Coaching Lessons from Iain Henderson, Director of The Bridge at Wellington College

As an educator and leader who has been spearheading coaching into the Wellington College family of schools, Iain Henderson has gained invaluable insights along the way.

We first met Iain and his wife, Cressida, Deputy Head of Wellington College, in Autumn 2010. Attracted by the school's pioneering approach to implementing a wellbeing curriculum ahead of many others, we visited their stand at a conference in London and immediately hit it off.

Our connection was immediate and genuine.

Iain had been eager to introduce coaching at Wellington and was keen to share coaching training for educators. We had the privilege of introducing our coaching model and curriculum to Wellington beginning 2012, and since then, they’ve been sharing coaching training in-house in the UK, China and Thailand.

Recently, we saw Iain speak at The Festival of Education at Wellington College. His talk, entitled “Coaching at Wellington – and well beyond” was filled with key coaching insights and experiences which we want to share to help others on a similar journey.

Iain shared quite clearly that…

Integrating coaching at Wellington College has enabled students to take ownership of their learning, exercise greater agency and develop strong self-awareness—leading to noticeable shifts in mindsets and outcomes. Students are leaving school with less fear and a much greater sense of self. Iain shared quite clearly that it has made a noticeable difference in student mindsets and outcomes.

However, it comes with a few challenges. For example:

  • It’s unrealistic to expect everyone will excel at coaching, as it’s a way of being that comes more naturally to some than others.

  • Initial over-enthusiasm led to some unrealistic expectations, such as trying to make every conversation a coaching conversation.

  • The school missed and early opportunity to foster teacher-to-teacher coaching, which would have strengthened their coaching culture.

  • Wellington encountered some misuse of coaching where it became a form of coercion through leading questions. This highlighted the need for ongoing, robust training.

  • Looking back, Iain wished he had included more Instructional Coaching best practices from the very beginning, so that staff understood the differences early on.

And if you’re thinking about out introducing coaching at your school, then Iain thinks you’ll want to know…

  • Coaching is not a quick fix—it requires a sustained commitment.

  • Coaches must remain vigilant about their intentions, always striving to empower those they coach.

  • A successful coaching programme depends on developing a shared understanding and ethical framework.

  • Humility, reflection, and the willingness to admit missteps are essential for any leader attempting to implement a coaching culture.

If you missed out on Ed Fest this year, we hope this gives you a glimpse into the event. We proudly attend both in the UK and USA as often as we possibly can.

A huge thank you to Iain for honestly and transparently sharing his journey. We are grateful to have been a part of it!

Curious about coaching and the journey other schools have taken? Schedule a call with us.

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Our Brains Are Begging Us to Step Outside Our Comfort Zones