What Keeps Me Up at Night as a Leader
Leadership Series | Its not budgets or board meetings...
After a decade-plus serving in top leadership, there is only one thing that really keeps me up at night. It’s not the budget deficit. Or the looming board meeting. Or figuring out our next strategic move.
It’s when things aren’t right with people.
When I sense someone is struggling and I haven’t checked in. When a hard conversation is coming and I’m dreading it. When I replay a meeting and wonder if I made someone feel unheard. When something didn’t land right and I can’t shake it.
That’s what I think about at 2 a.m.
I’ve had my fair share of not-so-great bosses, dysfunctional boards, and toxic coworkers. I’ve seen bad behavior ruin teams and really hurt people (sometimes irreparably) while leaders just stood by. Or worse, took part. Some didn’t care. Some didn’t know how to support their people and never bothered to learn. Others never had good leadership modeled for them, so they just replicated the cycle of hurt they knew. Things that could have been avoided with a little more compassion and competence and care.
If you’re like me… hoping to be the kind of leader worth following, one who can hold both humanity and accountability… this is for you. Below are some of the practices that I follow, but first, we need to talk about fundamental assumptions. Because that’s where real change starts.
Fundamental Assumptions
Fundamental Assumptions are deeply held beliefs about how the world and people work and influence how you show up.
For example, if you think people are not trustworthy, you’ll be looking for ways to control them. If you believe people are lazy, you’ll micromanage their time. If you assume people don’t care about quality, you’ll build systems around catching their mistakes instead of empowering their growth.
I’ve worked years to undo all the toxic mindsets around people that emerge from capitalism, and have aligned with these transformative assumptions.
People are creative, thoughtful, trustworthy adults capable of making important decisions.
People are comfortable being held accountable for their decisions if given the capacity and autonomy to take action.
People are fallible; mistakes and failure are a normal part of life, and also necessary for innovation.
People are unique, and both their lived and professional experiences have value.
People want to use their talents and skills to make a positive contribution to the organization, and the world.
What I do to do right by people
With those beliefs as my foundation, here are some of the things I do to try and show up at my best for the people I lead. It’s a living list I’m constantly fixing and adding to.
1️⃣Trust people out the gate.
I don’t care that some might think this is naive I think that the idea that you have to ‘earn my respect’ is outdated and toxic. You have my respect and my trust on day one, and it’s yours to lose. I’d much rather start from a place of belief in people than from suspicion. It’s how I would want to be treated and sets the right tone from the start.2️⃣Don’t dodge the hard conversations.
Radical candor means challenging directly: being willing to shine light on what’s not working. But here’s where most people mess up: you also have to care personally. It’s not just about delivering the feedback. It’s about demonstrating care by actually helping them get better. When there’s an area of growth, we keep talking about it. I try to find resources or mentors. I stay invested in their growth. Balanced with real gratitude for what people bring every day, my highest goal is simple: make sure people are actually happy where they are, and if they’re not, help them move on.3️⃣Fiercely protect and respect work-life balance. Theirs and mine.
That means setting clear expectations about on-site vs remote work and working hours, and then honoring that agreement until it’s explicitly altered. No texts on weekends or late at night. No praising people for working themselves into the ground. I audit time off records and making sure people are actually taking time off. I’ve said it before, rest is a leadership responsibility and boundaries necessary for longevity in our field.4️⃣Advocate for people behind closed doors.
I fight for their promotions, raises, resources, and recognition in rooms they’re not in… and let them know I’m doing it.5️⃣Make time for the conversation, not just the transaction.
I get to know the people I work with, up and down the organization, beyond their role or what they deliver. I ask about their lives, their interests, what matters to them. And I try to share the bits about myself that make me more human too. When someone needs to talk through a challenge, they get my full attention rather than me rushing to solutions or trying to resolve it in a Slack message. Work is relational, and relationships need more than status updates to thrive.
6️⃣Admit when you’re wrong & Create space for failure.
I try to model vulnerability and accountability by owning my mistakes openly, apologizing when needed, and showing that leadership doesn’t mean being infallible. If mistakes are necessary for innovation, then we can’t punish people for taking smart risks that don’t pan out. When things go wrong, I focus on what we learned, not who to blame. Plus, more often I have found that it is systems or supports that failed, not people themselves.7️⃣Give people authority and autonomy, especially if they’re the ones accountable.
You can't hold someone accountable if they don't have the authority to make decisions or the autonomy to execute. So I trust them to own their work, make calls in their domain, and I support those decisions (even when I might have done it differently) as long as the results are there. This doesn't mean they operate in isolation; collaboration is real. But ownership has to be meaningful or burnout and frustration will be right around the corner.8️⃣Default to transparency.
If people are trustworthy adults, they deserve context for decisions, even difficult ones. I share what I can about the "why" behind changes, constraints, and trade-offs. Not making promises I can’t keep
And when the hard calls come…
And then there are the moments I dread most: when I have to make a decision I know will hurt someone. Letting someone go. Restructuring a team. Delivering news that will change someone’s life.
It would be easier to distance myself, hide behind process, defer to HR, retreat into business-speak. But that’s exactly when humanity matters most. People remember how you treated them in their hardest moments far longer than they remember the rationale. So I try to show up fully: deliver the message myself, with honesty and compassion, and do whatever I can to help them land somewhere good.
A final thought
I don’t have this all figured out.
I’m still reflecting, still learning, still catching myself when I fall short. But I keep working at it…. because I want to be worthy of the respect and trust people place in me. I want to set a model worth copying. And more than anything, I want to break the cycle of workplace harm that I myself have been subjected to.
So yes, that’s what keeps me up. Not spreadsheets. People. Always people.
