The Many Ways Your Org Chart Is Breaking Your Organization
How good intentions create unscalable structures
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.
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).
“Give your best individual contributors somewhere to go besides management” This! Not every good worker wants or is cut out to be a manager. And management is a huge responsibility that takes away half of your time at least, so turning a good worker into a manager can actually be a very bad decision
Since you asked for the missing one: structure standing in for a constraint that isn't structural. Most of what's on your list is an adaptation rather than an error — the Frankenstein role absorbs work no funder will pay for on its own line, title inflation pays people in the only currency that isn't restricted. That's why they recur across very different organisations, and why unwinding them hurts as much as you describe: you're removing something that was holding weight. Worth asking what a role was compensating for before you cut it, or it reappears under a new title within the year.