I recently read that the oldest Gen Z-ers turn 29 this year. Aside from the fact that time is apparently flying by, it made me pause: I was 29 when I joined my first board. That means the generation many people still think of as ‘interns’ is now old enough to sit at the table… and over the next decade, boards that want to stay relevant will need to get serious now about recruiting, developing, and retaining Gen Z (and millennial) directors.

This isn’t just another diversity box to check. It’s going to be a growing governance need. Your organization is trying to hire Gen Z talent, sell to Gen Z customers, build for Gen Z communities. If nobody in the room has lived that experience, you’ll be making decisions with a piece of the picture missing. It's why many organizations create youth councils or advisory groups made up of the people they serve: someone, somewhere, knew the board itself wasn't covering that ground.

So this week I wanted to talk about what Gen Z brings to the table, how you need to change board recruiting and governing to make room for them, and what gaps you’ll need to manage as they grow into the role.

Seeing What the Next Gen Brings to the Table

Before I dive into how to attract and develop Gen Z board talent, I probably need to make a stronger case for why you’d want them in the room in the first place. Here’s what this next gen brings:

Digital fluency. Whether they’re early adopters or true digital natives, younger directors will bring an intuitive grasp of technology that boards increasingly need, both to inform and oversee digital strategy, and to run board operations more effectively.

A values-driven lens. ESG, equity, community impact, and transparency aren’t side issues to this generation…. they’re baseline expectations. Younger directors tend to ask the why and who does this affect? questions earlier and more often in a discussion, which can save you from an expensive problem later… and potentially help you better connect with your community.

An entrepreneurial instinct. This generation came of age as the gig economy exploded. Recent reports suggest that 34% of Gen Zers have a side hustle, with many having built something, freelanced, or worked adjacent to founders. That shapes how they tolerate risk and value innovation.

Tolerance for change. In the era of social media, trends move in months, sometimes days. A generation raised inside that pace tends to be less precious about “the way we’ve always done it” and more oriented toward experimentation. This can be a useful counterweight in boardrooms that can default to caution and traditionalism.

A different vantage point. Beyond the traits above, younger board members often see things longer-tenured directors miss entirely: how a decision will read externally to a younger workforce or community and where legacy processes could cost the organization credibility.

Changing how you recruit

Most board pipelines run on two primary filters: years of professional experience and giving capacity. They’re looking for people who bring 20-plus years of executive leadership experience, or a technical background in finance or law, or the ability to write a five or six-figure check. But that type of filter will likely exclude almost anyone under 35. If you want Gen Z on your board, you have to expand what you’re screening for and where you’re looking.

First, stop requiring past board experience for entry-level seats. Most boards don’t need to gatekeep as hard as they are: 82% of boards run on an operating budget of $250,000 or less a year, and at that scale, a first time director with no prior board experience isn’t much of a risk. To be clear, this isn’t the right call at every scale (an enterprise organization running $20M+ probably does want someone who’s sat in a boardroom before), but for the vast majority of seats out there, ‘no prior board experience’ shouldn’t be disqualifying.

Second, recruit outside your existing network. Boards fill seats through personal referrals more often than they’d like to admit, and personal networks skew toward people who look like the people already in the room. So, instead, look where this generation actually is: tap university alumni boards and industry-specific young professional groups and try posting openings publicly instead of relying on closed networks, using platforms like LinkedIn, Instagram, Reddit, and TikTok to promote the opportunity.

Third, rethink giving requirements. Some organizations have already made this shift in the name of equity: instead of requiring a flat $5,000 minimum gift, for example, they use language like ‘give at a level that’s meaningful to you.’ That can open a board seat to someone who has plenty to offer and just doesn’t have five figures sitting around (yet!).

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Retaining and investing in their talent

Getting a younger director to say yes is the easy part… once you’ve actually opened the door. But keeping them and getting the value you brought them in for takes a little more effort. Here are a few things that I think move the needle (and benefit not just your gen zers but all serving on your board)

• Education. Most directors, regardless of age, have never had their fiduciary duties explained to them or been provided with basic governance education. Build an onboarding experience that includes both written materials and hands-on sessions that walk through legal responsibilities, financial reports, operating norms and behavior expectations, policies, and current board business.

• Accessibility. Choose meeting locations reachable by public transit or without reliance on paid parking or expensive long-range travel: not everyone owns a car or can casually eat a $400/year parking bill. The same logic applies to timing. A 2pm Tuesday meeting works fine for a retiree who controls their own schedule, but not as well for someone earlier in their career who can’t just step out of the office midday, or a parent juggling pickup and drop-off.

• Tech-enabled operations. Gen Z doesn't just prefer good tools… they've never worked anywhere that lacked them. Build a board portal and leverage shared tools for async work and questions between meetings. Consider inviting younger directors to help you upgrade your tech stack and train fellow directors if this is still a gap.

• Sharper communication. In general, executive communication should be short, direct, and increasingly visual. Packets and supplemental materials should be layered, when possible (think a one-page dashboard ahead of a twenty-page narrative memo, or a five-minute summary before the deep dive). This helps those newer to the content orient in and retain more information.

• Collaboration. The board has to demonstrate genuine openness to different perspectives, especially from those with less tenure. Concretely, that means your facilitator needs to know how to draw out newer directors to weigh in before the room’s most senior voices anchor the conversation.

• A readiness to mentor. Pair every incoming director with a mentor on the board who debriefs with them after each meeting: what landed, what didn’t, and why. The less executive-room exposure someone has had, the more that debrief matters.

Acknowledging the Risks

Okay, but I won’t pretend this is all upside. Bringing Gen Z onto your board comes with a few risks to keep in view.

The experience gap. The older I get, the more I notice my own gaps from back when I started. The experience to know when to push and when to defer, the pattern-matching skill that only comes through having sat in the executive seat several times, the calm in the face of crisis because I’ve seen things like it before. First time directors are more likely to lean into what feels urgent vs what is actually important. Again, good onboarding an mentorship make a huge difference on this front.

Social media risk. Younger folk are more online and engaged in social media, and thus more likely to treat a board seat the way they’d treat any other part of their public identity, which can be a real mismatch with what a fiduciary role requires. Define early and clearly what can and can’t be shared publicly, and how to communicate professionally in ways that don’t compromise the organization. Put it in writing as part of onboarding, like a simple one-page policy covering what’s off-limits to post, screenshot, or discuss, and walk through it in the first meeting.

AI risk. Millennials and especially Gen Z are more rapid adopters of new AI tools, both at work and in how they process information generally. Its an asset when it comes to spotting useful applications early… but it’s also a governance risk if it outpaces the board’s own guardrails: sensitive material pasted into an outside tool, drafts run through an assistant without a data-handling policy in place, or decisions informed by outputs without enough rigorous review. This applies to the whole board, but younger directors will be the ones pulling AI into the boardroom fastest, so your policy work needs to keep pace with them.

The Bottom Line

I want to wrap by saying that I am not trying to convince you to lower your bar. Every director, regardless of age, still needs to meet the required time and financial commitment of your board, and bring domain expertise that adds value. Young directors still need to be competent and you shouldn’t rush to place just anyone just to check this box.

But the boardroom is going to look different over the next ten years, whether boards plan for it or not. The ones that get ahead of it, by updating recruitment practices, building in flexibility, writing policy, and welcoming in new and different perspectives will get sharper, more current, more resilient governance out of the deal.

❓How has your board expanded accessibility and diversity, and what moved the needle?

Over the last ten years, I’ve seen the inside of a lot of struggling organizations, as an interim exec and as an advisor to other leaders and boards. … and while there are many factors that come into play when it comes to org decline and dysfunction, the one contributing most often is bad design.

Organizational design is the set of decisions that determine how work gets done in your business: what each role is responsible for, who and how you go about filling that role, and how those roles connect to each other through reporting lines and decision rights. It’s not the org chart itself (that’s just the output). Design is the thinking that produces it.

Good design creates a reality where work moves along smoothly, decisions get made at the right level, and people are clear on accountability. Bad design, on the other hand, drives up costs, slows performance, and leads to conflict, confusion, and bottlenecks. It’s usually the real driver behind whatever the org is calling a ‘people problem’ or ‘execution problem.’

Few leaders get to build a structure from scratch. Most inherit what someone else built, or are promoted into making these calls without anyone showing them what good looks like versus bad. That’s how the same mistakes keep showing up across otherwise very different organizations.

The good news is that these pitfalls are learnable, and, once you know what to look for, avoidable. So here are the three things I think you should pay attention to when designing your organization.

1 | How You Design Roles

Role design is the decision of what a job covers and what it’s called: the title, responsibilities, and required qualifications that define a position. It’s the starting point, and thus, the first place things go wrong. A poorly designed role creates a host of issues downstream: wasted talent, roles nobody can backfill, and people set up to fail before they’ve even started.

🚩The Pitfalls

Here are ways I see leaders get role design wrong most often:

Frankensteining - You stitched together unrelated responsibilities, often spanning entirely different domains of expertise. Perhaps you have a top performer who wants to grow so you pile on disconnected work, or maybe you've got a handful of functions that don't each need a full-time person, so you bundle them into one catch-all role in order to hire a single FTE instead of finding a fractional or outsourced fit for each piece. Either way, you end up with a role nobody can backfill, doing several jobs poorly instead of one well.

Title Inflation. Someone valuable asks for growth, and instead of giving it to them, you give them a label: a bigger title with no change in pay or responsibility… which cheapens it for everyone else who holds the same title and operates at that level.

Title Invention. A manager asks to be a Director, so you make them one, not because the org needs a Director, but to keep them happy. Now you're paying director-level cost for work that hasn't materially changed, and you've set a precedent for what it takes to get promoted that has nothing to do with actual scope or impact.

The Equality Trap. Everyone gets the same title or comp in the name of fairness, regardless of actual scope or impact. The head of a 3-person team ends up with the same title as someone running a team of 20, and now titles stop meaning anything: nobody can tell who owns what, and you've lost the ability to differentiate pay or promotion based on real impact.

“We’ve Always Had This Role”. A position made sense years ago and nobody's revisited it since. Your Director of Major Gifts is still around even though your funding model has shifted almost entirely to grants. They find things to do, everyone does, but the role doesn't ladder up to where the organization is going.

✅ The Solutions

• Annually audit roles against strategy. If this role didn’t exist today, would you create it? If the answer is no, then it’s time to change the position into something the business needs now.

• Design growth paths that build depth, not breadth. When someone asks for growth, promote them into bigger responsibility within their domain, move them to a new function with clear boundaries, or invest in their development, … but only if the business needs it.

• Separate the title from the reward. If someone deserves recognition but the role isnt there yet, use a bonus, comp adjustment, or development investment instead of a title that outpaces the job.

• Be honest about career ceilings. If someone has outgrown their role and there’s no next level for them in your organization, tell them directly, give them runway to look elsewhere, and don’t punish them for wanting more.

• Differentiate based on scope, not fairness. Tie titles and comp to a clear rubric, team size, budget owned, decision rights, so the difference between roles is defendable.

• Fix Frankenstein roles before they become urgent. Once a frankestien role vacates, you will struggle to backfill it because you’re now hiring for a job that combines unrelated skill sets, and that person rarely exists in the market. Ask whether each bundled function is strategic enough to justify its own hire, even fractional. If yes, split it out now; if not, consider the cut.

2 | How you hire people

Staffing decisions are about who fills a role and when (hiring, promoting, and adding headcount). Even a well-designed role can add no value, or work against you, if you poorly timed or considered. Worse, while hiring decisions are easy to make, they are hard to reverse. Plus, a bad hire costs more than a salary…. it can erode culture, slow down teams around them, and set a precedent for what your organization thinks is acceptable.

🚩The Pitfalls

If you’re ramping up to add headcount or hire for a vacant role, try to avoid these traps:

Automatic Backfilling - Someone leaves, and you post the exact same role without asking whether you still need it, or need it in that form. The org has likely changed since that person was hired but refilling the seat as-is is easier than re-evaluating it.

The Counteroffer Trap - Someone gives notice, you scramble to keep them with a raise or promotion, and they stay …for now. Often they leave within a year anyway, because whatever made them look elsewhere didn’t get fixed. You’ve also just told everyone else on the team that resignation letters get results. Yikes.

Promoting Your Top IC to Management. Your best associate becomes a people manager, now handling forecasts and one-on-ones instead of the work they were great at. Theyre not particularly good at coaching, which is creating people problems, and you’ve lost your top performer in the process.

Hiring for a resume, without consideration to context - You picked the candidate with the most impressive background or fancy title over the person who fits what the role requires right now. Think: a former VP from a 500-person team joins your 15-person team and either gets bored, tries to build infrastructure you don’t need yet, or leaves within a year because the job is smaller than their ego expected.

Hiring to Relieve Pressure - You say yes to every request for more staffing, without digging into the real why. Sometimes this happens slowly: a team says they’re underwater, you approve headcount, and a year later they’re still underwater, just with more people and higher costs. Sometimes it’s a spike: a team drowns after a launch, you hire a few extra hands for the work, and the headcount stays long after the crisis passes.

Hiring for a Fantasy Future - You hire the team you’ll need in three years before you have the strategy or revenue to support it. It feels like investing in growth, but the money is really going toward capacity you can’t use yet.

✅ The Solutions

• Before you approve headcount, spend two weeks watching where time goes. Look for the bottleneck: is it bandwidth? Or is it messy scope, weak systems, or a manager who’s in over their head? If it’s any of the last three, more people won’t fix it, they’ll just spread the same problem across more headcount.

• Ask if this is a spike or the new normal. Has the team been underwater for a few months, or did this start right after a launch, a departure, a busy season? If it’s a spike, bring in a contractor or temp help… and only make it permanent once you’ve watched the need hold steady for a full quarter.

• Give your best individual contributors somewhere to go besides management. Build an IC track that pays as well as management does (if possible), so people don’t have to become managers just to get paid more. And if someone does move into management, train them for it, don’t just hand them a title and a calendar full of one-on-ones.

• Score candidates against a rubric. Write down what the role needs, and the context, then hold every candidate up against it. If you can’t explain why this specific person fits this specific scope, on paper, not vibes, then you might be getting into hot water.

3 | How You Draw Lines (Reporting lines)

Reporting structure is how roles connect to each other: who reports to whom, how many layers exist, where decisions get made. Get this wrong and decisions slow down, ownership gets blurry, conflict grows, and people spend more time managing politics than doing their jobs. Layers pile up that don’t need to exist, work gets duplicated across teams that don’t know who’s accountable, and managers end up stretched across more people than they can support. It is usually a symptom of problems upstream, poorly defined roles or headcount added for the wrong reasons, but the structure itself can compound the damage on its own.

🚩The Pitfalls

Vanity Hierarchy -You build layers to justify a title. Your Director wants to be a Senior Director, which means you need more Directors, which means you need Managers. Now you have many more layers where fewer would do… costs skyrocket and decisions crawl.

Autonomy Creep - You give a senior leader room to spot opportunities and run with them… and run they do! They pick up projects outside their scope because they’re capable and engaged, but over time, their role expands into adjacent territory, creates problems with other teams, and department lines blur.

Matrix Madness - You can’t decide whether your communication associate reports to Development or Marketing, so you make it report to both. Roles have dotted lines everywhere. It feels sophisticated, but nothing is owned. You’ve built accountability soup.

Too Many Direct Reports - One leader has 15 direct reports because you’re trying to stay flat or avoid adding a layer. But execution slows down, people can’t get time with their manager because they’re too busy, and the leader burns out trying to support everyone.

✅ The Solutions

• Map the critical path first. Before you design structure, understand the processes that create value and revenue, and design around those workflows.

• Design hierarchy based on work. Add a layer only when decision-making complexity or scope requires it. If someone has outgrown their role but you don’t need another layer, expand their scope horizontally or help them find the right level elsewhere (aka help them move on.)

• Set explicit boundaries on scope. When you give someone autonomy, be clear about where it stops. Review scope expansion regularly, and pull it back when it crosses into someone elses domain.

• Minimize matrix structures. Every role should have one clear manager who owns their development, priorities, and performance. Build cross-functional collaboration through process and shared goals, not reporting lines. If you must use a matrix, be precise about who owns which decisions.

• Respect span-of-control limits. Most managers can effectively support 5 to 8 direct reports, stretching to 10 to 12 on high-performing, low-touch teams. Past that, you’re likely setting people up to fail.

• Fix the real problem before the org chart. Before you reorganize, ask whether you have a structure problem or an execution problem. If teams aren’t communicating, build better systems. If there’s no trust, address it directly. If accountability is unclear, clarify it through goals and decision rights. Save reorgs for when the work itself has changed.

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The Takeaway

As an interim leader, I’ve had to unwind these decisions more times than I can count. The fixing is hard because it usually hurts people: de-Frankensteining a role feels like a demotion, solving headcount bloat usually means terminations or salary adjustments, untangling a matrix creates political fallout and frustration. It’s pain, start to finish.

But leaving things as they are is worse: your organization can’t scale, can’t adapt, and can’t execute, because its fundamental architecture is broken... and every shortcut you take today becomes someone else’s nightmare tomorrow, and that someone might be you (or me).

💡What’s the org design mistake I didn’t cover here? Tell me and I’ll add to this list!

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Happy summer, everyone!

I’m a voracious reader. Every year I chew through 100+ books across all kinds of genres. As summer rolls in, I’ve been pulling together my reading list for the season, and as always, a few books on leadership, boards, and the nonprofit sector find their way in.

If you serve on a board or lead an organization, and are planning to spend time on the beach with a book, below are some titles I’ve read and think are worth your time. It’s a bit of a mixed bag. Some help you understand the sector better, including its possibilities and its problems. Others are practical, focused on the skills that can make you more effective. Not all are explicitly about governance or nonprofits, but I think all of them can help make you a better leader.

Happy reading and see you next week as I resume my regular schedule of weekly articles!

Caitlin

📌P.S. I'd love to make this a two-way conversation. If you've read something recently that's made you a better board member or leader, hit reply or drop a comment. Always looking to add to the stack. :)

Books for Exploring The Sector, Its Possibilities, and Its Problems

Reimagining Nonprofits and Philanthropy: Unlocking the Full Potential of a Vital and Complex Sector by Vu Le

An obvious inclusion. If you’ve ever read Vu Le’s blog Nonprofit AF, you already know what you’re in for: sharp, funny, and consistently right about things the sector doesn’t want to hear. This book was published in late 2025, with each chapter tackling a different topic… which I look forward to assigning to my master students this fall! (Boards get their own chapter, and it is not flattering.)

Nonprofit Turnaround: A Guide for Nonprofit Leaders, Consultants, and Funders by Jan Glick

Don’t let the boring cover turn you away. This book is fantastic and a must read for nonprofit leaders. Glick walks through how to recognize crisis symptoms, build a leadership team under pressure, and make hard decisions about culture, programs, and the business model. Considering the state of the sector, better to read it before you need it.

Scene Change: Why Today’s Nonprofit Arts Organizations Have to Stop Producing Art and Start Producing Impact by Alan Harrison

Just finished this book earlier this year. Though framed for arts organizations, I’d encourage anyone to give it a read (at least the first few chapters). Harrison’s argument is simple: excellent art alone is not a nonprofit mission. If your programs aren’t creating real, measurable change in the community, you’re not fulfilling your 501(c)(3) purpose… no matter how good the art is. More broadly its a commentary on how to keep your organizations priorities straight,

Mutual Aid: Building Solidarity During This Crisis (and the Next) by Dean Spade

A short pocket read. Spade talks about community-based mutual aid networks as an alternative (or at least a complement) to traditional nonprofit service delivery. You don’t have to agree with his politics to benefit from understanding the critique.

Decolonizing Wealth: Indigenous Wisdom to Heal Divides and Restore Balance by Edgar Villanueva

Villanueva writes from his experience as a Native American philanthropist to challenge the colonial patterns embedded in how wealth moves through the nonprofit sector. The questions he raises about power, proximity, and whose judgment gets trusted are ones every board should sit with.

