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Transition Strategies for Founders and other Long-Tenured Execs: a convo with Bob Wittig

Over the years, Good Insight has worked with a number of founders and long-tenured executives on succession planning and leadership transitions. The departure of a long-time leader is inevitable – but it is also one of the organization’s most fragile points in history.

According to BoardSource’s Leading with Intent survey, only 1 in 3 nonprofits has a succession plan in place. Without a plan in place, all the different elements of the transition become simultaneously urgent. From revisiting organizational identity, shoring up donor relationships, retaining staff and board members, and communicating transparently about changes at hand… it’s a lot! And we haven’t even gotten to the executive search part of things!

Our friend and close colleague Bob Wittig recently presented a recent workshop, Founder Transition: Creating your Strategy and Plan, at the Nonprofit Village earlier this year. He’s joining us to share about his work with founders and long-time executives. We know that his insights into the emotional and tactical elements will be helpful to our colleagues considering a transition in the few years.

You have recently worked with the Nonprofit Village on a workshop for founders and long-term executives directors to plan a transition strategy. What is special about founders and long-term executives? Shouldn’t every leader have a transition strategy?

Yes, they should, but founders and long-term executives are special for distinct reasons. Founders conceived of a mission-driven organization and actually brought it into existence. Long-term executives stepped in at some point after a founder and brought new energy or purpose to the organization and sustained that over many years. What they have in common is a deep emotional commitment and passion for the mission and tremendous influence on the organization’s culture.

The emotional connection is the reason why these transitions can be more challenging.  It can be hard to for either the founder or long-term executive to let go or step back from something to which so much time, passion, and personal sacrifice have been given.

When I am with a group of founders I ask “When is a good time to start planning for your departure?” They all share different answers, however, the one I believe is the best is the first day your nonprofit opens!  In my experience, so much of the information about the running of the organization lives in a founder’s head. If the founder had to leave town for a period of time, would anyone even know the combination to open the front door?

From a risk management perspective, I would label this “high-risk!”

I advise clients to document workflows and other key information necessary to daily operations. By the way I believe this is a good strategy for all nonprofit leaders.

It’s also important that founders step back from being a voting member of the board as soon as they can—this enables the board to step into their role and become more independent, both critical to the long-term viability of the organization.

What roles do boards have to play in the transition of a founder or LTE? 

Boards are critical to transitions. For a founder-led organization, it is the first time that the board has had to hire for this key position. That is a daunting task for sure!

It’s important that boards drive the transition process, not the founder or LTE. That said, a partnership between the board, departing leader, and staff is important to develop an effective transition plan.  This plan includes, among other things, conducting a financial assessment, documenting workflows, revising (or sometimes creating) the ED job description, managing or conducting the search and hiring process, and celebrating and acknowledging the contributions of the departing leader.

It’s also important to add that the transition does not end the first day the successor is on the job—the board must remain engaged and supportive if the successor and the organization have the best chance to thrive.

Aside from getting a tactical plan in place, how can founders and LTEs process the emotions related to their transition? When should that process begin?

Often, the emotions that arise when a founder or long-term executive decide to depart are not fully dealt with. Everyone in the organization, the founder, board, staff and even participants, will have some level of anxiety and sadness. Think of it like a grieving process. Addressing these emotions across the organization is essential to a successful transition process.

Processing these emotions cannot be done in a vacuum. From my experience, a founder will reach exhaustion and simply say “I am ready to leave!” and that’s it. However, there are likely emotions under the surface. Left unchecked, they can undermine the transition process. Engaging a coach can help the founder, board, and staff.

A professional coach can provide space for the founder to process emotions before the successor is onboarded.

Another important piece of these transitions is what will the departing leader do next?  Going from a situation where almost every waking moment was devoted to the organization to the next life chapter can also create anxiety and uncertainty for these leaders. Having a plan on what’s next is crucial to the success of the transition. A coach can help the leader envision what’s next for them.

Ideally, an organization needs 8 to 12 months for a transition. This gives time to process emotions, create and implement a transition plan, increase board engagement, celebrate the departing leader, and hire and onboard the successor.

While each transition has similarities, often there are needs unique to the organization. Having an objective partner who can offer tailored support during these transitions is one of the best things that an organization can do.

And what kind of support do you give clients? What does it look like to work with you?

As a coach and consultant, I bring over 30 years of experience to nonprofit leaders planning transitions. For departing leaders, I have developed a method that combines coaching and consulting.

We start with individual sessions with the founder and board chair. I coach the founder/LTE through developing their exit strategy, announcing it and negotiating it with the board.  If the founder/LTE desires some kind of role after the successor is hired, I work to ensure that whatever that role may be, it does not impede the ability of the successor to fully step into their leadership role. Then depending on the situation, I provide additional individual or group coaching to the board and staff. An important part of my process is to help everyone envision the possibilities and opportunities that exist for the organization after the founder/LTE departs.

I also support the tactical elements of the transition, working with the board and staff to establish a transition committee that will be highly involved in the entire process.  I assist this committee to develop a transition plan, timeline, and determining whether or not to retain an interim executive director and/or an executive search firm. Buy-in from the founder/LTE, board, and staff is important. A good portion of my consulting is dedicated to the board, helping them to step more fully into their governance role to prepare for the transition and to support the successor.

In addition to leadership transition engagements, I coach nonprofit executive directors.  My goal is to create safe spaces where a leader can fully explore their leadership, identify what’s working well and areas for growth. My goal for every coaching engagement is to help the leader achieve their professional and personal aspirations.

Thanks, Bob! If leaders or boards want to learn more about your work, what can they do?

For more information about my coaching and consulting, visit and sign up for a free consultation.

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