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Ollie on Work

Author: Ollie Henderson

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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.


Hosted on Acast. See acast.com/privacy for more information.

241 Episodes
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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, and when do you stick with what works?Today we explore the exploration versus exploitation dilemma - the choice athletes face every race between sticking with proven strategies or risking everything to test new approaches. The same decision defines careers, businesses, and life.Alex's research reveals we have a "central governor" in our brains that pulls the plug early, protecting us from discomfort but also preventing breakthroughs.TALKING POINTS:Why the wall you think you've hit probably isn't your actual limitThe "central governor" theory and how your brain protects you by holding you backHow to build tolerance for uncertainty like elite athletes doThe exploration vs exploitation dilemma in careers and business decisionsWhy "optimism in the face of uncertainty" is the optimal mathematical strategyHow to know when to explore new paths vs exploit existing knowledgeThe danger of stopping exploration too early in life and careerLINKS:The Explorer's Gene book Endure bookAlex's writing at Outside Magazine Alex's LinkedInInterested in me sharing insights on these topics with your team? Book a free consultation - HEREOllie on WorkOllie's LinkedInOllie on Work newsletterMy Book Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 reaches 35,000+ readers across tech, finance, and government.Dror's insight? The predictable career path is shrinking fast. What used to be a 40-year "paint by numbers" journey is becoming more like showbiz - constant experimentation with uncertain outcomes.TALKING POINTS:Why the "productivity paradox" means more of our work will seem useless until it's suddenly valuableHow careers are becoming more like showbiz - constant experimentation with uncertain outcomesWhy AI might actually force us back to trusting what we can see and touch in personThe institutions that need to be completely rethought for a post-industrial economyWhy everyone will need to experiment constantly rather than following set career pathsHow energy constraints might save humans from being replaced by AILINKS:Dror's newsletter: Old/New Dror's LinkedInInterested in me sharing insights on these topics with your team? Book a free consultation - HEREOllie on WorkOllie's LinkedInOllie on Work newsletterMy Book Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 than ever in our distracted workplace, and how to build what she calls "unforgettable presence" without feeling fake or inauthentic.Her insight? Your manager isn't noticing your great work - not because they don't care, but because they're too busy dealing with their own challenges to spot your contributions.TALKING POINTS:Why the "lottery ticket" approach to career advancement is doomed to failHow to build unforgettable presence that goes beyond just showing up in meetingsPractical frameworks for speaking up when you're put on the spotWhy introverts actually have advantages in building visibility (and how to use them)The difference between being heard and being the loudest person in the roomHow to advocate for yourself without feeling like you're braggingLINKS:Lorraine's LinkedIn Unforgettable PresenceInterested in me sharing insights on these topics with your team? Book a free consultation - HEREOllie on WorkOllie's LinkedInOllie on Work newsletterMy Book Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 can now do that better, faster, and cheaper than any human. But he believes this creates the greatest opportunity in human history. The future belongs to what he calls "creator capitalists" - people who use AI and human creativity to build entirely new things of value.TALKING POINTS:Native analogue vs native digital humansThe death of knowledge workersCreator capitalists - how to use AI and human creativity to build new things of valueDiscovering your superpower - what people come to you for and how to monetise itWhy creativity got beaten out of you Building your moat in an AI worldLINKS:Christopher's LinkedIn Category Pirates Play Bigger The Existing Marketing TrapHigh AgencyInterested in me sharing insights on these topics with your team? Book a free consultation - HEREOllie on WorkOllie's LinkedInOllie on Work newsletterMy Book Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 anywhere"—and his research shows this isn't about working from home. It's about fundamentally rethinking how you build and scale teams.His book, The World is Your Office, reveals why the leaders who master this shift will have access to global talent pools while others remain stuck hiring from a single city.TALKING POINTS:Work from anywhere vs work from home - why the distinction matters for talent strategyEngineering serendipity - how to make in-person interactions actually productive instead of accidentalPerformance management revolution - measuring output quality rather than input hoursWhy introverts finally get their chance to lead in distributed teamsThe isolation myth - practical solutions beyond just "bringing people back to the office"Digital nomad villages and the future of coworking spaces as learning labsLINKS:The World is Your Office book Raj's LinkedInInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie on WorkOllie's LinkedInOllie on Work newsletterMy book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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: helping people avoid the career expiration trap and build momentum as the rules keep changing.Today, I'm joined by Eric Jorgensen, CEO of Scribe Media, the world's number one professional publishing company. He's the host of the Smart Friends podcast, author of The Almanac of Naval Ravikant (which has sold over a million