Nonprofit Strategy Revolution: Real-Time Strategic Planning in a Fast-Moving World by David La Piana

Most boards are still running traditional multi-year strategic planning processes that bear little resemblance to how the world actually changes. La Piana makes the case for a more iterative approach to strategy, where you treat the strategic plan as a living conversation rather than a document to ratify.

Books on my to-read list in this category this summer:

• Philanthropy: From Aristotle to Zuckerberg by Paul Vallely - I love books that blend together history, anthropology, and philosophy to help me better understand philanthropy. Hoping this stands up!

• Winners Take All: The Elite Charade of Changing the World by Anand Giridharadas - A critique of how wealthy elites use philanthropy to protect the very systems that generate inequality. Interested to see how it might change my viewpoint on donors in the boardroom.

Books for Building Skills and Ways of Being That Make You Better in the Boardroom

These are not board-specific books, but reads that helped me lead organizations and the boardroom better.

Radical Candor: Be a Kickass Boss Without Losing Your Humanity by Kim Scott

If you know me, you know this is one of my favorites. The ability to give and receive honest feedback is a critical facet of strong leadership… and boards are teams too. They face the same challenges with honesty and directness that any team does. Scott’s framework (care personally, challenge directly) is as valuable in the boardroom as it is in the executive suite.

The Art of Gathering: How We Meet and Why It Matters by Priya Parker

A lot of board meetings are, let’s be honest, not great. Parker’s book is about how to design gatherings that actually accomplish what they’re meant to accomplish. Every gathering should have a clear, specific purpose that shapes every decision about format, structure, and who’s in the room.

Reinventing Organizations by Frédéric Laloux

Laloux maps the evolution of organizational structures and makes the case that most organizations are still operating on management models that no longer fit the world we live in. His concept of “teal organizations” will either strike you as visionary or unrealistic. Either way, it will force you to examine assumptions about hierarchy and how decisions get made.

Books on my to-read list in this category this summer:

• The 2-Hour Cocktail Party by Nick Gray - Seems like a quick read with practical advice for building a stronger network (a key skill for any board member or leader!)

• Love and Work by Marcus Buckingham - I’ve always disliked the phrase ‘Do what you love.’ — and am curious how Buckingham will approach this mindset.

• Thinking in Systems: A Primer by Donella H. Meadows - On my quest to continue to collect frameworks and mental models. I already a believer of systems thinking, but don’t mind expanding on that.

There’s plenty of governance advice out there: Books, webinars, consultants, writers like myself, all telling boards what they should be doing. But most skip the question that matters first: what kind of board are you? A three-year-old all-volunteer organization and a regional hospital system with a $40M budget and 15 sites face different challenges, carry different risks, and are held to different standards of governance. Yet both tend to reach for the same playbook (and wonder why the advice doesn’t fit).

In my consulting work, I meet a lot of boards that feel stuck or dysfunctional. If you serve on one, your problems probably feel big and unique… but they’re usually neither. Most of what goes wrong on boards is predictable, and there often are solutions other boards have already worked through. You just need a lens to see it.

Reframing and building on Karl Mathiasen III’s work (see the author’s note below), I want to talk about four board operating modes. What determines your mode isn't size, budget, or age. It's how the board relates to power: where authority lives, how much risk and public accountability the organization carries, and who the board is loyal to. Once you better understand this, you better understand what’s expected of you as a director, what expertise is needed in the boardroom, how the board should relate to staff, strategy, and the public, and what pitfalls to watch for.

As usual, I've tried to make this a useful tool. Under each mode you'll find a way to identify whether it's you, the pitfalls that predictably show up, practical advice for governing well, and the forces that will eventually push toward change.

👁Quick Glimpse - The Four Modes

• Following Mode — decision-making authority flows through, and defers to, a single person.

• Working Mode — the board is the operational capacity of the organization.

• Governing Mode — board and staff hold separated roles and negotiate a shared power structure, with varying degrees of success.

• Enterprise Mode — the board governs at arm’s length, trusts professional staff, and focuses on risk, resources, and reputation.

Mode 1 | Following

📍This is the board that gets built around a person. Decision-making authority flows through, and defers to, a single person.

The defining characteristic of a Following Board is loyalty and deference: (1) Loyalty to the executive leader, before or instead of the mission. And (2) deference of authority, where decisions flow through one person and real accountability is largely absent.

Maybe it’s a founder who pulled together a board of family and friends who believe in them… or maybe it’s a long-tenured CEO who reshaped the board over time, nudging out independent voices and recruiting people from their network. The origin story isn’t important. What matters is the dynamic: authority concentrated around a single leader, the board following rather than governing, and the mission subordinated to the interests of one person.

Is This You?

• Are new directors recruited by the executive leader* or does the leader have significant influence over who joins?

• Do directors feel/seem more loyal to the exec leader (vs the mission)?

• Does the leader set the agenda, drive the conversation, or control what information the board sees?

• Is the organization's identity intertwined with the executive's identity publicly?

• Are major decisions made by the executive and presented after the fact?

• Does the board never pushback on the Executive leaders ideas?

• Does the board never hold the executive accountable?

*this could also be a founder or a board president

Common Pitfalls & Patterns

The Following Board has a predictable set of failures. Most share the common root of personal loyalty crowding out mission accountability. Rubber-stamping, where motions pass without real deliberation and challenging the leader feels disloyal.

• The loyalty loop, where new directors are recruited from the execs personal network, leading to a lack of independence.

• Conflicts of interest go unnoticed or unaddressed.

• Mission drift, as the organization’s focus shifts with the executive’s evolving interests and priorities, and no one willing or able to check it.

• Staff vulnerability due to board unwillingness to hear staff concerns if something goes wrong.

• Succession blindness, where things are going well enough that nobody thinks about what happens when the executive leaves… and the board isn’t built to govern independently when that day comes.

• Financial and compliance risk, where the absence of hard questions allows errors and mismanagement to go undetected longer than they should.

The Upside & Advice for Followers

A Following Board isn’t without its strengths. A small, tightly aligned board can move fast, and give a founder or executive the space to take risks, innovate and iterate quickly, and gets things done without gridlock. For organizations doing relatively simple work or still figuring out who they are, this mode can be perfectly adequate.

Unfortunately, all Following Boards have an expiration date. A Working Board can run for generations and a Governing Board can be a permanent home, but a board built around one person only lasts as long as that person does. Sooner or later, every Following Board is forced to evolve.

The tricky part is that the evolution rarely happens by choice. It takes a trigger: a leadership transition, a financial shock, a serious complaint coming to light, growth the organization isn’t ready for. And when the trigger comes, a board built to follow is suddenly asked to govern. The boards that navigate this best are the ones that didn’t wait for it: they built independence, accountability, and a succession plan while things were still steady. So don’t wait.

• Start asking questions. Take a personal interest in the organizations mission. Do your due diligence before meetings. Engage in discussions about strategy, rather than following blindly along.

• Hold the leader accountable for outcomes, financial performance, and the mission impact.

• Recruit at least one or two genuinely independent voices… people with no personal relationship to the executive who are there purely for the mission. Even one person willing to ask hard questions changes the dynamic.

• Establish basic governance infrastructure including a conflict of interest policy, an annual review process for leadership, and clear board roles.

• Take ownership of board recruitment. The leader should have input, but not control, over who joins the board. Break the loyalty loop!

• Separate the leaders identity from the organization’s identity, thinking about how you communicate publicly, how you recruit, and how you talk about the work. The organization needs to be able to exist without any single person.

• Start talking about succession early, not because anything is imminent but because a board that has never discussed it isn’t ready when it needs to be.

Mode 2 | Working

📍This is the board that is the organization.

The defining characteristic of a Working Board is shared ownership and distributed authority. Unlike the Following Board, there is no single person at the center. The vision (and work) belong to everyone in the boardroom.

Working boards are usually born from the community: neighbors coming together to make a difference or advocates for a shared cause…. so from day 1 there is universal buy-in to the mission. The structure is flat and decisions tend to get made by consensus, which, while democratic, can be slow and exhausting.

Working boards can persist for a very long time, decades even if the scale stays small. And there is nothing wrong with that. A working board that knows what it is, and maintains balance, can be incredibly effective.

Is This You?

(These don’t all have to be true for this to be you.)

• Does the org run on board and volunteer labor, with little to no paid staff?

• Did the board found the organization (vs. a single leader?)

• Is there a strong sense of personal ownership over the mission and the work?

• Do board members hold operational roles or responsibilities outside of governance? e.g. program direction, event coordination, and the like?

• Are board meetings operationally focused? Are committees mostly engaged in programs and operations?

• Is it hard to tell where board work ends and staff work begins?

• Does the budget rely on the networks and relationships of board members?

• Is the board apprehensive about hiring staff, or resistant to giving staff authority?

Common Patterns & Pitfalls

Common sources of pain can vary, but often stem back to the high investment of emotional energy and social component of service.

• Burnout, where board members are carrying both operational and governance responsibilities and neither gets the attention it deserves.

• Consensus paralysis, where the culture of shared decision-making makes it hard to move quickly, resolve disagreements, or hold anyone accountable.

• Mission and strategy stagnation, where the org keeps doing what the founding group knows and loves rather than what the community has evolved to need.

• Governance bad behaviors including side conversations, cliques, and informal decision-making that happens outside the boardroom.

• The insider/outsider dynamic, where founding members form an informal power center that controls decisions, leaving newer members feeling like outsiders.

• The ownership crisis, where staff are hired and a prolonged power struggle emerges between the board that built everything and the staff now being asked to lead it. (This muddy middle can drag on for years.)

• Board leadership determined by availability or popularity rather than expertise and capability.

The Upside & Advice for Workers

The Working Boards greatest strength is the individual investment in the mission. It is deep and personal and usually intense. These boards show up, do the work, and care about the organization’s success in a way that is hard to replicate. In the early stages and at smaller scales, that hands-on involvement is exactly what keeps the organization alive and moving forward. A Working Board that understands its mode and manages its boundaries well can be remarkably effective for a long time.

Here’s how to lead well on a working board… and through its evolution.

• Draw clear lines between board and staff responsibilities, ideally before you make your first hire. Treat it like a governance transition, not just an HR milestone.

• Document policies and procedures. Running on shared norms and handshake agreements works until it doesn’t.

• Invest in onboarding new board members to shared norms and decision-making expectations. In consensus-driven cultures, unspoken assumptions cause the most damage.

• Combat the insider/outsider dynamic with structure. Term limits prevent any one cohort from cementing control. A board orientation gives new members the context and confidence to participate. Rotating committee and officer roles keeps power from consolidating in the same hands.

• Actively recruit outside the founding community. Fresh perspectives break the insularity that keeps working boards stuck.

• Trust your staff. Delegate operational authority and build a professional relationship with defined lanes.

• Check the ego at the door. The organization belongs to the mission, not to the people who built it. It is going to change and the board needs to change with it.

• Exit directors who are unable or unwilling to make the shift as the org grows.

Scaling into Crisis

If your organization ever wants to grow, it will need paid staff. Volunteer labor can sustain a small operation indefinitely, but it can’t scale one. So at some point you hire… and that’s when the trouble starts.

It doesn’t show up right away. The first hire or two coordinate the work, the board keeps running the show, and the arrangement feels fine. But as the team gains size and independence, the questions pile up. Who actually runs operations? Who decides what? Where does the board end and staff begin? Every new hire turns up the tension, and it keeps building until the line gets drawn. It’s a power struggle that can drag on for years.

The boards that make it through check their egos, get clear on roles and responsibilities, invest in governance education, and think long-range about what the organization needs rather than what they want to hold onto. They evolve into a Governing Board. It’s hard work, but there’s no scaling without it.

Mode 3 | Governing

📍This is the board where authority is divided. Board and staff hold separated roles and negotiate a shared power structure, with varying degrees of success.

The defining characteristic of a Governing Board is the separation of authority: the board governs, management leads day-to-day operations, and neither side runs the other. The board’s job is holding management accountable for strategic direction, not doing the work (that’s the Working Board) or cheering on the leader (that’s the Followers Board).

Organizations at this stage have staff, carry real risk, and often manage facilities, assets, or liabilities that demand clear lines of responsibility. The division of roles is a necessity: someone has to be accountable for operations, and it can’t be the board.

Governing Boards sit on a spectrum from highly functional to deeply dysfunctional, and yours likely lands somewhere in between.

Is This You?

• Does the organization have paid staff with clear division of responsibilities between board and staff?

• Does the executive leader report to the board, and does the board exercise oversight rather than defer to them?

• Is the organization’s risk profile manageable without specialized legal, financial, or regulatory oversight at the board level?

• Are committees focused on governance and oversight work rather than running programs or operations?

• Does the board govern through policy? E,g, setting boundaries, delegating authority to the executive, and holding management accountable?

• Is the board recruited for skills, perspective, and expertise rather than their relationship to management or individual board members?

Common Dysfunctions

Because Governing Boards sit on a spectrum, a lot can go wrong in a lot of ways. Some boards are missing structure, some are missing real evaluation, some have most of the pieces but not all of them… and the gaps are where the problems grow. Here are some common ones:

• Governance theatre, where the board is just goes through the motions… meetings happen, votes pass but nothing meaningful gets examined.

• Strategic drift, where the organization keeps doing what it has always done without questioning whether it’s still working.

• Committees meet but don’t produce anything.

• Policies go without update or aren’t followed.

• Over-reliance on a successful executive, with the board rubber-stamping whatever comes through the door.

• Growing complexity without growing expertise, where the organization’s scale and risk profile outpace the board’s ability to govern it.

• Long-tenured directors with no end in sight, stuck in how things used to be and resistant to how things need to be.

• New voices welcomed into the room but the same people driving every conversation, leaving fresh perspectives unheard.

• Board recruitment that gets lazy, filling seats with whoever is available rather than whoever is needed.

• Executive evaluation doesn’t exist or is a formality rather than a real accountability tool.

Advice for Directors on a Governing Board

The Governing Board knows its role, respects the line between governing and managing, and has built the relationships and systems to back it up. For most organizations, this is the destination. It’s not a stepping stone to something bigger, but a garden to tend and grow. Here’s how to make the most of it.

• Treat board recruitment as a strategic exercise, not a social one. Every open seat is a chance to fill a gap in expertise, perspective, or community connection.

• Make your executive director evaluation process real. Set goals at the start of the year, revisit them mid-year, and do an honest assessment at the end.

• Audit your committee structure periodically. If a committee hasn’t produced anything meaningful, it either needs a mandate refresh or it needs to be dissolved.

• Keep asking as the organization grows: does this board have the expertise to govern what we’ve become? The answer changes, act on it.

• Enforce term limits. Long-tenured directors calcify thinking and block fresh perspective. Build rotation into your bylaws and hold to it.

• Keep self-assessment and board education as standing priorities.

• Develop a robust onboarding practice that welcomes directors into the conversation, not just the room.

The Case to Evolve

Most organizations will never need to move beyond the Governing Board mode. But some organizations find themselves being pushed toward something bigger. The trigger here is rarely a crisis. It’s more of a dawning recognition that the organization’s scale, risk profile, and public accountability have outgrown the board’s current practices. A few signals worth paying attention to:

• The organization has become a significant public institution with a level of scrutiny that demands more formalized oversight.

• Operations have crossed into enterprise scale: significant staff, budgets exceeding $25 million, programs delivered across multiple sites or states.

• The organization manages multiple entities, subsidiaries, affiliates, or chapters.

• Large government contracts or a highly regulated environment demand more sophisticated legal and financial oversight.

• Liability and risk exposure have grown to a level the current board isn’t equipped to govern.

• The board can no longer provide the financial capacity, expertise, or credibility the organization needs to compete at its level.

The question to ask is whether your current mode is adequate for the organization you are today. If the answer is yes, stay the course and govern well. If the answer is no, it might be time to read on.

Mode 4 | Enterprise

📍The board governs at arm’s length, trusts professional staff, and focuses on risk, resources, and reputation.

Not every organization makes it here, and not every one should.

The Enterprise Board is governance at scale. The organization has grown into a serious public institution: large budgets, significant staff, multiple sites, complex assets, and serious liability exposure. Think hospital systems, large universities, major social service agencies, national disaster relief organizations. At this level, the consequences of getting things wrong are public, and in some cases, life-threatening.

The defining characteristic of an Enterprise Board is governance at arm’s length from operations, with a primary focus on risk oversight, public accountability, and resource generation at scale. The board is not close to the work. It doesn’t need to be. It needs to be capable of governing an institution whose complexity no single person fully understands, and doing so with the rigor that level of public trust demands.

This is also the one mode where seeking prestige and access is not vanity. The ability to make significant gifts, open significant doors, and navigate high-level public relationships is part of the job at this scale. It has to be built into how the board is recruited and how membership is defined.

Is This You?

• Is the board large and formally structured, with directors who bring substantial financial capacity, executive-level expertise, or high-profile public influence?

• Are committees fully functional and independently operational across all major domains: finance, audit, governance, compensation, risk management?

• Is fundraising professionalized and staff-led, with the board activated as partners rather than drivers?

• Is governance infrastructure supported by dedicated staff, legal counsel, and formal board management systems?

• Are performance expectations set and actively managed for both board members and executive leadership?

• Is the board-CEO relationship defined by professional distance, with clear mechanisms for evaluation, escalation, and termination?

• Does board service carry visible public prestige and attract civic, industry, and philanthropic leaders?

Advice to the Enterprise Boards

The Enterprise Board, when it works, is governance at its most powerful: serious talent, resources, and public credibility in service of a mission operating at scale. Directors at this level have served on multiple boards before. They come in prepared, having done the work before they walk in the room. They understand the difference between governing and managing and don’t blur the line. They ask hard questions without micromanaging, and they bring deep expertise (legal, financial, sectoral, or relational) and deploy it in service of the board’s work rather than their own agenda. They take their fiduciary responsibilities seriously, engage with risk and compliance, and hold the executive accountable with rigor and respect. They give, they open doors, they are visible to the public, and they know when it’s time to leave.

Tips for functioning and growing well:

• Do not recruit first-time board members. This is not the place to learn what fiduciary duty means or how to read a balance sheet. By the time someone joins an Enterprise Board, they should already know how to govern. Your orientation should be about this organization, not governance 101.

• Build risk management into your committee structure. An audit or risk committee that meets regularly, has teeth, and reports directly to the full board is not optional at this scale.

• Be deliberate about board composition. Not every member needs to be a specialist, but the board as a whole needs the depth of legal, financial, and sector expertise to critically evaluate what it is being asked to approve.

• Govern the board itself with the same rigor you bring to governing the organization. Term limits, annual self-assessments, clear expectations for attendance and giving, and an offboarding process when members are not meeting them.

• Bring on dedicated staff to support governance. Volunteer-driven board management is no longer sufficient.

• Anticipate stakeholder activism. At this level, employees, community members, funders, and regulators all have opinions and will not hesitate to voice them. The board needs to be prepared for that scrutiny, not surprised by it.

• Maintain the connection to mission. The bigger the board and the more removed from operations, the easier it is to lose sight of why the organization exists. Build in regular touchpoints with the communities and people the organization serves.

Traps to Avoid

All modes come with their problems, and the enterprise board is no exception. When dysfunction sets in, it likely looks like this:

• Directors who are there for the credential rather than the work, expecting influence disproportionate to their actual engagement.

• Committees that operate so independently they create silos, and the full board loses visibility into critical information.

• Board size becoming unwieldy, making real deliberation nearly impossible and reducing full board meetings to ratification exercises.

• Over-reliance on staff to prepare and present everything, leaving the board in a passive, receptive role rather than an active governing one.

• Risk and compliance functions that exist on paper but lack real teeth (e.g. audit committees that meet once a year and call it good.)

• The gap between the board and the communities being served growing too wide, leaving the board out of touch with the mission it’s supposed to protect.

