In recent years, I’ve been leading workshops and webinars on leadership transition and succession planning. It’s a significant aspect of my business.

If you believe the maxim, “An expert is anyone who knows 5% more than most people,” then perhaps I qualify. I’ve read a little (and written a little) on this subject. I’ve talked with lots of peers. I’ve coached several clients. But mostly I’ve been stumbling my way toward wisdom, just like everybody else. 

Over the years, I’ve also designed and implemented three succession plans in my personal and professional lives. Each one yielded different lessons.

Round one: Leaving my day job and starting a business

Thirty years ago this month (!), I went to my very last boss and said, “I’m giving you two years’ notice.” 

I shared this story in a previous post, “How I Started My Consulting Business.” Here’s the simplified version. 

During year one, I dialed back my full-time fundraiser job to four days per week and began consulting during the other three days. In the second year, I shifted to half-time and we hired my successor, whom I supported and mentored while continuing to build my business.

By the start of year three, when I left the organization, my employer had a fully trained development director. By then, I had created a mature-ish consulting practice that could support me financially.

A shout-out to my very last boss for embracing this unusual transition plan. It worked well for everyone. 

Lesson one: Be intentional and transparent. Yes, I understand that not every employer will accommodate your long-term goal to take a new job, start a business, etc. However, if you’re a leader in your organization – for example, the executive director with a decade on the job – give your colleagues lots of lead time so you can figure out the transition together.

To begin this process, clarify your personal goals and timeline. What do you want? When do you want it? The clearer you are, the smoother the process.

Round two: Winding down my consulting business

As I shared in “How to Semi-Retire,” I’m gradually stepping back from my business. I say no to long-term gigs – strategic plans, mergers, coaching contracts – to focus on one-off projects, like webinars, workshops, and retreats. I might lead a training series – for example, three sequential webinars – but I don’t want to spend a year carrying a client around in my head.

I am also shedding some formal responsibilities. For example, my partners and friends Bob Osborne and Laurel McCombs of The Osborne Group are gradually taking over responsibility for Train Your Board, for which I am deeply grateful.

Like all experiments, this one has been imperfect. Some of the good parts: I wake up when I feel like it. I spend lots of time outdoors, walking in the woods and working in the garden. We cook really delicious meals.

On the other hand, you can still find me at my desk at 10:00 pm, answering emails. This workaholic mindset imbued by 1) my parents and 2) capitalism is deeply entrenched. It will take time to unwind those behaviors.

Lesson two: Whatever your transition plan, give yourself grace to do it badly. As noted earlier, treat this as an experiment. Try something, see what you learn, adjust accordingly. If you’re navigating a transition with colleagues, keep talking and adapting as you go.

Round three: Escaping the board presidency

I chair the board of a local grassroots group with one employee and an annual budget of $100,000. At the start of my second term, I gave one year’s notice, explaining that I planned to step down in July 2023.

For a variety of reasons, I am still the president. One reason: my board colleagues see how much time I invest in this volunteer position, and they can’t or won’t match my time commitment. Consequently, no one wants to follow me – and I don’t blame them. 

By setting an unrealistic example, I’ve made the position untenable. In response, we are developing an intriguing alternative. 

We’ve divided the president’s job into five or six categories: managing the board and facilitating board meetings, internal communications with our members, external communications, overseeing our sole staff member, etc. As a next step, different board members will (I hope!) claim each of these tasks. In this way, we are moving toward a distributed leadership model. 

Lesson three: Make it easier for others to step up. Nobody wants to follow a perfectionist, martyr, or drudge. 

Adapting a phrase from Gestalt psychology, sometimes you need to sub-optimize. By not always doing your best work, you create space for others to step up and do their best work.