copies), and a master at recognising genius in others. His upcoming book will share secrets from Elon Musk's entrepreneurial journey.TALKING POINTS:Career leverage - the craft of increasing your input-to-output ratio and why it changes everythingFour types of leverage - tools, products, people, and capital, and how to identify which suits youHigh agency as the single most important meta-skill for navigating career shifts in the AI eraWhy there's no "should" in career progression - breaking free from linear thinkingRecognising genius in others - how curation and connection can become your competitive advantageAI's impact on creative industries - why it will make the best better and more prolificLINKS:Eric's websiteScribe MediaThe Almanack of Naval RavikantGeorge Mack's High Agency essayInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie on WorkOllie's LinkedInOllie on Work newsletterMy book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 colleaguesWork Redesign: Humans + AI AgentsLINKS:Follow Ollie on LinkedInSubscribe to the Future Work/Life NewsletterMy book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 means to create a more sustainable, inclusive, and fulfilling workplace.Whether you’re rethinking your own career or looking for strategies to lead in the AI era, this episode is packed with actionable insights and thought-provoking ideas.TALKING POINTS:David’s transformative career pivot.The intersection of AI and human connection - how technology can amplify humanity in work.Building a culture of gratitude, recognition, and authentic leadership.Reskilling and upskilling for the AI-driven future of work.LINKS:David's LinkedInFollow Ollie on LinkedInSubscribe to the Future Work/Life NewsletterMy book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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. You'll enjoy this.TALKING POINTS:The importance of mental fitness in the workplace and why it's a growing challenge.How leaders can cultivate positive cultures in which employees are able to express who they are.The difference between assimilation and authenticity in leadership, and why acclimation matters more.How the next generation is changing norms for the better.Tips on where to focus your time and energy.LINKS:Donald's LinkedInFollow Ollie on LinkedInSubscribe to the Future Work/Life NewsletterMy book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 careers.If you've been thinking about how to manage talent in the age of AI, or how to future-proof your own skills, this episode is packed with insights.TALKING POINTS:The growing skills gap and why it’s here to stay.How AI can be leveraged to identify and bridge skills gaps within organisations.Moving beyond traditional credentials - why skills are the new currency.Practical advice for leaders on adopting a skills-based approach to workforce development.The importance of lifelong learning and how organisations can create a culture that supports it.LINKS:David's LinkedInDegreed websiteFollow Ollie on LinkedInSubscribe to the Future Work/Life NewsletterMy book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 this episode, I bring together the standout ideas and discussions from Season 15. We talk about how AI can augment human skills, the changing landscape of workplace connection, the evolving needs of different generations, and the importance of empathy and learning cultures.More great guests to come before the end of the year...LINKS:Ollie's LinkedInFuture Work/Life NewsletterMy book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 conversation feeling more confident about discussing these tough topics—and I hope this episode does the same for you.TALKING POINTS:How the loss of her mum inspired Amber to start The Grief Gang.The challenge of navigating grief at work and why it's often avoided.The power of creating a space for conversations about loss and vulnerability.Amber’s journey in building The Grief Gang community and why community support is crucial.Practical ways to be there for someone dealing with grief—at work and beyond.LINKS:The Grief Gang websiteThe Grief Gan InstagramAmber's LinkedInOllie's LinkedInFuture Work/Life NewsletterMy book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 leaders and executives looking to thrive.TALKING POINTS:The historic shift in work: from agrarian and industrial to decentralised and AI-driven.Why curiosity is a critical mindset for navigating the future of work.The rising value of hands-on, practical skills alongside tech-driven roles.How the “multi-stage life” concept is reshaping career paths and personal growth.Personalisation of work experiences through AI—making employee engagement more meaningful and tailored.LINKS:Cara's LinkedInPeopleTech PartnersInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie's LinkedInFuture Work/Life NewsletterMy book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 Your Leadership Story: How to Build Understanding and Motivate Teams Using Fables and Folktales.TALKING POINTS:The role of storytelling in effective leadership.How neurodiversity shaped Pat’s leadership approach.Navigating career growth in fast-paced, innovative industries.Lessons from leading HR in some of the world’s top companies.Insights on building inclusive, high-performing teams.LINKS:Pat's LinkedInUnlock Your Leadership Story: How to Build Understanding and Motivate Teams Using Fables and FolktalesInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie's LinkedInFuture Work/Life NewsletterMy book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 opportunities shaping the modern workplace. TALKING POINTS:The challenge of workplace disconnection and social isolation—why addressing this is crucial for employee well-being.The ongoing debate on work models: insights on remote, hybrid, and in-office work, and why “one size fits all” doesn’t work.The evolving role of AI in HR and how it can help reduce busywork, enabling people teams to focus on more meaningful human interactions.Rethinking performance reviews—shifting from individual assessments to evaluating team performance for greater impact.Practical steps HR leaders can take to foster genuine human connection and boost team performance.LINKS:David's LinkedInFlare's websiteInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie's LinkedInFuture Work/Life NewsletterMy book, Work/Life Flywheel, was a Business Book Awards 2024 finalist. