Leaving Well: Is It the Right Time?

In June, I announced that I will be retiring from Propel at the end of 2023. For real. After the announcement was made, I heard from friends, peers, partners, and others in the nonprofit sector with so many kind words. It was wonderful, overwhelming, and nourishing. There has been curiosity, too, including some common questions that I’ve asked myself: How did I know it was the right time? Why now?

Well, on the surface, the answer is easy: I felt ready. But the reality is a little more complicated. For a long time when the question came up, I didn’t feel like it was the right time for me personally or for Propel. But once I reached the 20-year mark in my position in 2020, my gut told me it was time to get serious.

I’ve been thinking about retiring from Propel for several years. I am one of the Baby Boomer leaders who have been the subject of many articles and commentaries about the upcoming wave of retirements, and a frequent topic of conversation among peers. Propel’s board has included this topic – succession planning – as part of my annual performance review for several years. If you have read literature on executive transitions, you know the subject of succession is taboo for too many organizations and I’m grateful that our board did not fall into that trap.

As I paid close attention to leadership transitions, read the few studies that have been done, and had conversations with leaders who have retired and leaders who have followed founders and long-time leaders, I observed that there are three key lessons about what makes a leadership transition more likely to be successful:

1. First, the retiring leader must be ready to leave. To let go and really step away.
2. Second, the organization should be positioned to thrive with a new leader with preparation and transfer of knowledge and relationships. This also includes stable finances and a team with skill and capacity to make decisions.
3. And third, boards of directors need to consider how their work will change with a new leader. What are the board practices and governing style, and how will these be developed, strengthened, and put into action?

These three lessons informed my thinking about our succession planning and then my personal preparation and our planning for this transition. With my goal to “leave well,” I hope that sharing what we – myself as the transitioning leader and the organization preparing to welcome someone new – are learning might be helpful to others.

So, how did I know when it was the right time? I have a memo that I wrote to our board in November of 2020 titled “Leading towards succession planning” with some background and a simple assessment of the organization’s strengths and weaknesses and areas that would need particular attention. It addressed some areas where we were strong and some gaps that needed to be filled with hiring, staff development, or infrastructure. The memo also addressed some needed board development. That was also when I signaled to the board that this was on the horizon, and it was time to prepare.

But what I’ve learned over the last few years in conversations with people who have retired and those following long time leaders, and with our strategic services team, it seems that the biggest obstacle to success is the readiness of the departing leader to leave. All the organizational preparation, fundraising, hiring, and board member recruiting in the world doesn’t replace the deeply personal work of getting ready for a major change in your life. Succession planning and retirement questions are emotional, financial, professional, and tied up in one’s personal identity. So how did I know it was the right time? When I trusted myself that I was ready to leave.

It’s frankly easier to say, “I have a grandchild now,” or “I want to travel more” (and both of those are true.) I’m excited about this change. I’m ready to use my energy differently, to have a different pace in my life, to learn about the world differently, to stay engaged in a different way, and to be the biggest cheerleader (from some distance) of what Propel will become with a new leader.

Over the next few months, I’ll be writing more about my efforts to “leave well.”  I’ll share more about organizational planning, staff development, leadership, and board planning. I hope you’ll follow along, tell us when something resonates with you, and share your experiences along the way.

Learn more about Propel’s Leadership Transition at our President & CEO Transition Page.

Hear from Kate about this series on our YouTube channel.