The Rethinking Work Show

The Rethinking Work Show

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.

Episodes

August 27, 2025 43 mins

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.

David Timis is a Global Communications & Public Affairs Manager at G...

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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.

Freddie Laker is a serial entrepreneur, growth strategist, and founding partner of Chamel...

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August 13, 2025 41 mins

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.

 

EPISODE CREDITS

Produced, edited and mixed by Ria Tobaccowala

Artwork designed by Ben Damiano

Additional music licensed through Premium Beats

LINKS

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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 powerhous...

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July 30, 2025 38 mins

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 ov...

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July 23, 2025 35 mins

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...

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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.

Naama Manova-Twito is the Co-Founder & CEO of Marketeam.ai, the world's first agentic Integrated Marketing Environment. Naama brings over 20 years...

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July 9, 2025 48 mins

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. His...

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July 2, 2025 37 mins

How is AI changing the way we collaborate, create, and make decisions at work? 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.

Kyle Csik is the CEO and co-founder of Adaly, an enterprise AI platform transforming how companies turn data into action. With a background in marketing and enterp...

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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.

Andrew Graff is the CEO of A&G (Allen & Gerritsen), an independent, integrated creative agency located in Boston and Philadelphia. Andrew is a leader who challenges the status quo ...

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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...

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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.

Matt Moog is the Founder & CEO of Career Bird, a talent development platform helping organizations unlock the potential of their workforce through skills-based career paths and learnin...

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June 4, 2025 38 mins

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 concepts, research and guidance discussed in this episode, please explore Dr. Prithwiraj Choudhary's new book called "The World Is Your Office: How Work from Anywhere Boosts Talent, Productivit...

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