Taking the Awkwardness Out of CEO Transitions

Replacing a long-tenured executive is a challenge even in the best circumstances. But it can be done smoothly with advanced planning and clear communication to members, stakeholders, and—especially—staff.

When Kristine Hillmer, CAE, was hired to be CEO of the Wisconsin Restaurant Association late last year, she had four months to prepare for day one—the day of the previous CEO’s retirement. The good news is that those months gave her plenty of time to understand WRA’s operations. But that long runway also created some awkwardness. As she prepared for her start date, she would work in the office one day a week, stationed in a corner of the outgoing CEO’s office while he was still there.

Management of expectations helps with that transition period.

“I sat a table, he sat at the desk,” she says. “We certainly made it work, and it really wasn’t a big deal. But to be relegated to a table in his office was a little uncomfortable.”

Hillmer’s experience is a concrete manifestation of a common question at associations: How do you best navigate the transition between CEOs? Especially, as was the case at WRA, when the outgoing CEO has been long-tenured, with more than three decades or routines and relationships with members, staff, and stakeholders?

Leadership consultant Cynthia Mills, FASAE, CAE, says potentially clumsy baton-passing periods will be inevitable when new CEOs arrive. But those CEOs should be empowered to make their own decisions as quickly as possible—and make clear to staff and others about who’s in charge.

“For an incoming CEO, the ability to from day one arrive and begin to build a relationship with staff and members and boards—that’s the foundation foundational underpinning to success,” she says. “And when you have two people who essentially have the same title and behavior patterns in play, it becomes difficult for that to happen.”

In Hillmer’s case, that meant establishing some ground rules about who had what responsibilities during the transition period. “He agreed that he was the CEO until his retirement date, but when there was a decision to be made that affected things after April 1, he let me make that decision,” she says.

She also made sure that there was a clean handoff when it came to the association’s lead stakeholders, such as suppliers and sponsors, scheduling in-person meetings to make sure those people could get to know Hillmer directly, and get the outgoing CEO’s in-person vote of confidence.

Meetings like that, Mills says, should be part of an outgoing CEO’s transition work, because it shares the institutional-memory stuff that often isn’t documented. Indeed, Mills advises creating a document with such material. “It’s a critical exercise for all departing CEOs,” she says. “The transition document literally outlines everything that’s in your head that you just know, and that you’ve forgotten you just know.” That can include stakeholder relationships, knotty staff issues, and important dates on the calendar.

Since April 1, Hillmer’s official start date, her predecessor has been out of the office, and though she knows he’s available to help, she hasn’t had a need to reach out. But that doesn’t mean that sticking points relating to a transition won’t come up after the past executive has left. For instance, Hillmer noticed that her senior staff was initially a bit cautious with her, which turned out to be the result of hallway chatter during the transition that a new CEO was likely to clean house. “I came into a situation where things were going really, really well,” she says. “So for that to be how senior staff were presented with me, without my knowledge, was really unfortunate, and we’ve since worked it through.”

Hillmer’s experience highlights the point that the more information the staff gets during a transition, the better. “Staff sometimes gets forgotten in onboarding,” Mills says. “It’s very important not just to communicate to staff that a person has been chosen and here’s the name and here’s the date they’ll arrive, but to also share with staff what that onboarding is going to look like. It’s the management of expectations that helps with that transition period, because the longer staff doesn’t know what next, the more they’ll try to fill that vacuum quite naturally.”

How have you handled CEO transitions at your association, and how were responsibilities divided between the exiting and entering CEO? Share your experiences in the comments.

(Dmitrii/iStock/Getty Images Plus)

Mark Athitakis

By Mark Athitakis

Mark Athitakis, a contributing editor for Associations Now, has written on nonprofits, the arts, and leadership for a variety of publications. He is a coauthor of The Dumbest Moments in Business History and hopes you never qualify for the sequel. MORE

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