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Happy Birthday, dear TOOS! Photo by Lan Gao on Unsplash
I can and I can’t believe it’s been three years since I started writing Talking Out of School, starting from nothing and now we are at just under 1,000 subscribers! It’s such a pleasure to write for this audience and it’s also been incredibly gratifying to talk to readers when I’m out and about in the independent school world.
So before I go any further, a big heartfelt thank you to you all!
Building a business from the ground up is hard, hard in a way I didn’t fully imagine or expect. In retrospect, I think I had no idea what to expect? Kind of like when I thought it was a great idea, in theory, to take out most of the lawn and replace it with a cottage garden from scratch.
The freedom and flexibility and room for creativity is an amazing gift. Creating and self-enforcing your own work structure is tiring. And also at times pretty lonely for someone like me who both deeply appreciates solitude and is a pretty social animal.
In the day to day grind to achieve what you think of in your head as definitive “liftoff,” you can often lose sight of the fact you’ve already created something solid and substantial - and it would not be possible without this amazing readership who keeps opening up these emails and forwarding posts to friends and colleagues who subscribe. Talking Out of School is the platform that helped launch Stony Creek Strategy in 2023 and it continues to give me a way to communicate directly and with nuance to people doing the hard work of leading schools.
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Fall, 2025 - Three Years, Four Trends, Four Solutions
A lot has changed in three years. In the fall of 2022, I don’t think I ever heard the word “chatbot” or had a fleeting thought about AI and cheating. The topic of the declining school-age demographics did not come up in almost every conversation. I did not imagine the US government trying to take away 1-20 granting status from a university or cancelling international student visa interviews or ICE detaining and sending a South Korean university student from NYC to Louisiana before releasing her without comment.
Yet here we are. The instability of our current moment has exacerbated longstanding trends at a pace that is difficult or even impossible to fully digest or appreciate but we all still have to move forward.
ONE
Independent schools are under ever-increasing stress, from all directions
Enrollment, Fundraising, Auxiliary Revenue
The majority of schools are significantly struggling with enrollment at some level - whether that’s having to re-gauge what a “full” school is in 2025 or reconfiguring the criteria for a student who will prosper in your community. The schools at the top of the food chain are still full, but the pools are smaller and every school seems to be reaching into the pool of the school down the chain. Everyone else seems to be reconfiguring budgets ranging from a tweak to a major cuts. Schools that never provided much int he way to learning support are adding it and schools that had it are adding more to serve a wider range of kids. There are no easy fixes.
Enrollment is the main conduit of revenue - but it’s astonishing to me how many schools treat fundraising and alternative revenue with much less intentionality. There’s no silver bullet - all three revenue streams need to be firing on all cylinders right now. As an admissions director said to me recently, “Even if you’re lucky enough to be in a good market, today you have to be totally on your game.” That goes for all revenue generating areas.
Academic Program
The rise of generative AI is so blatantly disruptive it can’t be ignored. I’ve heard faculty are sometimes struggling emotionally when trying to work together to create AI guidelines - they are often having to significantly modify or say goodbye completely to pedagogy that is, in some cases, an extension of their personal identity and conduit to interpersonal connection with students. Of course it’s emotional - but it’s hard for the people leading change to manage. But schools need to get a handle on how to manage this fundamental threat in a proactive way. For their tuition dollars, parents have a right to expect a philosophy around generative AI and sensible, student centered guidelines that go beyond when it’s considered cheating for a student to use it in an upper school course.
In summary
The fact that schools were slow to change could sometimes work in their favor in the past - they resisted passing trends and tended to be generally risk averse. But when all the predictions start to come true at once - lower cost private schools are benefitting from government supported vouchers, homeschooling continues to be on the rise, public schools are starting to engage enrollment consultants and all the while there are just fewer kids than ever before - the inability to fundamentally adjust to a new world could be fatal for schools who were already significantly wounded after 2008 and were barely managing year to year.
And I am particularly concerned with small boarding schools. I find myself reflecting on conversations I had years ago with Bill Kummel of Rational Partners who, just looking at publicly available information, thought many small boarding schools would be in trouble due to lack of large endowments, desperately aging facilities, relatively large debt loads and a shrinking pool of tuition capable families who would continue on to be generous donors long after they graduated (i.e. domestic families). My biggest fear is that these schools were in trouble decades ago and found a way to plug the holes in a zero-inflation environment, mostly without fundamentally changing. The options for revenue are vanishing before their eyes and the conditions in the current world made a continuing tightrope walk impossible.
TWO
Constituent pressures continue to intensify, including from trustees
Another handicap of the current norms of operating is that decision making is often driven by constituent opinions and pressure vs what’s best for the future of the school.
In day to day practice, trustees are often confused about their role and perceive they are limited to a binary choice between being ineffective figureheads or being enmeshed in the day to day like an employee, often with troublesome effects.
