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June 29, 2024

Bosses and Mentors

Whose voice do you hear years later—for better or worse? 

By  Rachel Toor

The Sandbox

Inside Higher Ed Insider
In illustration of a female leader choosing from masks of different emotions.

From Rachel Toor

There's a beautiful comment about mentorship in Ali Smith's novel, Autumn, about a long-term friendship between neighbors nearly seventy years apart in age. The young woman says, after too many years absent and wondering if the elderly man had even noticed it had been a decade since they'd been in touch, "Myself, I thought about you the whole time. Even when I wasn't thinking about you, I thought about you." If you've been the beneficiary of great mentorship, you know exactly what that's like.

Most presidents say that nothing they knew or did prepared them for the job until they were actually in it. Sure, they learned essential and important stuff at boot camps and leadership institutes, though many people say the most important thing they gained from those experiences were peers. 

Only a few mention former bosses.

In a conversation with one president, she answered many of my questions by sharing pieces of advice she’d gotten from others, often naming them (though not in a name-droppy way). Her list of mentors, most of whom she had never actually worked for, was long. 

While the most common advice former presidents offer to newbies is the (true but perhaps not all that helpful) nugget to "marry the right person," I have heard from many who say the person they really talk to is their executive coach. 

A current president who read our recent issue with contributions from a president and their coach, wrote about his own experience: "I am working with a coach, which has been tremendously helpful for all the reasons you note. My top staff person was a bit concerned, thinking people usually get coaches for remediation purposes. I don’t really talk about the coach with my executive team, but if I do, I sometimes use the word 'consultant,' as I don’t want them thinking that getting a coach was something the board insisted/mandated that I do. In fact, I am not sure I even told the board!"

I was surprised by this, since so many leaders not only have executive coaches, but also know to ask for this as part of their compensation package. He replied, "No one mentioned coaching to me until I realized that a few of my colleagues were using coaches. A great resource, tremendously helpful, particularly with board-related topics. Am using discretionary funding, so kind of in the budget, kind of not, but at least covered by the school."

At this point in history, I would have thought most people would realize there's no shame in asking for support. It takes, as most of us have learned, a village to succeed. We all mess up and need people on our side to help us dig out of holes, sometimes of our own making. And also, to prop us up after being laid low by the haters when they don't like what we do or even just who we are (the haters gonna hate). 

After I met with a current president and his leadership team, I commented on how well they got along. They really seemed to like each other and I asked if it was genuine and how he'd created such a good vibe. What I knew (from knowing him) is that a lot had to do with his personality. That's something you can't fake.

But I’ll share with you what he said.

The writer is a current president

Yes, our team gets along for real. I worked for a chancellor who operated that way, and by that way I mean really fostering a sense of collaboration, cooperation, and friendship among cabinet members, and I brought that approach with me. On the other hand, that same chancellor fought tooth and nail every single day with trustees and with campus faculty union leaders, and he was fired after three years. 

The first president I worked for pitted cabinet members against each other, I guess to reinforce his power over us. It took me a while to figure this out, but once I did it was so obvious, and there was a famous cabinet retreat where one VP burst out sobbing. 

The second president I worked for allowed no one on cabinet to contradict or disagree with her. You had to sit around the table nodding like bobble heads. This extended to one-on-one meetings with her, although, me being me, I stood up to her in private (but not in public). 

We hired a fantastic VP for Enrollment and in her first meeting with the president she asked: “Are you the kind of president who likes it when VPs say what they are really thinking?” The president’s response: “Only X is allowed to push back, and only in private.”

Don’t even get me started on working for this president who was sweetness and light in public, really, really sweetness and light, and a holy terror in private. A real bully. Eventually a trustee figured it out. I never spoke to anyone about it except my wife and my senior associate provost at the time. The president retired, and I don’t know if that was forced or not, but it was five years of hell for all of us in the provost’s office. 

The Sandbox is a benefit of IHE's Insider membership program. We anyone who wants to understand the lived experience of leading in higher ed and is willing to pony up a little extra coin to support Inside Higher Ed's free journalism.

If you’re a president or chancellor, current or former, from any sector, and there are things you think but cannot say with your name attached, this is your chance to write for no money, no prestige and no self- or institutional promotion. We’ll shield your identity; all conversations are confidential and off the record.

Harry Icicle ridge

Harry got to go for a hike with me, a former president, and our spouses (not pictured because: Sandbox.)

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 Worst of Times: FY 2025–26

October 3, 2026

Hiring a Leadership Team

September 26, 2026

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
View All
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