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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. Listen in to discover more...TALKING POINTS:How Arist leverages AI to deliver high-impact learning.The shift from legacy training methods to rapid, easy-to-deploy microlearning.The importance of meeting learners where they are - why training via SMS and tools like Teams & iMessage is so effective.The role of Stanford-backed research in Arist's development.Arist's new AI Agent, TeammateLINKS:Arist websiteMichael's LinkedInInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie's LinkedInFuture Work/Life NewsletterMy book, Work/Life Flywheel, was a Business Book Awards 2024 finalist. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 ReCulturing: Design Your Company Culture to Connect with Strategy and Purpose for Lasting Success.TALKING POINTS:Why consistent clarity on priorities is the key to team success.Leaders who encourage curiosity foster innovation and growth.How organisations can create environments where continuous learning thrives.What AI means for the future of leadership and learning.Skills-based organisationsLINKS:Melissa's websiteMelissa's LinkedIn profileReCulturing: Design Your Company Culture to Connect with Strategy and Purpose for Lasting SuccessCarolyn Wiley's study on motivation and recognitionInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie's LinkedInFuture Work/Life NewsletterMy book, Work/Life Flywheel, was a Business Book Awards 2024 finalist. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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. In this episode, Chloe dives into the key factors driving these generations' workplace preferences, from feedback culture to boundary setting, and explores how organisations can adapt to attract and retain the talent of tomorrow.TALKING POINTS:Feedback Culture: Gen Z and Gen Alpha expect constant feedback—just like in the rest of their lives.Boundaries Matter: Younger generations prioritise mental health and set clear boundaries at work.Career Aspirations: Gen Z and Gen Alpha are choosing entrepreneurship and creativity over traditional careers.Visibility Drives Motivation: Younger workers need to feel seen to stay engaged and perform at their best.LINKS:Chloe's websiteChloe's LinkedInInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie's LinkedInFuture Work/Life NewsletterMy book, Work/Life Flywheel, was a Business Book Awards 2024 finalist. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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 her analysis of speeches by Abraham Lincoln, Martin Luther King Jr., and Steve Jobs is legendary.Duarte Inc. has helped countless leaders and companies transform how they present ideas, blending empathy, storytelling, and data to craft powerful messages that resonate. In this episode, Nancy shares her insights on communicating authentically, leading with empathy, and adapting to an evolving technological landscape.TALKING POINTS:The Role of Storytelling in Leadership: Nancy explains why storytelling is key to authentic leadership and how leaders can use it to connect with their teams.Balancing Structure and Authenticity: Nancy discusses how to deliver scripted communications without losing authenticity and the nuances of using teleprompters effectively.Navigating Hybrid Work Challenges: Insights on maintaining visibility and transparency in distributed teams and why in-person communication remains critical.The Future of AI in Communication: Nancy’s take on the opportunities and risks of AI and how it might change how we communicate, both in business and beyond.Empathy as a Core Skill: The critical role empathy plays in leadership and communication, and how leaders can cultivate it to improve their influence and effectiveness.LINKS:Duarte IncInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie's LinkedInFuture Work/Life NewsletterMy book, Work/Life Flywheel: Harness the work revolution and reimagine your career without fear, was recently shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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.Culture Amp is the world’s leading employee experience platform, revolutionizing how 25 million employees across more than 6,500 companies create a better world of work. Culture Amp empowers companies of all sizes and industries to transform employee engagement, drive performance management, and develop high-performing teams.TALKING POINTS:AI and Technical Comfort: The importance of embracing technology and AI to enhance workforce and talent strategy.Cultural Transformation: From his start at Deloitte to leadership roles in tech, Nick discusses navigating shifts in workplace culture.Employee Experience as a Culture First Approach: How Culture Amp uses employee engagement data to enhance organisational culture and drive financial success.Performance Management Evolution: Nick’s take on transforming performance management systems to accommodate modern, hybrid work environments.Future of HR Technology: Expectations for integrating AI and analytics into HR practices to enhance strategic decision-making and organisational outcomes.LINKS:Nick's LinkedInCulture AmpInterested in me sharing insights on these topics with your team? Book me to speak with your team.Ollie's LinkedInFuture Work/Life NewsletterMy book, Work/Life Flywheel: Harness the work revolution and reimagine your career without fear, was recently shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.
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