I help leaders navigate AI, generational change, and the future of work

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Hi, I’m Ollie 👋

I've learned to escape the Career Expiration Trap by creating and maintaining momentum through uncertainty. Still experimenting and taking risks (although not always getting it right). But never getting stuck.

I've spent 15+ years founding and running businesses. Over the past 5 years, I've spoken to 1000+ business leaders and had 250+ conversations with thought leaders like Daniel Pink, Lynda Gratton, and Rory Sutherland, exploring what you need to keep moving forward, even as the rules of work change.

The key lesson? Building entrepreneurial skills that enable you to adapt and grow regardless of the context you’re working in. Helping you to keep moving forward.

Trusted by leaders at 100+ global organisations - including:

What I offer

Keynotes

High-energy presentations that cut through complexity and give your audience clear frameworks they can apply immediately.

You'll get practical insights on navigating transitions, implementing AI strategy, and building momentum through uncertainty.

The focus is on what's actually changing, why it matters to your people, and specific actions they can take. No generic future-of-work content - just proven approaches that help you lead effectively as the rules of work change.

Workshops

Interactive working sessions where your leadership team tackles real challenges together.

We'll design practical solutions for cross-generational collaboration, AI implementation that works, or building culture that unlocks performance. You don't just learn vague frameworks - you customise them for your specific context.

Teams leave with clear action plans, aligned understanding, and momentum to implement change immediately.

Advisory

Strategic partnership for founder-led and executive teams navigating major transitions.

You get 1-2-1 strategic thinking, access to my network of specialists who can accelerate execution, and ongoing support as you implement. Whether it's realigning leadership, sharpening strategy, or refining your point-of-view, we work together until you have clarity and momentum.

No cookie-cutter approaches - everything tailored to your specific challenge.

Podcast

Conversations with thought leaders like Bruce Daisley, Dorie Clark, Marcus Buckingham, Tim Harford and Tyler Cowen about building what comes next as work evolves.

Newsletter

Weekly insights on navigating major transitions and building what comes next as the rules of work change. Practical frameworks for ambitious leaders who want to stay ahead.

In their words…

  • "Ollie Henderson gives you the system you need to make bold changes in your career and the motivation to share your ideas with the world"

    Daniel H. Pink - #1 New York Times bestselling author of Drive and When

  • "For a more flexible and adaptive multi-stage life, we need to be bold and courageous. Ollie shows the foundations for this courage and shares the stories of those who have created momentum and energy in their working life."

    Lynda Gratton - Author of Redesigning Work, Professor at London Business School

  • “Work and leisure have become a false dichotomy. As Ollie Henderson shows using the superb Flywheel metaphor, done right, each can make you better at the other.”

    Rory Sutherland - Vice-Chairman of Ogilvy, author of Alchemy

  • "As people are beginning to reimagine work and reconsider their careers, Work/Life Flywheel is a brilliant resource to help you get started in redesigning your work/life"

    Elizabeth Akanbi-Ogabi - Author of Side Hustle in Progress

  • "Ollie will show you the practical techniques of reimagining your life and career and reveals how much better things could be for you, if you can adopt his hard-earned wisdom."

    Damian Hughes - Host of The High Performance podcast and author of High Performance

  • "We know how personal and complex worker issues are, and Ollie was able to delve into the topics with so much relatability, humour, and depth, which made everyone feel like they were part of an intimate conversation with a wise friend."

    Vanesa Pazos - Partner, NoBa Capital

  • "Ollie helps us finding that binding rhythm"

    Will Page - Author of Pivot and Chief Economist of Spotify

  • "Ollie has a warm and engaging, storytelling style and was able to blend his own experience running businesses to helping leaders understand how to successfully adapt and thrive as work evolves."

    Sarah Rourke - EMBA Coach, Henley Business School

  • "Ollie will help harness your mindset, spark your creativity, and lead to substantial breakthroughs for harmony and alignment in both your personal and professional life.".

    Dr. Kathrin Hamm - CEO, Bearaby

  • "Ollie ran an energetic, fun, informative and practical session with lots of takeaways for how to make the workplace more effective and efficient. His session was a highlight of the collaborative leadership course."

    Shân Wareing - CEO & Vice Chancellor, Middlesex University

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