Planning your leadership transition

I am reminded of the Paul Simon song “Fifty Ways to Leave Your Lover” when I think of the many conversations I’ve had with chief executives who have recently retired or are contemplating retirement or later-in-life transitions. 

The retirement/transition issue is ubiquitous these days as the baby boomers exit the field and new leaders emerge to take over the world we thought was ours to protect forever. Some in our field thought the new generation could never replace the one leaving. I feel the opposite. The world demands new talents, new sources of inspiration, new visions, new vocabularies. Our attributes got us this far, now it’s time for others to succeed us and own their own accomplishments and mistakes. 

After countless discussions receiving and dispensing advice with friends and peers over many years, I thought I would summarize a few of the most interesting features of leadership transition in the nonprofit sector. 

I will start with the premise that there are many ways to leave, with no single right way or correct collection of subjects or issues to be addressed. My focus will be only on voluntary transitions – avoided will be the more dramatic fate felt by many of our friends who have been, rightly or wrongly, gently or not-so-gently, terminated or “disappeared” from their positions of responsibility. Also, my understanding of this issue comes primarily from people who have been with organizations for long periods of time, not necessarily as founders but certainly as leaders who have been strongly identified with one or a few organizations and where transition is a challenging subject and more impactful than in short-tenured contexts.  

So, consider the following suggestions as you prepare to “drop off the key, Lee and get yourself free:” 

* Be planful well in advance of any contemplated transition. Having a plan in your mind, even if a bit fuzzy or incremental, is critical. This is step one –  before you think about other issues which then get subsumed within the plan. The plan must be in your head, and your heart, shared with others or kept secret, firm and strong enough to guide you through what will inevitably happen and flexible enough to adapt to unknown factors.

* Document as much as you can in writing. Make it available to targeted audiences before you leave and to others who may need it after you leave. This is a nonprofit management best practice that is often overlooked. What needs to be documented probably differs considerably with each leader and organization, but it is simply not possible to convey all the intricacies of your tenure verbally during even the most organized of transitions. The potential readers include your successor, staff, the board, and even possibly some outside stakeholders.

* Prepare your staff and board for the transition when the time is right, on a well scheduled and thought out need-to-know basis. Other folks will need to begin preparing as well and for their own reasons. Preparation can be substantive – such as delegating authority or sharing information, or psychological – for example, you may hint about changing personal priorities.

* Have those substantive conversations with senior staff and the board which you may have been avoiding. Most leaders know that there are certain things staff and board members have either never thought to ask about or have tried to avoid asking. Share with them. Transition time means you no longer have any excuses.  

* If you are using a search firm, make sure they understand what the real job is about. Search firms generally have set in their minds the standard definitions for what top leaders are about and the characteristics or qualifications which are needed, but these packaged job descriptions are frequently obvious and not instructive –  as well as being too naïve and simplistic. Write your own.

* To the extent possible, take care of as many leftover projects as you can. Allow that the “extent” may be minimal, despite the fact  that the temptation to leave as clean a slate as possible is unavoidable. Target items suggested by remaining senior management. 

* Do not start new longer-term projects that will transcend the timeline you have established for your transition. New projects may be tempting and the pursuit of them may be in your blood, but acting on them now would not be wise. Decide early in your planning stages which projects you’ll likely have to bequeath to others. 

* Think about your future, even if only loosely. The most consistent advice I received from others was to make no big plans or big decisions ahead of time. There should be no rush. Instead, prepare for uncertainty, prepare for the unknown, and prepare for choices never envisioned. 

* Figure out the money thing ahead of time. Many have told me they misunderstood the financial ramifications of the separation/transition they experienced or they incorrectly anticipated how much money they would need to support their desired lifestyle. Budgeting your own life can be much harder than managing organizational finances.

* Don’t think you will become a completely different person during or after transition. Transition is not the same as being reborn with a new persona. You are still your same old self. Deciding to leave does not mean you will suddenly become more wise or insightful or effective.

* Understand that the place you are leaving is no longer yours. Even if they miss you, people will start thinking about themselves and their futures the moment they know transition is about to occur. Some will stay, others will go. Some will be happy, others sad. Whatever the world thinks you did right or wrong will be the final word, at least for a while. Everything is a matter of perception, myths, facts, reputation, deserved or not. 

* Memory will shape and define the past,  as well it should. I can’t speak from experience as I’m only recently retired, but rumor has it that over time, all of the above items become less important … if you remember them at all.  

This article is one in a series of occasional columns from Michael Zisser, recently retired CEO of University Settlement and The Door.