Parents try to micromanage their child’s experience and are not afraid to be quite obnoxious and to use their donations as weapons.
Current faculty are still shell shocked from the pandemic, feel workloads are unfair and that they are underpaid. The next great teaching cohort is out there… somewhere?... asking about the potential of a hybrid work environment, moving up the ladder and the potential for pay increases in their interviews.
A belief persists that school cultures operate best with some level of vaguely defined “consensus,” a model that had some chance of more or less working when constituents - families, faculty and staff, trustees, alums - were more the same than different. More than ever, school communities are characterized by differences in expectations and values shaped by a much more diverse population, pandemic isolation, generational points of view, individual experience influenced by race, class, religion and country of origin, and pervasive anxiety. Long time school employees long for the “old days” and newer community members are frustrated that the pace of change is so slow.
And I don’t say any of this romanticizing the past. “Consensus” may have meant a congenial work environment for many people but it didn’t lead to much student-centered change. And there were many views that weren’t aired - although the people who loved consensus also love to insist all views were aired.
Trying to apply a consensus-type process to a complicated, quickly evolving topic such as AI is bound to end up in a mess.
I’ve heard a lot recently about schools undertaking a review of the basic faculty workload, the third rail of independent school decision making. If you’re making a tweak - maybe you can do it yourselves. If you’re trying to take on the basic structure of the faculty workload - I strongly recommend bringing in a consultant who has an outside perspective (Not self-promotion! Not my wheelhouse.)
THREE
Communications remains under-appreciated and misunderstood
Recently, I was casually chatting in a social situation with a new-ish head I’d just met. The head runs a large, established, thriving school. The head mentioned a new development at school that needed (and this is my description, not the head’s) an intentional communications plan. Not anything elaborate but it was information that needed to be managed. The head then described the decision that was made around the “who-what-when and how” of communicating the news and it made perfect sense - from one viewpoint. The decision was in motion and that’s why the person was thinking about it. And then we continued on, chatting about other things
But I felt bad because the sensible plan the head described was highly unlikely to have the desired impact - in fact, it was probably going to create the opposite effect. I could understand why the head made the decisions that were made. A lot of time and thought went into the decisions. I didn’t try to offer a different perspective because we were just making social conversation; the head wasn’t coming to me for advice - besides the fact, the wheels were in motion.
This kind of thing comes up so regularly that I think, as a sector, there is still just not a consciousness, let alone a respect or appreciation, about how helpful a communications professional can be in leading a school. When schools run on relationships and, as noted above, constituents are more complicated and sensitive than ever, professionals who are deeply skilled about how information is processed and understood by recipients are more important than ever.
I think the importance of marketing is more widely accepted than it has ever been, but for all the other crucial functions communications fulfills - that is still a work in progress. Largely, communications is a service office not an equal partner.
And this is related to Number Four…
FOUR
Leadership, including governance, is often operating on instinct, emotions (including what feels right in placating vocal constituent groups) and what worked in the past, in a very different context.
New leaders are thrown into complicated situations an experienced pro would struggle with, yet expected to excel. Well meaning and enthusiastic new trustees are left wondering what their actual job is and sometimes, in an attempt to be useful, they create operational headaches.
It’s not that there aren’t a lot of great leaders out there. Because there are - a lot of wise, courageous, calm leaders who, every day, get up and move their schools forward. But successful schools aren’t about one great leader. They’re about a great leader and a great team of senior administrators and a great board. One senior admin said to me recently, “I feel like all we do is struggle to address one problem after another.” Who wants that job?
Many people who rise through the ranks of schools have developed some very good instincts for how to manage and how to lead. But there is a lot about leadership that is counterintuitive and you only learn by a combination of experience, reflection and increasing your knowledge through working with others who are experts in their area, including senior team members and board members and seeking out helpful leadership development insights and programs.
It is not necessarily an instinct that, in a crisis, to be clear and transparent, don’t try to ignore it, deny it or cover it up. Complicated information? Try to deliver it straight and not bury it because the worms always end up leaking out of the can in the end. People complaining? Don’t shut it down or feel the need to immediately fix it but listen hard, be curious, ask questions, engage. And if they won’t engage, put your energy into the people who will. Senior admins disagreeing with you? It may feel like they’re questioning your authority but they are also comfortable enough to disagree with the boss, a real strength.
Twilight of the genteel all-volunteer board of trustees?
Since I started working on governance topics about 18 months ago, I’ve discovered the degree to which the governance function is struggling is quite eye opening. And the myriad ways this can manifest is also eye opening. And of course, if the governance function is not strong, the school is in a very poor position to deal with all the other challenges in front of it. The workaday tragedy of the governance struggle is that trustees really love and want to do right by the schools they serve, but often fail in the attempt. They need better tools and more support.
