Spotlight on Diana Osagie: Courage, Confidence & Leadership That Lasts
- EdEvents
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We are thrilled to welcome Diana Osagie, founder of the Courageous Leadership Consultancy and the Academy of Women’s Leadership, to EdInspire Singapore 2025. A seasoned headteacher, consultant, coach, and author, Diana is internationally recognised for her ability to cut through the noise and speak with truth, humour, and deep wisdom about the realities of leadership.
About Diana Osagie
With over 26 years of experience in education, Diana has led schools through some of the most challenging circumstances. She served as a London secondary school headteacher and later an executive head, establishing her reputation as a resilient and highly effective leader.
For nearly a decade, Diana also worked as an OFSTED inspector, scrutinising leadership and operational systems across schools. This background gives her an unparalleled insight into what effective leadership looks like — and how to build it in practice.
Her passion for empowering leaders led her to found the Academy of Women’s Leadership, where she supports women to strengthen organisational cultures and flourish as confident leaders. Diana has also authored four books on leadership, each offering practical, unvarnished lessons on leading with courage, humour, and strength.
Pre-Conference Masterclass: Courageous Leadership
📍 Friday, 7 November | Morning 8:30–11:30 AM OR Afternoon 1:00–4:00 PM
Why does leadership seem so effortless for some, whilst others struggle? In this 3-hour masterclass, Diana will demystify the “secrets” of courageous leadership. Whether you’re a new leader looking for practical tactics, or a seasoned leader seeking a refresh, this session delivers the real, hard-won insights you can’t just Google.
Through three interactive modules, participants will explore how to handle the pressures of leadership with clarity, confidence, and courage — leaving with tools and methods that make leadership not only more effective but more sustainable.
Workshop: Practical Strategies to Create Psychologically Safe Teams
📍 Saturday, 8 November | 10:00 – 11:00 AM
Teams that feel safe are teams that perform. In this hands-on workshop, Diana will outline the four stages of building psychological safety and show leaders how to create cultures where people can bring their best selves to the table. Expect practical strategies, relatable stories, and even a visit from the “well-being dog.”
Participants will leave not just with theory, but with the beginnings of a concrete action plan to implement in their own schools.
Plenary: Confidence is NOT a Feeling
📍 Saturday, 8 November | 16:00 – 16:30 | Main Stage
In this closing plenary, Diana will challenge assumptions about confidence, offering a transformative insight: “If my confidence is predicated on how I feel, I will never accomplish anything. How I feel changes with the wind.”
In just 30 minutes, she will equip attendees with a mindset shift that positions confidence as a superpower — one that fuels innovation, leadership, and self-esteem regardless of circumstance.
Why Attend?
Diana Osagie doesn’t just talk about leadership — she’s lived it in the most demanding contexts and distilled her lessons into practical strategies leaders can use immediately.
Whether you attend her Friday masterclass, join her Saturday workshop, or hear her plenary on confidence, you will walk away with renewed courage, clarity, and conviction.
👉 Be part of Diana Osagie’s sessions at EdInspire Singapore, 7–8 November 2025, and discover what it means to lead with courage.
VISIT THE EVENT WEBSITE: https://www.ed-inspire.com/ SECURE YOUR TICKET: https://www.ed-inspire.com/tickets
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