Entrepreneurial Thinking for Independent School Leaders

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What makes some schools thrive while others struggle to adapt? In this episode of the Independent School Moonshot podcast, I sit down with Dr. Brett Jacobsen, President, Southern Association of Independent Schools (SAIS), to explore how independent school leaders can think like entrepreneurs—not in the Silicon Valley sense, but in a way that fosters innovation, adaptability, and long-term success.

Brett brings decades of experience as a head of school and now works with nearly 400 independent schools across SAIS. He shares how leaders can spot trends before they disrupt their schools, balance daily demands with long-term strategy, and build cultures that embrace change. We also dive into the power of small, strategic shifts, why defining a 10-year target is critical, and how creating a shared language around innovation can transform decision-making.

Whether you’re leading a school today or preparing for leadership in the future, this conversation will give you fresh ways to align vision with action—and create a school built to evolve.

What You'll Learn From Brett Jacobsen:

• Entrepreneurial Mindset as a Leadership Tool –Being an entrepreneur isn’t about disruption for disruption’s sake; it’s about recognizing opportunities, scanning for signals, and iterating in real time.

• Start with Optimization, Not Overhaul –The most successful school transformations don’t start with revolution; they begin with refining what’s already working.

• Common Language Builds Momentum –Creating shared vocabulary around strategy and innovation strengthens alignment between leadership, faculty, and boards.

• Strategy vs. Daily Demands –Leaders often struggle to balance immediate challenges with long-term goals. Productivity tools, middle management development, and clear priorities are essential.

• The Power of the 10-Year Target –Successful schools use long-range visioning to guide decision-making, measuring progress with clear benchmarks instead of rigid plans.

• Cultivating Leadership at All Levels –Schools that act as “leadership factories” empower middle management, expanding strategic capacity across the organization.

Discussion Prompts

• What signals do we see in independent school education that could shape our school’s future? How are we responding to them?

• Are we balancing strategy with daily demands effectively? Where do we need better systems?

• How does our school define entrepreneurial thinking? Are we fostering a culture that encourages problem-solving and iteration?

• What is our 10-year target? Does our current strategic approach align with that vision?

• What small optimizations could we implement now that would have a compounding effect over time?