Initiating the Succession Planning Conversation – Advice for Board Leaders

It’s not surprising that nonprofit board members are timid about starting the succession planning conversation with their chief executives. There is the fear that raising the subject might suggest to the chief executive that the board thinks it is time for him or her to leave. There is also the fear that that they may hear something they would rather not: “She’s planning to leave us!”

I believe it is the responsibility of the board chair, and/or board officers, to remove the anxiety surrounding succession planning, to get these conversations out in the open, and to help the board and staff appreciate the value of planning ahead. It is in everyone’s best interest to avoid surprises that cause turmoil within the organization or lead to rushed decision-making.

My recommendation to the nonprofit leaders with whom I work is to make it a standard practice to build a discussion of succession planning into the annual chief executive evaluation process. With the assumption that the evaluation process will include a face-to-face meeting between one or more board officers and your chief executive, I suggest you set the stage for that meeting by sending out in advance an e-mail to your chief executive describing what you hope to accomplish during the meeting. One of the items should be “succession planning.” This removes it from the list of forbidden topics and brings it out into the open.

The goal here is to reduce the risk of being surprised and finding yourself with a much shorter time horizon than you might like. A 12-18 month “heads-up” is usually ideal, and that may be one of the messages to communicate to a long-time leader.

One board chair with whom I work had a very direct way of approaching the conversation: “I’ve told you I don’t like surprises, so if you have any thoughts of leaving in the next 12 months, tell me now.” Whether you have just delivered a glowing evaluation or one a bit less positive, this direct approach effectively starts the conversation!

Here’s another approach that accomplishes the same thing but a bit more gently: “I hope it is obvious from our conversation today that we respect your leadership and that we hope we’ll be able to count on the same for many years to come. With that said, I want to check-in with you now to make sure you can still see yourself being with us for several more years.”

You may not need to say any more, especially if you sit quietly and let the chief executive speak next. The goal here is to set the stage for this conversation and then be ready to offer encouragement, show relief, or engage in a conversation about how best to manage a transition. Whatever the result, it is certain to be better than being surprised somewhere down the road.

At Starboard Leadership Consulting, we take pride in the advice we offer regarding succession planning and leadership transitions. For more advice like this blog post authored by Jeff Wahlstrom, visit our website:, or click here to access our contact form and connect with a member of our team.