Heads and Boards Break Up. The Colbert/CBS Split Has Some Lessons.
When a certain set of circumstances combine, even stars can lose their jobs.
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Before the main event, an update about the month ahead. (Feel free to skip ahead to the “what to expect” paragraph if you’re not interested in the backstory!)
I have many, many topics swirling around in my head recently and they all feel substantial and worthy of considered exploration. I had one I was planning to publish today, on how the combination of the current state of governance and the traditional norms of the head search process are holding back schools on a number of levels, and then I realized I was going to have a chance next week to talk to someone about leadership search and transition from the the perspective of the private sector and I wanted to add that to the mix. So that will be upcoming.
And then there is also an increasing need to look at the now three year old Talking Out of School project in its entirety to figure out the next stage. I don’t think the next stage is going to look radically different. It’s fun to toggle between longer and shorter pieces. Every time I think the idea pot is empty, something else comes up. And writing this newsletter has been in general, really fun.
But what is becoming more and more apparent to me is that the newsletter/blog format has an aspect that is ephemeral in nature. And that is a feature not a bug - when you connect with a newsletter writer and subscribe to their work, you want their “take” and there’s a freshness and responsiveness that’s like a satisfying texting sesh with a friend. But when you look back on the texts, their “juice” is largely depleted. That thing that was hilarious is flat. It’s basically a collection of words.
But there are other aspects of this work that are more durable and I think there’s a lot of stuff in the TOOS archive that remains helpful and relevant for leaders. Some posts even achieve a semblance of thematic unity! :)
So the question is, is there value in going back and sharpening up some of these archival posts to take out some of the ephemera and leave the more enduring stuff - whether that juice is worth the squeeze - or whether to more seriously consider something I keep flirting with on and off about putting it together in a book.
There is a fair amount of grouchiness from Substackers who have published books about the huge effort to produce a book and how much authors are now expected to do once it’s been written to market it, even a book published by a legacy publishing house, and how the return is often minimal. The odds against even landing a contract with a legacy publishing house seem slim and while of course that’s the longstanding dream of a Gen X writer like myself, the reality of that seems significantly less glamorous and desirable than the old days. Then there’s self publishing and small, specialized no frills-ish publishing concerns. There’s a way to figure it out; it is a potential path.
I suspect there’s more than one reader out there who also has contemplated writing a book, so I’ll keep you posted as I explore the options!
And then there’s the ever morphing landscape of Substack itself which keeps marching forward, promoting more social media features, like Substack Live videos. I get the fact that snippets of video are more promotable and can enhance “discoverability” more than audio, but does everything end up becoming about the slick approach we take towards presenting ourselves as authentic? Bleck. I like nothing more than the idea of having a fun video chat with a fellow Substacker like Michele Levy, but now I have to buy a ring light and have camera ready outfits put on barely-there makeup? Jeez.
What to Expect in the Next Four Weeks
ANYWAY. This is a very long way of saying that for the next month (July 29 - August 26th) things are going to be a little different for the next four weeks as I take some time and headspace to think more expansively about some specific topics I want to delve into and reflect on the archive. I’m going to pause Tuesday’s posts except for the August “Happenings” newsletter (unless there is some snappy topic I just can’t resist) and the four Fridays I will split between two new posts and two from the archives.
Thank you for coming on this ride with me, whether you’ve been around since the beginning or are just joining in now!
Heads and Boards Break Up. The Colbert/CBS Split Has Some Lessons.
Logic and “business sense” only ever go so far, even at a multibillion dollar global media conglomerate. When a certain combination of circumstances collide, anyone can suddenly find themselves out of a job.
A few weeks ago, I heard someone say that June is a time of rough rapids for heads of school - some survive the ride and some get tossed in the river. I hadn’t thought about it that way, but it seems to be true, at least in the past few years - in July, that’s often where a handful of announcements come out from schools that it will be the head’s last year or even sometimes that the head is departing immediately.
It’s also a sign something went very badly wrong a while before. Maybe it started out as a a murmur far off by the horizon but through a series of events, or conversations or events and conversations that combine with some unfortunate outside circumstances beyond anyone’s control serving to heighten the problem, suddenly the current situation goes from bumpy to an unplanned head transition.
And as we all know, the unplanned head transition is just never ideal. Starting from zero with a new head, often a head new to headship, rather than trying to make it work with the incumbent (often an incumbent who has done some significantly positive things for the school), it will be a multiyear investment that may or may not pay off as the board hopes. Sometimes there are villains and high drama; most of the time it’s humans trying to figure things out until there is a sense of a tipping point. Heads aren’t perfect and neither are boards.
