Founders who step down often go through a process that parallels the five stages of grief. (Illustration by iStock/Vectorios2016)
I came up with the idea for Teach Plus, a nonprofit to build the leadership capacity of teachers in the United States, while rocking my daughters to sleep at night. After the organization launched in 2007, I tracked my daughters’ growth against the big logo wall in our Boston headquarters, the way other people do against the doorframe of their kids’ bedroom. It won’t be long now before I send them off to college, giving my babies over to the guidance of other adults, hoping I’ve equipped them what they need to thrive. As I listen to other parents facing the same transition, I can hear them talking through the five stages of grief—denial, anger, bargaining, depression, and acceptance—and I realize I’ve already been through the process with a different baby.
Every social entrepreneur thinks of their venture as “their baby.” Giving birth to it, keeping it alive, shepherding it through the rocky teen years—these are whole body-and-mind experiences that weave themselves into our DNA. To me, the decision to leave Teach Plus after a decade was equally holistic. I started to feel my work life, my personal life, and the larger social context were pushing me in the same direction, toward a new chapter. Still, it took three years to move from gut instinct to departure. Most of that time passed pre-announcement, getting square in my own head about how to lead through my final act in a way that set up the organization and my treasured colleagues for long-term success. While few in the social entrepreneurship community talk about these stages, I believe the “grieving and leaving” process is universal among founders.
Stage 1: Pre-Announcement (Denial)
I can remember the exact moment when the idea that I would leave Teach Plus slipped into my mind. Even today, it doesn’t feel like it came from me. I was in church in early fall 2014. It was suddenly in my thoughts. I didn’t want it there. It felt like a betrayal. It came with a strong feeling of denial that, for me, lasted almost two years. I still loved my work. I still knew there were things I needed to accomplish. The people who built the organization with me were like family.
For almost a year after that moment, leaving barely occurred to me. But then came a subsequent year of mental wrestling matches: I could never actually leave! Could I leave? No, I could never leave. Meanwhile, the organization and the context of our work continued to evolve, and I knew I needed to change in big ways I wasn’t sure I was capable of. Maybe there was someone better for the role?
During this time, I didn’t breathe a word to anyone except my husband and my therapist—and I over-talked to them. Founder departures make for good gossip. I didn’t want news to leak and accelerate my timeline. I didn’t want my leadership team, funders, or anyone else with a stake in the decision to influence me. I needed the time and space to back out if I chose.
Finally, one day I walked into the office and knew it was time. I hadn’t planned to announce it. It was like the early days when you work forever to get that first grant, and when you do, everything changes in an instant. I’d been mentally preparing for two years, and suddenly I was announcing my decision to my leadership partner and a new era was in motion.
In some ways during this stage, I was un-learning my entrepreneur’s bias toward action and speed. But I believe the extended period of processing the change, followed by a clear, quick decision served the organization well in the long run.
Stage 2: The Announcement (Anger)
A good founder transition announcement is a tightly orchestrated exercise in crisis-control communications. Everyone needs to be “the first to know”—your team, your funders, and prospective replacements. The board and I took a week to prepare “my letter” and organize contact information for everyone in our orbit. The letter was intended to share my news in a way that highlighted the logic of the timing and the health of the organization. In my draft, I wrote that I thought the organization would benefit from the perspective of a leader of color. The board reminded me that, while they didn’t disagree, I wouldn’t be the one to call the shots on the next leader. Once the letter was complete, we blitzed our universe. Within 48 hours, all letters went out and I made several hundred back-to-back phone calls.
The harder part happened after that. I’d given away 100 percent of my power in a single act, and it took losing it to see what I’d had. In a matter of days, my inner circle was not the inner circle at Teach Plus. The people I would have chosen to become politically powerful didn’t, the emerging queen bee of the transition bypassed me when she talked to the board, and the board took on a greater role in making high-level decisions I once owned. These were the people who agreed to take charge of my baby and get it safely to the other side. I was immensely grateful to them, but there was some anger and hurt along the way.
So, was I just expected to report to work each day at the company I founded and not be in charge?! The simple answer was yes, but knowing that intellectually and knowing how it feels day-in and day-out in practice are very different, particularly because you can’t know how long the transition will take.
