I help leadership teams navigate change and get unstuck on AI strategy

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Hi, I’m Ollie 👋

Most leadership teams are stuck when it comes to navigating change - whether that's implementing AI, managing multigenerational teams, or building culture that actually performs.

I've spent 15+ years founding and running businesses and the past 5 years exploring how work is evolving. Over that time, I've spoken to 1000+ business leaders and had 250+ conversations with thought leaders like Daniel Pink, Lynda Gratton, and Rory Sutherland, exploring what leaders need to keep moving forward.

Through keynotes, workshops, and advisory work, I help leadership teams cut through complexity and get unstuck - whether that's on AI strategy, organisational change, or building momentum when you can't see the full picture.

Trusted by leaders at 100+ global organisations - including:

What I offer

Keynotes

High-energy presentations that help teams create clarity and momentum when technology is reshaping how work gets done.

Topics include leadership through technological change, managing multigenerational teams, building culture that unlocks performance, and navigating uncertainty when you can't see the full picture.

You'll get practical frameworks that cut through complexity and show what people need to do differently.

Workshops

Collaborative sessions where leadership teams dig deeper into growth opportunities, strategic narratives, and unlocking performance.

We work on the bigger questions:

What story are you telling internally and to customers?

How do you turn generational differences into competitive advantage?

Where are the growth opportunities you're not seeing?

Teams leave with shared clarity on priorities, compelling stories they can use, and practical plans for leveraging multigenerational talent.

Advisory

I work with leadership teams to get unstuck on strategy, growth, and implementation challenges - whether that's AI adoption, organisational change, or building systems that deliver results.

Recent work includes AI workflow implementation, performance culture redesign for scaling companies, growth strategy development, and narrative crafting that positions leaders credibly in their markets.

You get deep research into your business context, clear direction on opportunities, and access to my network of specialists for execution. I work as a high-trust sparring partner who challenges assumptions, helps prioritise, and gives you conviction to move forward when you can't see the full picture.

Podcast

Conversations with business leaders, operators, and thought leaders about how work is evolving and what leaders need to do differently.

I speak with business and thought leaders on implementing change today and reimagining what's possible tomorrow.

Recent conversations explore AI implementation, building culture that unlocks performance, leading multigenerational teams, and navigating change when you can't see the full picture.

You'll get practical insights from operators alongside fresh perspectives from people shaping the future of work, 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

Get in touch