A Nonprofit CEO's Guide to Letting Go - 5 Questions to Ask


​When I first became a CEO, I didn’t expect to miss having a boss. And, for the most part, I didn’t. I loved the leadership challenge, the ability to work in partnership with the board to set a new direction, the opportunity to lead the team, and the expanded feeling of autonomy and independence.

But I was surprised to discover that there was one way in which I missed having a direct supervisor: I missed having someone who could help me “let go” when something hadn’t gone the way I wanted it to.

It sounds like a small thing, but for many – if not most – nonprofit and foundation CEOs, it’s actually a very big thing. That’s because, as the top leader, there’s no one there to tell you that you’ve worked hard enough, done well enough, or learned enough from your mistakes or shortfalls. There’s no one there to help flag that it’s time to move on – for the sake of your work, your organization, and your own health and wellness.

No one, that is, except yourself.

But learning how to let go is something that many nonprofit CEOs haven’t been taught. That’s why “Letting Go” is the final in my series on Nonprofit CEO Survival Skills. In my experience, both as a CEO myself and as a coach and advisor to other Nonprofit CEOs, I know the damage this can cause. 

Consider for a moment the CEO who:
  • Struggles to focus on the work ahead because they are beating themselves up about something that happened in the past
  • Hesitates to celebrate large-scale team wins or organizational progress because not everything went perfectly
  • Consistently goes to the board looking for comfort or encouragement when things haven’t gone as well as hoped or planned
  • Can’t sleep or enjoy time with family or friends because they are too upset with themselves or their situation
  • Defines their leadership effectiveness – or their identity as a leader – by the mistakes they’ve made or the things that haven’t gone well
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These are real and challenging dynamics. The inability to move forward by letting go not only creates significant wear and tear on leaders as humans, it also decreases their leadership effectiveness and resilience over time.

In a workshop with nonprofit CEOs earlier this year, we talked about these dynamics and I shared a set of questions designed to help leaders find a way to let go when it’s time to do so.
Previous Posts:

Was I the Leader I Needed to Be?

As nonprofit and foundation CEOs, leaders sometimes have to make tough decisions or do things that may not be universally well-received. Because of that, external definitions of success such as “Is everybody happy with me?” or “Does everyone agree with the decision that was made?” are sometimes counterproductive. This question invites you to center on the leadership moment you’re in, and whether or not you rose to the moment, which is a more internalized – and useful – definition of “success”.

Was I True to my Values and Intentions?

Building on the first question, this helps a leader think through if their leadership actions or choices were aligned with their personal – or organizational – values. If they were, you can take comfort in the fact that you are acting in a way that is consistent with those values. If not, this is an invitation to reflect on why that is, and what it means to you.

Are there Any Ways in Which I Need to Make Amends?

After reflecting on the first two questions, a leader may decide that they did not operate in the way that they would have liked. And sometimes this means that there is a need to make amends to mend relationships and trust. If an apology or acknowledgment of harm is appropriate, that’s an important precursor to letting go.

What do I Want to Learn from this Experience?

Often, we learn the most from the situations that are the most difficult. Taking a moment to mine the experience for learning is a valuable next step. It’s important, however, not to use this as an invitation to stay mired in the past. Instead of “I should have…” or “I wish I would have…” statements, ask yourself “How do I want to incorporate these new insights and learnings into my leadership in the future?”

What Else Might I need to Do, Say, or Internalize before I Let this Go?

This is a catch-all. A metaphorical “last call” on living in regret. Ask yourself what else might be important, do that thing, take a deep breath, and then give yourself permission to let go.
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A Final Note to Nonprofit CEOs
As many leaders in the room named, this process of letting go is easy in theory but difficult in practice. And they’re right. But they also named that there was relief in knowing that their fellow CEOs were struggling with this, and a lot of value in naming that – to survive – CEOs must learn how to do this for themselves.
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And, for many of us, acknowledging that letting go is necessary and useful is an important first step.