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I had to do a double take when I saw this—54% of visitors to the registration page have signed up for my webinar, What is a School Operating System? That kind of response is exciting (and frankly pretty uncommon in my experience) and tells me school leaders are eager for better ways to execute their strategic plans. Coming up with a strategic plan is one thing, but actually making it happen? That’s where things get tricky. The School Operating System (SOS) is designed to help leaders turn priorities into action, and tomorrow, I’m pulling back the curtain to show you how it works. If you’re looking for a way to bridge the gap between strategy and execution, join me tomorrow at 1 pm ET for a free webinar. I can’t wait to share.

In the past few weeks, I’ve had several conversations with school leaders who are concerned that their differentiators aren’t coming through clearly in the market. Families have more choices than ever—charter schools, public schools, micro-schools, online schools, and even homeschooling. That’s a radically different market than most schools faced just 10 years ago. And here’s the challenge: if a prospective parent can’t quickly and clearly explain what makes your school worth the investment, you’ve lost ground—no matter how strong your program or mission might be. Too often, the essence of what makes a school special is vague, generalized, or buried under layers of language. Here’s a question worth asking: If you talked to five parents in your community, would they all say the same thing about why your school is special? If not, it might be time to take a fresh look at how your school shows up in the market.

We’re not that far from wrapping up the school year, so we’re right on the edge of planning season. •Strategic plans will be reviewed. •Goals will be set.  •Priorities will be debated. But the real work? Figuring out how to actually get it all done. Behind every strategic plan—successful or stalled—is a set of habits, structures, and routines that guide how work gets done. Whether you call it this or not, what you’re relying on is your school’s operating system. The reality is that most schools already have one. They may not realize it. It’s how you plan, prioritize, run meetings, communicate, make decisions, and hold each other accountable. The question isn’t if you have an operating system. It’s whether that system is intentional or just evolved over time. When strategic plans stall or priorities start to blur, it’s usually not a vision problem. It’s a systems problem. As the author James Clear puts it: “You do not rise to the level of your goals. You fall to the level of your systems.” So here’s the invitation: Before locking in next year’s goals, take a moment to reflect on the system that will help you get there. •Are you clear on your annual goals? •Are you breaking them into 90-day sprints?  •Are you tracking the Key Performance Indicators (KPIs) that matter most? •Do your weekly meetings drive momentum or just burn time?  •Is your team aligned on what matters most? We fall to the level of our systems. Do you need help building an intentional school operating system? I’d be glad to talk.

There can be a natural roadblock to asking for money. For some, fundraising feels overwhelming. Who has money? Who doesn’t? The fear of making the ask. But as Jill Goodman shares in this episode of the Independent School Moonshot Podcast, the ask is actually the smallest part of the process. 🔗 https://lnkd.in/gue4V-2C The real work? Building relationships. Connecting with donors and aligning vision and inviting them to collaborate on ideas energizing the school and the donor. By the time you actually ask, it’s a natural next step. Check out this short clip, then listen to the full episode for a deep dive into the head of school’s role in fundraising, building donor relationships, and what makes a development program successful. #IndependentSchools #Leadership #Fundraising #SchoolGrowth #MoonshotOS

What’s one system you could install next week to make your leadership team more effective? It could be a shared dashboard. It could ask: “What are we solving for this week?” It could be committing to one 90-day goal—and aligning your team around it. Small systems, repeated consistently, build strong schools.

Independent school leaders, I’m curious: What’s your biggest challenge right now? Hiring and retention? Managing competing priorities? Executing strategic plans? Feeling stuck in a cycle of reacting instead of leading? These are the issues I hear every single week when I talk to heads of school. This Thursday, I’m hosting a free webinar to dig into a solution: The School Operating System. It’s a way to bring structure to leadership, prioritize the right work, and actually execute strategic goals. Join me: Thursday, March 20 at 1 PM ET Register here: https://lnkd.in/gT5SqMvb I hope to see you there.

