What You Need to Know Before You Become a Head of School

This episode of the Independent School Moonshot Podcast is sponsored by Searchality. Designed exclusively for K-12 education, Searchality makes hiring easier for schools and job searches smoother for teachers, both in the US and internationally.

What does it actually take to be ready for headship in today's independent schools, especially when the job increasingly focuses on running a complex business operation rather than solely leading academics?

In this episode, we sit down with Leigh Toomey, CEO and founder of LeadHERship Educational Solutions and former head of school, to unpack what leadership readiness really means.

Leigh brings a rare blend of business training and school leadership experience, offering a practical lens on operational fluency, board relations, and the realities new heads often underestimate.

The conversation centers on a familiar challenge for many aspiring and current leaders, particularly women coming from academic pathways. They are already leading and making decisions, but often lack clarity, confidence, or exposure to the business and governance sides of schools.

Leigh shares concrete strategies for building that capacity before stepping into headship, from advocating for access to finance conversations to reframing budgets and advancement as strategic tools. This episode is a grounded, honest look at how schools can better prepare leaders for the full scope of the role.

What You'll Learn from Leigh Toomey:

1. 1. Leadership often starts before the title: Many aspiring leaders are already doing the work of leadership through influence, decision-making, and team leadership. The gap is recognition, not capability.
2. Operational fluency matters as much as vision: New heads often underestimate how much time is spent on finance, enrollment, advancement, and systems. Understanding these areas early reduces overwhelm later.
3. Budgets tell a story about priorities: A school's budget is not just numbers. It reflects mission, values, and strategic choices. Heads must engage budgets as narratives, not inherited checklists.
4. Delegation requires trust and accountability: Sustainable leadership depends on building strong teams, trusting expertise, and holding people accountable through clear systems and expectations.
5. Boards need clarity, not reaction: Effective heads manage up by helping boards distinguish between urgency and importance, grounding decisions in strategy, and consistently reinforcing shared priorities.