The rethinking work show
Rethink How We Work, Why We Work, And What Work Should Become.
Rethinking Work is a show hosted by Rishad Tobaccowala about how work is changing and how we can change with it. In each episode, Rishad sits down with bold thinkers, builders, and leaders to explore the future of work across industries. From remote work and AI to purpose, creativity, and culture, we uncover the ideas reshaping how we live, lead, and grow in today’s world.
Subscribe to hear fresh, human conversations about what work can and should become.
THE COURAGE TO CHOOSE YOURSELF | September 10 2025
What if the most important approval you’ll ever need is your own?
Author and coach Jillian Reilly discusses her book The Ten Permissions, and why we struggle to let go of others’ expectations, and how to start giving ourselves permission to live and work on our own terms.
How AI Reshuffles The Knowledge Economy | September 3 2025
How is AI reshaping who holds power in the knowledge economy?
Sangeet Paul Choudary, the best-selling author of Platform Revolution and Reshuffle explains how artificial intelligence is re-stacking the way knowledge is created, distributed, and monetized, and what this means for workers, companies, and the future of competitive advantage.
Building Skills is the Future of Work | August 27 2025
What if the key to the future of work isn’t jobs themselves, but the skills that unlock them? David Timis, Global Communications & Public Affairs Manager at Generation, shares why building adaptable skills is more important than chasing job titles and how organizations like Generation are helping people prepare for meaningful, resilient careers in a changing world.
Turbo Charging Through Talent Augmentation | August 20 2025
What happens when work stops being about full-time jobs and starts being about outcomes? Paul Suchman, Freddie Laker, and Juan-Carlos Morales of Chameleon Collective share how the rise of fractional leadership is reshaping companies, giving professionals more flexibility, and challenging traditional ideas of careers, culture, and collaboration.
TALENT IN THE AI AGE | August 13 2025
How do you spot and grow the kind of leaders who can thrive in the age of AI? Jay Haines, co-founder and global president of Grace Blue, shares how expectations for leadership are shifting, what skills will define success in an AI-driven world, and why human potential still matters most.
A Next Generation Agency For A New World | August 6 2025
What if you could tap into top talent, anywhere in the world, exactly when you need it? Luke Smith, CEO and co-founder of Croud, unpacks how the “talent on demand” model is reshaping teams and blending speed, scale, and flexibility without sacrificing culture or creativity. Luke Smith is the Global CEO and co-founder of Croud, a leading independent digital agency.
Since 2011, Luke has helped grow Croud into a full-service powerhouse, serving clients like Amazon Prime Video, Nespresso, and Ford. The company now spans 600 employees and a global network of on-demand experts known as “Croudies” across 118 markets and 86 languages.
Own Your Work, Shape Your World | July 30 2025
What if being a company of one wasn’t just a structure, but a strategy? Flavia Barbat, editor-in-chief of Brandingmag, shares how professionals can build careers around clarity, substance, and intention in a world where content is everywhere but meaning is rare.
As founder of Brandium, Inc. and Editor-in-Chief of Brandingmag, Flavia has been responsible for nurturing and promoting the creation of purposeful thought leadership for over a decade. She represents undiscovered talent within branding and beyond, and vouches for the industry’s collective responsibility to safeguard human creation in an age of synthetic content. Flavia also consults leading B2B organizations on building scalable content platforms through her “editorial marketing” mindset.
How to build a portfolio career | July 23 2025
What if your career wasn’t just one job, but a collection of roles that reflect your skills, interests, and values? Ben Legg, co-founder and CEO of The Portfolio Collective, shares how the portfolio career model is helping professionals design more flexible, purpose-driven lives, and why the future of work may look more like a mosaic than a ladder.
Ben Legg helps business leaders and investors navigate the rapidly changing world and position themselves and their teams for success. Early career included relieving the siege of Sarajevo in 1995, McKinsey strategy consultant, turning around Coca-Cola India, COO of Google Europe and global tech CEO. In 2020 Ben cofounded The Portfolio Collective, to help professionals understand, launch, manage and grow successful portfolio careers - as a community.
How AI Coworkers Are Transforming Work | July 16 2025
What happens when AI becomes part of your workforce, not just your toolkit? MarkeTeam.ai Co-Founder Naama Manova-Twito and Board Members Clive Sirkin and Tony Weisman, share how AI coworkers are reshaping marketing workflows and why the future of marketing will be human-led, AI-empowered.
Andy Spence, Reskilling for the Age of AI | July 9 2025
How do we retrain millions of workers for jobs that don’t exist yet? Workforce futurist Andy Spence joins Rishad to talk about closing the skills gap, preparing for AI-driven change, and why retraining is the most urgent challenge facing the modern workforce. Andy Spence is a leading voice in workforce strategy, with over two decades advising global organisations and the C-suite on how to build better, people-centric workplaces.
Originally from Manchester, Andy now lives in Lisbon, helping CHROs and senior leaders navigate the shifting landscape of work.
Kyle CsiK, CEO and co-founder of Adaly | July 2 2025
Kyle Csik, CEO and Co-Founder of Adaly, joins Rishad to explore how intelligent systems are reshaping our roles and how we can stay curious, creative, and in control in an AI-powered workplace.
Andrew Graff, CEO of Allen & Gerritsen | June 25 2025
What happens when a CEO rethinks office culture from the ground up? Andrew Graff, CEO of Allen & Gerritsen, shares why he brought his team back together—not out of tradition, but through intention, trust, and a bold redesign of how people connect at work.
Dan Cheetham, founder & managing principal of FYOOG | June 18 2025
Can a workspace make us feel more connected, creative, and alive? Architect and artist Dan Cheetham shares how design—rooted in art, music, and human experience—can turn ordinary offices into places of meaning and collaboration. Dan Cheetham is the founder and managing principal of FYOOG, an IA Interior Architects Company. Inspired by his musical background and after stops in New York, London, San Francisco, and Shanghai, Dan formed FYOOG, a studio based in Austin, TX. FYOOG is devoted to creating one-of-a-kind immersive sculptures that reflect and celebrate the unique essence of each client and place in a multi-layered composition, often supplemented with elegant architectural enhancements that transform space into places that engage, inspire, and delight.
Matt Moog, Founder & CEO of Career Bird | June 11 2025
What does a modern career path look like when the job market keeps changing? Career Bird Founder & CEO Matt Moog joins Rishad to explore how AI and data can help people navigate their skills, goals, and growth in a world without straight-line careers.
Dr. Prithwiraj Choudhury | June 4 2025
If work isn’t a place, how do we measure impact, build culture, or grow careers? Harvard Business School professor and author Dr. Prithwiraj Choudhury shares insights from the front lines of the remote work revolution. To dive deeper into the concept, research and insights from today's guest, please consider purchasing his new book, "The World Is Your Office: How Work from Anywhere Boosts Talent, Productivity, and Innovation".