From Headteacher to Executive Leader: Letting Go to Lead Well

“I think I’m a bit controlling,” James (not his real name) said with a smile in one of our early coaching conversations. He wasn’t talking about micromanaging staff or making every decision himself. He meant what many successful headteachers would recognise: being present, hands-on, and holding the reins. Knowing what’s happening in every corridor, being visible at the gate, fielding questions from parents, offering a listening ear to staff. The leader who sees, hears, and steers.

But in September 2025, James will become Executive Principal of two secondary schools. And that kind of leadership no longer scales.

This article explores what it means to step into executive leadership across two schools with very different contexts. It’s a story of transition, of identity shift, and of learning to lead through others. And it offers a wider reflection on what executive leadership requires; in mindset, in strategy, and in self-awareness.

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Two Schools, Two Realities

James is currently the substantive principal of a securely ‘Good’ secondary school. It’s around average in size and pupil demographic, with low EAL, SEND levels in line with national, and deprivation levels around the national average. He’s been in post for several years, has established a strong leadership team, and enjoys the trust of his staff, students, and community.

In September, he’ll step into an executive role across two schools. His current deputy will take on the substantive head of school role, supported by the strong team and systems already in place.

His second school is more complex. It’s larger, with over 1,100 students. The deprivation indicator is significantly higher (43% compared to a national average of 27%). It’s less secure in terms of performance and is due an Ofsted inspection within the year. The new head of school is less experienced and unfamiliar with James’s leadership style.

This is where the leadership challenge begins, not just logistically, but emotionally and strategically.

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Situational Leadership: One Size Doesn’t Fit All

James is already asking the right questions: How do I balance my time and focus across the two schools? How do I show up differently without compromising my leadership identity?

This is where the theory of situational leadership becomes particularly relevant. Hersey and Blanchard (1982) argued that effective leaders must adapt their style based on the context, task, and readiness of those they lead. In other words, leadership is not static; it’s responsive.

In one school, James will need to step back, giving space to a capable deputy to establish themselves as head. In the other, he’ll need to provide more visible support, modelling leadership presence while being careful not to eclipse the new head of school. As Goleman (2000) suggests in his work on leadership styles, emotionally intelligent leaders are those who can shift fluidly between approaches, based on what the situation demands.

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The Visibility Paradox

We spent time in James’s coaching session exploring the paradox of visibility in executive leadership.

As a headteacher, visibility is one of the most powerful tools in a leader’s repertoire. Being seen by students, staff and families creates a sense of presence, authority, and approachability. But in executive leadership, that visibility must be intentionally repositioned.

In his current school, James will need to step back to allow his successor to lead confidently. In the new school, he plans to be more present initially, not to take over, but to signal that strong leadership is in place and that the school is on a recovery journey.

But we also discussed a crucial risk: that colleagues or families might bypass the new head of school, deferring to James for decisions or approval. And this is where executive leadership becomes a delicate balance of presence and absence.

The most effective executive leaders are often invisible to the wider school community. They lead from the shadows, enabling, advising, mentoring, and strategically directing. Their leadership isn’t diminished; it’s simply expressed differently.

“Executive leadership is not about being the hero on the stage. It’s about being the director in the wings, ensuring the right people are in the spotlight, with the right script and the right support.”

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Control: Letting Go Without Letting Down

The question of control mirrors that of visibility. As a headteacher, James was the decision-maker. He had oversight. He had a handle on everything.

Now, control needs to be redefined.

The outward control must sit with the heads of school. They are the ones who will lead operationally, build team culture, and respond to the day-to-day needs of staff and pupils.

James’s role is no longer about doing, but about designing the conditions for success. This means:

Setting clear strategic direction

Building systems of accountability and assurance

Spending time in both schools to stay connected and informed

Creating a culture where feedback flows upwards as well as downwards

Ron Heifetz, in his work on adaptive leadership (Heifetz & Linsky, 2002), highlights that leadership is less about control and more about navigating uncertainty, helping people face challenges for which there are no easy answers. James will do this by guiding, not gripping.

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Coaching the Shift

Through coaching, James has begun to unpick his identity as a leader. He is highly reflective and plans meticulously, qualities that serve him well. But coaching has also helped him recognise where his instincts (to step in, to stay close) might need to evolve into new habits (stepping back, scaling perspective).

We’ve focused not only on operational strategy but on leadership identity; who he needs to become to succeed in this new role. He’s learning to lead through leaders, to create clarity without overreaching, and to prioritise culture over control.

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What Can We Learn?

James’s story isn’t unique, but it is instructive. As more school leaders move into executive roles, the system must support them to understand that executive leadership is not a bigger version of headship. It’s a different discipline altogether.

To those stepping into executive leadership, I offer this:

Trust your heads to lead. Empower them to act, then hold them to account with clarity and care.

Be intentionally visible, and intentionally invisible. Know when your presence empowers, and when it overshadows.

Redefine control. Replace direct oversight with strong systems, high expectations, and strategic presence.

Protect your thinking space. Executive leadership is cognitive leadership. Hold the long view, even when the urgent clamours loudly.

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Final Thoughts

Leadership is always contextual. But executive leadership requires a shift not just in strategy, but in identity. It’s a shift from being in the work to being over the work; from solving problems to building people who solve them.

James is doing that work with courage and care. And his story is one that many others will follow.

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I’d love to hear from you:

• What changed for you when you stepped into an executive leadership role?

• What helped you learn to lead through others?

• And how do you balance visibility, presence and trust across multiple schools or settings?

I have limited availability for up to 10 new coaching clients in 2025 - 2026.

Could one of them be you?

Email me at info@claireplattcoaching.co.uk to find out more.