Peter Baron's Linkedin Analytics

It so often comes down to execution. #schooloperatingsystem

Advisor Spotlight: Mattingly Messina Meet Mattingly Messina, one of our Moonshot Lab Advisors. Mattingly and his firm, Throughline, help organizations reimagine their fundraising to be relationship-first, strategic, sustainable, and rooted in trust. He brings a unique background: former Director of Advancement at Bentley School, alumni leader and trustee at St. Margaret’s Episcopal School, and previously a negotiator at Google, where he crafted arguments in high-stakes legal and regulatory environments. That rare blend of advancement expertise, communications strategy, and negotiation chops makes him an incredible asset to school leaders looking to rethink their development approach. Why it matters: Mattingly helps Moonshot Lab members shift from transactional fundraising to long-term relationship building, while aligning advancement efforts with their broader financial strategy. Moonshot Lab members can access Mattingly and other top experts at no extra cost. Whether it’s about engaging boards, building sustainable giving programs, or refining how you communicate your case for support, he’s here to help. If you could ask Mattingly one question about fundraising strategy or relationship-building, what would it be? Drop it in the comments.

Advisor Spotlight: Bridget Johnson Meet Bridget Johnson, one of our Moonshot Lab Advisors. Bridget is a longtime advocate for student life professionals and a leader who understands the deep connection between community, care, and culture in schools. She founded the Deans' Roundtable in 2012 after recognizing a clear need: student life leaders lacked sufficient support and professional development. Since then, the Roundtable has become a go-to hub for connection, learning, and growth among deans nationwide. Before entering consulting, Bridget served as Dean of Students at Milton Academy, where she led initiatives on restorative discipline, health services reform, emergency response systems, and residential life. She later became Associate Executive Director at Prep for Prep, helping prepare high-achieving students of color for success in independent schools. Why it matters: Bridget helps Moonshot Lab members think critically about leadership, culture, and care, especially how student life and school operations intersect with strategy, equity, and organizational growth. Moonshot Lab members get access to Bridget and other top experts at no extra cost. Whether you’re building systems to support student well-being or navigating leadership challenges across teams, she brings wisdom, clarity, and a restorative mindset to the conversation. If you could ask Bridget one question about student life leadership or restorative practices, what would it be? Drop it in the comments.

How to increase your strategic leadership skills as an aspiring head of school: • Ask more “why” questions • Engage more with financial data • Practice more cross-functional collaboration • Stress-test more ideas with your team If you’re aiming for headship, you need to be fluent in how schools operate, not just educationally but financially and strategically.

Advisor Spotlight: Dr. David Hanson Meet Dr. David Hanson, one of our Moonshot Lab Advisors. David brings decades of experience in finance, operations, legal affairs, and risk management to his work with schools, and he does it with an eye for strategy that’s both precise and expansive. He currently serves as Chief Financial and Operating Officer at The Branson School in Marin County, CA. He is a partner at Winthrop & Associates, where he advises schools and nonprofits on long-term sustainability. His past leadership roles span Phillips Exeter Academy, a global nonprofit foundation, Virginia Commonwealth University, and Emory University. David also has a deep legal background, including being a U.S. Army JAG Corps veteran, a former federal staff attorney, and a Fulbright Scholar twice. His expertise helps leaders move from reactive management to strategic decision-making grounded in data, clarity, and strong governance. Why it matters: David helps Moonshot Lab members make sense of the complex financial and operational realities facing independent schools while sharpening their ability to lead with confidence. Moonshot Lab members get access to David and other top experts at no extra cost. Whether you’re staring down a tough financial decision, thinking through risk, or working to align operations with strategy, he’s someone you want in your corner. If you could ask David one question about financial leadership or operational strategy, what would it be? Drop it in the comments.

