I want to begin this episode by saying some things out loud. The things so many CEOs and Executive Directors are thinking but rarely admit.
This is the first of a two-part series, because this conversation deserves space. It deserves nuance. And most of all, it deserves honesty.
My goal is simple.
I want you to feel seen.
I want you to feel heard.
As a former founder and Executive Director for a decade, I understand this role in my bones.
I know what it feels like to carry responsibility quietly.
I know what it feels like to second-guess every word coming out of your mouth – while still showing up strong for everyone else.
Last year, I conducted a research project. I personally spoke with nonprofit leaders across multiple sectors — different missions, different budgets, different stages of growth.
I asked each of them the same set of questions about their greatest challenges and their deepest desires in the CEO or ED role.
The purpose was to serve them better. What emerged was not a collection of isolated frustrations. It was a pattern.
And in these next two episodes, I’m going to share that data with you — not as theory, not as advice — but as reflection of shared identity.
Because the consistency of what I heard was deeply revealing. And when you hear it, I believe you will feel less alone.
Humanizing the Journey of the Modern Nonprofit Leader
Together, we’re going to humanize what it actually feels like to lead in this sector right now.
Here is the exact language nonprofit leaders shared with me:
“I’m not always totally aligned with my board. They sometimes hinder, not help you. It takes time to build the board we want.”
“The staff feel whiplashed in a turnaround phase. They are tired of change.”
“I don’t want to admit that I don’t know things.”
“Right now, we’ve been thrown into a lot of uncertainty.”
Those are direct statements. Not dramatic or exaggerated. Just honest, and I’m so grateful for the courage these participants had to share with me.
So what I want you to hear is this: These are not isolated experiences. They are sector-wide patterns.
If you have felt any of that — the fatigue, the misalignment, the self-doubt, the quiet pressure to have answers — you are not alone in that experience.
You are operating inside a system that has been under strain for years.
Let’s dive deeper into the identity-level challenges CEOs & EDs are having right now.
When leaders said, “People are tired of change,” what they were naming was the quiet exhaustion that comes from asking your team to pivot again… and again… and again.
Our social impact sector has not had the luxury of steady conditions.
We do not operate in stable markets with predictable margins. We operate in living systems.
Funding shifts with policy.
Community needs evolve — sometimes overnight.
Staff transitions happen faster than succession plans can keep up.
Boards cycle in and out.
Strategic plans that felt solid eighteen months ago suddenly require revision.
Change is not an interruption in our sector.
It is the baseline.
And that means one of the most important reframes for CEOs and Executive Directors is this:
If evolution will always be the norm, how do we lead in a way that protects what matters most — while intentionally saying no to what does not?
Because without clarity, everything feels urgent.
And when everything feels urgent, leaders carry more than they should.
Working with an “Empty Bench”
Then comes the next reality.
“A key person leaves and then another person is covering.”
That sentence sounds simple, but it carries so much weight.
When someone leaves, you do not just lose labor.
You lose institutional knowledge. You lose relational continuity with donors, partners, or clients.
You lose the rhythm of how things were done & even the informal knowledge that never made it into a handbook.
And if the person who leaves is a fundraising leader — especially a high-performing one — the financial impact can be immediate and destabilizing.
Revenue drops. Relationships wobble. Forecasting becomes uncertain.
And in many organizations, there is no bench waiting to step in. So someone absorbs it.
Often a program director stretches beyond capacity.
Sometimes a development associate steps into leadership without adequate support. And sometimes — often — you absorb it.
I recently worked with a client who, for a few months, was wearing three hats at once.
Executive Director. Development Director. Program Director.
Three separate leadership functions all layered onto one human being.
When she told me that she had finally hired both a new Development Director and a new Program Director, she laughed and said, “Now I only have one job.”
Only one job. We both smiled at that.
Because in this sector, “only one job” can still mean 50+ hours a week, board management, fundraising oversight, staff development, community relationships, and strategic planning.
No one is sipping pina coladas on a beach because they finally reduced from three executive roles to one.
But that moment — when she moved from absorbing everything to redistributing responsibility — was pivotal.
Board Alignment and the Art of Managing Up
Then there’s board alignment.
“I’m not always totally aligned with my board. They sometimes hinder, not help you. It takes time to build the board we want.”
