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What if strategic planning in independent schools wasn’t a one-off exercise but a living, breathing practice woven into daily culture? In this episode, Alanna McKee, founder and CEO of Scarlet Oak Consulting, challenges schools to move beyond glossy one-pagers and accreditation checklists.

She makes the case for strategy as a continuous leadership mindset, anchored at the board level, carried through senior leadership, and embedded across faculty and staff.

Together, we explore how schools can balance bold ambition with realistic execution, operationalize strategy so it doesn’t collect dust, and create a culture of innovation where testing small ideas builds the muscle for bigger shifts.

Alanna also shares candid thoughts on revenue diversification, board governance, and how overwhelmed heads can get started without overcomplicating the process.

What You'll Learn from Alanna McKee:

Strategy is not a document; it’s a culture: Effective schools embed strategic thinking into boardrooms, leadership meetings, and faculty practices.
Boards set the tone: Strong orientation, generative thinking, and tools like “Elmo, Enough, Let’s Move On” help keep them at the right altitude.
Operational plans are non-negotiable: Without them, even the boldest strategic vision struggles to gain traction.
Ambition must be matched with achievability: Schools must prioritize, make trade-offs, and build the endurance to test and scale ideas.
Innovation grows from small experiments. Celebrating both wins and failures creates a safe environment and builds the innovation muscle across the organization.

Recommended Next Steps

Audit your school’s current approach. Do you have a true operating plan tied to your strategic vision?
Train your board and leadership team in generative thinking and strategic decision-making.
Introduce small, low-risk experiments that test new ideas and build confidence in innovation.
Tie KPIs directly to your strategic goals and make them a standing agenda item at board and admin meetings.
Begin revenue diversification discussions with an openness to non-traditional streams that don’t dilute mission impact.

Everyone in Your School Should Be a Strategist

Independent School Moonshot Podcast