• Governance becoming overly bureaucratic, with policies and processes that slow the work beyond what is reasonable.

Wrapping this up

If you’ve read this far, you probably recognized your board somewhere in here… maybe in more than one place. That’s normal. Real boards drift between modes, blend traits, and carry habits from what they used to be. The goal isn’t a perfect label; it’s a clearer view of how your board actually operates.

🫧Authors Note

This article builds on Karl Mathiasen III's work, published by the National Center for Nonprofit Boards in 1990 (cited at the end). It has held up well for 35 years and I've returned to it many times as a teaching tool. This article is just an attempt to extend it, adding observations from my own practice, and working through a few places where my experience led me somewhere different. I'm not claiming to have it more right. Just more to add.

Semantics: I’ve made the semantic choice to relabel Mathiasen ‘stages’ as modes. A stage implies a ladder, a progression from simple to sophisticated. But that’s not how boards actually work. Not every board needs to evolve, and not every one that does moves in a straight line. A Working Board that stays a Working Board isn’t behind. It might be exactly where it needs to be (and can be for a long time). Do I think ‘mode’ is perfect? No, but I think it is better than Stages.

Stage/Mode Definition: Mathiasen described boards through demographic markers: board size, fundraising capacity, formality, committee structure, board-staff relationships. All useful, and much of it carried over here. But the more defining qualities are how a board relates to power: how authority flows, how decisions get made, the scale of risk and liability carried, and the degree of public accountability the organization is subject to. I more directly am interested in this.

Breaking up Stage 1. Mathiasen treated his first two board types as variations of the same startup condition. I disagree. The Following Board and the Working Board can both exist far beyond the founding era, and the governance dynamics, challenges, and standards of good leadership in each are distinct enough to deserve their own treatment. Collapsing them misses too much. I don’t think I’ve fully worked this out here, but I also have seen boards regress and fit all the markers of a following board, without a founder in place.

Changing Institutional to Enterprise. I renamed the institutional board as the Enterprise Board, which is another semantic choice, and shifted the definition away from board size and fundraising expectations, which dominated his framing. Instead, I think better markers of an enterprise board is the scale of risk and liability the board carries, the complexity of the decisions it governs, and the degree of public accountability the organization is subject to.

Additional Stuff. Beyond this, I added in my own advice and observations, which I hope serves as a useful addition and resource for boards.

Mathiasen III, Karl. “Board Passages: Three Key Stages in a Nonprofit Board’s Life Cycle.” National Center for Nonprofit Boards, c1990

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P.s. Have a question? Disagree with something I said? Catch a typo? Tell me below :)

Here’s the big lesson learned over the course of nine executive assignments: How I build trust, how fast I move, who I talk to first, how I collect information all depends on the situation I’m walking into. Showing up the same way in a turnaround as I would in a healthy, growing organization isn’t only less effective, it would be damaging.

Any executive leader stepping into a new role needs to assess the business situation before they can determine the right strategy. The problem is that most people don’t make enough transitions in their career to develop strong instincts for it… so they default to what worked for them last time. And that's often where the struggling starts, or worse, where leaders fail and find themselves out the door.

So this is exactly where a good framework can be of help. Today I’m sharing with you the STARS model, which I first came across in Michael Watkins’ book The First 90 Days. Though that was almost ten years ago, I still pull it out every time I step into a new role. It helps me get my bearings and start acting quickly and confidently.

🔖(This is a long one, so bookmark it and come back when you’re ready to dive in!)

The Five STARS Situations

STARS stands for Startup, Turnaround, Accelerated Growth, Realignment, and Sustaining Success. These are five fundamentally different business situations, and thus require fundamentally different approaches to leadership. The model isn’t about neat lines and tidy boxes. Every situation you walk into will be unique… But the five situations here will give you a common language and a starting point. They help you find patterns more quickly, anticipate common challenges, and make better decisions before you have the full picture.

I’m not going to go deep-dive into each, but here is a high level overview.

Startup

If you’re in a startup situation, you’re building from scratch. On the upside, teams here usually bring high energy and enthusiasm for the mission, and you’ll get to take action without having to navigate legacy or bad habits. On the other side, structure will likely be weak, processes manual, resources tight, and culture? While full of potential, it can quickly spiral into misalignment if you’re not deliberate about it early. Expect to be hands-on and all-in.

⭐Leadership Tips

• Be decisive about what matters, and flexible about everything else. Save conviction for the things that are truly foundational in these early stages.

• Establish the fundamentals early. Culture, priorities, ways of working will form whether you shape them or not. Set your expectations clearly and hold people to them from the start.

• Own hiring and onboarding. Culture-setting begins during recruitment, and ripples out. A bad hire in a small team does big damage, so you’ll want your attention here.

• Stay focused on your core opportunities and problems. There will be an endless number of doors you could walk through. Be discerning about which ones you open. Losing the plot in the frenetic energy of a startup is easier than it sounds.

• Pilot before you commit. Early decisions have a way of becoming foundational, for better or worse. Take smaller bites, test ideas before scaling them, and don’t get attached to anything that doesn’t have the data to back it up.

• Know yourself. A startup will test your stamina and your ego. Set realistic boundaries around your energy, own your strengths and weaknesses, and ask for help before you need it.

• Delegate early, even when it’s uncomfortable. You cannot be everywhere, and trying to be will slow the most important things down.

Turnaround

The organization is in crisis and something has to change, and it has to change fast. Maybe funding has been pulled or a program failed or your leadership team collapsed. The pressure is intense, the timeline is short, and the stakes are high. Paradoxically, this can actually be one of the more straightforward situations to lead into. When things are clearly broken, people are primed to be led. They want direction and even small wins generate momentum. But make no mistake…. hard calls will have to be made, and quickly.

⭐Leadership Tips

• Triage! Deal with critical survival issues before anything else. Do you have enough cash? Can you make payroll? Are there a major grant or donor about to walk? Is there an accelerating staff exodus? Don’t take up large-scale, long-term transformation projects, such as launching a new programming or strategic planning, until the foundation is stable.

• Get consensus on the diagnosis before you reach for solutions. Don’t assume shared understanding just because there’s shared panic. Deep dive into the data, talk to staff at every level, and determine whether the problem is strategic, structural, cultural, or some combination. You don’t have time to treat the wrong problem.

• Secure early wins, as you need credibility and momentum in order to be effective. If there are obvious pain points you can resolve with a quick decision, make it… and then advertise it. (As Stephen Covey says about building trust: say what you’ll do, do what you’ll say, and advertise!)

• Learn your ‘power grid’. Figure out who actually influences the team… both directly and softly. I’m talking staff culture-keepers, board leaders, major donors, key stakeholders. You’ll need them on your side because formal authority only gets you so far.

• Get the right team in place fast. Identify your strong leaders and change champions early, ally with them, and position them where they can have the most impact. Where you find serious, entrenched resistance… move them on. If left in place, resisters will undermine everything you’re trying to do.

• Over-communicate. Silence breeds panic in a turnaround. Be transparent about what you’re doing and why. Test ideas with a small trusted group, but communicate broadly and often.

• Manage your energy. Turnaround environments are exhausting. Closed doors, time pressure, high emotion — it accumulates fast. You cannot lead well on empty. Protect yourself.

📌PS. I wrote about leading through crisis a little while back, with more detailed advice.

Accelerated Growth

Things are working … and working well! The organization is growing fast, demand is strong, and there’s real momentum behind the mission. This is an exciting place to lead. The challenge isn’t fixing anything, but to build the infrastructure and team that can support ongoing growth

⭐Leadership Tips

• Build ahead of the growth. Systems and structures need to be in place before you need them, not after. Anticipate what the next stage requires and start building toward it now… and don't fall into the trap of holding onto ways of working just because they're familiar. What got you here won't always get you there.

• Tend to your culture. As you bring people on, it becomes more important than ever to ensure new team members are really integrated… and that your values are consistent universally across the org.

• Shift from operator to orchestrator. As the organization grows, your job changes. You can no longer be close to everything… and you shouldn’t be. Build systems and develop leaders who can make good decisions without you in the room.

• Put the right people in the right roles. Growth creates new roles and new demands. Assess honestly whether your team has what the next chapter requires, and invest in developing them or bringing in new talent where needed.

• Over-communicate. Alignment happens naturally on small teams. It doesn’t at scale. You need to be consistent, and you need good downline discipline.

Realignment

This is a sneaky one, and in my experience, the most underestimated. Things aren’t on fire… but they’re drifting. The organization was successful, maybe still looks successful on the surface, but the signs are there if you look closely. Donor retention is slipping or financials are trending negative. Program participation is flattening. Staff turnover is increasing. The mission is starting to feel tired. This is the stage before a turnaround, and the defining challenge isn’t fixing a crisis, it’s convincing people one is coming. You’re fighting complacency, and sometimes willful blindness.

⭐Leadership Tips

• Lead with facts. People won’t accept a problem they can’t see. Use data, benchmarks, and external assessments to make the case objectively of the current situation.

• Create urgency without creating panic. Your job is to shift people from things are fine to we need to act … without triggering fear. Name the moment as an opportunity, use data, and avoid over dramatization.

• Shore up culture, systems, and skills. Unlike a turnaround, the strategy here is often still sound. What needs attention is how people and systems are working together or what capabilities are missing.

• Bring in outside voices. External perspectives, consultants, advisors, peer benchmarks, can help you say things you can’t. Use them to validate and amplify your case for change.

• Rebuild the top team where needed. Surround yourself with people who can see the drift and are willing to fight to correct it. Resistance at the leadership level will kill your efforts.

• Be patient but persistent. Realignment takes longer than a turnaround. Change here is deliberate and gradual. Don’t mistake slowness for failure… but don’t let patience become an excuse for inaction either.

Sustaining Success.

You’re inheriting something that is really working! The mission is clear, the team is strong, the funders are giving and happy, and your predecessor left big shoes to fill. This might sound like the easiest situation to walk into… but it comes with its own kind of pressure. With high expectations from all sides, many leaders are tempted to make their mark by changing things. But that instinct can be dangerous. The organization doesn’t need (or want) disruption. It wants continuity and steady leadership.

⭐Leadership Tips

• Resist the urge to change things for the sake of it. You were brought in because something is working, so be sure to understand what that is before you touch it.

• Honor what came before. By acknowledging the legacy of your predecessor, you can build trust and signal that you’re a steward (not a bulldozer).

• Listen before you lead. Your credibility here will be built through curiosity. Take time to understand why things are done the way they are before deciding what should be different.

• Keep the team motivated. Success can breed complacency, so your job will be to keep people energized and connected to the mission.

• Invest in what’s next. Sustaining success doesn’t mean standing still. Start looking for the next evolution, including new opportunities, emerging risks, the question of what this organization needs to become in 5-10 years.

• Develop your people. A healthy organization is the right moment to invest in leadership development and succession planning. Build the bench while you have the runway to do it well.

Using the STARS Model as a New Executive

As I said, I keep this model in mind whenever I start a new executive role. Here is some of my advice:

First of all, the diagnosis process starts before your first day. In fact, it begins when you’re interviewing for the role! You should research what’s publicly available, and make sure to ask targeted questions to the board of directors to get an early read on the organization. Some I like to use are:

• What does the financial picture look like over the next 12 months, and are there any significant risks or pressures on the horizon?

• How would you describe the organization’s culture right now, and how has it changed in the last few years?

• Are there any major strategic decisions either on the horizon, or have been delayed?

• Where do you think the organization is falling short of its potential?

• How aligned is the leadership team and board around priorities and direction?

• What has to go well in the next 90 days for this to be considered a successful transition?

• If you’re being completely honest… what’s the one thing you’re most worried about?

Second, take those answers with appropriate skepticism. Everyone has a perspective, and no single conversation gives you the full picture. Especially if you’re interviewing with a Board, where their visibility into the organizations day to day can be limited. So be sure, when you walk in through the door, to further validate, pressure-test, and fill in the gaps.

Finally, I also think its important to know yourself. Not every leader is built for every business situation. Turnarounds require a different kind of leadership skillset than a start-up . Some people thrive in chaos and grow bored in stability. Others are masterful stewards of success but freeze up when hard calls need to be made. The leaders who are honest about the situations where they thrive and where they don’t, tend to be the ones who do their best work. You need to know when to walk away from a role simply isn’t the right fit.

A final thought…

The biggest trap in any leadership transition is assuming what worked last time will work this time. Maybe it will. But you shouldn’t assume. Every situation is different, and the leaders who struggle most are usually the ones who never stop to ask what this moment actually requires of them.

STARS doesn’t give you all the answers but it can get you started in the right direction, faster.

🔗Read more! An HBR article by Michael Watkins can be found here, and you can of course pick up a favorite book of mine, The First 90 Days where he talks about it, and other transition strategies, too!

🔗You might also enjoy: People Work in Nonprofits Because They Can’t Cut It in ‘Real’ Business and Nonprofit Means No Profit!

The people sitting on your board will make or break your organization’s next chapter. They’ll approve the budget, hire and fire the ED, set strategy, and open doors. So why do most nonprofits leave that to chance, treating recruitment as an administrative task rather than a strategic one? You probably recognize the pattern: a seat opens up, someone knows someone, a name gets floated, a vote happens. It might keep the numbers up, but it doesn’t build a board.

Impactful recruitment requires intention, and a different model entirely. That model is cohort recruitment.

What Is Cohort Recruitment?

Think of it like a school year, because that’s exactly what it is.

Schools don’t admit students one at a time or whenever a space opens up. They plan for an incoming class, shape it intentionally, welcome everyone together, and move them through a shared arc of learning and growth. And the entire rhythm of the institution, from recruitment through graduation, is built around that model.

Your board can (and should) work the same way.

Cohort recruitment means deliberately recruiting multiple board members at the same time, as a group, with shared onboarding, shared orientation to the organization’s culture and challenges, and a built-in peer relationship from day one. Instead of welcoming one new member into an established room and hoping they find their footing, you bring in a class. Three people. Four. Maybe five. They learn together, ask questions together, and enter the culture together.

When you adopt that board year mindset, the governance calendar reorganizes itself around a more predictable and usable rythm. Spring is recruitment season: the pipeline is active, candidates are being cultivated, the incoming cohort is taking shape. Summer is transition time, departing members closing out, incoming members beginning their orientation. Fall is the launch of the new board year, the full board convening with shared context and renewed energy.

This school-year approach benefits everyone. Long-tenured members know when to expect new faces. Staff can plan around it. The board chair can design the year as an arc rather than a series of disconnected meetings. And the organization stops lurching from vacancy to vacancy and starts moving with intention.

Why It’s Worth Doing

Cohort recruitment is a shift, and that shift takes work, but the changes it brings to the overall board dynamic makes it worth doing. While I could write you an essay on this, I’ll trim it to my top three:

• Strategic recruitment and succession planning. A cohort model asks you to assess what the board actually needs and then recruit for it. Does the organization need a lawyer to help revamp the bylaws? Someone with real estate experience if a new facility is on the horizon? You can survey your current board, map gaps in skills, expertise, and diversity, and recruit deliberately to address them. That kind of intentionality is nearly impossible when a single vacancy is driving the process. Urgency crowds out strategy every time. And, bonus, the same rhythm that makes recruitment strategic also makes succession manageable. When directors join and rotate off in groups, vacancies become more predictable.

• Stronger relationships and better onboarding. When directors join as a cohort, they go through the experience of being new together. Like an incoming class of college freshmen, that shared moment creates a natural environment for community: new directors feel safer asking questions, admitting uncertainty, and learning alongside one another. It also gives you the opportunity to design a real, structured onboarding program rather than handing someone a binder and hoping for the best. It can be a real program you deliver, refine, and improve each year, using each cycle as a moment to refresh educational content for the full board, not just the newcomers.

• Energy management. Recruiting is time-intensive. Treating it as a constant background task means it never fully gets done and never fully goes away. An annual cohort model lets the board focus their energy for a fixed season, make a big push together, and then turn their full attention back to the actual work of governance.

Getting Started

If you’ve never recruited in this style before, it can feel a little daunting to formalize the process But, with a little work on the front end, recruitment will progressively become a smaller lift with better returns. Here are five things that will help you build a process that’ll work for you:

📍Get your paperwork in order. Before you recruit anyone, pull together the materials a serious candidate would expect to see: a board job description, a board service agreement, a copy of your financials, an impact report, and any other materials you think a candidate might benefit from seeing during your recruitment process. Having these ready makes the whole thing go easier and shows your candidates you are well organized.

📍Set a timeline and stick to it. Cohort recruitment only works if it’s timeboxed. A reasonable cycle looks something like this: one month to get your materials together, then two to three months to post publicly, source candidates, meet people, and conduct interviews, with enough runway at the end to propose a slate for a board vote. When everyone knows the window and what’s expected, the more likely they can support.

📍Build a multi-touch process. Recruitment is a two-way street. The candidate is getting to know your organization just as much as you’re getting to know them, so one lunch with the ED isn’t enough for either side. You want to create a real sequence: an exploratory conversation that’s more than a pitch, a deeper dive that might include a site visit, a program observation, or a walk through the financials, a sit-down with a few board members. Each touchpoint gives you both more to work with, and can also be spread out throughout the year as you build the pipeline.

📍Teach your board how to help. Current board members can be your best ambassadors and recruiters, but without some guidance, they won’t know who to refer or how to make a good introduction. They’ll pitch too hard and scare people off. Or they’ll get excited about someone and make informal offers before the process is anywhere near done. Before recruitment season opens, get everyone on the same page: here’s who we’re looking for, here’s how to make an introduction, here’s what to say and what not to say, and here’s where the formal process picks up. Give them some talking points, templated text for a linked in post that they can customize. Every little bit helps.

📍Design a full onboarding arc, not just an orientation packet. This is where the cohort model can really pays off. Because you’re bringing people in together, you can design an experience that unfolds over time rather than cramming everything into a single day. A session on organizational history. A team building breakout with the board. A strategy conversation with the ED. A finance 101. A site visit. Each can builds on the last. It’s also a chance to mark the moment: celebrating the people joining, honoring those rotating off, and treating board transitions as the significant event they actually are.

🤞One more thing: don’t feel like you have to get it perfect the first time. This is an iterative process. Your first cohort will teach you things no article of mine can. Go and collect feedback, notice what worked and what didn’t, and try to do a little better with each class. The boards that do this well didn’t start out that way… they just started.

💭A final thought…

The annual cohort cycle isn’t just good for new members, it’s good for everyone. Welcoming a new class is a natural moment to reset as a group, revisit your culture, and let the energy of new people remind long-tenured members why they joined in the first place. That’s the deeper promise of the school year model: it doesn’t just change how you recruit. It changes how the whole board shows up.

💡What’s the hardest part of board recruitment for your organization right now?

I’ve been recruiting a new cohort of board members every year for almost ten years now. Different boards, different organizations… but the same thing happens every time. Someone brand new walks into their first meeting, and you can tell they’re a little … uncertain?

Honestly, it’s not hard to see why. Walking into your first board meeting can feel a lot like showing up to a party where everyone already knows each other. You’re not sure where to sit, how things work, or what the unspoken rules are. There are inside jokes you don’t get, shorthand you haven’t learned, and a whole layer of norms nobody thought to write down or explain before you showed up.

So this year, I’m going to be trying something new. I’m calling it the First Board Meeting Survival Guide, and I want to share that idea with you.

What is it?

Exactly what it sounds like: a short guide, handed to every new board member before their first meeting, with the tips and tricks I wish someone had told me. I’m no talking about a copy of the bylaws or governance101s, but the small, human stuff. Things like: Where should I park and can I attend remote? How much open discussion is encouraged and when is it appropriate to ask questions? Where can I find that document they’re talking about? What does that acronym mean!?

In addition to making the social facets of a board meeting more smooth, I also want to signal to new board members: we thought about you. We’re organized. We care about inclusion and culture. And I think that will matter more than people realize when it comes to building a board that actually enjoys and is effective working together.