Stage 3: The Search (Bargaining)
Exactly a year passed between the day I announced I was leaving and the day my successor began, and despite the changing dynamics, I stayed in my role the entire time, which allowed me to codify the history and lessons that so far only existed in my head into a book. It also allowed me to raise some additional money, and make a few program and staff adjustments to ease the transition for my successor. But while time is a necessary component of a healthy transition, we arguably had a little more than we needed.
As an organization active in politics, Teach Plus had always courted controversy. Yet, riding the roller coaster of the search for a successor beat it all. During this stage, I did a lot of bargaining. First, I reached out to a few prospective leaders and tried to pitch them on how great the job I was leaving was. (Awkward!) Then there were hot-and-heavy negotiations around two different potential mergers, which would have led the organization in very different directions. (Neither ended up working financially.) Finally, I had to help sell my eventual successor on the job, with the best combination of truth and sweet talk I could muster.
I also spent a lot of time bargaining with myself. This is the time when you begin to consider your legacy. Previous leadership training had urged participants to ask: Does your legacy matter? At the time, I said no, legacy is hubris. But in the purgatory of this phase, I learned that a legacy mattered to me, arrogant or not. What if the organization couldn’t find the right leader? Would it shut down? Would I stay? I debated these questions for months.
Stage 4: The Transition (Depression)
The last month before the transition team announced my successor was arguably the hardest. Staff were begging for a glimmer of hope and losing faith that my replacement would ever materialize. At one point, I was 99 percent certain who it would be but couldn’t breathe a word. During a staff planning retreat originally scheduled to align with the arrival of the new leader, I had to stand up and lead the staff I had resigned from 11 months earlier. Every interaction, from big to small, was cringeworthy. Strategy talk ignored me and was peppered with, “Well, we can’t settle this without input from the new leader.” Small talk was worse, knowing the only real topic people wanted to chat about was when I’d be clearing out my office. We were in a collective state of depression.
Dawn finally broke, however, and the team was overjoyed to hear who their new leader would be. I had very minimal overlap with him, because my co-leader of 10 years had agreed to stay on for a month. But I was there for his first day in the office, and because my office was now his, I waited for our new leader on the couch in the lobby. I sat with a brand-new junior staffer who was waiting to be onboarded. He was the future of Teach Plus, and I wasn’t. This was a moment for all of the emotions.
I went straight from my last day at Teach Plus to teach at Harvard that evening. I had a place to land, but the role wasn’t full-time. It was the next day, when I had no place to go, that a new, personal depression hit. I hated not being “full-time” on a passion project. I hated the loss of identity that followed spending a quarter of my life in one role. I hated that I could just sit on my couch and do nothing at 11 am. I knew in my gut that the time was right and did not doubt my decision, but I still needed to process a loss.
Stage 5: The Future (Acceptance)
Ruth Bader Ginsberg once said that the key to a successful, long-term marriage is to “Be a little deaf.” That may be the best advice for departing founders as well. I have a ton of empathy for someone whose job is to bring a fresh set of eyes to another person’s organizational vision—a vision that, after a decade of operation, can easily calcify into established practices, team-wide blind spots, and sacred cows. I knew I didn’t have the vision for the next stage. I also knew my continued participation (asking for a board seat, for example, or keeping tight relationships with team members who stayed) might inhibit my successor from creating his own. Giving my successor the freedom to lead was the best I could offer.
In my first year away from the organization, the first question people in my professional network asked me was, “How do you think Teach Plus is doing?” I told them I didn’t know, and that was the truth. People offered me unsolicited tidbits of information, both positive and negative, about the organization all the time. But I knew that every day and month I had when I was CEO generated a long tally sheet of wins and losses, many of which no one knew about but me. I felt it was my responsibility to not read too much into single stories, do behind-the-scenes public relations for the organization, or engage in gossip.
Some intentional distance and a healthy dose of “deafness” helped me accept who the organization is without me and who I was without the organization.
Final Thought
Teach Plus thrives today in a way that it probably wouldn’t have under my leadership. When my intuition told me it was time to leave, I had no idea how psychologically involved the process would be. I see the faces of Teach Plus’s network of teachers every day on social media, and it reminds me how special the organization is. I love what I built and that I gave it away. And what I know now is this: I mourned it, because it matters.
Support SSIR’s coverage of cross-sector solutions to global challenges.
Help us further the reach of innovative ideas. Donate today.
Read more stories by Celine Coggins.