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What does it truly mean to be a head of school today?

In this episode, guest Mark Crotty, former Executive Director of NWAIS and now Consultant and Partner at Educators Collaborative, explores how the role of headship has evolved.

He unpacks the shifting expectations for heads, the growing complexity of the job, and what aspiring leaders should know as they consider stepping into this demanding but rewarding role.

From loneliness in leadership to the board–head dynamic, Crotty offers hard-won insights from more than 40 years in independent schools.

For school leaders and boards, this episode is both a wake-up call and a guidepost. Crotty emphasizes the importance of clarity, self-awareness, and team building, while also challenging schools to rethink how they prepare and select future heads.

The conversation frames headship not simply as management of an institution, but as a calling grounded in service, vision, and the ability to see possibilities for others.

What You'll Learn from Mark Crotty:

Headship is now more complex and externally focused: Today’s heads must juggle marketing, fundraising, facilities, and brand management in ways that weren’t as central 25 years ago.
The loneliness of leadership is real: With no true peers inside their school, heads need intentional coaching, mentorship, and support systems.
Boards are both vital and challenging partners: Misalignment around strategy vs. operations creates tension; boards must see hiring a head as their most important strategic decision.
Aspiring heads must start with the “why”: Motivation matters. A desire for service, not just the title, sustains leaders through the demands of the role.
Team building is ongoing, not a one-time event: Heads must continuously shape leadership teams and practice distributed leadership to thrive.

Recommended Next Steps

Aspiring leaders should reflect on their motivation: Write down why you want to pursue headship and test it against the realities Crotty describes.
Current heads should build intentional support systems: Invest in a coach or peer group to counteract leadership isolation.
Boards should reframe head searches: Evaluate not just resumes but the person’s long-term potential and how the board itself will support them.
Leadership teams should embrace constant evolution: Use regular check-ins to assess how the team needs to shift as the school advances its vision.
Schools should integrate business acumen training: Provide aspiring leaders with exposure to finance, governance, and external relations early.

The Changing Role of Headship: Then vs. Now

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