Most school leaders inherit an operating model they never learned to question. The budget. The meeting formats. The org chart. The tuition strategy. All passed down, rarely reimagined. We don’t go deep enough in preparing future leaders for the business of running a school. That’s why I built this framework. These eight business competencies are the foundation behind MoonshotOS. They’re what every independent school leader needs to understand... not just heads but anyone aspiring to lead. I hope you can use them to direct your learning to help you today and down the road. #independentschools #schoolleadership #aspiringleaders #moonshotos

Strategic plans are often ambitious, and with good reason. Schools want to grow, stay relevant, and meet the evolving needs of their communities. That kind of ambition is healthy. But when everything feels urgent, it’s easy to lose traction. The plan gets crowded. Priorities compete. And eventually, the work stalls. The most effective plans don’t try to do everything. They help schools clarify what matters most — and do the hard work of deciding what can be left behind. That process takes honesty. It takes courage. And it takes a shared commitment to focus not just on what’s possible, but on what’s essential. This isn’t about cutting back. It’s about aligning your energy with your purpose so the work that matters has room to succeed. That’s what real strategy makes possible.

If you can’t execute your strategic plan, your vision doesn’t matter. Most schools have big ideas. The problem is turning them into action. It’s not about working harder. It’s about building the best structure. Even the best strategy will stall without an operating system that sets the right meeting schedules, progress check-ins, and accountability practices. Vision without execution is just wishful thinking. Execution without vision is just spinning your wheels. You need both. A School Operating System gives your team the foundation to make real progress, not just talk about it. If you’re serious about moving forward, it’s time to ask the hard question: Are we better at dreaming or doing? #MoonshotOS #IndependentSchools #SchoolLeadership #StrategicPlanning

This was a good week. Welcomed new folks into Moonshot Lab. Always gratifying to see the community grow. Hit six weeks post-ankle surgery and officially out of the boot (yah!). And heading into a quiet weekend before a busy stretch with two graduations. I appreciate weeks like this. Happy weekend, everyone!

Independent schools aren’t just mission-driven. They’re market-driven, too. Sustaining success today requires leaders who can: • Stay true to the mission • Build the skills to create a sustainable business model Great ideas aren’t enough anymore. You need great strategy, too.

I built Think Like a Head of School because too many aspiring leaders are left to figure out the business side of school on their own. The course is a free six-part email series that introduces the financial, strategic, and operational skills every school leader needs but most were never taught. Reading the testimonials from those who’ve taken the course means so much to me. Their words are a reminder that the time and energy behind this work matters. It’s clear the next generation of leaders is ready to grow. If you’ve taken the course and found it helpful, thank you. Truly. If you haven’t yet, you can check it out here: 🔗 https://lnkd.in/g6UcGMQ6 #independentschools #schoolleadership #aspiringleaders #moonshotos

Signs your school’s strategic plan is at risk (and how a School Operating System can save it): 1. There’s no shared understanding of priorities. 2. Everyone’s working hard, but not necessarily on the most important things. 3. Teams operate in silos, and strategic goals get lost between departments. 4. Decision-making feels reactive. 5. Instead of steering toward the vision, the leadership team is stuck putting out fires. The truth is, a great plan isn’t enough. Even the best strategy will stall without a system underneath it, the structure, rhythms, and accountability to keep it alive. That’s where a School Operating System makes all the difference. It keeps your leadership team aligned, focused, and moving forward together, week after week. If this sounds familiar, it might be time to take a closer look at how your operating system is (or isn’t) supporting your vision. #MoonshotOS #IndependentSchools #SchoolLeadership #StrategicPlanning

The week’s almost done. If you’re like most school leaders I talk to, this time of year is packed. You’re closing out the year celebrating students, planning, managing transitions, and still finding time to show up for your community. So, if it’s felt like a sprint lately, you’re not alone. Here’s your reminder: • You don’t need to have it all figured out. • Progress beats perfection. • Rest is part of the work. Keep going. You’re doing meaningful, often invisible, work that shapes lives. See you next week. #independentschools #schoolleadership #aspiringleaders #moonshotos

I really appreciate Brendan Schneider’s vulnerability in sharing his story. What stood out to me: no career path is linear. Embracing adaptability isn’t optional. It’s essential. Worth your time:

