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
Udemy's Melissa Daimler on clarity, curiosity & leadership
This week, Melissa Daimler, Chief Learning Officer at Udemy, returns to the podcast.
Melissa brings decades of experience shaping leadership, learning, and organisational culture at some of the world’…
Chloe Combi: Understanding Gen Z in the Future of Work
This week, I speak with Chloe Combi, an expert on Gen Z and Gen Alpha, who’s spent years researching and advising on how these younger generations are reshaping work, education, and culture.
Chloe is …
Nancy Duarte: Communicate with Authenticity in the Age of AI
This week, I speak with Nancy Duarte, CEO of Duarte Inc. and the world's leading presentation expert.
Nancy’s career is a masterclass in the art of communication. She has advised TED, worked with Al G…
Nick Matthews: Culture, Engagement & Performance
This week, I speak with Nick Matthews, VP and GM of Europe, Middle East & Africa at Culture Amp.
Nick brings a unique blend of experiences from his early days teaching Liam Neeson’s kids to swim to hi…
Isabel Berwick: The Future-Proof Career
In this episode, I interview Isabel Berwick, presenter of the award-winning Financial Times' Working It podcast and co-writer of the Working It newsletter.
Isabel's new book The Future-Proof Career: S…
Hannah Grady Williams: Unleashing a new generation of talent
In this episode, I had a fascinating chat with Hannah Grady Williams, the founder of d'Skills.
We explored the challenges of the traditional education system and how new technologies, particularly AI…
Matthew Dicks: How to become a better storyteller
In this episode, my conversation with Matthew Dicks sheds light on storytelling as a craft that everyone can master, offering insights into life and work.
Matthew Dicks is an internationally bestselli…
David Green: Growing people and organisations using data
In today's episode, I sit down with David Green, Host of the Digital HR Leaders podcast, co-author of Excellence in People Analytics, and Director of Insight222 and myHRfuture.
David's round-up of the…
Vanesa Pazos: Human-centric investment in the future of work
In today’s episode, I speak with Vanesa Pazos, a Partner at NoBa Capital.
NoBA is a venture capital firm that invests in early-stage tech-enabled businesses shaping the Future of Work. Their portfolio…
Jenny von Podewils: Enabling a new generation of leaders and workers
In this episode, I had the pleasure of speaking with Jenny von Podewils, co-founder and co-CEO of Leapsome.
Leapsome is revolutionising how companies engage with employees and foster a culture of cont…
Tonille Miller: Flourishing at Work
Today's guest is Tonille Miller, Transformation & Experience Leader, and author of The Flourishing Effect: Unlocking Employee Thriving and High Performance as Your Competitive Edge.
This was a great c…
Noelle London: Helping HR Leaders Make Data-Driven Decisions
Today's guest, Noelle London, is the founder and CEO of Illoominus. She's focused on unlocking the full value of companies' HR tech stacks, enabling leaders to foster people-first workplaces.
This con…
Debra & Ken Corey: Bad Bosses Ruin Lives
My guests today are Debra and Ken Corey, authors of the new book Bad Bosses Ruin Lives: The Building Blocks for Being a Great Boss.
Debra Corey is a global HR thought leader, recently recognised amon…
John Winsor: Open Talent
In this episode of the Future Work/Life podcast, I speak with John Winsor, formerly an advertising founder and exec and now a pioneer, entrepreneur and thought leader on open talent.
John is the Execu…
Tyler Cowen: Creativity, Talent & AI
It’s a special episode today. We recently celebrated the 200th episode of the Future Work/Life podcast, which coincided with the same milestone for my guest’s show, "Conversations with Tyler."
Tyler C…
Matt Abrahams: How to speak more confidently
Today’s guest is Matt Abrahams, a Lecturer in Organizational Behavior at Stanford University’s Graduate School of Business and an expert in communication.
With decades of experience as an educator, a…
Nick Bloom: What's driving where and how we work
Welcome back to a new series of the Future Work/Life podcast.
Today’s guest is Nick Bloom, a Stanford Economist who has been studying remote work for over two decades. He is the co-founder of www.wfhr…
Best of 2023: Jennifer Moss
BEST OF 2023 EPISODES:
Today's guest is Jennifer Moss, a workplace speaker and strategist.
Jen's also an award-winning author, journalist, national radio columnist, and the author of The Burnout Epidem…
Best of 2023: Tom Goodwin
BEST OF 2023 EPISODES:
Today's guest is Tom Goodwin, a digital business transformation specialist and the founder of All We Have Is Now, a consultancy created to help companies unleash the power of ne…
Best of 2023: Bruce Feiler
BEST OF 2023 EPISODES:
Today's guest is New York Times bestselling author Bruce Feiler.
Bruce's last book Life is in the Transitions greatly impacted Ollie and featured in his book Work/Life Flywheel. …