So let’s get into what I’m going to be putting into this guide!

Part 1 - The Basics

I’m starting this off with the boring, practical stuff. Maybe you think it sounds too simple to mention, but trust me, knowing where to park or how to find the Zoom link removes a surprising amount of first-day stress. These are the details people are embarrassed to ask about, so they don’t... and then walk into their first meeting with anxiety.

📍Ease the first-day jitters by sharing:

• Where is the board meeting, what are directions, where do they park, and how do they get into the building? Who should they call if they have a problem?

• If it’s virtual, what is the video link or meeting details?

• If its hybrid, is the general expectation to be in person or is being online actually ok? Are virtual attendees able to actually participate or is it realistically just them listening in? (P.s. if the latter, maybe take it as a sign you should abandon them…)

• If in person, is seating assigned, or is there an informal ‘that’s always Dave’s chair’ situation? Are there name tags that need to be picked up?

• How long do meetings usually run? Do they actually start and end on time?

• Where are the bathrooms?

• Is food or coffee provided, or should they grab something on the way?

Part 2 | How Meetings Actually Work

Every board has its own rhythm, and nobody should have to figure it out on the fly on their first day. Sure, your bylaws and board policies will cover a lot of this, and yes, new directors should read them. But that’s a lot to read through and absorb before meeting #1. This part of the survival guide is a cheat sheet to get them up to speed on the things that actually matter in the room, right now.

📍A few things newcomers might want to know include:

• How’s the agenda put together and who runs the meeting?

• How far in advance can directors expect meeting materials, and how will they be delivered? If they’ve already been sent, include a link.

• Do board members typically read materials in advance, or is the meeting itself the first real look?

• Is open discussion encouraged throughout, or are there designated times for it?

• Is it okay to ask a clarifying question in the moment, or is that better saved for after?

• Who else will be in the room? Just the board? Staff? Members of the public? Community partners? Every organization is different.

When someone understands who is in the room and how the room works before they walk in, they’re a lot more likely to engage appropriately and speak up.

Part 3 | The Unwritten Rules

Think about what took you a year to figure out — the stuff that wasn’t in any handbook. The things you were a little embarrassed about, or didn’t even realize were ‘a thing’ until you accidentally stepped over a line or said something that landed wrong.

📍Help other navigate a little easier by sharing the ‘silly’ stuff like:

• What’s the dress code, really? Suits? Business casual? Jeans and a nice top?

• Phones on the table, or put away? Can people bring a laptop and take notes? Are AI notetakers permitted? (Please no.)

• Is there pre-meeting chit-chat or social time? Is showing up early a thing, or are you fine to roll in right at the start?

• Similarly, do people generally stay after the meeting to catch up, or does everyone leave right away?

• Is humor welcome in the room, or is it kept pretty buttoned up?

• Is it okay to step out to take a call, or is that frowned upon?

Additionally, new board members often feel like they need to prove themselves in the first meeting. They don’t… and it’s worth stating explicitly that it is totally fine (actually, it’s smart) to listen more than you speak your first few meetings, and that there are no dumb questions. If something’s confusing, ask.

Part 4 | After the Meeting

The final bit that should be shared early on is what happens after their first meeting, as it reinforces expectations and behaviors you will want to see from board members moving forward.

📍Reinforce working practices by answering:

• When and how are minutes shared? Do they need to acknowledge these?

• How do follow-up tasks get assigned and tracked?

• Who do they call if they walk out with a lingering question?

• Is it common for people to weigh in between meetings, or is the board mostly ‘meeting driven?’

• How do board members communicate in-between meetings? Email, text, group chat?

• Is it normal to reach out directly to staff, or do all communications go through the ED?

• What’s next up for onboarding?

A quick note from a board buddy or the chair… even just a hey how’d it go? can also make a meaningful difference and open up an early channel of communication. It makes people feel more welcomed and settled, while also giving you (as an existing board member) some real-time insight into gaps.

One Last Thing

Remember, this First Meeting Survival Guide isn’t supposed to be the one-stop-shop for all things related to how your board operates and fulfills its governance obligations. It doesn’t need to be long, and it definitely doesn’t need to be formal. A short, well organized document is more than enough to ease the first day jitters for your new directors and set the tone for board culture and behavior.

🔗P.S. - A ready-to-use First Meeting Survival Guide template is available exclusively for paid subscribers. Grab it here and customize it for your board.

💡Help me write a better guide - what’s something you wish you knew before your very first board meeting? 📨 Hit the reply or drop a comment, and I might just add it in!

I spent the beginning of this year on the hosting side of a gala. Now I’ve got several coming up as an attendee this spring…. and I must say, switching roles has a way of sharpening your eye.

There’s a lot that goes into making a gala successful. The storytelling, the guest experience, the programming, the follow-up. Most of it gets plenty of attention in the planning process. But one thing that often gets overlooked is the role of the board.

Too many board members will show up to their organization’s biggest fundraising event of the year and treat it like a night off. They catch up with friends, enjoy the dinner and drinks, clap for the program, (cut a check), and head home… and the organization leaves enormous opportunity on the table.

As a board member you don’t attend your gala, you host it. When board members show up and own their role as hosts, they amplify everything else in the room. They make guests feel welcomed, connected to the mission, and excited about the work—which means more dollars raised and a growing community of people who actually care.

Below, I’ll be diving into what showing up as a host actually looks like, from the moment you arrive to the days after you leave. Real, practical advice to get your board into action.

Before You Arrive

What happens before you walk through the door matters more than you realize. The conversations you’ll have, the connections you’ll make, the moments where you can really move someone… it all goes better when you’ve taken a little time to prepare.

🔵Make or commit your gift before you arrive. Either make your donation ahead of time or decide what you’re going to give that evening. It’s much easier to invite others to give when you’ve already done it yourself, and you’ll be able to say so with genuine confidence when the paddle raise comes.

🔵Know the story of the night. Review the fundraising goal and have one or two recent program wins in your back pocket. You don’t need to memorize a fact sheet. Just enough to anchor a real conversation when someone asks what’s going on with the organization.

🔵Prepare your ‘why I serve’ story. Someone will ask how you’re connected to the organization. Have a warm, personal, 60-second answer ready. Specific and genuine beats polished every time. Practice it once out loud a few times so it doesn’t feel stilted when the moment comes.

🔵Bring a guest or fill a table. Think about who in your network would genuinely connect with this mission and invite them. Tell them specifically why you thought of them. Bonus if you can buy a few extra seats and offer them to friends for free (I find it’s easier to get first-timers to take the leap when dinner is on me!). And if you’re a more seasoned fundraiser, consider leading a table and filling it yourself.

🔒If you're a paid subscriber, I've got you covered with a set of ready-to-adapt email invitation templates. You can find them here.

When You Arrive

This one sounds obvious, but: get there early. The first 30 minutes of a gala are often the easiest time to move about, meet new people, and have genuine conversations. The room is quieter, guests are still finding their footing, and there’s no program pulling attention away. Once dinner starts, that window gets much smaller.

And, when you walk in, own your role. Don’t wait to be introduced. Mill about and greet people warmly. Introduce yourself as a board member. Thank people for coming out. You’re a leader of this organization. Let that show from the moment you arrive. (I talk more about this next).

Working the Room

This is where board members can make the biggest difference, and where most fall short. It’s easy to spend the whole night with people you already know. Don’t. The room is full of people who care about the same things you do, and your job is to find them.

🎊Spread out and meet people. If someone is standing alone, that’s your cue. Walk over, introduce yourself as a board member, and say hello. It’s that simple. As a host, you don’t need a reason to approach someone. Your presence and warmth are enough.

• For shy or newer board members, pair up with a fellow board member to work the room together. It’s sometimes easier to approach people as a duo and you can introduce each other.

• Give yourself a goal… commit to meeting three new people before dinner starts. Having a number makes it feel manageable.

🎊Lead the conversation with curiosity (not a pitch). Ask people what brought them to your event, or how they’re connected to your organization. You’ll learn more, the conversation will flow naturally, and people will leave the interaction feeling good. A few additional tips:

• If you’re not sure what to say after hello, a genuine compliment about the event or the venue is an easy opener.

• Listen more than you talk. The best conversationalists make the other person feel like the most interesting one in the room. Nobody wants to feel like they’re being talked at.

• Keep one hand free. Don’t juggle a drink and a plate at the same time if you want to be able to shake hands comfortably.

• … And don’t rush. One genuine 10-minute conversation is worth more than five quick surficial ones.

🎊Be a connector. In my opinion, this is the fun part! Introduce guests to each other, to staff, and to the executive director. If you meet someone whose interests connect to someone else in the room, make that introduction. People love meeting other people at these events, and you’re uniquely positioned to open those door

🎊Work your table. Don’t go quiet once you sit down. The people seated around you during dinner are some of the best conversations you’ll have all night. If you’re the sole board member at the table, introduce yourself, talk about the organization and your service, and get curious about everyone else.

🎊Don’t forget to exchange contact info. If you have a genuine conversation with someone, get their information before you part ways. A digital business card makes this easy. Don’t leave it to chance or assume you’ll find them later.

During the Paddle Raise

A paddle raise can be the emotional peak of the evening, and board members play a surprisingly critical role in it’s success.

🙋Be one of the first to raise your paddle. When your giving level is called, put your paddle up confidently and quickly. A hand in the air gives others permission to follow. It’s contagious in the best way.

🙋Consider making a leading gift. Talk to your development team before the event about anchoring a giving level. A board member who can kick off a level with a pre-committed gift sets the tone and gives the fundraiser something to build momentum from.

🙋Cheer others on. Applaud when others give, make eye contact, lean in, smile. Your body language matters throughout the entire paddle raise. The energy you put into that room (or keep from it) is felt by everyone.

After the Event

The gala doesn’t end when you walk out the door. The 48 hours after the event are when board members can make a real difference in who stays connected (and who quietly drifts away.)

✨Check in on the guest you brought. Send a thank you note following the event. It could be as simple as an email or text. But follow up directly and ask what they thought. That conversation is the beginning of their relationship with the organization, and you’re still the bridge. It also is a great chance to point them to upcoming events or volunteer opportunities. (For paid subscribers, find my templates here!)

✨Follow up with new connections within 48 hours. If you had a meaningful conversation (and followed by advice to get their contact info…) try to send a personal note. Don’t leave it to staff alone. Your voice carries different weight than an organization email, and a warm, specific message from a board member is meaningful.

✨Brief the development team. Share who you spoke with, what they expressed interest in, and any next steps you mentioned. These handoffs are where momentum lives or dies.

What Not to Do

Just as important as the playbook is knowing what kills the energy. A few things to avoid:

✖️Don’t overdo it at the bar. You’re there to make connections and represent the organization. Keep it to a level where you’re able to still be present all night.

✖️Don’t be on your phone. Except for snapping a photo or two, put your phone away for the night. Give your organization the attention, and respect, it deserves.

✖️Don’t make asks. Unless you’ve been specifically coached to, leave the formal solicitation to staff and program. Your job is to build relationships, not close gifts.

✖️Don’t disappear after dinner. The paddle raise and the moments right after it are when board visibility matters most. Stay present through the end of the program.

Don’t leave without saying thank you to someone. A donor, a volunteer, a member of staff, a sponsor… by name, in person. It takes 30 seconds and makes a difference.

The Bottom Line

Everything in this guide is practical. But the thing that actually determines how a board member shows up at a gala is simpler than any checklist.

Above all, I want you to remember: Your enthusiasm, warmth, and genuine belief in the mission are the most powerful fundraising tools in the room, more than any paddle, program, or talking point.

You are not attending a fundraiser tonight. You are hosting one. Your job is to make every person in that room feel welcomed, valued, and connected to something worth caring about. The asks, the paddle raise, the follow-up — all of it flows naturally when you start from that place.

Go make it a great one.

💡 Question: What is something you do to make your organizations gala rock? Drop it in the comments or hit the reply and help others raise the bar.

After eight years in boardrooms, I’ve earned this opinion: hybrid meetings are the worst of both worlds, and we need to stop pretending otherwise.

The premise sounds reasonable. Someone’s traveling, several time zones away, managing a health situation, or running late… and Hybrid feels like the problem solved. But in practice, hybrid meetings are a compromise that consistently costs your organization the one thing board meetings exist to produce: genuine, high-quality conversation.

Bear with me. Here’s what actually happens.

1. Unequal Experiences

The people online don't engage the way the people in the room do.
They're muted.
They're multitasking.
Sometimes the room forgets they exist (because that's how human attention works).

Questions in the chat get missed. Side conversations happen in person that never quite make it through the speaker. Non-verbal cues are invisible to anyone on a screen.

Tell me, can you really stand beside this as good governance?

2. A higher bar for facilitation

Facilitating a truly engaging meeting in person or online requires a high level of skill. Pulling off hybrid adds more work and another layer of complexity entirely (you literally have to plan two sets of logistics). It also requires someone in the room dedicated to managing the tech while someone else runs the meeting. And when things go wrong, part of the group is stuck on the outside while the room has to waste time troubleshooting.

3. Weaker governance.

As a board member, you have the legal duty of care: to be fully present, read in, and genuinely participating in the decisions in front of you. Your headcount contributes to quorum, and quorum exists for a reason: to ensure major decisions have the benefit of real representation and diverse viewpoints. A board member half-present on a laptop in an airport lounge checks the quorum box, sure. But are they actually fulfilling their legal responsibility? That's a harder question, and hybrid makes it far too easy to avoid asking it.

Make the change.

I’ve heard every argument for why it’s necessary. I’ve made some of them myself in the past.

But I’d challenge you to challenge your board: what would it actually take to make it work in person? And if someone can’t be there? As long as it’s not a pattern, that should be okay. That’s genuinely what minutes are for.

And I’m realistic about what the shift requires. Moving to a single format might mean some people can no longer make it work, and that’s a real cost, worth acknowledging. But it’s also worth asking: is the current arrangement actually serving your governance, or just serving convenience? Not every board role will be the right fit for every season of someone’s life, and the best decisions are made in the interest of the organization… not around individual schedules.

On the other side, the fully remote meeting, done right, can work too. Everyone’s on equal footing and the facilitation challenges are consistent and manageable. Do I think the quality is lower than in-person? Yep. But it’s leagues better than hybrid.

Whatever you decide, be flexible, but be clear. You can even do some meetings in person, others fully online! That’s fine. What isn’t fine is defaulting to hybrid because it feels easier. Proactively manage attendance expectations, set the format in advance, and hold the line.

My bottom line? Stop optimizing for convenience and start optimizing for conversation

Get your board aligned on what a one-format meeting makes possible, reset expectations, and pick a lane: Everyone together, or everyone online.

Because your board, and your mission, deserve better than being stuck in the middle.

📌P.S. If this got you thinking, subscribe for free — I write regularly about nonprofit governance, board leadership, and the hard-won lessons from my own experience in the boardroom.

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Every spring the board I serve on launches its annual recruitment effort, and the questions come rolling in from board members: What do I say when I reach out to someone? What if I don’t have a big network? I want to help, but I’m not sure what I’m supposed to do. When talking with board members (on my own board and others) some feel awkward reaching out and some assume it’s someone else’s job. But mostly, what I hear is that board members would step up in a heartbeat if they just had clearer guidance.

A key thing to remember is that the board you build is one of the most important things you’ll do as a board member. The people in the boardroom will work alongside you year in and year out, shaping strategy, stewarding the mission, and tackling challenges as they arise. You should want a voice in who joins that room, and the responsibility of recruitment belongs to everyone sitting around that table.

So whether you’re an individual board member wondering how to contribute or the person responsible for driving the process, here are practical ways everyone can show up for recruitment, no matter how long they’ve been on the board.

First, Get Organized.

Before you launch into recruitment, there is a little bit of ‘prework’ you need to do, both as a board and an individual board member, in order to be successful.

Create a Reference Doc

Board members need to feel confident talking about what they’re inviting people into. The board chair or governance committee should put together a simple one-pager… this can be as lean as a cheat sheet just for internal reference, or something more robust like a designed prospectus that can be shared with prospective members. Either way, think of it as a go-to resource for all your conversations about service.

Basic things to know and include are:

• The mission and impact

• Top impact statistics from the prior year and a high-level sense of the organization’s size (budget, people served, reach)

• The basics of board service (monthly time commitment, meeting cadence, giving expectations, etc).

• An outline the recruitment process steps

• A clear point of contact or link to a landing page, so people know what to do if they’re interested.

You also need a story to tell, either your own or one that resonates with you from the organization, that answers the question ‘why does this matter to me/my community?’ I recommend taking a little time to reflect on this and write a few notes down before jumping in.

Have a Job Description

Board service is a job… a volunteer job, yes, but a real one nonetheless, with legal responsibilities and fiduciary duties. A job description is critical for recruitment, as it calls out what you're specifically looking for in a board member: areas of expertise, professional background, community ties, or other qualities that reflect what your board actually needs today. It should be updated every year to reflect the evolving composition of the board.

Create a Landing Webpage

Finally, your organization needs a webpage about the board and recruitment. This landing page should include information about who is on your board, the job description, the application process, and the application itself. This improves transparency and helps bring credibility and polish to the process.

If you’re just getting started, nonprofit leadership lab has a sample application here.

Now, The Practical Stuff.

Alright - you have your talking points, a job description, and a place to point people. Now here’s how you, as an individual board member, can contribute to the overall success of the process.

1 | Share and amplify the opportunity

Help make it easier for the right people to find your organization by sharing and amplifying the opportunity in both your real and digital life:

• Post once on LinkedIn this month (ask staff for sample language if you need it), and tag 2-3 people.

• Reshare one or two organizational posts and add a sentence about why you serve.

• Drop the opportunity in two or three relevant online spaces. This could be alumni networks and newsletters, linkedin groups, professional associations, community organizations, etc.

• Attend a local community event, panel, or professional gathering with recruitment in mind, and talk about your org and the opportunity.

• Text or DM 1-2 people with the recruitment website link, with something like: “Thought of you when I saw this… Do you know anyone who might be a good fit?” Because, you don’t have to know the right person yourself, sometimes the best candidates come one connection removed.

2 | Make warm introductions

Personal outreach is the single most effective recruitment tool available… and yet this is where most board members hesitate. (‘I don’t really know anyone’)

Here’s the thing: you probably know more people than you think, but you need to think beyond your immediate circle: colleagues, former coworkers, people you volunteer with, folks you’ve met through community work or networking.

• If no one comes up, keep recruitment in the back of your mind as you move through your normal week. The right person might be closer than you think.

• If you find someone you think could be a match, reach out with a short, genuine note explaining why you thought of them. Offer to grab coffee or introduce them directly to the right person on your board, and follow up once to keep the momentum going. You don’t need to push them through the whole process, you need to get them excited about the opportunity.

• If someone expressed interest last year but never followed through, follow up again. Timing matters and people’s circumstances change

Learning something about board recruitment? My stack is full of free (real free!) guides and resources for boards and nonprofit leaders looking to grow.

Sign me up, Scotty!

3 | Tap other boards and past board members

This one gets often overlooked: great board members often know other great board members!

Look around your city and take note of who is showing up on other nonprofit boards, civic committees, or community organizations. Those are exactly the kinds of people you want in your orbit. These are people who already understand what board service looks like and are likely passionate about community service. …And, just like your board, organizations everywhere have people cycling off every year who may be looking for another opportunity to serve.

Reach out to people who serve on other boards (even if its a cold connection), share that you're recruiting, and ask if they know anyone who might be a good fit. If you're an experienced board member yourself and get this type of outreach, don't be shy about trading talent across organizations.

Additionally, reconnect with past board members who have rotated off. They already know and love the organization and may be ready to return or refer someone great

4 | Support building the pipeline

People join boards of organizations they feel connected to, which means recruitment actually starts years before someone finally says ‘yes!’ to board service. There are so many ways that you can help build relationships that may eventually lead to the boardroom.

• Invite people to an organizational event or program site visit so they can see the work firsthand.

