The Party’s Over – Knowing When and How to Make a Graceful Exit From The Executive Director Role

As I was exploring the idea of blogging, I emailed some trusted colleagues to ask (1) if I should and (2) if so, what topics I should address. After having heard me shoot my mouth off on a variety of topics, these were the people who would be honest with and who knew what might be of interest to others.

This post is the result of their input. People wanted to know how I had decided it was the right time to leave a place that I had spent the last thirteen years as the Executive Director – New York Cares. If you are not familiar with the organization, please get to know its meaningful mission and amazing team. You’ll be glad you did.

So, where to start – how to know that “The Party’s Over.” Let me work back from the day of the announcement. For that important milestone, I knew my friends, colleagues, staff, donors, and community partners would have two immediate questions: “Why are you doing this?” And “What are you going to do next?” (The answer to the second question is HERE, and that answer was clear – more or less – to me at the time).

Most leaders leave their job for one of three reasons:

  • They quit to go to another job. Not my case.

  • They get fired. My six-month lead time was a sign that was also not the case.

  • They retire. I have dreaded that word for years (starting around the ripe old age of 50 when AARP started sending me weekly membership offers). I don’t think I am ready for whatever it is people do when they retire. I owe this topic a blog post at some point.

The long and short of it was … I left … because it was time.

So, the answer to “WHY?” was hard to distill down into a sentence I could share with all those who asked. As I thought of how to structure the response to the question of: Why are you doing this? I started by thinking of the reasons why I was NOT doing it:

  • I’m not being fired, retiring, going somewhere else (see above).

  • I’m not being driven crazy by my Board. As a matter of fact, I rather enjoyed Board members, our debates, and the way we pushed each other to be better. I found this relationship to be energizing.

  • I’m not tired of fundraising. As I noted in this blog post, about 50% of my time, at a minimum, was dedicated to fundraising, just like most nonprofit leaders. I loved building partnerships, and fund-generating relationships. Building networks is one of the many reasons I loved this role.

So, I was clear on what I would respond if someone asked me, why not? As I kept thinking of the succinct and accurate answer to, why was it time?, I remembered the stories of colleagues through the years who had talked to me about stepping down from their roles. I had heard many reference leaving their jobs totally drained – “on hands and knees.” I knew that I wanted to walk out, not crawl out.

As I’ve thought about this , I believe there were two things to parse out: (1) the organization’s readiness; and (2) my readiness.

In terms of the level of readiness within the organization, since we had time for a planned transition, I wanted to (and did) see:

  • A stable and engaged Board. I was working with an experienced Board President and a highly engaged Board. The exit of a leader and the search for their successor is arguably the time that a Board is taking on its most important duty, so this was especially important to me.

  • Regular succession planning. One executive committee meeting per year was dedicated to succession planning (and had been for the last eight years or so of my tenure). This was not only about me and my role. It was about staff morale, advancement for staff, the pipeline for senior roles in the organization, and Board of Directors membership. All of this was critical information for navigating the impending period of transition.

  • A generally understood strategy. We were at a point where all stakeholders understood the direction the organization was going. It wasn’t that everything was crystal clear (and there will always be unknown elements), but the general direction was clear and the conversations we needed to have were actively taking place. What a perfect time for a Board to decide on a new leader.

As to my readiness, we all know that a good Executive Director fully inhabits their role (while, in my case, reading lots of articles about work/life balance). As a result, the line was more than a little blurry between Gary, the Executive Director and Gary, just Gary. All of the sudden I was asking myself: Could I walk the dog without texting with a Board member? Could I talk about what I was doing without a PowerPoint deck? Could I survive without saying, “Thank you for your generous support” or “That is SO interesting; I’ll think about that?” or “Thursday’s all-staff meeting will be a chance for you to give critical feedback on everything I’ve said and done over the last month?” Coach, spouse, friends, and trusted colleagues helped me loosen my grip on that identity.

I also needed to grapple with ideas that I knew were irrational but kept popping up:

  • I need to achieve (fill in the blank) before I leave. I needed to reframe this for myself as “I need to set this organization for the next person to succeed.” And I needed to feel good about whatever I had made happen up to that point.

  • There is a perfect time to leave. That moment never comes. Waiting for the time when everything was running exactly the way I wanted was a fool’s errand (especially in the midst of a pandemic).

  • The organization can’t run without me right now. Well, of course it could. I was just one person within a large group of capable people and an even bigger supportive network. It would all get figured out, and if it didn’t, that was a statement on how I had guided us during the past thirteen years.

I went into the decision imagining that there would be some balance between its being right for me and right for the organization. In hindsight, I see that it was up to me to create that moment – to decide “The Party’s Over.”

Maybe most importantly, I want to share how I made the decision, and how I found the right time. Here are some of the tactics that worked for me that you may want consider if you are at a similar crossroads:

  • Get outside help. I preferred an executive coach, but you can also turn to your family, therapist, friends, or colleagues. You will likely consider many options, as did I. Having someone to help me throughout the process of examination (without falling into analysis paralysis), remind me of what’s important to me, and cheer me on as I gained clarity was invaluable.

  • Revisit your purpose. Through the coaching process, I was reminded that purpose evolves, sometimes with age, sometimes with experience, sometimes just because it does. I needed to acknowledge that my purpose (being of service) had not changed, and that my job was just one way to be of service among many (paid and unpaid).

  • Decide what is next. Even if you decide to take time to unwind and replenish (a thing I did a lousy job of – something I will share about in a future blog), have an intentional plan and timeline for charting your new course. I do suggest staying in touch with a coach during this time so as ideas begin to bubble up, you can balance how you go about exploring them.

  • Pick an end date. Putting an end date on your tenure makes it real for you and everyone else. You can be flexible and provide a little support if the organization needs you for a bit longer, but the understanding that you are finished and providing some additional support is a good, shared understanding for you, your Board, and your team.

These are some of the ways I decided “The Party’s Over” and to start the next chapter of my professional career. By the way, if you know the song I am referencing – congrats. If not, it’s from the musical “Bells Are Ringing.” You can hear great versions from Leslie Odom Jr (my current favorite), Judy Holliday (the original), Julie London, Nat King Cole, Peggy Lee…the list goes on.

If you are thinking the party might be over and want to work through the many aspects of this decision that await you, email me at or schedule a time to chat HERE.