Let’s talk about uncertainty because it’s hard to get a clear read on where the broader economy is headed. If you’re leading an independent school, that ambiguity can be unsettling. Some pressures are already here, like rising costs and admission yield concerns. Others may surface later this year. What I’m noticing: schools that prepare for multiple scenarios, instead of hoping for stability, are in a stronger position. That’s certainly how I operate. I like to have a Plan A, B, and C—and then keep D in my back pocket. Here are a few questions I’m encouraging Moonshot Lab members to ask: • What assumptions are baked into next year’s budget that need stress testing? • How would a dip in enrollment or philanthropy affect your model? • Are you exploring new revenue opportunities, or just maintaining the existing ones? • What early signs are you watching that might hint at bigger shifts ahead? No need to panic. But it is time to plan with purpose.

Most independent school boards have an advancement committee. But is that structure serving your school's mission or just maintaining the status quo? In the latest episode of the Independent School Moonshot Podcast (Is It Time to Rethink Advancement at the Board Level?), I talked with Mattingly Messina, founder of Throughline and an advisor at Moonshot Lab, about rethinking advancement at the board level. Here's some of what we covered: • Why organizing boards by function (finance, facilities, development) limits impact • How to embed philanthropy across every committee, not just the fundraising one • Why we need to stop apologizing for fundraising and start leading with clarity If you're a head of school, an aspiring leader, or a trustee, this is worth a listen. Listen here: https://lnkd.in/gRcpPtpg. You can also find it on your favorite podcast app (Apple Podcasts, Spotify, and more). Thanks to RG175 for sponsoring this episode of the podcast!

I was talking to a head of school today who didn’t realize I host a podcast about exploring the business side of independent schools. Totally fair. It’s easy to miss with everything going on. But if you didn’t know either, let me introduce it to you: I host the MoonshotOS' Independent School Moonshot Podcast. It’s where I share stories of schools rethinking the business model and the leaders driving that change. Here are a few recent episodes: • How Auxiliary Programs Can Transform Your School’s Bottom Line • Should Independent Schools Think Like Businesses? • Winning Recruitment Strategies for a Competitive Independent School Market • How Daycroft School Grew Enrollment by 99% in Just 5 Years You can listen on your favorite podcast app: Apple Podcasts: https://lnkd.in/gx7YPvf7 Spotify: https://lnkd.in/gUG-gVHp Or check out all episodes here: https://lnkd.in/gmXhFhax If you’re an independent school leader or aspire to be, I hope you’ll give it a listen.

It felt good to be back out in the world post-ankle surgery on Tuesday, sharing what I’ve learned from more than 100 conversations with heads of school about the independent school business model Huge thanks to the Northwest Association of Independent Schools for inviting me to speak at the Business Officers Conference and to all of the CFOs in the room. It was a privilege to connect with so many of you. Also… first time presenting while balancing one leg on a scooter. Grateful to be mobile and back in the mix.

Really excited about the next few episodes of the Independent School Moonshot Podcast. It’s a terrific lineup. Susan R. Perry, PhD, MSW, LCSW joins me to talk about leadership growth and how to be intentional about your development. Mattingly Messina breaks down the connection between successful fundraising and strong board governance. And Julie Faulstich shares why learning to say no is one of the most powerful tools a leader can use effectively. If you work in or around independent schools, these conversations are well worth a listen. Subscribe on your favorite app: Apple Podcasts: https://lnkd.in/gx7YPvf7 Spotify: https://lnkd.in/gnu2RNhx

Excited to speak at today’s Northwest Association of Independent Schools Business Officers Conference! I’ll share what I’ve learned from 100+ heads of school about the independent school business model. I’ll be presenting while balancing on one leg and resting the other on my scooter (ankle surgery makes things interesting!). Big thanks to Mark Crotty and Emily McGrath for the opportunity to join this important conversation. And to my wife, Akiko Baron, for driving me to Tacoma today!