Navigating financial strategy, executive leadership, and the impact of AI on modern business.
Get new insights by email. Subscribe
Passion is a feeling, and feelings get shaky when the ground under your profession keeps moving. What separates leaders who thrive from institutions that stall is purpose and curiosity working together. In an AI-native world, purpose has to be rewritten until it's clear enough to test against, for every decision a human or an agent makes.
AI capability is advancing on a curve that doubles every six to twelve months. AI diffusion, the rate at which organizations actually absorb that capability, moves much more slowly. That gap is the strategic window every leader should plan around.
Not-for-profits, independent schools, and most mission-driven organizations are running their teams at the edge of capacity. Budgets are flat, expectations are rising, and the people doing the work cannot imagine adding "redesign our entire operating model" to their week. That is exactly the moment to bring in outside capacity that does the building so the inside team can keep delivering.
Every week now, the dinner table conversation turns to AI, and someone proudly announces that their company is using it. That is a real and important first step. It is also Level 1. The work that will separate leaders from laggers is Level 2: rebuilding the business from the ground up for a world where the cost of answers and the cost of execution are both approaching zero.
Most organizations bring in fractional CFO leadership later than they should, and a smaller number bring it in earlier than they should. Here are the honest signals (and the faulty ones) that tell you it's time.
As artificial intelligence drives the cost of answers toward zero, the scarcest resource is not information, analysis, or execution. It is the human capacity to identify which question is worth asking. Organizations that master this skill will have a durable competitive advantage that technology alone cannot replicate.
Independent schools and education organizations are getting pressured to do something about AI. Most of what's being recommended is the wrong place to start. Here's where the real first steps are, and the order they should happen in.
Most organizations are asking the wrong question about AI. They ask: "How can we use AI to improve what we already do?" The better question is: "If we were starting from scratch today, how would we design this organization?" That shift in framing changes everything.
Most conversations about nonprofit financial sustainability start with the budget. That's the wrong place to start. The strategic moves that actually shift a nonprofit's long-term trajectory begin with a different question entirely.
Independent schools sit in an unusual financial spot: tuition-funded, mission-driven, and governed by volunteer boards. Hiring a fractional CFO who understands all three is harder than it should be. Here's what to actually look for.
The not-for-profit sector has a financial leadership problem. Many organizations are large enough to require sophisticated financial management, but too small to justify a full-time CFO. The result is a gap that costs organizations dearly, and it is entirely avoidable.
The people doing the work have already picked up AI on their own, and the gains are landing before leadership has a plan. For a 10-to-75-person shop, the move isn't a six-figure full-time hire or doing nothing. It's fractional senior leadership a few days a month to set direction and put sensible controls around what your team is already doing.
The term "first mover advantage" is being applied carelessly to AI adoption. The organizations that gain durable advantage are not those who adopt AI first. They are those who rethink fastest. There is an important difference.
Independent schools face a unique set of financial pressures: enrollment volatility, aging infrastructure, and a donor landscape with rising expectations. The schools that will thrive over the next decade are those that build genuine financial resilience now, not as a response to crisis, but as deliberate strategy.
Your second-best finance worker just closed the month three days early, and the only thing that changed was she started running reconciliations through Copilot. Before you write the next job ad, look at what's already happening under your own roof. Find the quiet adopter, learn exactly what they're using, and figure out what would have to be true to trust it across the team.
We are living through exponential technological change, and AI adoption alone is not a predictor of success. The organizations that will thrive are those that develop rigorous discipline around question formation: asking the right questions before investing in answers, and designing for genuine customer value rather than organizational convenience.