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September 26, 2026

Hiring a Leadership Team

“You cover building a cabinet in “becoming a president” school. You don’t get the full magnitude of what you could face.”

By  Rachel Toor

The Sandbox

Inside Higher Ed Insider
Image of people running

From Rachel Toor

When I talk to presidents in their first couple of years, I always ask about their team.

How many inherited people in executive positions remain?

Not many, if any.

How many VPs did they know were going to be a problem?

Plenty.

How long did it take to make a change?

Too long.

Usually a couple of VP slots become open because those who have been around a few blocks know the drill. Some presidents tell cabinet members that they will have to apply for the jobs they currently hold; others manage to shock folks who couldn’t read the (neon) writing on the wall and thought they were indispensable. Of course there are leaders who want to surround themselves with mini-me’s.

Who can leaders turn to to learn where the bodies are buried and who can fill them in on the history? Most say to beware of those who row out quickly to greet the ship. Early on one president told me, “I take long-serving administrative assistants out for coffee. They know everything and are rarely asked their opinions.”

All this hiring must happen when a new person is learning the culture of a place, uncovering icky financials and other surprises, and forging a relationship with a board that may or may not be, um, functional.

And then, just when they think they’ve got it covered, someone leaves.

***

Last week’s Sandbox seems to have hit home for way too many presidents. So I want to remind you that if you need a supportive ear, reach out to me. (It should never go without saying: Everything is always confidential and off the record.) At this point, I have a great network and may be able to find some kind of help for those who need it. I’m also always delighted to hear good news, so please don’t be stingy with that, either. I’m rooting for all of you.

I’m interested to hear what you think board chairs could benefit from knowing—that they could hear from someone like me, not the presidents who report to them. If you have ideas, bring them on.

The writer is a current president

Looking back, the creation of our current executive team seems to have just happened—a normal transition in institutional leadership. It did not.

As everyone who has done it knows, building a cabinet is far from a routine administrative task; it is a painstaking, surprisingly high-stakes process where every single detail matters.

Weeks before my arrival at the campus, I had to deal with three retirements. Key leadership seats sat empty, and they needed to be filled quickly. Lots of people told me this was a tremendous opportunity to shape the landscape from day one.

At an intellectual level, I understood that perspective. But it all felt too quick. I was just getting used to the reality that I was going to be leading an institution. There was no time to take that in. I was in search mode. And it was daunting, like being thrown into the proverbial deep end.

While managing the three high-visibility searches, I simultaneously began to learn things about the institution that were not shared with me during my own search process: a structural deficit that was more than double what I had been led to believe; a toxic culture caused by the former president having “checked out” of the role for a number of years before leaving the position; a Foundation that had a deeply dysfunctional relationship with the administration; a slew of “homegrown” systems and processes that were completely disconnected from mainstream best practices in higher education; and, finally, a lack of respect for expertise in administrative roles, a truly disconcerting feature of the institution. All of this was hitting me in rapid succession.

Back to the cabinet openings. I knew that the campus search process for vice presidents and cabinet officers would be intensely public. In addition, each search committee action, candidate presentation, and interview schedule would be scrutinized as a direct reflection of my leadership style.

Because the stakes were so high, I chose to be deeply involved in every step of every search and personally oversaw each hiring process: crafting and refining position descriptions, working closely with the University Senate and Office of Human Resources, charging the search committees, shaping the campus visit itineraries, spending extensive one-on-one time with candidates, personally making all reference calls, and ultimately making the final decision.

Once the first three positions were filled and the initial momentum was set, we faced four more vacancies, including the most pivotal administrative role on campus: the provost. Two national searches required multiple iterations before we found the right candidate.

It was during these difficult moments that my normally positive mindset was truly tested. I had to find interim support for two important roles, temporarily pivot away from festering issues, and then reset and search again.

My full team is now assembled. But getting people into these roles does not complete the job. The even harder work comes next: forging separate, highly accomplished individuals into a cohesive team capable of executing a unified agenda.

I have recently become very concerned about one of my hires. I have lost sleep over this person’s judgment, alignment with my priorities, and most importantly, core competence and expertise. I am trying to give the individual the benefit of the doubt, but I am also coming to the realization that this isn’t going to work. My mentor asked me, “Can you see this person working with you five years from now?”

The answer to that question is now forcing me to think through the personal and professional implications of an impending decision regarding that person, the impact it will have on the campus and the cabinet, and the weight of all of this on me and my relationships.

You cover building a cabinet in “becoming a president” school. You don’t get the full magnitude of what you could face—the entwined challenges that have marked my experience thus far. I don’t really know if my experience is unusual. It’s not something I have spoken to my peers about. But my wife, mentor, and therapist know. Without them, I’m not sure where I’d be.

From the Boss

We’re inviting all presidents and chancellors to New York City next month for our U.S. Universities & Colleges Summit—a day and half of off-the-record conversations about leadership, board relationships, M&A, accreditation and more. We’ll kick things off with reflections from Jim Ryan, the former president of the University of Virginia, and finish the second day with a Sandbox live session led by the Odd Couple, Rachel Toor and Gordon Gee. We have a lot more good stuff planned in between.

If you haven’t already signed up, learn more here. Or reach out to me directly. I hope to see you there!

Sara Custer
Editor in chief

Feel free to forward this email to anyone

Photo of Harry and Squid (dogs)

Teams require individuals with different strengths (and sizes). Sometimes they can grow in ways that are surprising. (Harry's BFF Squid is now a year old and has 30 pounds on him.)

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

The Real Text Messages of Lady Presidents

September 19, 2026

Retreat Rights

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
View All
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