Boston University now has TWO full time administrators who both serve on the board and support the board - a general counsel and a chief of staff equivalent. The days of the genteel volunteer board may be coming to a close - how will schools embrace this fact?
FOUR SOLUTIONS
I do truly think that given how fundamental the shake up is right now, this could be a huge opportunity - if school leaders can effectively harness the moment.
ONE
Align and differentiate
I believe most schools aspire to be the best version of themselves. And I also believe the gap between identifying effective strategy to move a school forward and implementing that strategy lies mainly in a lack of alignment. A lot of time and money can be invested in developing a very exciting new vision for the school that has little correlation with who the school really is and how it truly operates. Once a school aligns, gets energized by realizing existing strengths, identifies where it can amplify to create differentiators and then develops language to capture who the school is, how people at the school truly behave and where it is headed in the future, that is the only silver bullet.
“Differentiation” has been repeated so much I expect it lands on deaf ears or feels like a facile cliche. But schools need to explain how they are different from competing public schools, other independent schools, homeschooling and the demanding opportunity to play with that elite travel team that holds out the hope for your kid to get that D1 scholarship. Besides, isn’t it a real pleasure to really explore what makes your school, your school, that place you love so much and have so much belief in?
If you do this work and create the language to discuss your vision and values, you don’t need an elaborate implementation system - you have a simple litmus test for whether or not that initiative is strategic in nature or not. At Westover, we did a brand refresh around the concept of “Confident and Connected” and before we even had a strategic plan, we knew it was real, relevant and living at the school every day. As leaders, we also understood to make decisions based on whether it was supporting the development of the student’s confidence and enhancing their connections to each other and to the wider community.
TWO
Grind away on all revenue sources - no silver bullets.
It is amazing how many schools neglect the fundamentals in admission. Always have a human answer the phone. Make sure you have contact name rather than an admissions@ address for people to make an initial contact. I could go on. Also make sure you’re on your financial aid game and don’t leave tuition dollars on the table. You can also take similar simple steps to start to optimize your fundraising. Evaluate your price points and popularity of your offerings for auxiliary programs. These are all examples of doable, mostly free of charge steps you can take, right now.
THREE
Leaders at all levels - Increase your skills at leading change and navigating conflict. Appreciate that both communications and management often are counter intuitive and don’t just lean into the relational patterns that perhaps served you in the past.
This summer, I’ve found myself saying, “leadership happens one conversation at a time” on repeat. Yes, some people are naturally good at connecting with and managing people. Most people are not naturally good at managing people because people are messy and complicated, they change as individuals over time and stress generally doesn’t bring the best out in anyone. Besides the fact that if you’ve been doing this kind of work for more than ten years, the makeup of the school, at all levels, has fundamentally changed and your tactics may have worked great in a different time and context.
You can’t lean on charm and charisma or micromanaging every detail or wielding your authority to force people on board. We need to get away from thinking that magic personalities will come and lead our schools out of darkness by dint of their incredible and rare gifts. Leadership is hard and the skills it demands need to be developed intentionally. We all have the potential to be our own worst enemy when it comes to leadership.
This goes for boards, too.
Trustees are people, too! They are people in powerful, ill-defined, high status, volunteer jobs. They need to be spending time on how to lead consciously, generously and wisely, appreciating how to use their power to support the school. This will often mean navigating complicated situations and interpersonal interactions to establish what the greater good indeed is and how best to get there over time. It means getting their chapter right in the greater book of the life of the school.
If the definition of insanity is repeating the same actions but expecting different results, independent school governance might just be accurately described as insane at this point. It’s time to think about truly new and innovative solutions that will genuinely help passionate volunteers do their jobs well.
FOUR
If you’re a school leader and you don’t really “get” what I’m saying about communications, here’s a place to start.
And then get curious! Talk to your comms person! If you have a small office with a small purview, reach out to a few other schools with bigger offices - see if you can talk to the heads and the comms director. Become an annual subscriber to TOOS and use your two free sessions to deconstruct some constituent communication that didn’t go as well as you liked. Often a bad communications rollout can fester in certain quarters and it can eventually lead to much bigger problems…
This might all feel a little daunting - but truly, I’m excited about the year ahead. The pilot Boss Skills Lab launches Monday August 18th. Brand strategist extraordinaire and generally fabulous human Michele Levy and I are polishing up a one page marketing piece about our Align and Advance strategic planning offering. I continue to be deeply energized by leadership coaching. The only way to deal with all the norm disruption is to believe there is hope for new and exciting possibilities, even if it take a while for us all to get there. Humans are resilient and our schools will be resilient, too - they need to be for our kids!
Enjoy the weekend, everyone!
The birthday sale is on - from now until September 1, get 20% off an annual subscription to TOOS that includes TWO one on one, 45 minute coaching or consulting sessions with me - for $79.20 That price is in-sane!