I read this very thoughtful and nuanced piece by Nate Silver from his Substack, Silver Bulletin, that analyses The Late Show cancellation and it struck me that while we think that a gazillion dollar legacy media conglomerate has its act together in ways our small independent schools never could, at bottom it’s also just people making decisions, sometimes driven by hard financial reality and sometimes by optics or exhaustion or a sense that, “this doesn’t seem to be working anymore.” Even if the heart of the legacy media conglomerate is both cold as ice and as green as the color of money, even if they are run by hundreds of sophisticated, experienced executives with fleets of accountants and analysts and McKinsey on speed dial.
I think you can read this piece as puncturing that fantasy. People are people and at a certain point, however the cost/benefit may still transactionally end up on the “benefit” side of the ledger, things fall apart. Losses are cut. Everyone moves on. And it doesn’t matter if you’re an international star who the actual Pope asked to gather a group of American comedians and fly to the Vatican to discuss the importance of comedy and laughter in a tough time. You can still get the boot.
Silver starts off by linking to an article about his departure from ABC/Disney when they had a mass layoff that included most of the team at FiveThirtyEight, his statistical analysis org that was part of ABC News. They woke up in the AM with jobs and had none by the end of the day. His description of running that org was, I think, a pretty good one sentence description of headship in 2025: “We were still building the plane as we flew it and there was an obstacle course of successes and failures.” (I love that image of an “obstacle course of successes and failures” because successes can cause as many adaptive headaches as failures and you pinball between dealing with first one and then the other - and sometimes an issue can be a particularly confounding combination of the two!)
He goes on to make observations that can be just as applicable to schools as they are to CBS:
“Rather than skate towards where the puck is going, media executives chronically fight the last war.” Yep.
“While CBS probably has some basis to justify the $100 million figure, there are a lot of ways to run the numbers.” There are choices to be made in this area and it’s not uncommon for a head to inherit one level of transparency around finance that may have been adequate in the past. However, when in a much more dynamic environment, the board needs another level of transparency altogether, and one that may expose much greater struggle and operational vulnerability.
“Until recently CBS might not have been motivated to examine the budget because the show was making money.” It has crept up on some schools the way the admissions pool has been shrinking or family capacity to pay rising tuition has been gradually reduced. It’s like the Hemingway quote about going broke - it happens little by little and then all of a sudden.
“Why not trim the budget, as painful as that might be, rather than throw the baby out with the bathwater?” Silver notes that mass or broad category layoffs avoid internal/stakeholder politics, surgical layoffs of specific roles and that employees have trouble accepting pay cuts. So there can be incentive for a drastic solution that avoids some interpersonal/political yuck. The organizational culture can work against you.
And then there’s this:
ABC News executives often had shockingly little knowledge of what features of FiveThirtyEight were bringing in traffic, how to monetize the site or understanding of detailed contract terms for me or other employees. If a bloated dinosaur of an organization - CBS was founded in 1927 - never develops the muscle memory for scrutinizing expenses or maximizing revenues, it may struggle to do so even when the economics make it vital.
I enjoyed how Silver points out CBS has been around since 1927 with a kind of amazement. But the point taken is that while our schools may not be “bloated dinosaurs” we are certainly not used to a culture that is continually optimizing for financial efficiency or questioning our program choices in terms of revenue generation.
Maybe things aren’t a bed of roses at the school and maybe for some very observable reasons totally outside of the head’s control. Schools are getting pummeled by so many outside forces right now. I just talked to a parent recently who is so unhappy about a school’s head-in-the-sand (as yet) approach to AI where the AI use guidelines are vague and contradictory and good kids trying their best to make choices are getting in trouble. Demographics are just bad in some formerly populous areas. No one foresaw all the layoffs that would hit the professional class in the DC area this spring. Inflation has made budgeting and tuition setting a nightmare. And parents are really mad about that newbie teaching Physics who replaced the last newbie who washed out and left midyear.
But often the finger gets pointed at the head because it’s much easier to attribute the problems to a person rather than the much harder to fix problems.
And then there’s this:
The Late Show is still a rounding error to Paramount Global, which took in 29 billion dollars last year.
One of the lessons I took away from my tenure at Disney is that, if you’re a barnacle clinging on to a whale of a very large media brand - CBS’s current NFL contract runs 2.1 billion a year for 11 years - your performance doesn’t matter as much as the opinions of investors about the overall direction of the company or the political incentives of your bosses.
If a new executive comes in who is interested in cleaning things up - whether it’s because it’s an actual economic need or to make a point, or to score points - if your area is in the red, you can be a sitting duck.
To Silver’s point, even if The Late Show is a rounding error to Paramount Global, the combination of business losses, which they interpret as indicative of the losing direction the whole late night sector is headed towards, and political headaches can easily come to seem like not worth the effort or putting off the inevitable. As Silver writes, “You might be able to survive losing money and you might be able to survive being a political headache for the suits, but probably not both at once.”