For most CEOs and Executive Directors I know, effectively engaging their Board is one of the most complex parts of the job.
I’m thinking of a client of mine who inherited what she described as a “friends and family” board.
People who loved the mission. People who believed in her. But people who had never really been asked to function as a governance and fundraising board.
As the organization grew, the expectations grew too. The budget expanded. The staffing model became more layered. The strategy required sharper oversight.
But the board structure stayed the same.
And so she found herself in this awkward, in-between place — actively trying to transition toward a governance and fundraising board while still honoring the people who had helped build the organization in the first place.
That transition takes time and patience. It takes emotional intelligence. It takes a strategic recruitment plan.
Many Boards genuinely do not understand their fiscal responsibilities. They do not understand oversight versus operations. They do not understand what healthy governance looks like at scale.
This same client told me something that stopped her mid-sentence when she said it.
“I’ve never gotten a performance evaluation. Not once. In years.”
And what she said next was even more revealing.
“I actually crave feedback. I want to grow. But no one is giving it.”
That is not a disengaged leader. That is a growth-oriented leader who wants partnership, not just approval.
And when you do not have structured evaluation, when you do not have clear governance guardrails, when you do not have alignment around roles, it creates ambiguity.
Ambiguity at the board level trickles down into the organization. It affects confidence. It affects decision-making speed. It affects how much authority you feel internally.
If this resonates for you, you already know what “managing up” feels like.
It means offering training on fiscal responsibilities rather than waiting for it to be requested. It means introducing governance best practices gently and strategically.
Succession as an Act of Stewardship
It means bringing succession planning to the table, even when it makes everyone slightly uncomfortable.
And let’s talk about succession planning for a moment. So many boards are behind on this, not because they are negligent, but because they are not educated about it.
I’ve been asked to give a lot of presentations on succession planning to boards and nonprofit associations.
What I do first is clarify that succession planning is not about someone leaving tomorrow.
It is about continuity. It is about stewardship. It is about protecting the mission beyond any single leader.
When succession is unclear, anxiety rises even if no one says it.
You are actively building the board you want: the board that thinks strategically, supports decisively, understands nuance, and operates at the level your organization now requires.
Another unspoken experience as a CEO or ED is that “The staff feel whiplashed in a turnaround phase.”
This one is especially heavy. Because you care about your team. You want stability for them. You want clarity for them.
But when strategy shifts, when funding changes, when leadership recalibrates direction — they feel it.
And you feel responsible even when the change was necessary.
The Power of “I Don’t Know”
Here is a theme that came up repeatedly.
“I don’t want to admit that I don’t know things.”
This one is quiet but powerful.
Executive leadership carries an unspoken expectation of certainty. You are the one others look to. You are the one expected to steady the room.
Admitting uncertainty can feel risky.
Especially when you are the Executive Director. Especially when people look to you for steadiness.
And yet, imposter syndrome is real.
That quiet voice that says:
“You should know this by now.”
“You’re the leader…you’re supposed to have the answers.”
But here is what decades of research and lived experience continue to show us:
The antidote to the fear of admitting you don’t know something is not pretending.
It is transparency.
When you name uncertainty appropriately — not chaotically, not without direction — but thoughtfully — psychological safety increases.
And when psychological safety increases, performance increases.
Innovation increases.
Inclusion deepens.
People contribute more fully when they do not feel they are protecting themselves.
One of my previous podcast guests, Kelly Dunkin, said something that has stayed with me:
“The team is always smarter than the individual.”
That does not diminish your authority.
It strengthens it.
Because leadership is not about having every answer.
It is about creating the conditions where the best answers can surface.
And that requires courage.
The courage to say, “I don’t have the full picture yet. Let’s think this through together.”
The courage to invite input without abdicating responsibility.
The truth is no one has all the answers. No one. Not in this economy. Not in this moment of change.
But when you are brave enough to say that out loud in a grounded way, something shifts.
Morale grows and respect deepens. And your team begins to experience your leadership not as performance but as partnership.
And that is a far stronger foundation for moving your organization forward in a way that honors your humanity.
If any of this resonated with you, schedule a Burnout to Boundaries session with me. All of these areas are fixable with the right support. Go to CultureCARES.com and click on Burnout to Boundaries.
Always remember you are meant for great things, and you don’t have to burn out to prove it.