Meet Diane Thompson
Hi, I’m Diane — Executive Coach, experienced Headteacher, and founder of Courage Over Comfort Coaching.
With over 20 years of leadership and coaching experience, I’ve successfully led and transformed schools, mentored aspiring leaders, and coached professionals at every stage of their journey to overcome barriers, build resilience, and create lasting impact.
I work with individuals, schools, and organisations to create coaching cultures that prioritise psychological safety, inclusion, wellbeing, and leadership development. I take pride in empowering clients to build confidence, deepen self-awareness, and fulfil their full potential — both personally and professionally.
I hold an ILM Level 7 in Executive Coaching & Mentoring and am the author of Mindful Moments: Wellbeing Journal for Educators and Mindful Moments for Everyone, bringing both expertise and lived experience to this work.
I’ve walked the path. Now, I help others rise with courage, clarity, and conviction.
Our
Story
Courage Over Comfort Coaching was founded on a bold belief: that leadership should be inclusive, human-centred, and transformative. At its heart, our name reflects a deeper truth — that true growth lies beyond our comfort zone.
After more than two decades leading schools and coaching leaders at all levels, I saw the same barriers holding people back: imposter syndrome, underrepresentation, burnout, and a lack of meaningful support. At the same time, I witnessed the profound, life-changing impact of coaching — and I knew something had to change.
I created Courage Over Comfort Coaching to challenge the status quo — to build psychologically safe spaces where people feel seen, supported, and stretched. To make leadership coaching not just a luxury, but a powerful tool for equity, wellbeing, and sustainable change.
Our name says it all. Choosing courage over comfort means daring to challenge limiting beliefs, push boundaries, and take purposeful action. It means developing the confidence to lead, speak up, and create meaningful change — not in isolation, but with the right support beside you.
At Courage Over Comfort Coaching, our mission is threefold:
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Empowering women to build confidence, overcome imposter syndrome, and thrive as authentic, impactful leaders.
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Transforming leadership culture in schools and organisations by cultivating strong coaching cultures that prioritise inclusion, wellbeing, and continuous leadership development.
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Making coaching accessible to traditionally underrepresented groups in leadership by offering subsidised coaching — made possible through organisational partnerships and commissions.
Our
Mission
Our
Vision
We believe everyone deserves the opportunity to achieve greatness, regardless of their background or starting point in life.
We envision a world where coaching is no longer a luxury, but a catalyst for equity, inclusion, wellbeing, and meaningful leadership. By creating safe, supportive environments that encourage courage and growth, we empower leaders at all levels — especially those from underrepresented backgrounds — to lead with clarity, confidence, and purpose.
Through organisational partnerships and commissions, we are building a sustainable model that drives systemic change — enabling us to open doors for those who have traditionally been left out of leadership conversations.