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October 11, 2025

The Art of Leaving Well

“I made myself available for confidential conversations on any topic (though, to my surprise, [my successor] never took me up on this offer).”

By  Rachel Toor

The Sandbox

Inside Higher Ed Insider
image of two people sharing secrets

From Rachel Toor

When I talk to long-serving presidents who have stepped down, I often ask about their relations with their successors. I mean, if I took a job following someone who could tell me which donors needed to be asked about their dogs children, which executive team leaders should be sent away, and which faculty members will never be won over, I would exploit that knowledge for all it’s worth. Which is, I think, a lot.

But every time I have this conversation the former says, “I don’t want to hover, but I have made myself available.” And when we get into it, they confess that their feelings are hurt not to be consulted.

Sometimes a new person coming in finds financial messes, trips over bodies that had been long buried, and discovers what seem to them to be plain old bad decisions. Plus, it’s hard to follow someone who has been in the job for a long time, especially if you don’t come from the same demographic.

A word to new presidents (and others) based on what I’ve heard: It doesn’t make you look weak to exploit the shit out of avail yourself of your predecessors’ knowledge. Just the opposite, in fact. You can be selective in the advice you seek and still follow your own path.

And to those out of the job, especially if you haven’t been president since 2019, you may not know as much you once did, so maybe don’t publicly second-guess those who have followed you. The new folks are facing challenges you could never have imagined. None of us could have predicted this is where we’d be now. Please, don’t be part of the problem. Current leaders have enough battles without having to deal with friendly fire from peers.

https://bit.ly/4iZ5wlB

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The writer is a former president.

It may be said that leaving well is a good leader’s last gift to an organization. If so, nowhere is this more important than in presidential transitions at higher education institutions.

I stepped down last year. Having served as president of two institutions and a consultant to several others, I have seen departing presidents support their successors by preparing the way for their arrival and passing the baton smoothly. I have also seen those who struggle with letting go and undermine their successors by continuing to meddle in their institutions’ affairs.

My experience in my first presidency was a case study in the latter. My predecessor had served for well over a decade and hoped for a different outcome of the search that selected me. He had someone else in mind, a former student whom he had mentored. Living just blocks away in retirement, he frequently was on campus finding fault with the changes I implemented. He was an alumnus of the institution (I was not) and was in constant contact with many trustees and alumni, spreading rumors and criticizing my priorities and team. It was painful, frustrating, and ultimately led me to seek another opportunity after it was clear the trustees he recruited to the board were unwilling to address his behavior.

I have since heard similar stories from peers who have wondered why it is so hard for some departing presidents to let go. The role uniquely embodies a university’s identity/brand and is the primary point of contact with the institution’s most important relationships. It isn’t surprising that the all-consuming nature of the job can lead some to imagine they are irreplaceable. And more than a few fall headlong into an identity crisis after retiring.

As a former president, I now understand this better than before. My explicit commitment to my successors is to keep a respectful distance, to not meddle or criticize, and to be available anytime to answer questions or assist. Yet I must admit it is disappointing that I am never consulted. Like most, I like to think any successor would want the benefit of my treasure trove of invaluable insight! Then again, I will confess that I failed to consult any of my predecessors and perhaps should have.

When I announced plans to retire from my most recent presidency a bit over a year ago, I reflected on what I could do to ensure a smooth transition and leave well. How could I set up my as-yet-unknown successor for success? Over the next year, I met with faculty, staff, administrators, donors, and others to encourage them to support the next president and explain what a new leader needs from them. I gave a presentation to the Board of Trustees to help them understand the true nature of the president’s job and how better to support the next person in the office. After my successor was named and before I left office, I made myself available for confidential conversations on any topic (though, to my surprise, the individual never took me up on this offer).

From what I have observed at institutions large and small, a good approach for a departing president is to do everything possible to pave the way for a smooth transition; to offer advice and assistance to one’s successor, but only if requested; to disappear from the scene and not accept a president emeritus’s office on campus; and to refrain from criticizing the new president, despite what you may think privately.

I have also found that I am happier not following my former institutions’ day-to-day activities or visiting their websites, for it is too easy to feel slighted or disappointed as changes inevitably come with a new administration.

If you want to get this newsletter, please become a member.

All previous issues of The Sandbox are available here. 

We invite presidents to write here under the cover of anonymity about their experiences in ways that make visible the challenges of the job. And to send in photos of their dogs (otherwise it’s all Harry all the time). Email me. 

Harry the dog running through burned area

Maybe don't leave scorched earth in your wake.

JOIN TODAY

 

The Sandbox

Not your typical weekly newsletter. This is a space where presidents and chancellors can say what they really think without fear. Everyone is welcome to read, but only those who have been in the top job can submit to us. The Sandbox, by Rachel Toor, is an exclusive benefit of our paid Insider membership program.

 

 

The Sandbox Archive

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September 12, 2026

What Does a College Student Look Like?

August 29, 2026

Wackadoodle Newsletter Turns 3

August 22, 2026

Presidents: Quit Yer Whining

August 15, 2026

“Life Changes in the Instant”

August 8, 2026
View All
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