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November 14, 2026

The Pipeline to the Presidency

Plenty of people still want the job, but are we creating the conditions that make it possible to do it?

By  Rachel Toor

The Sandbox

Inside Higher Ed Insider
image of one person chasing another

From Rachel Toor

Last month I had the opportunity to talk to a whole bunch of board chairs of well-resourced private colleges. The guy who invited me started the conversation by asking his peers if the presidency had become an impossible job. Was it too much for one person? Were institutions going to be able to recruit good people to do something that seems so awful challenging?

Let me tell you, this conversation gave me hope for the future. Because if boards are getting it—or at least board chairs are, or at least a few of them are—that means they know they have to do better at supporting the leaders they choose. I saw in this meeting people who knew their role was to let the president manage the campus and it was on them to keep the board on task.

They asked questions that showed how aware they are of the challenges facing all of higher education. These volunteers, all of whom have their own big jobs, are using their time and treasure (as my Odd Couple buddy likes to say) to give back to institutions they care about.

Not everyone has such well-informed board chairs, and it’s a real tribute to those presidents who have forged good and transparent relationships. We can’t blame people for what they don’t know or haven’t been told. Many leaders just want to put on a dog-and-pony show to assure their bosses that everything’s great. Except we all know that even at the richer-than-God places, everything is no longer great.

What I’ve been hearing from the boards I speak with is that they want to help. But first they have to know about problems, even if it can be scary to share the bad news.

Today’s seasoned president talks about the fact that we need a support pipeline. If you have a good board chair, maybe forward this issue.

The writer is a current president.

It occurs to me that the presidential pipeline may be full while the presidency itself is becoming increasingly difficult and less sustainable. What worries me is not whether people are capable of becoming presidents but if the jobs we are offering are ones they will want to keep.

As I think about my own 18 years as a president across three institutions, and more than 40 years over all in higher education administration, I find myself somewhere between optimism and concern. I am not sure I would encourage my younger self to pursue the presidency in exactly the same way today. I still meet extraordinarily talented women and men who care deeply about higher education and who are capable of leading institutions through significant change. The pipeline does not seem to be empty. In fact, I suspect there are many leaders who possess exactly the skills higher education needs.

The role has changed dramatically in the past decade. Presidents have always faced financial pressures, enrollment challenges, fundraising expectations, and governance complexities. What feels different today is the degree to which every issue is amplified. Social media has accelerated criticism. Political polarization has turned colleges into public battlegrounds. Demographic shifts and financial pressures have made difficult decisions unavoidable. Constituents who once assumed positive intent increasingly assume the opposite. The result can be exhausting, even for leaders who remain deeply committed to the work. And perhaps most difficult, many presidents spend as much energy managing internal conflict as external challenges.

I have mentored women wanting to advance through ACE and through the NCAA. I often tell aspiring leaders that the hardest part of the job is not making difficult decisions but doing that while maintaining relationships with people who may never agree that those decisions were necessary. A president can communicate openly, share data, invite participation, and listen sincerely, yet still face accusations of secrecy, indifference, or incompetence. I had that experience just last week.

I see this reflected in a friend’s observations as well. She is a talented leader who once seriously considered a presidency. She watched institutions hire leaders into nearly impossible situations. She watched highly capable women subjected to relentless criticism. She ultimately chose a role where she could have impact without sacrificing the quality of her life. I suspect there are many leaders making the same calculation.

That raises a question that I think higher education is only beginning to confront: Perhaps the issue is not the leadership pipeline itself. Perhaps the issue is the support pipeline. We spend considerable time preparing people to become presidents. Leadership institutes, executive coaching, mentoring programs, and search firms have all helped strengthen preparation for the role. We spend far less time preparing institutions to support them once they arrive. Maybe that is where the next generation of leadership development should focus.

Too often, presidents are hired specifically because change is needed. Then, when they begin making the changes they were hired to make, support evaporates. The expectations placed on leaders sound like the speech from Barbie: be bold but don’t upset anyone; be transparent but never make a mistake; solve financial problems without changing anything people value; create a vision while simultaneously reflecting every competing constituency. Over the years, I have been told both that I was moving too slowly and too quickly, communicating too much and not enough, protecting traditions and disrupting them. The presidency often requires navigating expectations that cannot all be satisfied simultaneously.

As we have read many times in The Sandbox, leadership competencies celebrated in women during a search can become liabilities once difficult decisions must be made. Women leaders are frequently expected to be collaborative, empathetic, and relational, yet they can be judged harshly when circumstances require them to be decisive, direct, or disruptive. Many women end up navigating a narrower path with less room for error. And as we know, the tenures are shorter. Despite all this, I remain hopeful.

I remain hopeful because I continue to see exceptional leaders emerging and I see institutions adapting and evolving. Even amid the challenges, the work still matters. We all believe this: Higher education changes lives every day.

But if we genuinely care about the next generation of college presidents, especially women presidents, we need to do more than encourage them to step forward. We need to create environments in which they can succeed, grow, and stay. We need stronger mentoring networks, governing boards that understand the realities of institutional change, and spaces where leaders can speak honestly about their experiences without fear that candor will be held against them. Maybe The Sandbox is helping create one of those spaces.

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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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November 7, 2026

A Grieving President’s Thank-You

October 31, 2026

Mentor, Consultant, Coach: Which Do You Need?

October 24, 2026

The Loneliness of the Long-Serving President

October 17, 2026

A Proposal for Fundraising

October 10, 2026
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