I’ve had so many great conversations with heads of school about turning strategic plans into action. It’s not always easy—good systems play a huge role in making it happen. That’s why I’m hosting a free webinar on March 20th at 1 pm ET to explore how a School Operating System (SOS) can help bring your strategic vision to life. If you’re looking to move from big ideas to real results, I’d love for you to join me. 👉 Register here: https://lnkd.in/gT5SqMvb #SchoolLeadership #IndependentSchools #StrategyExecution #MoonshotOS

Julie Faulstich’s Talking Out of School newsletter (a must-subscribe, by the way) recently pointed me to an insightful piece by Trace Urdan: Surviving the Higher Ed Apocalypse. While higher ed is grappling with declining enrollment, shifting demographics, and financial pressures, independent schools are navigating their version of these challenges. The dynamics may differ, but the need to adapt and make thoughtful decisions is the same. One key takeaway? Schools that actively shape their future will be in the strongest position to thrive. Trace notes that many institutions have struggled to adapt because “for a sector that has known nothing but volume and price growth for generations, it has no instincts or muscles to manage contraction and consolidation.” For independent schools, give thought to: • Understanding your market position. Where is demand shifting, and how is your school responding? • Investing in your value proposition. Stand out in an era where families have never had more schooling choices. What makes your school compelling today—and tomorrow? • Strengthening financial resilience. Are you exploring sustainable ways to grow beyond tuition? Independent schools have always evolved to meet the moment. The key is doing so with intention. Read the article—it’s worth your time:

One of the biggest takeaways from my conversations with heads of school is this: Crafting a strategic plan is one thing (and incredibly important thing, mind you)—executing it is a whole different challenge. Many leaders feel stuck in the gap between big ideas and everyday realities. I get it. It’s easy to lose momentum when there are a thousand competing priorities. That’s why I’m hosting a free webinar on March 20th at 1 pm ET to introduce the concept of a School Operating System (SOS). My goal is simple: help school leaders turn strategy into action with clarity and confidence. Here’s the thing—good systems increase your odds of both short- and long-term success, especially if you’re tackling your school’s business model. Having the right framework in place can make all the difference. If you’ve ever felt the frustration of seeing a great plan stall, this session is for you. 👉 Register here: https://lnkd.in/gT5SqMvb #SchoolLeadership #IndependentSchools #StrategyExecution #MoonshotOS

What a week! I spent a terrific few days working with customers to implement the School Operating System and running a business model retreat. Nothing beats the energy of helping independent schools build exciting futures. Next, I’m headed to Boston on Tuesday to give the keynote address at next week’s SPARC Summit. Hope to see you there!

“If your strategic plan doesn’t feel like a risk… it’s just a plan.” That quote from Tom Olverson has stuck with me. In an episode of the Independent School Moonshot Podcast, Tom—former head of school and consultant with RG175—joined me to share lessons from his book Leading Through Strategy: How Business Principles Can Help Independent Schools Thrive. We unpacked: •Why strategic plans often share similar themes •How schools can clarify their market position without simply following others •Ways to bring a strategic lens to leadership without needing an MBA •What it means to make intentional choices—and why that can feel uncomfortable Tom offers a practical, grounded take on approaching strategy in independent schools. Whether you’re leading strategic work or just starting to build your thinking in this area, the conversation offers plenty to consider. Listen to the podcast: https://lnkd.in/eQ-dq7r3 Check out the book Leading Through Strategy: https://a.co/d/9BbfvYB #IndependentSchools #SchoolLeadership #Strategy #MoonshotOS #AspiringLeaders

Most independent school leaders know something has to change. But iterating the school’s business model isn’t easy work. It’s complex. It’s layered. And it’s easy to second-guess your thinking when you’re tackling it alone. That’s exactly why I created Moonshot Lab. And why I just launched the Moonshot Lab Advisors Program. These aren’t one-time speakers dropping in for a webinar. They’re experienced, trusted professionals. People who understand how schools work and what it takes to build a more resilient, sustainable model. Now, Lab members have direct access to that insight. Whether you’re pressure testing a tuition strategy, refining your marketing approach, or building your enrollment pipeline, you don’t have to do it in isolation. You have a bench of advisors ready to support you. If you’re serious about evolving your school’s business model, this gives you an immense advantage. Learn more and join the Lab: https://lnkd.in/gz-wgEmt

More and more schools are turning to auxiliary revenue to help balance the budget, and it makes sense. Costs are rising, and what may have once been considered a "nice to have" is quickly becoming a critical part of the financial model. I’ve gotten to know the folks at SPARC, Summer Programs and Auxiliary Revenue Collaborative (Nat Saltonstall, Karen McCann McClelland, Bob Rojee, and David Sullivan), and their work with independent schools is critical right now. They help schools think intentionally about how to grow non-tuition revenue—aligning new opportunities with mission, brand, and long-term goals. Here’s what I’m hearing and learning from them: • Auxiliary programs need ownership. When it’s just tacked onto someone’s existing role, reaching its potential is a real challenge. •Treat it like a business unit. Strategy, P&L, goals—it all matters. •Listen to your market. Families, local partners, and alumni can surface ideas you haven’t considered. • Know your numbers. A financial deep dive often reveals which programs are pulling their weight. • Think beyond summer. There’s opportunity in before/after care, adult learning, global ed, and more. Auxiliary revenue is coming up frequently in my Business Model Retreats—not as a trend, but as a necessary response to rising costs, increased financial pressure, and the need to create more resilient school models. If your school invests here, I’d love to hear what’s working. #independentschools #schoolbusinessmodel #auxiliaryprograms #moonshotos #sparc