• Bring a prospect as your guest to a fundraiser, annual meeting, or community gathering.

• Share a recent impact report, news story, or program update with someone you think would care about it.

• Connect people with volunteer opportunities so they can build a relationship with the mission on their own term.

5 | Be intentional about who you recommend

Before making a recommendation, think about what gaps exist in skills like finance, legal, fundraising, or communications, but also in lived experience and community representation. Recommend people even if you don’t know them deeply, as long as you can genuinely vouch for their potential. And resist the urge to self-filter others out before they’ve had a chance to learn more.

Bottom Line

The board you build is one of the most consequential things you'll do as a board member. A committee can run the process, but they can't replicate your relationships, your credibility, or your personal story. Pick two or three things from this list and get started. Recruitment season doesn't last long… but the board it produces will.

💡 Question: What is a tip or piece of advice you’d give a board embarking on recruitment this year?

Send this to a board member who is busy recruiting for your board this year!

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Most nonprofit closures don’t happen over night. Nanowrimo’s collapse was years in the making. This is the story of what went wrong, and what every executive and board member can learn from it.

Every November for most of the 2010s, people around the world attempted a crazy challenge: to write a 50,000 word novel in just 30 days. What began as a small experiment among friends quickly became an international movement, with more than 400,000 participants, complete with paid staff and student programs and summer events. Hundreds of volunteer leaders organized local ‘write-ins’ and buildt regional communities. Books were published. People were inspired. I mean, by many measures, NaNoWriMo (short hand for National Novel Writing Month) looked like a success story.

And, holding it all together was a set of shared values: that creativity matters, that anyone can tell a story, and that showing up for your art counts.

… So when leadership began making decisions that seemed to contradict those values, you can imagine how quickly things slid south. In fact, it only took five years for NaNoWriMo to go from international success to doors shuttered.

Let’s dive in…

(This case study is particularly poignant for me, as I personally participated in NaNoWriMo nearly every year from 2006-2018. I wrote and cheered other writers on… and even recommended NaNoWriMo to my friends. It was small and magical and now, sadly, gone.)

🤸‍♀️Jump to a section:

• The Case Recap

• Lessons Learned

• Downloadable Resource

Case Recap: 3 governance failures that compounded into collapse

No organizational failure is black and white… and what brought Nanowrimo down wasn’t one catastrophic mistake… it was multiple ones, compounded over years, each making the next one harder to survive.

Failure #1: Declining financial and program performance

This is the problem that amplified the impact of all other problems.

For four of it’s final six years, Nanowrimo operated at a deficit, surviving only because of a loan taken out during the pandemic. The majority of revenues were from merchandising and sponsorships, which was risky on it’s own, and individual giving was on a multi-year downward trend. By 2023, the organization was nearly out of cash, with very little runway left to course correct. A board reviewing financial and programmatic performance regularly should have caught this trend far earlier and demanded a plan.

Look, lots of organizations struggled post COVID… and had this been the only challenge, Nanowrimo might have survived. It had a loved brand and a committed community. A transparent call for help might have worked.

But they never had a chance to get ahead of it because… problem number 2 arrived:

Failure #2: No safeguards for children

In 2023, the board received complaints about child endangerment and staff misconduct. They quickly launched an investigation and shared findings 10 days later. On the one hand, impressive speed. But what they uncovered was alarming: no background checks, no child safety training, missing data protections, and lack of moderation across broader community platforms. The board then went on to make changes to leadership and implemented a remediation plan.

So far, a reasonable response.

But then, the new volunteer agreement they released to address these gaps was found to protect the organization more than the volunteers. When volunteers pushed back, the organization removed all of them from their systems.

And just like that, hundreds of regional communities and brand trust, built over years, disappeared overnight.

The community was fracturing. And then came the final blow.

Failure #3: Misaligned messaging

Facing a cash shortage and a shrinking base, NaNoWriMo sought new sponsors to keep afloat, including an AI writing tool company. They released a public statement essentially endorsing AI writing, and then went a step further to say that anyone who condemned AI was being ‘classist and ableist.’

Supporting AI in a writing community is a rocky position on its own… but calling critics classist and ableist is a different kind of mistake, and using marginalized communities as a shield for a sponsorship decision was met with rapid fire. NaNoWriMo later acknowledged the misstep, but with a tone that was perceived as blaming the community for the backlash.

Cue the end credits:

At this point, major media was all over it. Board members began resigning.. publicly and loudly. Community members spoke out. ..but the message from the organization read as: if you don’t like it, you can leave.

So people did.

Lessons Learned

Good governance can’t prevent every crisis, but it does create the conditions where you are more likely to catch problems early. Any one of those issues Nanowrimo faced could have been survivable. Maybe all of them, if handled with transparency, humility, and sensitivity. But all we can do now is learn from their mistakes.

Here are some lessons I see in this case, and things you should be thinking about as a board member.

Lesson 1️⃣: You need strong financial oversight with easy to understand reports.

A key responsibility as a board member is to provide oversight of the organizations finances. I don’t mean managing the numbers day to day, but making sure you are getting the right information at the right time, in a way that is legible. Then, ask questions if anything seems off and take action. A few things you can be doing as a board include:

• Use a dashboard to track key program and financial metrics, and review it every quarter.

• Look at trends across the last 3-5 years. A bad quarter is easy to explain, but a three year+ slide tells a different story.

• Ask hard questions of management if things aren’t tip-top. What’s driving the problem? What’s the plan? Don’t accept vague assurances.

• If management isn’t acting on concerning trends, demand a course correction.

• Share your financials publicly. Go a step farther to ensure they are easy to understand. This builds donor trust.

• Know your revenue risk. If most of your income comes from one or two sources (e.g. a single donor or set of contracts), that’s a red flag you need to have a plan for.

Lesson 2️⃣: You need safeguards when working with kids

If your organization works with minors in any way, your board needs to ensure there are protective policies and practices in place, and that those practices are monitored and held to the highest standard.

• Require background checks for staff & volunteers (and board members!) who interact with youth. Confirm this actually happens.

• Ensure child safety training is completed and tracked.

• Maintain up to date data protection policies that takes into consideration the involvement of minors in your programs.

• Have a volunteer management framework that is fair, documented, and supportive.

• Carry adequate liability insurance, ensure it covers working with minors, and review it annually.

• Have management conduct a periodic audit to ensure policies on paper actually match what’s happening on the ground.

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Lesson 3️⃣: Communications in a crisis can save you… or crush you.

How your organization speaks during a controversy can be make-or-break. Your board needs professional infrastructure and a plan on how to respond before the crisis responds.

• Know your community deeply, including who they are and what they care about.

• Have a crisis communications plan, including identifying who approves messaging, who advising the organization, and your response timeline. You don’t need prepackaged messages, but you need to know how the message is getting written and delivered.

• Loop in legal counsel and communications professionals early (this isn’t a time to wing it or skimp on the cost.)

• If something goes wrong, lead with accountability and humility.

The Bottom Line

Nanowrimo didn’t collapse because of one bad statement or one missed policy or one bad year. … Small governance failures added up over time and trust with the community eroded faster than leadership could repair it. The writers who loved it are still writing but the organization that served them is gone.

If you find that you see gaps in your organization or your board, don’t panic. No organization is perfect. Instead, use this as an opportunity to catalyze change. Bring this case to your fellow board members or leadership team, explore and learn more about your own organization, and act now, before there is a major issue.

Stress test your organization

⚡I've turned these lessons into a one-page questionnaire that you can bring to your next board meeting. Free to download for the first 24 hours… after that, it moves to the subscriber library!

A Governance Stress Test Nanowrimo Edition

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💡 What case of nonprofit mismanagement or governance failure should I cover next?

This article is part of Nonprofit Case Files: real stories of nonprofit mismanagement, platform failures, and governance breakdowns … and what leaders can learn from them. Subscribe to follow along.

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🔗Read More…

NaNoScandal | MSN | | Reactor | Little Village | Publishers Weekly | TheManuscriptEditor | Techcrunch | Vice

At any given time, many people are running a mental scale. On one side are all the Good Things: the mission, the team, the compensation, the relationships, the work they’re proud of. On the other sits the Bad Things: a board that doesn’t have their back, a culture that’s turned toxic, a workload that never lets up, the creeping feeling that nothing they do is ever enough.

They keep adjusting the balance, trying to find more good things or ‘reframe’ the bad things to lighten the weight, hoping that if they just get the math right, the scales will finally settle somewhere that feels okay. That they’ll feel a little less burned out.

But they never do… because that’s the wrong model.

When it comes to your happiness at work (or the project you’re working on, or the relationship you’re in, etc) good and bad aren’t weights you can balance against each other. At a certain point, no amount of good can cancel out the bad.

Because good and bad aren’t a scale. They’re a floor and a ceiling. They are two separate thresholds that operate independently of one another. And once you see that, you’ll realize the balancing act you’ve been doing was never going to make you feel better.

The Maximum Bad, Minimum Good Thresholds

This is my Floor and Ceiling mental model.

When deciding whether to stay in a job, or continue a project, or remain in a relationship, you should have two separate thresholds:

• A Minimum Good Floor

• A Maximum Bad Ceiling

For something to be worth continuing, you need to be above the floor AND below the ceiling, at the same time, always.

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The Good Floor.

First, your situation has to clear a floor. At work, that might mean the work needs to align with your passion or offer a certain salary or provide opportunities for travel or come with a kick ass team. In a relationship, it might mean respect, support, and feeling seen. Whatever your situation, these things are the bare minimums, and if what’s going on doesn’t meet or exceed these, you already have your answer. It’s a non-starter.

The Bad Ceiling.

There are also things that simply cannot be exceeded. Not balanced out, not justified, not waited out. I mean dealbreakers. At work, it might be a boss who undermines you, a culture that’s contrary to your values, boundaries that get crossed. In a relationship, you probably know your red flags, maybe the smoke or they don’t live in the same city as you. It’s different for everyone, but these are your non-negotiables. Once one of them is crossed, it’s over, full stop.

The Hard Part

That all seems straightforward enough. Problem is, people don’t feel things in such a black-and-white way.

You will find yourself one day in a position where the good is genuinely, undeniably good. The mission lights you up or the team is the best you’ve ever worked with or the work is some of the most meaningful you’ve done. And then something crosses your bad ceiling. And suddenly you’re facing the most disorienting version of this problem… because leaving doesn’t feel logical. You’re walking away from something that still feels, in a lot of ways, remarkable.

I don’t dismiss that. The good is real. Its value is real.

But Good can’t determine the outcome on its own. The two thresholds shouldn’t talk to each other. The ceiling doesn’t care how high the Good is. And if you choose to stay after your maximum Bad has been crossed, you’ve started a clock, waiting for the situation to correct itself. Asking the question again and again, running the math one more time.

But you already have your answer.

The ceiling doesn’t care how far above the floor the Good is. When the Bad Ceiling gets crossed, it’s crossed, No amount of good brings you back.

This is the moment your integrity and self-respect are most hard tested. Stop the project. End the Relationship. Quit the Job. Your happiness and health and your principles need to come first

The Expensive Miscalculation

It’s easy to brand suffering as perseverance. To tell yourself the sacrifice is admirable, that commitment means pushing through. Let me hold your hand when I say this: no. That’s an expensive miscalculation. The cost of staying past your Maximum Bad will show up in your decisions, in how you lead, in what you’re able to give the people who actually need you at your best. The damage rarely stays contained.

I never tell people to ‘look on the bright side’.

I ask: has something crossed your line? (Not a line you’re drawing in frustration, or a bad week or a hard quarter… but a genuine dealbreaker, something you knew mattered before it was tested.)

And most of the time, they already know. Maybe they’ve known for a while. They just needed a model that stopped asking them to keep doing the math.

When your maximum bad threshold is crossed, the answer is clear and simple.

Questions You Can Ask Yourself

• Has something happened that I previously said was non-negotiable?

• If a friend described this situation to me, would I tell them to stay?

• Am I staying because the situation is healthy or because leaving feels hard?

• What would have to change immediately for this to fall back below my ceiling?

• If nothing changed for the next year, would I still choose to be here?

Final Thought

You need to know your floor and respect your ceiling. The good and the bad are not in conversation with each other. They don’t negotiate. Your floor tells you what you need to stay. Your ceiling tells you when it’s time to go. Know both. Honor both. That’s the whole model.

Somewhere right now, a board is sitting through the dreaded two-hour meeting-that-could-have-been-an-email. Think: the executive reading through their report, every committee chair taking their turn, one or two people doing all the talking, and no real invitation to contribute. It’s just one, long status update with maybe a chance to ask questions at the end.

This is not uncommon and its a serious problem

Think about what’s actually happening here: You have done a difficult thing… You pulled together a group of experienced leaders, with diverse perspectives and a genuine passion for the mission, who carved out time in busy schedules to focus on the organization. …And you're wasting it on status updates. That's a missed opportunity and, frankly, disrespectful of everything those people bring to the table.

⚡But no more! There are a few targeted changes that can go a long way to ending boredom in the boardroom. Before we get there, though, there’s a prerequisite that makes everything else possible.

The Prerequisite: Someone has to really own the meeting.

Ownership is more than deciding what should get discussed, its shouldering the responsibility of figuring out out how it it gets discussed (and then actually facilitating it). This responsibility falls first to the Board President, and then to the executive committee as a whole.

Ownership means preparing the agenda well in advance, in partnership with executive leadership, with an eye on your strategic priorities and a bias toward interactivity. It means doing pre-work to think through actual facilitation (Breakouts, share-outs. possible action items, etc.) and always asking: how do I move this group from a presentation into a real conversation? This is the real difference maker between running a meeting that people check-out of and one that leans them in.

Ownership, more than subject matter expertise or governance knowledge, is what makes the biggest difference in the boardroom: someone who is both willing and skilled enough to facilitate and understands that their job is to move the room into dialogue.

Without that person, even the best structural changes will fall flat. That being said,, let’s assume you have it! Here are the two tips I have that can get you moving:

(P.s. If you’re a board chair, check out my basic & advance tips for being a rockstar leader!)

Change #1: Use a Board Packet to Eliminate Report-Outs

The most reliable way to kill momentum in a board meeting is to spend the first hour listening to executives and committee chairs read updates everyone could have read themselves.

⚡The single most valuable thing you can do is to eliminate the dreaded round robin of committee report outs. Here’s the fix:

1. Require written reports. Have every committee chair submit a report before the meeting using the same template, every time: top three headlines, critical need-to-knows, and anything that needs a decision. Your executive should do something similar. For anything coming to a vote, request a one-page memo, detailing context, and have it live first on the consent agenda.

2. Create a board packet. Bring all your written reports, plus agenda, past minutes and financials, together in one packet.

3. Send the packet at least five days before the meeting. …which means whoever owns the packet needs reports and the agenda done two weeks out. I know that sounds like a lot of lead time. But it’s not. Just plan for it.

4. Explicitly set the expectation that people to read it ahead of time. And I mean really read it… not ‘I skimmed it in the parking lot’ read it. Part of being a responsible board member is taking time to sit down and read, take a few notes, and come with a question or two. This is a reasonable ask and anyone unwilling, or unable, to meet it should not be serving on your board.

5. Slate Q&A time on the agenda. With all these reports, you need to give time for board members ask questions (Ideally questions that are clarifying or building on the content.) If everyone came prepared and there are no questions, move on. That means the written report did exactly what it was supposed to do.

6. Uphold real consequences. If someone shows up unprepared, they don’t vote on anything that requires the context of the packet. I’m not trying to be punitive: It’s just simple fact that you cannot exercise your legal duty of care on content you haven’t read. It’s that simple.

This single shift, of moving committee report outs to pre-read, can reclaim enormous amounts of time and creates space for the board to do what boards are actually there to do.

❓But what if a committee has something it wants to discuss with the whole board? Great. Your chairs should share topics with the board president so it can be balanced against other critical conversations and factored into the agenda thoughtfully (see Change #2 below)

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Change #2: Build Agendas Around Discussions

Once your board packet is relieving you from report outs, you get to have a little fun: what do you actually want to talk about?

At first, this can feel harder than it sounds. You’re so used to filling the agenda with updates that real conversation feels almost unfamiliar. But it gets easier, I promise.

Start by picking one to three things. and be honest with yourself about how much time you actually have. A good conversation, especially around a meaty question, will always want more time than you give it. That’s fine, but be ready to manage it.

Topics can come from anywhere: a strategic priority worth going deeper on, a decision the executive needs the board’s thinking on, a challenge that deserves collective brainpower, a question a committee has been wrestling with. Whatever it is, conversations becomes the heart of your agenda.

⚡Here’s the key trick: when you write your agenda, list the topic headliner AND include an actual question or two for people to sit with beforehand.

For example, instead of:

Write:

That small shift gives people the chance to do some thinking before they walk in the room. The conversation starts a level deeper, and you’re far more likely to hear from more than the usual two or three voices. (Also see how I included how much time is allocated for the discussion?)

Facilitation Tips

You should be aiming to make every board meeting interactive because that’s how you actually use the expertise sitting around that table.

If you’re the facilitator, there are so many cool techniques/tools out there you can draw on to create an engaging and productive room. Yes, it takes work to learn how to use these, and a little courage to try new things, but man, people will love you for doing the work to get them to lean in.

A few things I personally use to engage people & keep things on track:

• Timeboxing conversations. This is non negotiable for me. Telling people they have 30 minutes for a conversation gives you the mandate to manage time and refocus the group when things drift.

• Using a parking lot! When a good idea starts pulling the group off track, park it. It gets acknowledged, and you keep moving.

• Teaching ‘Step Up, Step Back’. Directors need to be self-aware of how much airtime they're taking. If you're talking a lot, step back and create space for other voices. It's an executive-level skill, and one you should expect from a board member.

• 1-2-4-All: Have individuals reflect individually, then pairs discuss, then fours, then the whole group. It surfaces ideas that never get airtime in open plenary, and ensure people feel heard.

• World Cafe: When you have lots of questions, try this! Rotate small groups through different questions at different tables. Generates cross-pollination and breaks up the usual seating dynamics.

• Breakouts + Share-Outs: Split people into smaller groups before a full-group discussion, and invite those groups to come with share outs.

• Closing the meeting well. What will you be doing between now and next meeting? Is there a pressing topic on the horizon? Use your final touchpoint to orient and task people. Note any action items, assign owners and deadlines, and have the secretary follow up with those assignments.

One last thing… ditch hybrid meetings

I get this is a hot tab, but after eight years in boardrooms —(in-person, fully remote, and hybrid) I think I’ve earned this opinion: hybrid meetings are the worst of both worlds, and we need to stop pretending otherwise.

The people online almost never engage the way those in the room do. They’re muted, they’re multitasking, they’re half in the room and half not. Sometimes people even forget they exist. And pulling it off well requires a level of facilitation skill and tech management that, honestly, most boards don’t have or cant sustain. I include myself in that.

I know it feels like the compassionate, flexible thing to do…. but it isn’t. It’s a compromise that’s costing your organization the quality of the conversation it deserves every single time.

So pick a lane. Everyone together, or everyone online. And if someone misses a meeting? Well that’s what minutes are for.

The Bottom Line

A few small changes, and a whole new boardroom:

One owner who takes facilitation seriously.
Reports where they belong (in the pre-reads.)
Agendas built around real conversation.

That’s really it. Those shifts can transform your board meetings from something people yawn and endure through into something they actually look forward to.

Remember: Boards exist to think and talk together. Your time all in one room is too rare to waste on sharing updates that could have been in an email.

You know what a great board meeting could look like…. now go run one!

📍P.S. If this helped you, forward it to your board and follow along! Everything I write comes from real experience… things I've actually done, tested, and can stand behind. No theory, no fluff. Free.

(Though you can become a paid subscriber too and help me keep this publication free for all!)

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Last week, I made my position clear: AI notetakers in nonprofit board meetings are a governance risk you shouldn’t take on. Discovery exposure, broken trust in the boardroom, potential legal violations… the potential problems are serious.