Maybe a school leader can weather the rapids of circumstance and steer as skillfully as humanly possible, besides the fact they are likely dragging around all of the institution’s past decisions as well - debt, timidity with raising tuition, a culture allergic to fundraising to name just a few.
But if then the political headaches keep coming - the complaints about the quality of new faculty or disgruntled employees or rumors about why certain families left the school or ongoing upset over a struggling program that was phased out or the college list not being what parents expected - it can be easy for a board to start to see the solution as “a new head.”
Trustees don’t join boards to get up to their ears in ugly or messy internal politics or hear repeated, somewhat complicated, context-setting explanations for why (fill in the blank group) is unhappy or why enrollment is struggling for yet another year. While there are trustee outliers who do truly believe their job is to “run the school” if they see something they believe is amiss, or to get the insider gossip or they join to protect their beloved institution from AI or from the new head or from…modernity, I really believe the average trustee doesn’t have a specific agenda.
I think trustees generally love the school because it was great for them or their kid and occasionally, they have some more distant connection, like their beloved aunty loved it or it has a niche mission that is in line with a personal passion and even, occasionally, they think the whole place is just worthy and cool and they find it fascinating to watch a highly skilled group of professionals deal with everything from leaky old pipes to pandemics. (When you get a trustee like that - strong recommend!)
And never forget, trustees are volunteers and even when things are going smoothly, it’s a huge time commitment and a big responsibility. They have busy lives and for most people, board service to an independent school is one small-ish part of that busy life.
There are typically a handful of trustees, mostly officers but sometimes just those with the interest and the moral authority, who can swing things one way or another. And even these super dedicated volunteers who are head of school cheerleaders and understand the nuance and also realize swapping out personnel is probably not, realistically, the answer, can get worn down; the fight seeps out of them.
In the last section of Silver’s post, he goes on to discuss the state of late night and comedy and how it’s struggling in the current era in large part because, as he says,“Outside of sports and maybe Taylor Swift, there is really no mass culture any more.” Gone are the days everybody understood a Carson reference, even if they didn’t regularly watch or weren’t part of his “core demographic” - or a Leno reference, for that matter. Now before bed, we’re all watching niche YouTube channels or repeats of The Office we’ve seen a thousand times before. “People are struggling to connect” is a slide I use in pretty much every presentation or workshop I give. We’re all in our own, customized cultural bubble.
Of course, this is the long predicted death of legacy media, the collision of personal tech/social media culture, related political polarization but I also think fundamentally exacerbated by the existential crisis of the pandemic we are still only barely beginning to acknowledge let alone unpack.
And I mention this at length because this state of interpersonal alienation and lack of social fabric glue is making the always nuanced partnership between heads and boards even more complicated and it most certainly is helping usher the culture wars through a school’s front door.
You can be an excellent head and still lose your job. The outside forces are powerful, the circumstances can be unrelenting and internal politics can be gnarly, contradictory and have few long term solutions beyond the impossible option of blowing it all up and starting again.
What is a head and a board chair to do? Try to be honest. Try to be optimistic. Don’t over promise. You do need to explain when you under-deliver. Most importantly, preserve your integrity and do what’s right for the kids in your care. Sometimes doing the ideal thing will be too complicated or costly or be too much of a sacrifice of some kind, including to the school’s self image, and you’ll choose the work around. There’s no shame in that from time to time.
But if the financial circumstances are tough and the board doesn’t have it in them to stand up to another round of constituent criticism - and let’s be honest, it’s easy to be brave in theory but it is very hard to be brave in practice and then to be brave repeatedly. People can be big hearted and well intentioned - and tired and distracted. And our industry’s can-do culture of leadership succession tells a story that there is another incredibly talented leader just right around the corner.
As Silver says about Colbert - he’ll land on his feet. I don’t watch The Late Show but I can highly recommend the podcast episode he did with Anderson Cooper on grief. He’s talented and charismatic, reportedly a benevolent and inspiring boss and from that podcast, I would say a reflective and sensitive human. He didn’t deserve to be unceremoniously and publicly dumped (though they are giving him ten months) and neither do a whole lot of other good people out there.
But as one of my school attorneys said to me many years ago, “Everyone has a sell-by date.” You have to trust the next chapter will be worthy of your star power.
Stony Creek Strategy featured services
I’ve had a lot of conversations about governance training recently nd it’s been fun to talk to heads and board chairs, co-creating the right program to support a board for wherever stage they might be in. The most important factor in a successful governance training isn’t the content; it’s a session that connects with board members, acknowledging the challenges and rewards of the trustee role and then facilitating an open discussion about the priorities in the year ahead and what meeting those priorities - doing that job - looks like in practice.
Here’s a link to my Summer, 2025 collab on governance basics in Independent School magazine.
Reach out or hit return on this email if you’re interested in a conversation about a governance training session, on site or virtual.