Yesterday, I had an incredible conversation with someone who took my free email course, Think Like a Head of School. They told me they started it while on vacation—yes, on vacation—and within days, they were already texting their head of school about what they were learning. That hit me. When I created Think Like a Head of School, my goal was simple: help aspiring school leaders connect the dots between the different moving parts of running a school. Too often, we get siloed in our roles—admissions, development, teaching, finance—without seeing how they fit together. I designed this course to change that and give leaders the tools to think more strategically and holistically. Hearing how this person, who has experience across multiple areas of school leadership, found the course genuinely impactful was deeply gratifying. They even added their course certificate to their LinkedIn! This is why I do what I do. To help leaders build confidence, see the bigger picture, step into their next role prepared, and think about how to iterate the business model. If you’ve taken the course, I’d love to hear what stood out to you. If you haven’t, maybe now’s the time? 🔗 https://lnkd.in/geBrNc3f #independentschools #leadership #schoolleadership #professionaldevelopment #career

In a webinar late last week, someone asked me if I knew of any schools wrestling with Baumol’s Cost Disease—and I loved the question. It sent me down a rabbit hole, flipping through my podcast interviews to see where this challenge shows up. Admittedly, I wasn’t familiar with Baumol’s Cost Disease, so I looked it up. Here’s what I learned: If you’re new to the concept, Baumol’s Cost Disease is what happens when salaries rise in labor-heavy industries, like education, not because productivity increases but because wages in other sectors go up. Unlike manufacturing or tech, where efficiency gains allow companies to produce more with fewer people, schools still need roughly the same number of teachers per student as they did decades ago. So when salaries rise (because they have to), tuition has to go up, too. Independent schools are living this reality every day. If you’re thinking about how to navigate this, here are a couple of podcast episodes worth a listen: Transparency in Action: How McGillis School Reimagined Tuition to Support Teachers and Sustainability https://lnkd.in/gx-uSB58 Cultivating a Culture That Attracts and Retains Great Teachers https://lnkd.in/gs_jYHcH I would love to hear how your school approaches this—reply below or DM me to let me know what you see.

About to take the podium at the SPARC Auxiliary Revenue Summit! Grateful for the opportunity to keynote and dive into how a School Operating System (SOS) can help schools build stronger, more sustainable auxiliary programs. Thanks to SPARC, Summer Programs and Auxiliary Revenue Collaborative, Nat Saltonstall, Karen McCann McClelland, Bob Rojee, and David Sullivan!

The podcast is on fire right now. Every time I'm at an event, I hear from multiple people who are tuning in and using the episodes in fundamental ways. One school leader recently shared that they used several episodes to facilitate a board meeting and inform their business model conversations. That completely blew me away. Playing even a small role in that kind of work is an honor. And that's just one of many conversations I've had lately. Curious what's coming up on the pod? Here's a quick preview: • You'll learn how one school doubled enrollment • You'll hear about the power of saying no • You'll get insights from a higher ed expert on the challenges facing the industry • You'll discover what one leader's research uncovered about teacher retention • You'll hear from a strategic planning expert And much more. If you're an independent school leader, advocate for our schools, or just passionate about the work—and you haven't discovered the podcast or hit subscribe—I suggest checking it out: 🎧

I’m happy to share that I obtained a new certification earlier this year: Certified Top Coach™️ from Top Teams! I'm excited to support independent schools in executing their strategic plans. Drop me a DM to learn more!

Just wrapped up an incredible few days at #NAISThrive, and I’m feeling deeply appreciative of the chance to reconnect with so many amazing people—some of whom I’ve known for two decades. And I can’t wait for next year in Seattle! Thrilled for everyone to visit my hometown and experience a little of what makes the Pacific Northwest so special. To get you excited for the trip, here are some photos I’ve taken of Mt. Rainier and other cool spots. Plus, my dog is always ready to say hi! #IndependentSchools #Seattle2026 #Leadership #MoonshotOS

Heading to Colorado to work with schools—and of course, wearing my ASSOCIATION OF COLORADO INDEPENDENT SCHOOLS beanie. Seems fitting!