But I’m also a realist. Even with my warnings, some of you are going to use AI tools anyway. Maybe your board secretary already decided and this ship has sailed. Maybe the executive director demoed a tool at the last retreat and people loved it. Maybe you’ve been using one for months and are just now reading this wondering if you’ve made a terrible mistake.

(You may have. But let’s fix it.)

Below I talk about how to use AI tools while minimizing legal and governance risk. If you're still on the fence, last week's piece lays out why I'd still steer you away entirely.

Bottom line, up front: If you’re going to use AI in board meetings, these are my recommended essential protections you cannot skip.

Jump:

• 📄AI Transcripts are not your official minutes, full stop.

• 🗑️Immediate destruction after approval

• ✅All-Party Documented Consent, Every Time

• 🏢Enterprise-Grade Tools Only

• 🔍Vet Your Vendors Like Your Risk Depends on It (Because It Does)

• 🔒Make Sure This Doesn’t Conflict With Your Existing Data Privacy Commitments

• 📋Write a Policy.

• Human Review Is Not Optional

• ➡️Before You Move Forward, Answer These Questions Honestly

• 🎯The Takeaway

• Up next in my AI & Nonprofit series…

The Non-Negotiables

📄AI Transcripts Are NOT Your Official Minutes. Full Stop.

AI tools should only produce draft materials for reference, and should never substitute for proper board minutes. Your board secretary or governance professional should still prepare official minutes that:

• Document only essential information (quorum, decisions, due diligence, resolutions)

• Exclude preliminary discussions and speculation

• Maintain confidentiality of sensitive matters

• Meet your state’s legal requirements for nonprofit records

Why does this matter? Because if an AI transcript becomes your official record, you’ve massively expanded what’s discoverable in litigation.

⚡The action: Write this into your AI usage policy explicitly. AI transcripts are working documents. Official minutes are prepared by a human.

🗑️Immediate Destruction After Approval

Once your board approves final minutes, there is no legitimate business reason to keep the raw recording or AI transcript. None. .

Not “eventually.” Not “when we get around to it.” Immediately.

I know it feels wrong. What if someone has a question? What if there’s a dispute? Here’s the thing: your approved minutes exist precisely to answer those questions. That’s what they’re for. Keeping transcripts “just in case” creates more things that can go wrong.

Auto-delete features in your software are not good enough. You need a documented process where a human confirms deletion actually happened, and that confirmation goes in the meeting record.

⚡The action: Your record retention policy needs explicit language requiring destruction of transcripts upon minutes approval. Assign someone responsibility for confirming it and track it.

✅All-Party Documented Consent, Every Time

About a dozen states require all-party consent to record a conversation. If you’re in one of those states, or if participants are calling in from one, recording without consent is potentially a criminal violation. What documented consent actually looks like in practice:

• Announce at the start of every meeting that AI recording is in use.

• Get explicit verbal confirmation from each participant (not just silence).

• Document who consented in the meeting record.

• If someone joins late, pause and get their consent before continuing… yes, even if it’s awkward.

• Make it clear that anyone can object and the recording will stop.

⚡The action: Build a consent script into your meeting agenda template. Make it routine so it doesn’t feel like a big deal.

🏢Enterprise-Grade Tools Only

Free AI tools and standard consumer platforms are not appropriate for board meetings. Consumer AI tools (the free versions, the standard tiers) often explicitly retain your data, use it to train their models, and may share it with affiliates. Your board’s discussions about strategy, donors, personnel, and legal matters would become training data for a profit-driven company.

What you need from any tool you use:

• End-to-end encryption.

• Explicit no-training-on-data policies (your conversations won’t train their AI).

• Data residency controls (you know where data is stored geographically).

• Security certifications (SOC 2, ISO 27001, etc.).

• Contractual right to data deletion (not just user-side deletion).

• No third-party data sharing.

⚡The action: If you’re currently using a free or consumer tier of any AI tool in board meetings, stop. Evaluate enterprise options before your next meeting.

🔍Vet Your Vendors

Third-party vendors are one of the most common sources of data breaches and privacy violations. And here’s the thing: if your vendor mishandles your data, you are still on the hook legally. ‘Our vendor did it’ is not a defense.

Before adopting any AI tool:

• Read the complete privacy policy and terms of service

• Understand exactly how long they retain data and how deletion actually works.

• Verify their security protocols and certifications.

• Confirm compliance with relevant regulations for your sector (HIPAA if you’re in healthcare, FERPA if you’re in education, applicable state privacy laws everywhere).

Why this matters: Most data breaches and privacy violations happen through third-party vendors. You’re legally responsible for how your vendors handle your data.

🔒Make Sure This Doesn't Conflict With Your Existing Data Privacy Commitments

There is a good chance your organization already has data privacy commitments (to funders, to clients, to beneficiaries, to employees, etc). AI use in board meetings needs to be consistent with all of them. This means thinking through:

• Data minimization: Are you collecting more than you need to?

• PII protection: Are donor names, client details, employee information showing up in transcripts?

• Regulatory obligations: Healthcare organizations, educational institutions, and social service agencies face stricter rules that may conflict with AI transcription entirely.

• Funder and partner commitments: Some grants and partnerships include data privacy requirements you may not remember agreeing to.

⚡The action: Have someone review your existing privacy commitments before you finalize your AI policy.

📋Write a Policy.

“We’ll be careful” is not a policy. Policies have specificity, accountability, and teeth. Your written AI transcription policy needs to cover:

What can and cannot be recorded:

• Executive sessions: never

• Personnel matters: never

• Conversations with legal counsel: never

• Sensitive donor or client discussions: never

• Routine business meetings: only with unanimous consent

Who can authorize recording: From leadership to individual directors

How transcripts are controlled: Who has access, how they’re stored, how (and to whom) they can be distributed

When transcripts are deleted: Define this specifically. “After approval” needs to be defined —- 24 to 48 hours.

Accountability: Who is responsible for compliance? What happens when the policy is violated? When does the policy get reviewed?

⚡The action: This policy needs to go through your full board for adoption. Everyone who participates in meetings should be bound by the same rules.

👁️Human Review Is Not Optional

AI transcription is impressive, but it makes mistakes. It misattributes quotes. It mishears names. It transcribes things that were clearly off the record or were part of a sidebar conversation.

More importantly, AI has no judgment about what should and shouldn’t appear in a written record. A human who understands governance is more likely to. Every transcript must be:

• Reviewed by a human who understands governance requirements

• Edited for accuracy (AI makes mistakes constantly)

• Checked for proper attribution (AI misattributes speakers)

• Redacted for sensitive content before any distribution

⚡The action: Assign this review responsibility to a specific person with governance knowledge (your board secretary, your governance committee chair, or an outside governance professional, etc.).

Before You Move Forward, Answer These Questions Honestly

1. Can you actually implement all of this? Can your organization, with your current capacity, meet all these requirements consistently? Including during your busiest periods when shortcuts are most tempting?

2. Do you have the budget? Enterprise AI tools cost more than consumer versions. In addition to software fees, you should account for legal review costs for vendor contracts, policy development, and compliance monitoring.

3. Who owns compliance? Someone specific needs to be accountable, by name and role.

4. Have you talked to your insurance carrier? Does your D&O coverage address AI-related governance failures?

5. What’s your plan when something goes wrong? Maybe a transcript gets forwarded too widely. A recording captures a privileged attorney-client conversation. A vendor has a breach. You discover you’ve been violating consent laws for six months. What do you do?

6. Is it actually worth it? Honestly calculate the time you’d save against the full cost of doing this right … the enterprise tools, the legal review, the compliance monitoring, the staff time. Then compare that to what it would cost to invest in training someone to write better minutes.

If you can’t answer all of these questions confidently, you’re not ready to move forward.

🎯The Takeaway

I said last week you shouldn’t use AI notetakers in board meetings and I stand by it. But if your board has decided to proceed anyway, do it right. My non-negotiables above are my professional opinion on the minimum required to avoid serious legal exposure.

Governance failures are expensive. Do the work now.

💡P.S.! Next up in my AI & Nonprofit series

How to build your AI policy from scratch … and how to get ahead of the AI tools quietly embedded in platforms your organization already uses. Subscribe for free to follow along.

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🔗References & Continued Reading

• TeDesco, B. S., Yurko, B. J., By: Chris Cannon & Michael Felberbaum, & Dressely, B. D. (2025, September 29). Responsible ai: How donorsearch is Shaping Nonprofit Tech. DonorSearch. https://www.donorsearch.net/resources/responsible-ai/

• Polanco, H., Tiernan, K., & Lodewyck, S. (2025, May 6). A guide to nonprofit AI implementation for nonprofit leaders and staff. BDO. https://www.bdo.com/insights/blogs/nonprofit-standard/a-guide-to-nonprofit-ai-implementation-for-nonprofit-leaders-and-staff

• How to ethically use AI for nonprofit organizations. Orr Group. (2024, July 29). https://orrgroup.com/your-roadmap-to-ethical-ai-organizational-readiness/

• AI regulations: What Nonprofit Boards Need To Know. BoardEffect. (n.d.). https://www.boardeffect.com/blog/regulations-ai-nonprofits/

• Deloitte. (n.d.). AI governance for Board members. Deloitte. https://www.deloitte.com/us/en/what-we-do/capabilities/applied-artificial-intelligence/articles/generative-ai-governance-risk-management.html

Most nonprofit boards believe their executive left for reasons beyond their control.

Most of them are wrong.

Executive turnover is at a record high, and I’ve spent the last five years inside dozens of those transitions. What strikes me most isn’t the volume… it’s how consistently the board’s version of events doesn’t match the outgoing executive’s.

Boards tend to land on burnout or compensation. Something external, something inevitable, something beyond their control.

Meanwhile, the executive is telling a different story: they didn’t feel supported. They were asked to deliver the impossible with no resources. The board was either checked out or overreaching. Feedback was rare. No one thought to say thank you.

These aren’t two perspectives on the same story. They’re entirely different stories. And until boards reckon with that gap, turnover will keep climbing … and they’ll keep being surprised by it.

📍This field guide is for boards who are ready to do the work to retain their executives.

Jump to Section

1. 🛠️Set Them Up to Succeed

2. 🧹Clean Up Your Governance

3. 🔋Make the Job Sustainable

4. 🤝Be a real partner

5. 🎯The Takeaway: Turnover is a Governance Issue, Not a Leadership Resilience Problem

1 | 🛠️Set Them Up to Succeed

The success of your executive leader starts long before day one.

🛠️Stop writing job descriptions with everything and the kitchen sink.

If your CEO or Executive Director job description reads like five roles stitched together, that’s exactly what you’ve created. No one person can realistically serve as chief executive, chief fundraiser, CFO, HR lead, program director, and board wrangler …and yet, that’s what many job descriptions describe. Then boards wonder why their leader burns out in 18 months.

A few things that actually help:

• Bring real executive expertise to design the role. Many board members have never held an executive position. That’s fine! But it means they probably shouldn’t be the ones writing the JD. Search firms and experienced community leaders can help you calibrate what’s realistic.

• Define what success actually looks like. Not ‘we’re in a better place’. I mean specific financial targets, operational benchmarks, strategic milestones. If you can’t articulate what winning looks like in the first 12–24 months, you haven’t finished designing the role.

• Plan for a 90-day reset. Look, you won’t get the JD perfectly right from the outstart. Build in a structured check-in with your incoming executive to revisit it together to make sure expectations stay aligned with realtiy.

• Debrief with your outgoing executive. If they're willing to be candid, an exit conversation can surface exactly where the role broke down. If they're not, talk to senior staff….they usually know what’s up. Fold what you learn into your next search.

🛠️Hire by rubric, not by vibes.

Boards get swept up by compelling candidates all the time. Maybe they’re a fantastic storyteller or have real passion for the mission. But passion can rarely close the competency gap.

If a capital campaign is on the horizon, you need someone with major gift experience. If you’re in turnaround mode, this isn’t the moment to hire a first-time executive. Relevant experience will always outperform enthusiasm.

The fix is straightforward: build a scoring rubric. List the qualifications the role actually requires, pair each with specific interview questions, and use it consistently across your search. A good rubric keeps your committee aligned, surfaces real tradeoffs, and keeps “vibes” from driving the final decision.

🛠️Pay what the role deserves.

The idea that working for a cause should come with financial sacrifice is so embedded in nonprofit culture that many boards don’t even think to question it. But nonprofit leadership is serious, complex, high-stakes work… and if you want talented people doing it, you have to be willing to pay for it.

Market benchmarking is a useful starting point. But you also need to look honestly at what you’re asking this person to carry: the size of the budget, the complexity of the work, the level of risk involved. Compensation should reflect that reality, not just the sector average.

2 | 🧹Clean Up Your Governance

Make sure your board is lightening the load … not becoming the source of it.

🧹Establish a Functional CEO–Board Chair Partnership

The relationship between the CEO and Board Chair is the most important governance relationship in your organization, and it requires structure to work well: regular check-ins (monthly or biweekly), clear escalation protocols, and a genuine commitment to no surprises on either side.

I’ve written pretty extensively on how to get this right, so go jump there to read about this one in depth.

🧹Show up prepared to meetings.

When board members arrive uninformed or misses a call, someone has to get them up to speed. And that someone is almost always your executive (or their staff). Multiply that across a full year of board meetings, committee sessions, and one-off calls, and you’ve created a significant drain on leadership capacity.

Preparation is a baseline expectation of board service. Read materials before you arrive. Ask questions in advance. Come ready to make decisions. And if you’re in board leadership? Hold people accountable. If someone consistently isn’t showing up prepared or at all, it may be time to help them transition off.

🧹Right-size your committee structure

Over-built committee structures are an invisible tax on staff time.

Here’s an exercise worth doing: calculate the actual staff hours consumed by your current committees: in meetings, prep, and follow-up. A monthly one-hour committee with 6 people costs 72 hours of meeting time alone, before anyone even opens a laptop to prepare. Now put a dollar value on that time. How much of it is genuinely advancing strategy?

Every few years your board should be asking:

• What committees do we actually need to effectively administer the board and advance strategic priorities?

• Are these committees up to date with our current needs?

• Are any of our committees duplicating staff work?

• What would actually happen if you cut committee work by 30%? Meet every other month? Cut that meeting by 30 minutes?

You might be surprised.

🧹Address bad board behavior early.

This one probably should have come first. You probably have seen it:

• Side conversations.

• Bypassing leadership to give “suggestions” to staff.

• Re-litigating decisions that were settled last meeting.

• Passive-aggressive silence during discussion, followed by complaints afterward.

• Directors cultivating independent donor relationships in ways that create parallel power structures.

These behaviors, and others like it, create real work and real stress for your executive. The board chair should lead on culture at the board, but every board member should know how to recognize these patterns and feel empowered to name them. Every month a bad dynamic goes unaddressed is a month your executive is probably thinking about leaving.

🧹And, yes, major donors don’t get an exception

This one can be uncomfortable to navigate, but it matters: significant donors do not get a pass to be disrespectful to staff, undermine the executive, blur authority lines, or expect special access to internal operations.

When a major donor starts crossing lines, that’s a governance problem, and the board has to be willing to address it. If the board isn’t ready to step up, the executive absorbs that friction indefinitely. That’s not a sustainable arrangement.

3 | 🔋 Make the Job Sustainable

Telling your CEO they’re doing great is kind. Building systems that support them is better.

🔋Use an Executive Session, and Use it Well

Every board meeting should include a standing, board-only executive session. Not as a reaction to a crisis. Not as a workaround for hard conversations. As a regular, normalized part of how the board governs itself.

Used well, executive session creates space for three things:

• Board self-governance. Are we aligned? Operating at the right altitude? Is our behavior helping or hindering leadership?

• CEO performance and support. Are expectations clear? Does the CEO have what they need to succeed? Do we have any real-time feedback?

• Sensitive risk management. Litigation, investigations, compensation, succession planning, and crisis response require confidentiality.

What it is not: a place to vent about staff, a forum to reopen closed decisions, or a substitute for direct conversation with your CEO. If concerns are discussed in executive session, they need to be communicated back clearly. Executive session should never become a shadow conversation your CEO can feel but can’t see.

Here are some more tips from Boardsource.

🔋Conduct annual executive assessments that actually mean something.

Many executives never receive structured feedback. They hear praise in passing and concerns when something breaks. That’s not helping them grow.

An annual executive review should be a formal process: clear expectations, progress against agreed goals, and an honest assessment of where support is needed. It should never be the first time concerns are raised. And it should happen every single year.

I’m a strong advocate for bringing in a third-party facilitator. They can gather input confidentially, synthesize themes more objectively, and help both the board and the CEO work through difficult feedback productively. This is more than an investment in your leader. It’s an investment in organizational stability.

🔋Resource the Role & Infrastructure

A CEO cannot succeed in a structurally underfunded organization. If you expect growth and strong leadership but resist funding overhead, you’ve built a burnout machine.

Resourcing the executive means:

• Allowing them to hire the talent they need

• Funding back-office and administrative capacity

• Planning for succession below the CEO level.

When staffing is thin and infrastructure is weak, complexity rolls uphill …and it lands on the person you most need focused elsewhere.

🔋Normalize real time off, and sabbaticals.

An organization that cannot function without its CEO for a short period of time is structurally fragile.

Sustainable leadership requires genuine rest. Boards should ensure their leaders get meaningful vacation time, enforce real disconnection while the executive is away, and adopt a formal sabbatical policy for long-tenured leaders.

And as to Sabbaticals: they aren’t an indulgent benefit. They’re a legitimate retention strategy. If you want an executive who stays for the long haul, you need to build renewal into the structure of the role.

🔋Invest in professional development and coaching.

Executives operate in unusual isolation. They carry confidential personnel issues, donor tensions, political pressure, and strategic uncertainty… often without a true peer inside the organization.

Every CEO needs a place to think out loud, test assumptions, and process risk without consequence. Providing access to coaching, peer networks, or experienced mentors strengthens judgment and increases staying power.

Boards should budget meaningfully for executive-level development and coaching and encourage its use. At this level, serious education and advisory support cost real money, and that investment reflects the complexity of the role.

4 | 🤝Be a Real Partner

A lot of board-executive relationships deteriorate because the board stops showing up as a genuine partner. The relationship only works if both sides are actually in it.

🤝Provide Cover During External Conflict

Executives often absorb pressure that belongs to the whole organization: community backlash, donor dissatisfaction, staff resistance to necessary change. When the board goes quiet during those moments, it can feel like abandonment.

Strong boards instead:

• Publicly back difficult decisions

• Align in advance with clear, written talking points

• Refuse to undermine leadership in side conversations

Visible unity during times of distress can really build confidence and credibility.

🤝Don’t use the CEO as a Buffer Between Board Members

As a board member, routing conflict or political tension through the CEO may feel easier in the moment, but disagreement between directors is board work …not management. Executives should not be mediating interpersonal disputes between directors or carrying messages between colleagues.

Strong governance means directors address conflict directly with each other, and the chair steps in when behavior needs to be corrected. When the board manages its own dynamics, it protects the CEO’s focus and authority.

🤝Make Fewer, Clearer Decisions

Boards create instability when they drift into operations, reopen settled decisions, or hesitate to delegate once a direction has been set. Good governance means setting strategy and guardrails, not managing execution.

Strong boards stay at the strategic level, commit to decisions once they are made, and delegate authority to the CEO with clarity. They distinguish between high-stakes, hard-to-reverse decisions and those that can be tested and adjusted over time. (Here’s a mental model you might like.)

Not every choice requires exhaustive analysis. Leadership needs room to move, learn, and iterate.

🤝Respect the CEO’s Professional Judgment

Respecting the CEO’s professional judgment is essential to leadership longevity.

Constantly second-guessing staff expertise, overriding management decisions, or demanding certainty in ambiguous conditions erodes trust and accelerates burnout. Nonprofit leadership operates in complexity, and perfect foresight is neither realistic nor required.

