The Nonprofit Leadership Paradox That’s Rarely Discussed
To the CEO Who Finally Showed Me the Way
(#3 in the Letters We Never SendLetter Series)
There is a dynamic in nonprofit leadership that is rarely discussed, though it should be…and at length.
A nonprofit’s CEO reports to the Board. Their employment, their performance review, and their future with the organization sit in the hands of the very people they are also responsible for developing, educating, and gently, diplomatically growing into the philanthropic leaders the mission needs them to be.
Think about that for a moment.
The person with the least institutional power in that relationship is also the person most responsible for shaping it. The CEO must look up at the board, the body that holds authority over their career, and find a way to say: “I need you to understand your role differently. I need you to show up in ways nobody has ever asked of you before. And I need you to trust me enough to follow my lead, even though on paper, I follow yours.”
That is not management. That is not governance. That is one of the most sophisticated acts of leadership in the nonprofit sector, and it happens quietly, without fanfare, in one-on-one conversations and carefully chosen moments, and resources handed across a table with nothing more than a gentle suggestion.
It is also, when done well, the single most powerful thing a CEO can do to build a culture of philanthropy.
Because a culture of philanthropy does not begin with donors. It does not begin with campaigns or cases for support or fundraising events. It begins with the board. Whether the board understands its role. Whether they believe in the mission visibly and vocally. Whether they see themselves as partners to the work rather than overseers of it. The CEO who understands this and has the courage and skill to cultivate it changes everything.
This letter is written from a board member who was on the receiving end of that leadership. It is addressed to the CEO who gave them something no one else ever had: clarity about what their role had always meant to be.
It is fictional. But it is not made up.
And if you are a CEO reading this, we see you. This work is harder than it looks. It matters more than most people know.
Dear [CEO],
I have been trying to find the words for this for a while now. You sat down with me one afternoon and asked me a question nobody had ever asked before: ‘What do you think your role here actually is?’ Not as a challenge. As genuine curiosity. And when I answered, you listened. Then you told me, quietly and without judgment, what I had been missing.
You told me the truth. Not harshly. Not in a way that made me defensive. But clearly enough that I could not talk myself out of it. That is harder than it sounds, especially when the person you are talking to technically signs your performance review.
I want you to know what happened after our conversation. I not only realized I hadn’t been fulfilling my role, but also finally understood everything that had come before. I served on this board for four years before that moment. Four years of showing up to meetings, voting responsibly, reviewing financials, and asking what I thought were good governance questions. Four years of genuinely believing I was doing my job well.
And I was. Just not all of it.
What I did not understand, and what nobody had ever helped me understand, was that my role did not end when the meeting ended. That the most important work happened not in the boardroom, but in every conversation I had outside of it. Every dinner. Every coffee. Every time someone asked me what I was involved in, I gave a vague, careful answer because I did not want to seem like I was “fundraising.”
I was protecting myself from a role I had never been properly invited into. Here is what I need to confess to you, and I do not say this lightly:
I watched our development director work herself to exhaustion. I saw the weight she carried. I attended enough events to notice when she looked tired in a way that had nothing to do with the hour. And I told myself she was just passionate. That this was what fundraising looked like and that it was not my place to intervene or ask.
I did not understand that my presence, my voice, my willingness to simply say to a donor, “I serve on this board because I believe in this mission with everything I have,” would have lightened her load in ways I could not measure.
I did not understand that I was not a bystander to her work. I was a partner she never got to have.
That realization did not feel good. It still does not, entirely. But it is the most useful thing I have learned in four years of board service, and I learned it because you trusted me enough to hand me something that told me the truth.
What has changed since then is hard to fully describe, but I will try.
Something shifted in me after that conversation. Where I once carefully steered around the mission, I now speak directly to it. I say the name of this organization. I tell people why I serve. I have made four introductions in the past three months that I would never have made before, not because I was asked to, but because it finally occurred to me that my network belongs to this mission as much as it belongs to me.
I attended the last two events not as an obligation but as an opportunity. I stayed longer. I talked to donors I had never spoken to before. I stopped waiting for someone to tell me what to do and started asking what was needed. I talked to my friends and colleagues about my personal connection to the organization and, when appropriate, how I was personally supporting it financially.
And the most unexpected thing happened. It felt natural. Not like fundraising. Not like selling. Like leading. Like the version of board service I had always wanted to offer but never knew how to find.
Here is what I want you to understand about what you gave me:
You did not add to my responsibilities. You clarified them. You took something that had always felt vague and uncomfortable and made it concrete and achievable. You showed me that I did not have to become a different person to do this work well. I just had to show up as myself, more deliberately and more often.
I only wish it had not taken four years.
That is the part that stays with me. Not with regret exactly, but with a kind of quiet accountability. There were fundraisers in those four years who needed me to be the partner I am now becoming. There were donors who might have said yes sooner. There were relationships that might have deepened faster. I cannot go back and give those years a different shape.
But I can be different now. And I can tell other board members what I wish someone had told me on my first day:
This work is not about asking for money. It is about showing up with belief. It is about letting the people around you see that you trust this mission enough to carry it into your life. It is about understanding that your presence is not a courtesy. It is a contribution.
None of that is hard. What is hard is not knowing it.
Thank you for helping me know it.
I am still learning. But for the first time in four years of board service, I feel like I understand what I am learning toward.
With genuine gratitude and a commitment to show up differently,
A Board Member Who Finally Showed Up
What’s Coming Next in This Series
The series continues. Each letter holds a mirror up to a moment that nonprofit leaders rarely speak aloud.
If this letter made you feel something, share it with a Board member who needs it. Forward it to a CEO who is wondering whether it is worth the effort to invest in their Board. And if you are a Board member reading this, consider this your invitation to find out what you might have been missing.
If you missed the earlier letters in this series, you can find them here: When Good Fundraisers Leave: A Letter Series for Nonprofit Leadership and When Good Fundraisers Leave: To the Board Member Who Meant Well.
If you are a CEO who recognizes yourself in this letter or another nonprofit leader struggle with difficult Board-level conversations, you already know that direct conversations about board engagement can be complicated by the very power dynamic this article describes. Getting to the Yes: A Board Member’s Guide to Philanthropic Leadership gives you another way in. A resource you can share without pressure, that opens the door to exactly the kind of shift this board member describes.
Available from the Getting To The Yes bookstore or on Amazon.