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July 20, 2024

Can A President Be Too Well Liked?

How do you know if your closest staff members are telling you the things you don't want to hear (but need to know)? 

By  Rachel Toor

The Sandbox

Inside Higher Ed Insider
Thumbs

From Rachel Toor

Given recent events in the news cycle, I have found some solace in cows. There’s been expert advice arguing cows are the new puppies. Plus, Bruce. 

If you need to practice a speech, grazing bovines make a great audience; they tend to listen more attentively than graduate students and appear far more compassionate than faculty in a senate meeting. 

But we all have plenty of other work to do and not everyone has access to cattle.

Last week we offered insight from presidents who left jobs they loved. This week, I've been wondering about how leaders can protect themselves from living in a deluded happy bubble.

In a recent conversation, I asked a relatively new president, clearly an empathetic and kind leader, who tells him the hardest things, the truths he needs to hear? 

He thought for a while. He hoped everyone, he said. But really, if he was being honest with himself, it wasn't entirely clear. It was, he said, a good question.

We all know cabinet members who outlast many bosses by simply keeping their mouths shut. Those who serve at the pleasure of the president are often careful not to displease her. 

Some of you know presidents who claim they can handle the truth, but in real life squelch any hint of dissent. Those leaders don't want to play in The Sandbox and so I never speak to them. 

It's easy to see foibles in others. How much do we really admit to and about ourselves? 

Most presidents say they want staff to push back and tell them when their ideas are stupid. But what does that look like in practice? 

When I asked one president, he responded, “Any time I am feeling good about a decision-to-be, I immediately let my self-doubt loose and elicit questions from my team intended to find all the cons of the decision."

He continued, “I will say to my inner circle, ‘Look, I am having doubts about this and need your thought partnership to explore all the reasons we shouldn't go down this route.’ When I believe I have our best thinking, I move forward one way or the other. Eighty percent of the time I decide to stay the course. On other occasions, this exercise has made a huge difference in my batting average.”

Another president weighed in: “There are always a couple of people who will always agree with you no matter what. We have one on cabinet now. He does great work, and we just know that we can’t count on him to push back on ideas and proposals. That’s okay. We have others that are good at doing so.”

Someone else texted, "My cabinet members are great at saying ‘One thing you might want to consider is—’ or ‘I agree in principle but practically speaking, might it make more sense to—’ In any number of ways, they help me avoid self-inflicted wounds.”

We all need editors, all the time.

And we need people who show their love for us by pointing out when we’re wrong, wrong, wrong. When we’re letting our egos get the best of us. When we get stuck escalating a commitment instead of changing course. No one wins when advisors tell the naked emperor his new clothes will still look great in four years.

And yet, most of us are human, with all-too-human egos. 

Even some editors don’t take editing. After a friend in publishing sent me a copy of legendary editor Robert Gottlieb’s memoir about his career working with the most important authors of our time, I confessed that while I thoroughly enjoyed the book, a kind of People magazine for literary geeks, I wished it had been, well, better edited.  

My friend who worked with the great editor said, “Bob accepts only praise, not criticism.”

While puzzling over all this during such a weird time, I reached out to a recently retired president. He said, “I believe hiring for humility, as well as building a culture of listening and curiosity in the senior team, are among the most important things a leader can do—even though they’re among the most counter to our hiring and reward practices in the sector.”

He went on to explain that leaders from historically disadvantaged groups can suffer from corrosive self-doubt, wondering whether they are good enough and experiencing imposter syndrome. The other side of that, however, is that some are able to turn those feelings into a strength and benefit from healthy questioning of their ideas. 

As we head into another academic year guaranteed to bring even more turmoil to a FUBAR world that feels off-kilter, it seems more important than ever that we all learn how to listen better, to take harsh critiques seriously but not personally, and to be as civil and as kind to each other as we possibly can. 

Or we could just spend time getting ready with Bruce.

If you've got ideas about how we can improve The Sandbox, or what the Insider program could provide to help you do your jobs, bring them on. We accept criticism (and praise).

BAD NEWS (BUT WITH A HAPPY TWIST)

Doug Lederman (co-founder of Inside Higher Ed and aka the "work wife") headed west for a fabulous vacay with his (doctor-filled) extended family at Lake Tahoe. He'd never been to that part of the country. I warned him it was heart-breakingly beautiful.

Well, the dude got his heart broken all right.

From Doug: "My vacation was rudely interrupted on the second day by an aortic dissection. For those blissfilly ignorant as I was until a week and a half ago, this requires emergency open-heart surgery, from which I am (thankfully—wasn’t a sure thing, apparently) slowly beginning to recuperate." 

Ed's note: as we'd expect from our Energizer Bunny-esque editor, his recovery has actually been shockingly speedy and he is now fine. Those of us who care about him are still reeling from this close call and are trying to keep him away from work. Go ahead and spam him with good wishes.  But please do not mention anything about higher ed or give him any news tips.

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. Email me.

Doug at Tahoe

Hours before the heart gasket blew, Doug claimed he was trying to teach his sister's puppy to swim. Or did he think this was a cow and he was practicing a speech? 

JOIN NOW

 

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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