Boards retain strong executives when they ask good questions, set clear guardrails, and then let leadership, well, lead.

🤝Plan for Absence, Not Just Exit

Few boards plan for resignation. Even fewer plan for temporary absence. In addition to resignation or termination, there are a wide array of reasons your executive might be Medical leave, family emergencies, or burnout recovery require clear protocols. Governance maturity includes interim coverage plans, cross-training, and board readiness to step in temporarily if needed.

Preparing for absence strengthens continuity and reduces pressure on the executive to carry everything alone. Come back in a few weeks as I write more on this exact thing!

🎯This Is a Governance Issue, Not a Resilience Problem

The nonprofit sector doesn’t have a CEO resilience problem. It has a governance maturity problem. A role design problem. A support system problem.

We keep framing burnout as a personal failing… as though more grit or better boundaries will somehow compensate for unclear authority, misaligned expectations, and boards that drift into operations while neglecting strategy. Resilience matters. But it was never meant to be a substitute for structure.

In a sector where leadership turnover is accelerating, the ability to retain stable, effective executives is a real strategic advantage. Continuity builds donor trust, steadies staff, and lets organizations execute on long-term strategy instead of constantly resetting.

If boards want CEOs who stay, they have to become boards worth staying for.

💡P.S. Did you find this useful?

Share it with a fellow board member! This conversation is only valuable if it reaches the people who need it. Subscribe free to follow along, and if you’re able, consider a paid subscription. It’s how I keep this work free and accessible to our community.

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🔗References, Resources, and Additional Readings

• Kittleman Search. CEO Departures at Record Levels in 2025. Retrieved January 2025. https://www.kittlemansearch.com/insights/ceo-departures-at-record-levels-in-2025

• Challenger, Gray & Christmas. (2025, July 29). The rise of the CEO gig economy: Turnover in the corner office. Fortune. Retrieved January 2025, from https://fortune.com/2025/07/29/ceo-gig-economy-turnover-highest-in-decades/

• BizJournals. (2025, July 28). A turnover tsunami is hitting the C-suite — and sparking a ‘CEO gig economy’. Retrieved January 2026, from https://www.bizjournals.com/bizjournals/news/2025/07/28/record-turnover-ceo-gig-economy-challenger.html

• Johnson Center for Philanthropy. (2025, January 14). The nonprofit workforce is in crisis. Retrieved August 2025, from https://johnsoncenter.org/blog/the-nonprofit-workforce-is-in-crisis/

• Sigma Assessment Systems. (2025, May 27). Crisis in the C-suite: How to prepare for the wave of CEO exits. Retrieved August 2025, from https://www.sigmaassessmentsystems.com/crisis-in-the-c-suite-how-to-prepare-for-the-wave-of-ceo-exits/

• Urban Institute. (2025, April). Nonprofit leaders’ top concerns entering 2025 [PDF]. Retrieved August 2025, from https://www.urban.org/sites/default/files/2025-04/Nonprofit_Leaders%E2%80%99_Top_Concerns_Entering_2025.pdf

A few years ago, I joined a board meeting and noticed an unfamiliar participant listed: Otter.

I assumed it was someone’s assistant with an odd name… but then came the post-meeting minutes: A complete transcript of everything said, including a personnel discussion that was confidential. Otter turned out to be an AI notetaker, invited by our board secretary to ‘help’, that had recorded and distributed our entire meeting.

I was shocked. And, if I’m honest, a little embarrassed that I hadn’t noticed.

This experience isn’t unusual. Across boardrooms today, AI notetakers are showing up uninvited (or at least unannounced). An unfamiliar name appears in the participant list. A transcript lands in your inbox after a meeting you didn’t know was being recorded. A colleague mentions, almost in passing, that they ‘use AI for all their notes now.’ Perhaps, even, you realize the notetaker at the table is someone’s phone, propped up discreetly.

These aren’t just awkward moments.

As a board member, you are given access to sensitive information, financial details, and strategy that are confidential by necessity. When AI enters that room, the consequences can extend well beyond embarrassment…. They reach into legal exposure, eroded boardroom trust, and a compromised ability to govern.

Here’s what every board member should understand.

Jump to a section:

• ⚠️The Real Risks

• 🚨The problem is just getting worse.

• 🙋What You Can Do As A Board Member

• 🎯A Final Note

• 👉Next up in my AI & Governance series…

⚠️The Real Risks

1. Everything You Say Suddenly Becomes a Legal Record

Board meeting minutes should be carefully curated, capturing key decisions, discussion points, and rationale. What they include is as important as what they leave out. Preliminary thinking, exploratory debate, and half-formed ideas are part of how good boards work. They are not meant to be preserved verbatim.

AI, on the other hand, transcribes everything.

That offhand comment made while still settling into the room. The frustrated remark before a difficult vote. The joke a colleague made to break tension. None of it is filtered and all of it is likely discoverable in litigation.

Consider a director who arrives flustered and jokes: ‘I barely had time to glance at the materials this week.’ Everyone laughs and moves on. But if that board later faces a contested decision, that offhand comment is now a record of a director who, by their own words, voted without preparation. That's a breach of the legal duty of care waiting to be argued.

Read more about the legal risks + here + here too!

2. Your Confidential Information Doesn't Necessarily Stay in the Room

When AI records your meeting, that conversation leaves the room immediately. It moves to vendor servers, where it may be stored indefinitely under data retention policies you didn’t negotiate and can’t control. Vendor employees may have access and the content of your discussions may be used to improve the AI product itself.

Think carefully about what that means: Personnel discussions, financial commentary, strategic considerations…. All of it now held by a third party, under their terms, not yours.

The legal consequences reach further. Attorney-client privilege, one of the most important protections available to a board navigating serious risk, can be waived when confidential communications are disclosed to a third party. If your board engages legal counsel in confidence and an AI tool is routing that conversation through an outside vendor, that privilege may already be forfeit.

3. AI Dampens Candor

Good governance depends on frank conversation. Directors need to feel free to debate, challenge assumptions, float half-formed ideas, and voice minority perspectives without worrying how it will look on the record.

When sensitive topics are on the agenda and AI joins the room, you can bet that people won’t be as forthcoming. I’ve seen board members who are usually more direct chose careful words over candid ones, and some not participate at all. And their caution isn’t unfounded. AI misses context, flattens tone, and, when multiple people speak at once, mix up words and makes mistakes.

So it’s not so safe to speak up.

But a board that can’t speak up can’t govern well.

4. You May Be Breaking the Law

Federal law requires only one-party consent to record a conversation. But eleven states, including California, Florida, Illinois, Pennsylvania, and Washington, require all parties to consent. If even one participant is located in one of those states, that standard applies to everyone in the meeting.

Directors joining late, missing a consent notice, or dialing in from a stricter jurisdiction create legal exposure, for themselves and for the organization. It doesn’t require bad intent. It just requires not knowing, and that is increasingly easy in a world where recording features are being built directly into the platforms your board already uses.

One More Thing: It’s Not Even More Efficient

The pitch is that AI notetakers save time. The reality is that someone still has to convert an hour-long verbatim transcript into proper minutes.. and an unfiltered record, full of errors and crosstalk, is harder to work from than a well-prepared set of notes.

👀Unless, of course, you're using a second AI to summarize the first one. Which raises its own questions and opens an entirely new layer of risk.

The boardroom is one of the few places where the promise of efficiency should not be the deciding factor.

🚨The problem is just getting worse.

Unfortunately, AI transcription is becoming unavoidable. Zoom, Microsoft Teams, Gmail, and other platforms are building these features directly into their products … and this isn’t always something you choose. Maybe it gets enabled by default when you update your software, or turned on by a single participant without announcement, or activated accidentally.

There also is a less-named force at work: tech companies really want you to use it. There’s been a flood of content being released praising how AI can ‘transform board governance’. It reads authoritative.. but often these are marketing materials produced by companies with a financial interest in your adoption or individuals getting a kick-back. Their enthusiasm isn’t neutral

The reality:?

⭐AI transcription in board meetings presents well-documented risks that can compromise confidentiality and decision-making integrity.

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🙋What You Can Do As A Board Member

Watch for these red flags:

• 🚩Unfamiliar names in the participant list.

• 🚩Automated ‘this meeting is being recorded’ messages you didn’t authorize.

• 🚩Transcript emails after meetings.

• 🚩Colleagues treating AI note-taking as routine/expected.

• 🚩No board policy on recording or AI tools.

The first line of defense is simply paying attention. Before and during any meeting, watch for unfamiliar names in the participant list. Tools like Otter, Fireflies, and Notetaker are common, but they don’t always announce themselves clearly. An automated ‘this meeting is being recorded’ message you didn’t authorize is another signal. So is a transcript arriving in your inbox after a meeting you thought was private.

If a colleague mentions they use AI for all their notes now, that conversation is worth having directly. What tool? Where does it store data? Who has access? These are reasonable questions, not paranoid ones.

It’s OK to say no.

If you join a meeting and see AI at work, you have the right to raise the question. For most private organizations, even in one-party consent states, board members typically have a reasonable expectation of privacy, especially in executive session.

If recording continues over your objection, document it and leave if necessary. You’re not being difficult…. you’re protecting the organization and yourself.

(Note: boards of public institutions operate under different standards and should seek specific legal guidance.)

Advocate to get a policy in place.

Your board needs a written policy that addresses what may be recorded, which tools are approved for use, and where AI fits into your governance processes. This isn't optional. It's governance hygiene for the modern era.

And the boardroom is just the starting point. AI is quietly making its way into every corner of organizational operations: communications, fundraising, HR, finance. Your policies need to grow to meet that reality. But it starts here, with the room where your most consequential decisions are made.

🎯A Final Note

I say this as someone who grew up in a tech household and has always been excited about what new tools can do. Technology amplifies human choices, for better or worse.

In nonprofit governance, where trust and honest deliberation are foundational, we need to be thoughtful about which tools we invite into the room. AI transcription may work well in other lower-stakes contexts….The boardroom is not one of them.

Keeping Reading Part II >

💡P.S.! If your board insists on using AI despite these risks…

Subscribe for free and follow along. I’ll be covering the practical steps legal experts say boards must take to reduce exposure, including how to begin building your AI policy, and how to address the broader wave of AI tools quietly making their way into every platform your organization already uses.

Subscribe now

🔗References & Resources

• https://www.shumaker.com/insight/ai-notetakers-in-the-boardroom-privilege-and-privacy-considerations/

• https://corpgov.law.harvard.edu/2025/11/29/using-ai-in-the-boardroom-new-opportunities-and-challenges/

• https://www.bsk.com/news-events-videos/artificial-intelligence-in-the-boardroom-key-legal-governance-amp-risk-considerations

• https://www.wagenmakerlaw.com/blog/always-listening-ai-automatic-note-takers-and-related-risks

• https://www.babstcalland.com/news-article/eavesdropping-by-algorithm-legal-risks-of-ai-meeting-assistants/

Every time I step into a new organization to assess their health and strategy, one of the first things I do is look through their historical records. Time and time again, the minutes are useless. I can usually bet on finding pages and pages of ‘he said, she said’ with no easy way to track ongoing issues, find what I’m looking for, or get a clear sense of what was actually decided or why.

I know this sounds basic, but since I see it so often, I thought, perhaps you are struggling with this too. So let me save you some time: here’s how to write minutes so they might actually be used and properly protect you and your board.

Jump to a section:

• Your Basic Setup

• Don’t Do This (And Why)

• Field Tested Tips for Your Secretary

• Common FAQs

📄The Basic Setup

Here is a basic outline of what your minutes should contain and why:

• Logistical Data.
  Date, time, location, type of meeting (regular or special), and method (in-person, virtual, or hybrid).

• Notice of Meeting.
  How and when notice was provided to all directors. If notice was waived, include written waivers or consents with the minutes.

• Attendance.
  List who was present and absent, and confirm quorum was met (this determines vote validity). Note any guests or non-voting participants. If anyone leaves during the meeting, note their exit time.

• Agenda Items.
  A brief description of each item discussed and what was reviewed.

• Motions and Votes.
  The exact wording of each motion, who made it, who seconded it, and the vote count. Note directors who abstain or vote ‘present.’

• Documented Conflicts of Interest.
  List any disclosed conflicts and how they were managed (recusal from discussion, leaving the room during votes, etc.).

• Materials Provided.
  Identify materials given to directors that are directly relevant to board decisions. These should generally be attached as exhibits unless they’re sensitive or confidential.

• Action Items.
  Who is responsible for what, and by when. Be specific.

• Key Decisions and Rationale Here’s where you strike the balance. Capture essential context that demonstrates due diligence without creating a verbatim record. Use bullet points to note the main considerations. Phrases like ‘discussion ensued’ or ‘the board considered multiple factors including...’ capture the conversation’s substance while avoiding excessive detail that could create legal problems.

Remember: to protect from potential liability issues, keep minutes as concise as possible. Unnecessary information may provide little value while potentially opening up legal complications.

⚠️ Don’t Do This (& Why)

Verbatim Quotes and Attribution / Play-by-Play

Detailed accounts of ‘who said what’ are dangerous, as they provide fodder for opponents in lawsuits, as minutes can be requested in legal proceedings. Beyond legal risk, they personalize and politicize discussions, shifting focus from what the board decides to who said it. When individual arguments are documented, board members may become intimidated and guarded, and fail to express their true opinions. Board members need to be able to speak in draft, to test ideas, and change their minds without creating a permanent record. Documenting every turn in the conversation creates unnecessary exposure (and makes minutes unreadable).

Inaccuracies

The more detail you attempt to capture, the more likely you are to get something wrong: misattributing a comment or mischaracterizing a position. Over-documentation doesn’t just create legal exposure… it likely creates factual errors that may undermine the credibility of your records.

Lack of Detail (The Other Extreme)

On the flip side, being too vague or omitting critical information can lead to equally serious problems. Minutes that say only ‘the board discussed the budget’ without noting what was actually decided leaves no evidence of due diligence. You need to find the sweet spot between transcript and telegraph. (Check out the tips section below for how to get this right.)

Full Report-Outs and Copy-Paste from Presentations

If staff presented a 20-slide update, your minutes don’t need to reproduce it. That’s why you have attachments. Instead, reference attachments in your minutes and note where they’re filed. For example: ’The CFO presented the Q4 financial report (attached). The board accepted the report as presented’ is more than sufficient.

Personal Opinions, Judgments, and Interpretations

Leave your editorial opinions out of the minutes. Phrases like ‘the board was frustrated’ or ‘it was a heated debate’ are interpretations, not facts, and they can create problems down the road. Don’t polish what people said to make it sound better, and resist adding what you think they ‘really meant.’ Stick to what actually happened and let the facts speak for themselves.

🎯 Field-Tested Tips For Your Secretary

So you've got a basic template and you know the big mistakes to avoid. Good start. But here's what will make your life easier and separate minutes that work from minutes that sit in a folder gathering dust.

1️⃣Before the Meeting

Use The Agenda As Your Minutes Structure.
Create a copy of the meeting agenda and log key decisions, discussion points, or actions under each item. This creates consistency and ensures nothing gets overlooked.

Template & Track Attendance.
Make a templated checklist of your board members and key staff that you can mark off as people arrive, with slots to write in guest names. Create a clean copy for each meeting to fill in fresh.

Know Your Bylaws.
As the secretary, you should help ensure the correct execution of board process in the boardroom. Understanding your organization’s bylaws will help you know what requires a vote, what constitutes quorum, and what procedural requirements must be met.

2️⃣During the Meeting

Highlight Votes and Actions.
Mark action items with ‘VOTE’ or ‘ACTION’ in caps and highlight them in yellow so they’re easy to find later when someone is reviewing or following up.

Use The Three-Sentence Rule.
A good rule of thumb is that if something is asking more than three sentences to summarize, you might be including too much detail. Make sure to focus on outcomes, not process. What was decided? What was approved? What happens next?

📍Example: ‘The Executive Director presented the Q4 financial report. The board accepted the report as presented. Finance committee to monitor and report progress in Q1.’

Use The ‘Discussion Followed’ Framework
When the board decides to engage in a longer discussion, here is a framework you can use to capture the key points of that without dropping into the weeds:

The board discussed X. Key points included:

• Bullet point

• Bullet point

• Bullet point

📍Example:

The board discussed the marketing budget presented by the CEO. Key points included:

• Donor acquisition costs up from last year and whether current spending levels are sustainable.

• The ROI on digital campaigns compared to traditional outreach methods.

• Alignment with strategic priorities outlined in the three-year plan

Don’t Document Sidebar Conversations.
If it was important, they’ll bring it up on the record. Don’t include anything said during breaks either.

3️⃣After the Meeting

Send Drafts within 48 Hours.
Waiting a week guarantees you’ll forget critical details. Send them to the board marked as ‘DRAFT’ in the subject line and header, with a message requesting review for accuracy. Don’t forge to set a deadline!

Manage Change Requests.
This is a record of what occurred during the meeting, not individual positions after the fact.

• ✅ Accept: Corrections to factual errors

• ❌ Decline: Requests to add ‘what I meant to say’ or ‘for the record, I want it noted that...’ This is a record of what happened in the meeting, not a personal accounting on a topic. Remind folks they can bring their opinions up on the record at the next board meeting.

Keep It Neutral
Write in third person. ‘The board discussed...’ not ‘Jane argued that...’ Remove personality and attribution from the record.

Organize & Name Your Files

• Keep approved minutes in one folder, all supporting documents in another

• Name files consistently: ‘2025-02-Board-Minutes-APPROVED.pdf’

• Keep a running action item tracker separate from minutes so you’re not hunting through documents

🔍 Common FAQ

These are my professional recommendations based on working with private nonprofit organizations. Depending on your organization’s bylaws and legal requirements, you may be required to do things I recommend against (e.g. recording). Use your best judgment and check your governing documents.

Who Takes the Minutes?

This responsibility should fall to the board secretary, though it can be assigned to any board member. However, whoever takes minutes needs to understand they’re not a court reporter. They’re creating a strategic document that protects the organization while fulfilling legal requirements. This requires editorial judgment, not comprehensive transcription.

Could staff take the minutes for us?

I do not recommend staff take your minutes. Your board needs to have confidential conversations sometimes, and the moment staff is in the room, that’s compromised. Plus, minutes are a legal record of board decisions. The board should control what gets captured, not hand that off to someone who isn’t in the room for governance reasons. If your secretary is struggling, rotate the role among board members instead.

Should we record the meeting?

I do not recommend you record your board meetings. While convenient in some regards, people are less likely to be candid if they’re being recorded, and it’s risky for the same reason verbatim notes are risky. If you absolutely have to record: get consent from everyone in the room and remember that video does not replace written minutes. Delete the recording once you’ve drafted the minutes from it.

Should we use AI?

That’s a hard no for me. I’ve thoroughly answered this here.

Do I record everyone vote?

Only if asked or required. You don’t need to list individuals unless a director has formally requested to have their position explicitly recorded. Otherwise you can just say 7 yes, 2 no, 1 abstention.

What do I record if a vote fails?

Record it exactly as you would successful motions. Note: ‘Motion failed 3-5’ or ‘Motion tabled until March meeting.’

💭Final Thought

Good minutes aren't complicated…. but they are different from what most people think they should be. Stop trying to capture everything. Focus on decisions, actions, and who's responsible. Keep it simple.

Your future self, your board, and your lawyer will all thank you. Now go forth and write minutes that people might actually read.

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🛠️Resources + Downloadables

💡Paid subscribers make it possible to keep this platform free for everyone. Join them to get downloadable tools and templates, and help me keep writing practical guidance that's accessible to all. You can find downloadable resources related to this article here!

Plus here are some legal references on writing minutes:

• https://www.501c3lawblog.com/mastering-board-meeting-minutes-for-nonprofits/

• https://charitylawyerblog.com/2021/04/26/taking-nonprofit-meeting-minutes-like-a-pro/#common-mistakes-when-taking-nonprofit-meeting-minutes

• https://www.abelajlaw.com/non-profits/guide-to-non-profit-board-meetings-minutes-and-agendas/

⏱️Got a minute?

