Ollie on Work
Helping ambitious leaders avoid the Career Expiration Trap.
I'm Ollie Henderson. I've spent 15+ years founding businesses and I'm still experimenting today. I've learned what keeps leaders ahead. Entrepreneurial skills that create momentum regardless of what shifts.
Real conversations with business and thought leaders like Daniel Pink, Rory Sutherland, and Lynda Gratton about leading multigenerational teams, implementing AI strategy, and building what comes next as the rules of work change.
No generic future-of-work trends. Just practical insights for leaders who refuse to expire.
You can also read more about these themes in the Ollie on Work newsletter.
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- Update frequency
- every 4 days
- Average duration
- 26 minutes
- Episodes
- 240
- Years Active
- 2020 - 2025
Alex Hutchinson - Breaking Through Mental Barriers & Exploration vs Exploitation
Most people think they've hit their limits when they're actually nowhere close.
Alex Hutchinson returns to the show for his second appearance. As a journalist and author, he's spent years studying the…
Dror Poleg - Why Careers Are Becoming Like Showbiz
Most people are still planning careers like it's 1995.
But time itself has compressed. ChatGPT reached 100 million users in eight weeks. The Ford Model T took 70 years to hit the same milestone.
Today …
Lorraine Lee - Why Hard Work Isn't Enough, Building Visibility & Getting Noticed
Most people assume hard work speaks for itself. Lorraine Lee knows that's a dangerous mistake.
As the author of Unforgettable Presence and former LinkedIn editor, Lorraine has seen firsthand how talen…
Christopher Lochhead - Finding Your Superpower & The Death of Knowledge Workers
Most people think AI will just make their jobs more efficient.
Christopher Lochhead thinks it's about to make their jobs extinct.
Christopher returns to the show for the third time. The co-creator of C…
Raj Choudhury – Work From Anywhere & Engineering Serendipity
Most leaders are still fighting yesterday's battles about remote work. But the conversation has already moved on.
A few leaders have figured out that this isn't a policy question - it's a talent quest…
Eric Jorgensen – Career Leverage & Why AI Will Make The Best Better
Welcome back to Ollie on Work after a six-month hiatus. I've been speaking to hundreds of people - founders, leaders, workers who've been laid off - trying to understand what's really happening as wo…
Marcus Buckingham on the Hidden Signals of Career Success
This is the final episode in a mini-series focused on setting you up for a successful and fulfilling 2025.
Today, I'm sharing my conversation with Marcus Buckingham, bestselling author and renowned re…
Dorie Clark on Playing the Long Game in Your Career
This week, I'm resharing my 2022 conversation with strategy consultant, executive coach, and keynote speaker Dorie Clark.
Dorie has twice been named one of the Top 50 Business Thinkers in the World by…
Daniel Pink on making bold career decisions using mental time-travel
This week, I'm resharing my conversation with Daniel Pink, in which we explore how to make better decisions using mental time-travel.
Dan is the author of five New York Times bestsellers, including hi…
Grace Lordan on Thinking Big in your Career
This week we're revisiting a standout conversation with Grace Lordan, Associate Professor in Behavioural Science at the LSE and author of Think Big.
Grace shares her approach to goal setting, building…
AI Agents: Our new colleagues
This week I share some thoughts on why 2025 will be the year of the AI Agent.
Plus, how it will affect roles in B2B marketing, learning & development, and law.
Finally, I share some advice on how you c…
David Landman on The Long Exhale and Leadership in an AI World
This week, I’m joined by David Landman, former Goldman Sachs executive turned advisor and educator.
After two decades leading performance management, talent mobility, and talent development at Goldman…
Donald Knight on mental fitness & designing a fulfillfing work/life
This week, I'm joined by Donald (DK) Knight, SVP of People & Culture at Warner Bros. Discovery.
Donald has had a varied career, working in senior HR and people roles and serving as a venture partner a…
David Blake on the Skills Gap, AI, and the Future of Learning
This week, I’m joined by David Blake, CEO of Degreed and a pioneer in the world of lifelong learning and skills development.
Degreed, founded in 2012, launched with the mission of “jailbreaking the d…
Season 15 so far: AI, leadership & the multigenerational workforce
Welcome to this special episode of Future Work/Life, in which we take a step back and reflect on the key themes and insights from Season 15 so far.
It’s been a busy few months—between speaking events…
Amber Jeffrey on grief and having tough conversations at work
This week, I’m joined by Grief Gang's Amber Jeffrey, a podcaster, speaker, and grief mentor.
Despite tackling a challenging topic, I thoroughly enjoyed our conversation, which was filled with laughter…
Cara Brennan Allamano on staying curious, adapting & thriving
This week, I’m joined by Cara Brennan Allamano, cofounder of PeopleTech Partners and experienced people leader at startups and high-growth companies. Cara has been instrumental in scaling people func…
Pat Wadors on Unlocking your Leadership Story
This week, I'm joined by Pat Wadors, newly appointed CHRO at Intuitive, a leading medical technology company. Pat has previously led HR at UKG, ServiceNow, LinkedIn, and Yahoo and is widely recognise…
David Hanrahan on workplace disconnection & AI in HR
This week, I’m joined by David Hanrahan, Chief People Officer at Flare.
Flare’s software platform is transforming the delivery of professional services within the legal sector. By simplifying complex …
Arist's Michael Ioffe on redesigning learning with AI
This week, I’m joined by Michael Ioffe, co-founder and CEO of Arist.
Arist is used by leading organisations to deliver behavioural training and critical knowledge through the messaging tools employees…