Ollie on Work

Ollie Henderson
  • 5.0 (19)
  • CAREERS
  • UPDATED WEEKLY
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. Hosted on Acast. See acast.com/privacy for more information.

  1. Marcus Buckingham on the Hidden Signals of Career Success

    30 JAN · BONUS

    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 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 education firm, and now leads research at the ADP Research Institute. He's the author of 10 books, including his latest, Love + Work, which explores how we can find meaning and fulfilment in our professional lives. TALKING POINTS: Identifying "Red Threads" - the unique patterns of work that naturally energise youAttention as a creative act - how paying attention shapes your career opportunitiesRedefining strengths beyond performance - understanding what truly motivates youThe specificity of professional passion - why precise activities matter more than broad interestsBrain chemistry and career fulfilment - how doing what you love changes your neurological response LINKS: Marcus's website Love + Work book Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE Ollie's LinkedIn Future Work/Life Newsletter My 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.

    42 min
  2. Dorie Clark on Playing the Long Game in Your Career

    23 JAN · BONUS

    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 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. She's also the author of several books, including the WSJ bestseller "The Long Game" (Harvard Business Review Press, 2021), as well as "Entrepreneurial You," which was named "one of the most important business books of the year" by Inc. magazine and one of the Top 5 Books of the Year by Forbes. I really enjoyed our conversation in which we discussed: Prioritising your time to focus on the things that matter mostThe importance of tracking your progressSharing your ideas with the worldBecoming a recognised expertExperimenting with new ideasNetworking LINKS: Dorie's website Dorie's LinkedIn The Power of Regret: How Looking Backward Moves Us Forward, Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE Ollie's LinkedIn Future Work/Life Newsletter My 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.

    39 min
  3. Daniel Pink on making bold career decisions using mental time-travel

    15 JAN · BONUS

    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 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 is Human, and Drive, which brought the ideas of intrinsic motivation within business and management to the masses. His books have won multiple awards, have been translated into 42 languages, and have sold millions of copies worldwide.  Our chat was packed with insight, and like all the best podcasts I’ve hosted, I learned loads. We discussed why the philosophy of ‘no regrets’ neither reflects reality nor is desirable. As well as breaking down the main types of regret and how we respond to them, Dan explains how harnessing the lessons we learn from these experiences can serve us well in the future and why anticipating regret can be a useful mental model for decision making in the present. We explore why so many people look back on their careers and wish they’d be bolder, whether by going it alone, starting a business or speaking up more. Dan also shares why he became fascinated by the topic in the first place, including what he wished he’d known about maintaining connections with people earlier in his career. Finally, we cover some broader trends related to the future of work, including the pros and cons of remote and the office and whether our work/lives are destined to be defined by independence and autonomy.    LINKS: Dan's website The Power of Regret: How Looking Backward Moves Us Forward, Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE Ollie's LinkedIn Future Work/Life Newsletter My book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  This is what Daniel Pink says about it: "Creating new opportunities requires fresh thinking. With the Work/Life Flywheel model, 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.”aniel Pink from 2022, when we explored how to make decisions using mental time-travel. Hosted on Acast. See acast.com/privacy for more information.

    34 min
  4. Grace Lordan on Thinking Big in your Career

    9 JAN · BONUS

    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 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 practical steps to help you think big and take small actions that make a lasting impact. Talking Points: Building Resilience: Learn how to reflect on your energy levels and interactions to reduce emotional drain and preserve your well-being. Three Types of Resolutions: Grace outlines three categories - quick wins, skill-building goals, and habits to quit - and explains how timing impacts success. The Role of Luck: Discover how to increase your chances of serendipitous opportunities by expanding your network and putting yourself out there. Thinking Big: Grace emphasises the importance of focusing on long-term goals and the small steps that make them achievable without overwhelming your life. Links: Grace's LinkedIn Think Big: Take Small Steps and Build the Future You Want  Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE Ollie's LinkedIn Future Work/Life Newsletter My 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.

    37 min
  5. AI Agents: Our new colleagues

    17/12/2024

    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 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/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.

    12 min
  6. David Landman on The Long Exhale and Leadership in an AI World

    11/12/2024

    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, 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 LinkedIn Follow Ollie on LinkedIn Subscribe to the Future Work/Life Newsletter My 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.

    35 min
  7. Donald Knight on mental fitness & designing a fulfillfing work/life

    04/12/2024

    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 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 LinkedIn Follow Ollie on LinkedIn Subscribe to the Future Work/Life Newsletter My 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.

    24 min
  8. David Blake on the Skills Gap, AI, and the Future of Learning

    20/11/2024

    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 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 LinkedIn Degreed website Follow Ollie on LinkedIn Subscribe to the Future Work/Life Newsletter My 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.

    29 min
See All (234)

5
out of 5
19 Ratings

About

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.

Information

  • Creator
    Ollie Henderson
  • Years Active
    2020 - 2025
  • Episodes
    234
  • Rating
    Clean
  • Copyright
    © Ollie Henderson
  • Show Website
    Ollie on Work

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