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Diana Osagie

Diana Osagie

Diana Osagie portrait

Coaching Bio

Diana started coaching in 2010 and specializes in coaching head teachers in challenging circumstances. She uses skillful questioning to help her clients forge a plan of action and new ways of thinking in the midst of difficult situations. Diana is expert at helping clients navigate leadership challenges that arise when working with multiple teams, she is adept at helping clients find new levels of clarity and courage.

Coaching Experience

Diana has coached over 30 head teachers in various stages of their career, helping clients to navigate system leadership and culture development. She has coached senior teams in 9 countries in the state and independent sector. Diana has developed successful individual and team coaching programs under the banner of Courageous Leadership – coaching senior teams to reflect deeply on their culture and practice.

Career Experience

22 years’ experience leading secondary education, including six years as a successful head teacher in a London secondary school and subsequently an executive head; Diana works at the cutting edge of leadership development. She is known as a resilient, skilled in urban leadership under challenging circumstances. Diana couples sound strategic vision whilst giving clear operational direction. Diana was a school inspector for 9 years with developed expertise scrutinizing operational systems and leadership competency. She founded The Academy of Women’s Leadership; specializing in supporting women to grow the leadership cultures of their organisations and to flourish as leaders supremely confident leaders.

Coaching Qualifications


Coaching Accreditations

Fierce Conversations

Five Dysfunctions of a Team

This enabled us to be open, honest, and up front with each other. Whilst we are an extremely cohesive and positive team who work on our strengths, we have never really considered our weaknesses. This was quite liberating and gave plenty of food for thought. This exercise allowed us to strengthen our trust and relationship, which is crucial as a leadership team. Quite liberating…

Nicola Howard, Vice-Principal, The Alice Smith School, Malaysia

The work Diana did with us encouraged my team and I to think differently…

Given she spent only one day with us, it is amazing how often we use the phrase ‘ as Diana said…’ The work she did with us has encouraged my team and I to think differently about tricky conversations and situations, and given us additional tools with which to handle these.’ The work Diana did with us encouraged my team and I to think differently…

Dinah Hawtree, Principal, Prince of Wales International School, Malaysia

I would highly recommend working with Diana. She has coached me over the last year and we have explored a range of complex leadership issues. What I found most useful is that Diana went straight to the root of the issues which required me to carry out some very deep self-reflection. Diana is a highly skilled coach and utilises her extensive experience and I always enjoy our sessions – they are challenging progressive and fun. In a short time Diana has helped me grow as a leader and I anticipate I will be using her support and expertise in the years to come.

Nick Langham, Head teacher, Langdon Park School