Ollie Henderson
Ollie on Work
Conversations about work, AI, and careers - what's changing and what to do about it. Previous guests include Azeem Azhar, Daniel Pink, Lynda Gratton, Rory Sutherland, and Tyler Cowen. You can also read more about these themes in the Ollie on Work newsletter. Hosted on Acast. See acast.com/privacy for more information.
Author
Ollie Henderson
Category
Podcast website
Latest episode
Aug 20, 2025
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Episodes
Alex Hutchinson - Breaking Through Mental Barriers & Exploration vs Exploitation 20.08.2025 44:49
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 science of human performance. His first book Endure was a New York Times bestseller. His latest book, The Explorer's Gene , tackles a fundamental question: when do you push into unknown territory, an...
Dror Poleg - Why Careers Are Becoming Like Showbiz 13.08.2025 33:35
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 I'm joined by Dror Poleg for his second appearance on the show. He's an economic historian and one of the sharpest minds thinking about how this time compression changes everything. His newsletter re...
Lorraine Lee - Why Hard Work Isn't Enough, Building Visibility & Getting Noticed 06.08.2025 31:07
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 talented people get overlooked while less qualified colleagues get promoted - simply because they knew how to make themselves visible. Today I'm joined by Lorraine to explore why visibility matters more th...
Christopher Lochhead - Finding Your Superpower & The Death of Knowledge Workers 30.07.2025 50:42
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 Category Pirates and author of Play Bigger believes we're witnessing the end of the knowledge worker era - the 70-year period where getting paid meant applying existing knowledge to solve problems. AI...
Raj Choudhury – Work From Anywhere & Engineering Serendipity 24.07.2025 28:14
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 question. Today I'm joined by Professor Prithwiraj Choudhury, who recently moved from Harvard Business School to the London School of Economics. Raj has spent years studying what he calls "work from anywhe...
Eric Jorgensen – Career Leverage & Why AI Will Make The Best Better 18.07.2025 23:08
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 work fundamentally changes. Those conversations convinced me it was time to refocus. The podcast and newsletter have a new name, and I'm doubling down on what I think I'm uniquely placed to tackle: helpi...
Marcus Buckingham on the Hidden Signals of Career Success 30.01.2025 41:43
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 research director, about understanding the hidden patterns that drive career success. Marcus spent two decades at Gallup Organization co-creating the StrengthsFinder tool, built his own coaching and edu...
Dorie Clark on Playing the Long Game in Your Career 23.01.2025 39:15
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 Thinkers50, and the #1 Communication Coach in the World by the Marshall Goldsmith Leading Global Coaches Awards, as well as one of the Top 10 Communication Professionals in the World by Global Gurus....
Daniel Pink on making bold career decisions using mental time-travel 15.01.2025 33:46
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 his latest, The Power of Regret: How Looking Backward Moves Us Forward , published this month . His other bestsellers include When and A Whole New Mind, To Sell...
Grace Lordan on Thinking Big in your Career 09.01.2025 36:34
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 resilience, and embracing uncertainty as essential ingredients for creating the future you want. Whether you're reflecting on your career path or planning new habits for 2025, this episode offers pra...
AI Agents: Our new colleagues 17.12.2024 11:37
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 can prepare your company and team. READ: AI Agents: our new colleagues Work Redesign: Humans + AI Agents LINKS: Follow Ollie on LinkedIn Subscribe to the Future Work/Life Newsletter My book, Work/...
David Landman on The Long Exhale and Leadership in an AI World 11.12.2024 35:22
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, David embarked on what he calls The Long Exhale - a transformative sabbatical that reshaped his outlook on work and life. David shares his journey into purpose-driven work, reflecting on what it mea...
Donald Knight on mental fitness & designing a fulfillfing work/life 04.12.2024 23:46
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 and advisor for Valor VC, PeopleTech Partners, and Lattice. We had great fun discussing various topics related to company culture, wellbeing, and the skills you need to build a fulfilling work/life...
David Blake on the Skills Gap, AI, and the Future of Learning 20.11.2024 28:44
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 degree”, where all skills are recognised, irrespective of how they are acquired. More than 9 million learners from hundreds of global companies now use Degreed to gain the skills to grow in their...
Season 15 so far: AI, leadership & the multigenerational workforce 13.11.2024 6:46
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 and connecting with people leaders, I've had the privilege of speaking with incredible guests about the future of work, leadership, learning, and what it means to be human in an AI-powered world. In...
Amber Jeffrey on grief and having tough conversations at work 06.11.2024 41:15
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 and positivity. We explore how grief is often hidden in the workplace, how creating space for these conversations can help people heal, and why connecting during tough times matters. I finished our c...
Cara Brennan Allamano on staying curious, adapting & thriving 30.10.2024 19:43
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 functions at Pinterest, Udemy, and, most recently, Lattice. In this episode, we explore the biggest challenges and opportunities in the world of work, how AI is reshaping jobs, and Cara's advice for people...
Pat Wadors on Unlocking your Leadership Story 24.10.2024 40:40
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 recognised for her transformative leadership in the people space. In this episode, we explore leadership, storytelling, and the power of human connection. Pat also shares insights from her upcoming book, Unlock...
David Hanrahan on workplace disconnection & AI in HR 18.10.2024 17:12
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 processes, Flare empowers lawyers to deliver an elevated experience, ensuring clarity and support during key life events. In this episode, David and I dig into some of the biggest challenges and oppor...
Arist's Michael Ioffe on redesigning learning with AI 09.10.2024 38:31
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 use every day, like WhatsApp, Slack, and Teams. Michael’s background is fascinating—from his early entrepreneurial endeavours to building a platform that’s reshaping how people learn on the job. List...
Udemy's Melissa Daimler on clarity, curiosity & leadership 04.10.2024 33:48
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’s leading companies, including Adobe, Twitter, and WeWork (you can listen to what she learned during her brief spell at the latter on her previous pod appearance ). She's also the author of ReCulturi...
Chloe Combi: Understanding Gen Z in the Future of Work 25.09.2024 45:22
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 the author of Generation Z: Their Voices, Their Lives and a consultant to some of the world’s leading brands. She helps them connect with and understand the next generation of workers and consumers. I...
Nancy Duarte: Communicate with Authenticity in the Age of AI 18.09.2024 42:57
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 Gore on the documentary An Inconvenient Truth , and helped some of the world’s biggest companies communicate effectively. She is famous for her deep understanding of storytelling and empathy, and...
Nick Matthews: Culture, Engagement & Performance 20.06.2024 45:16
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 his career in tech. He started his career at Deloitte Consulting before moving to Yammer, which was later acquired by Microsoft, where he worked for four years before joining Culture Amp in 2016. Cu...
Isabel Berwick: The Future-Proof Career 10.04.2024 40:04
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: Strategies for thriving at every stage is published this week. We had a brilliant conversation about careers, management and changes in how we work. The book is a great read, so make sure you order a c...
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