These might be the most expensive three words in your workplace. This seemingly harmless question (delivered as a desk drop-by or a Teams ping) can destroy your team’s ability to do deep work and your ability to move the needle on the big stuff.

I learned this the hard way. Early in my career as a new exec, I’d sit down at my desk in the morning, get that first ping, and before I knew it, the entire morning had vanished. Person after person would show up with their ‘quick question.’ ...And my desire to help and be a resource ended up undermining my own effectiveness.

Here’s what I eventually realized: If you don’t decide what deserves your attention, other people will decide for you.

Every got a minute is someone else deciding what deserves your focus. And if you let them, your entire day... entire quarter ...entire year becomes a series of other people’s priorities.

The real problem ultimately is that this got a minute behavior becomes a shortcut around critical thinking and planning. Instead of staff reflecting on whether something is truly urgent, crafting a clear question, or batching communication, people default to instant interruption. It’s easier to grab someone than to think through what you actually need. But that ease comes at a massive cost to everyone’s productivity.

Make the Fix

Have I convinced you to break the habit but not sure where to begin? Great, I got you. Here is a laundry list of ways I’ve tried to set (or reset) this norm at the places I work.

• Leaders start here: You must admit your guilt & set the new expectation. I’m sure you have also been guilty of this got a minute behavior. When you own your contribution to the problem, people are more willing to own theirs. I named the impact, spoke to what everyone was feeling (the need for deep work time), and set a new expectation with my department heads... then follow through by modelling.

• Staff start here: Ask yourself three questions before interrupting. Is this blocking my immediate work? Can I work around it? Can I write it down clearly? If not truly urgent, maintain a running list for your one-on-one or send a single, well-composed message.

• Stay Curious but hold the line: When someone approaches you, ask: Is this urgent? If not, you need to resist the urge to help in the moment and redirect. Tell them to add it to your next 1-1 agenda, put it in an email, or that you’ll get back to them by end of day. But whatever you do, don’t solve it in the moment... you’ll only reinforce the behavior.

• Calibrate sense of urgency. Similar to staying curious, don’t just ask is this urgent, by Why is this urgent? or Could this wait? And, if someone truly thinks they need your help, figure out the timeframe: Do they need you right now, or by end of day, or can it wait until your one-on-one?

• 🚗Use a Parking Lot. This is a place where you literally ‘park’ ideas. Note issues as they arise in a shared document, teams/slack thread, or meeting notes, then batch them for discussion later. As a leader I also have a parking lot for ideas that pop up as I’m working on something, to help me keep focused.

• ⛔Use office hours or open blocks. Set specific times (e.g., 3-4pm daily) when you’re available for drop-ins. Outside those hours, everything goes to the parking lot unless genuinely urgent.

• 📄Create a shared running doc for each direct report. Maintain a shared document both you and your direct report own. Both of you add items throughout the week, then work through it in your 1-on-1. You can grab mine here, if you need a place to start.

• ❓Batch your questions. Keep a note on your phone or your notebook of things you need from each person, then send one message with 3-4 items instead of four separate interruptions. (Or use your shared documents/Wait until your 1-1s)

• ⏱️Time-block your calendar for deep work. Literally put ‘Deep work, no meetings’ on your calendar. Treat it like any other meeting. It’s not rude; it’s professional.

⭐And finally, most simply, you just have to get comfortable saying no. It only gets easier through practice.

A quick word on being ‘approachable.’

I know that people worry that setting boundaries will make them seem uncooperative or unapproachable (especially as a woman). Totally fair, and I’ve experienced it myself. Here’s what’ I’ve seen in the field though: if everyone understands the expectation, and its set as a team value, it’s easier to enforce without this negative repercussion. It is critical that leaders actually lead this culture shift by setting and holding the line with the whole team, reminding people proactively over a period of months, and immediately addressing out-of-sync behavior.

Final Note

It will take time to calibrate your team, but this is about protecting attention so deep work can happen. The habit of got a minute? reveals a team that hasn’t established communication protocols or learned to distinguish urgent from important. Fix this, and you’ll reclaim not just your morning... but your team’s ability to do work that actually matters.

💡Leaders: What are ways you set and protect deep focus time on your teams?

My first interim role was supposed to be a career side quest. A temporary pause. Something a little slower and a little easier than the relentless pace of long term leadership. I imagined myself as a helpful bridge, stepping in for a few months to keep the lights on, and stepping back out with minimal drama.

Boy, I was so naive.

Nine interim roles later, I’m still here, having fallen in love with leading in the liminal: that strange, potent space between what was and what’s coming. But I’ve also learned some hard lessons along the way, in ways I could have never expected. The hardest one? Interim work will require something very specific and difficult from you: To go deep, build real trust, put the full weight of yourself and your expertise into a mission… and then leave before you see what grows.

It’s easy to find and read up on the skills needed to be successful when leading through turbulence and transition: strategic thinking, financial acumen, decisiveness, communication, adaptability, etc.. But rarely do I see anyone talking about what it would really require of you professionally, personally, emotionally.

So I want to name it, and share what’s helped me keep saying yes, again and again.

What Makes This Work Hard

📍You rarely see the impact of your work.

As hinted, many leaders spend years, even decades, at a single organization, stewarding initiatives from conception to maturity, building lifelong friendships, and witnessing the full arc of their impact.

An interim leader’s experience is very different. We arrive, often thrust into making major decisions that will shape the organization for years, and leave before seeing most of them fully play out. I've helped organizations completely overhaul their mission and strategic plan, launch new programs, initiate partnerships and funding relationships… I mean, major, foundational work.

But I didn’t get to carry it all the way through. I left and had to watch from afar to see if the calls I made the right calls. The responsibility is heavy, and sometimes I'm only left with hope that the work will hold.

📍Relationships are intense, then over.

Any time you join a team, you build real relationships. You learn people’s anxieties, celebrate their wins, sit with them through hard conversations and sometimes tears. You become someone they trust. And these relationships can be more intense than typical work relationships, as you’re often going through hard things together, under a lot of pressure, in compressed time.

I once joined an organization where the entire C-team had collapsed. I spent months recruiting and integrating a whole new leadership team, setting up shared values, coaching them through their first big decisions, celebrating when things clicked. We went through the intensity of culture redesign and enterprise-wide systems change together… and we became a real team.

But then the assignment ended, and I had to hand over the work and step back. Unlike most professional relationships though, you don’t get to let this evolve into something long-term. There’s no shift from boss to mentor to ex-colleague I grab coffee with. You have to cut cleanly and create space for the next leader… only to just jump in and do it all over again with a new team.

📍High Stakes, Little Grace.

A typical new leader gets 90 days to learn before they’re expected to act…. Interim leaders sometimes get half that. Heck, sometimes day 1 arrives with a crisis that needs solving immediately.

I once walked into a an organization facing a multi-layered crisis: a double executive transition, a call-out that threatened donor relationships, financial gaps that required immediate audit, and governance problems that had festered for years. There was no orientation period, no grace for learning the culture first. Day one was triage.

And I've found that as an interim, the margin for error is thinner than usual. People are less resilient during transitions… tired and anxious. Trust is fragile and small mistakes can more easily amplify into crisis. You need to make people feel heard, while also making hard calls.

Hardest of all though is that the learning and the doing has to happen simultaneously. You sometimes have to make a decision today without all the information you want or need… and just stay humble and flexible in the execution.

📍Sometimes you can’t move the needle.

Not every problem can be solved in an interim window (…though, id argue, not every problem should). Some challenges require longer timelines than the time you have or more resources or, simply, a long term leader’s authority and longevity to see through.

In worse situations, sometimes the solution will be crystal clear to you… you can see exactly what needs to happen and the path forward is obvious… but the board or staff aren’t ready to move. They need more time, more trust, or a different messenger (or something…!)

So, in these cases, you do what you can, document what you’ve learned, name what still needs attention, and hand the rest to the next person, hoping they’ll have better luck. It's frustrating and unfulfilling.

📍The isolation is real.

Long-tenured leaders get to build networks counterparts at similar organizations over years, whereas interim leaders tend to move between missions. And the people who truly understand this work are few, and we’re often mid-assignment and unavailable to one another.

And gosh, the problems I confront…. every assignment is similar but different, and I long for peer guidance. But it’s so hard. How do you bring someone up to speed about all the complexities in an organization, its people, its problems, its politics... in an hour, with time left over for actual advice? And when the environment is shifting rapidly, week to week sometimes, the context you shared last month is already outdated. It gets lonely fast. You start to realize that you need to get way better at seeking advice in fragments, at trusting your own judgment more, at making peace with the fact that no one else will ever fully understand the situation you’re in.

📍No proper goodbye.

When a permanent leader leaves after years of service, there’s usually a farewell… a party, a toast, moments of collective gratitude. Interim leaders don’t often get that. The new person starts, the organization’s energy shifts toward them, and you fade out. This is appropriate; it’s their moment, not yours. But it means you often leave without ceremony, without much acknowledgment of what the work took.

I once spent a year with an organization, leading through a painful downsize, pivoting programs, and championing some serious culture change. When the new executive was hired, I got ready for transition. In many of my assignments, I’ve been lucky to get a few weeks of overlap with a new executive… you know, time to transition knowledge and relationships, to get closure. But this one? Four days. All virtual. When Friday came, I signed out of my email, and just like that, I was done. The organization just moved on, quickly, with problems still left to solve and work still unfinished.

Though this doesn’t happen often, you need to be ready to pack up quietly and move on.

📍Change is constant and exhausting.

New organizations, new teams, new cultures, new problems… again, and again and again. It is both exciting and draining. It is both exciting and draining.

Just as you’re hitting your stride, building real momentum… it’s time to leave and start over. Most of my assignments last about a year, which means every twelve months I'm starting from scratch on relationships, credibility, and context. The weight of that change is cumulative, even when each individual assignment goes well.

My 7 Tips for Sustaining Yourself in This Work

So, what's helped me keep saying yes? Here's what I've learned. Not all of these might be right for you, but maybe they'll give you some inspiration for finding the right rituals and guardrails to make the work sustainable.

• 1️⃣Develop a toolkit for leading under constraint.
  Interim leadership requires different skills than permanent leadership. Here are some of the core practices I’ve learned to rely on:

  • Use the 80/20 principle. 80% of your results will come from 20% of your efforts. Identify what truly matters and concentrate there

  • Use frameworks to cut through complexity. Tools like the pyramid principle and MECE can really help you make sense of massive quantities of data quickly and structure your thinking under pressure.

  • Understand one-way and two-way door decisions.. You need to be an expert at figuring out what decisions you should make vs the long term leader, and why.

  • Define decision-making authority up front. Make sure everyone knows who can decide what, and how quickly.

  • Timebox decisions. Give yourself or your team a clear deadline to decide, then move. This prevents analysis paralysis.

  • Treat early decisions as drafts. Master provisional decision-making… make the best call you can now, stay open to adjusting as you learn.

  • Admit mistakes quickly and publicly. This builds trust faster than pretending you had it right all along.

  • Set clear expectations. Be honest about what you can and can’t promise in your window.

  These skills, and more, are learnable. You can check out more of my some of my specific advice for leading under pressure here or subscribe and follow along as I share my toolkit over the next few months.
  

• 2️⃣Find a trusted partner inside the organization.
  External peer support is hard to access when you're deep in the complexities of a specific organization. You need to find a trusted staff member or board member who can really go side by side with you… someone who understands the nuances without needing constant context and who can be your sounding board in real time. This internal partnership can help bridge the isolation gap and give you someone to think through decisions with when outside advisors can't fully grasp the situation
  

• 3️⃣Protect the new leader by protecting your boundaries.
  This might be a hard take, but when I leave an organization, I maintain low or no contact with former staff for at least six to twelve months. This gives the new leader room to build their own relationships and prevents the team from splitting their trust. When a former colleague reaches out for advice, the kindest thing I can do is redirect them to their new leader. The boundary can feel severe, but it serves everyone. Eventually the connection can be reforged, but I found honoring that space is best for everyone.
  

• 4️⃣Create rituals for closure.
  Find your own way to mark endings. For me, I take a picture somewhere on site and frame it in my home office. I write goodbye notes and give small gifts to staff and board members and donors. I schedule final coaching sessions and exit coffees. I take a weekend away with my husband. And I write a reflection right away, then revisit it a few months later once I’ve got some distance. You need to find a way to make peace and prepare for the next assignment.
  

• 5️⃣Build real community outside your assignments.
  The only way to do this work well is in community with others doing the work. Seek out other interim leaders. Stay connected through your state np association or informal groups. For me, this looks like a group chat with peers in similar roles, attending conferences, and staying active in online spaces. I also serve on a board and have volunteer commitments, which keep me connected to the sector in a different way, grounded in relationships that extend beyond any single assignment.
  

• 6️⃣Anchor your identity outside the role.
  When your position is always temporary, it’s easy to lose track of who you are professionally. Identify what stays constant across assignments: your values, your craft, your approach to leadership. Write about it. Talk about it. Let your sense of self travel with you rather than depending on any single organization.
  

• 7️⃣Rest between assignments when you can.
  If you have the option and flexibility, building in time between roles to decompress can make all the difference. Even a few weeks can help you arrive at the next organization with a fuller tank. (Truthfully, I’m not great at taking my own advice on this front, but when I have been able to honor it, I feel the difference.)
  

And… 8️⃣Recognize that the weight you’re feeling is not weakness.

The exhaustion after an intense assignment, the sadness of leaving a team you’ve come to care about… these are not signs that you’re unsuited for the work. They’re the natural cost of doing it well. Caring about places you cannot stay is hard.

Honor it, feel it, and give yourself real time to recover before diving back in.

Why I Do It Anyway

As I said at the start, I never expected this to be my career path. I came into interim leadership by accident and fell in love with the dynamic nature of it. I get to see organizations at inflection points, when they’re most alive to change. I’ve built diagnostic intuition that only comes from variety. I’ve learned to travel light, emotionally and operationally, and there’s freedom in that.

And I get to help people—really help them--navigate those moments. To walk alongside someone as they find their courage, rebuild their confidence, or finally feel heard. The organizational work matters, but it's the human moments that stay with me.

So, if you’re considering this work, or already doing it, know that it is both rewarding and costly. To repeat: The weight you’ll feel isn’t weakness. It’s the natural cost of caring about places you cannot stay.

❓Are you an interim leader? What do you do to make the work sustainable?

📖Looking for your next read?

You’ve probably heard the standard advice: build a strong partnership with your CEO, come prepared, run efficient meetings, manage committee work, make time for the role, and handle conflict when it arises.

All true, all important. But becoming an exceptional board chair requires going deeper. I’ve served as chair of four boards and worked with several dozen more. Here’s what I wish someone had told me about how to grow into being great.

🎯1. Learn how to actually facilitate… and I mean really facilitate

Most board chairs think running a meeting means working through an agenda. Real facilitation is a skill that requires training and practice.

• Get trained → Invest in learning facilitation techniques from professionals, not just winging it based on meetings you’ve attended. Read Sam Kaner's Facilitator's Guide to Participatory Decision-Making. Check out the wealth of free resources, including facilitation tips from Boardsource or this training from Standford Graduate School of Business. Better yet, ask a board chair in your network if you can shadow one of their meetings to see skilled facilitation in action. You could even take a course like Voltage Control’s Facilitation Certification or the Technology of Participation.

• Design for interaction → Build agendas that aren’t just informational updates but interactive sessions where board members grapple with real questions and decisions together. Use a timer to cap informational updates at 10 minutes and protect 40+ minutes for real discussion. Get rid of generic committee updates (that could have been an email). Send a one-page briefing doc on a discussion topic five days before meetings with a clear ask: "Come prepared to share one concern about X."

• Create accountability → At the end of each meeting, read back the action items and owners out loud. Send a follow-up email within 48 hours listing commitments and deadlines. At the start of the next meeting, spend two minutes reviewing what was completed. This isn't punitive… it's how you build a culture of follow-through.

• Lead by example → Model the kind of engaged, thoughtful participation you want to see. Ask questions you already know the answer to when you sense others are confused but hesitant to speak up. When someone shares an idea, pause before responding and say tell me more about that instead of jumping to your own view.

📚 2. Commit to continuous governance education

The best board chairs are forever-students of governance, and appreciate that real leadership requires ongoing learning and adaptation.

• Build your network → This month, message three board chairs on LinkedIn with something like: "I chair [org name]'s board. Would you be open to a 20-minute call to compare notes on [specific challenge like 'ED evaluation' or 'board recruitment']?" Ask your ED to introduce you to board chairs at peer organizations they know or you partner with. Subscribe here for free and join my subscribers chat and commit to posting one question per quarter! Peer learning is powerful learning.

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• Stay current → Find and follow folks writing about good governance on substack and linkedin (check out my recommendations). Subscribe to established platforms like Stanford Social Innovation Review as well as folks like like Vu Le, who are challenging sector norms. Set a monthly calendar appointment to read about governance… even 15 minutes of intentional learning compounds over time.

• Share what you learn → Pass along articles, ideas, and insights with your fellow board members rather than keeping your learning to yourself. Try adding a standing five-minute "Governance Insight" slot at the start of each board meeting where you share one article or idea that made you think. Create a shared Google Drive folder for governance resources. When you read something relevant, forward it with a one-sentence note like… This made me think about how we handle X—curious your reaction. This uplifts a culture of collective growth.

• Model growth → When you share an article or bring a new idea to the board, be explicit that I’m still learning about this too. This signals that governance isn’t static and that everyone (including the chair) should be growing in their role.

🤝 3. Do the behind-the-scenes work that makes everything else possible

The most important work of a board chair often happens outside the boardroom, in the one-on-one conversations and relationship-building that create the foundation for effective governance.

• Prep the ground → Bring people along before meetings, especially when you’re introducing new ideas or approaching sensitive topics, so nothing feels like an ambush. Before any meeting with a significant decision, schedule 15-minute calls with two or three board members to hear their initial reactions and concerns… especially folks who tend to be more quiet or are new. For sensitive topics, send a brief ‘heads up’ email to the full board 48 hours in advance. Something like: I want to flag that we'll be discussing X on Thursday. Happy to chat beforehand if you have questions or concerns. Nothing should feel like an ambush. No vote should be a surprise.

• Onboard with intention → Orient new members thoroughly with genuine conversation about culture, expectations, and how they can contribute, not just a binder and a handshake. For every new board member, there are 3 one-on-one conversations they should have in their first 3 months: one with you, one with the ED, and one with a tenured board member who can share unwritten norms. Create a ‘First 90 Days’ checklist that includes attending a program site visit or volunteering, social activities, and other ‘get to know the org’ type things. At day 60, ask them directly: ‘what is still unclear about how we work together?’. Constantly be looking for ways to improve this process, as its the cornerstone of great governing teams.

• Socialize ideas early and personally → Before bringing a complex proposal to the full board… float it one-on-one with key members. A quick call or coffee gives people time to process, ask questions privately, and surface concerns you might not have anticipated. By the time you're in the boardroom, you'll know where the friction points are.

• Proactively Connect people → Facilitate personal connections between board members so they build relationships beyond formal meetings. Try using ‘board buddies’ and pair new members with veterans who can answer the how do things really work here questions. Host one social gathering per year with no agenda except to get to know each other better. When running break-outs in board meetings, try to pair people up who don’t usually interact. The trust and social capital you build makes it possible to navigate difficult decisions together.

A final note

The best boards I’ve seen have one thing in common: a chair who never stopped growing. That growth comes from intentional practice, continuous learning, and investing in relationships.

My challenge to you: pick one action from this list and start building today.

📌 P.S. If this was useful, share it with a fellow board member. Subscribe to get more like this, and if you can, consider a paid subscription… it’s how I keep this all free for those who need it most!

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