The Rethinking Work Show

Rishad Tobaccowala

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.

Play

Open in

21 episodes
fortnightly
Avg 38 min
English

Episodes 21

Newest Oldest Longest

All20 Unplayed20 In progress0 Played0

Counted on this page — what you have heard stays on this device, so it is not something the list can be paged by.

#37
September 2 · 45 min
Doing More With Less
What if building a bigger business doesn’t require building a bigger team? Tim Huelskamp, co-founder and CEO of 1440, shares how a small, focused team reaches millions of readers, and why staying lean, curious, and intentional can create outsized impact.
#36
August 12 · 38 min
Career Rewired
How do you keep evolving when the world around you won’t stop changing? Marketing leader Lou Paskalis explores what it takes to reinvent your career, stay relevant through disruption, and embrace change before it’s forced upon you.
#35
July 22 · 31 min
The Human Edge
As AI becomes more capable, what will make humans indispensable? Matt Lewis, founder and CEO of Transformental, explores why the future of work depends not just on smarter technology, but on strengthening human judgment, leadership, and the qualities that AI can't replicate.
#34
July 16 · 29 min
Finding Your Fit
How do you find work that aligns with who you are, not just what you can do? William Vanderbloemen, founder and CEO of Vanderbloemen Search Group, explores how understanding your strengths, behaviors, and motivations can lead to more fulfilling careers and more effective leadership in a rapidly changing world of work.
#33
June 24 · 39 min
Rethinking Career Growth
Is career success measured by moving up or moving forward? Cliff Maxwell, co-founder and CEO of Vocation, explores the difference between career progression and career progress, why fulfillment matters as much as advancement, and how individuals can take greater ownership of designing meaningful careers in a rapidly changing world of work.
#32
June 18 · 43 min
Identity Reinvention
What happens when you leave the career you've spent decades building? Julie Fedele, a Future of Work strategist and portfolio career mentor, explores why career transitions are as much about identity as opportunity, and how more professionals are moving beyond traditional employment to build a body of work that’s truly their own.
#31
June 3 · 44 min
Collaboration Revolution
In a world overflowing with productivity tools and AI assistants, are we actually working better together? Toby Daniels, co-founder of ON_Discourse and Domain, explores why the future of work depends on better collaboration, stronger networks, and systems that help us think and not just work more effectively.
#30
May 13 · 42 min
The Talent Shift
As AI transforms marketing and reshapes organizations, what skills and leadership qualities will matter most? Richard Sanderson, Partner at Spencer Stuart, explores how companies are rethinking talent, adapting team structures, and balancing automation with human judgment.
#29
April 29 · 31 min
Dynamic Teaming
What if teams weren’t built around roles, but around problems? Britt Gage, founder and CEO of oAT (of All Trades), explores the shift from static org charts to dynamic teaming, where generalist operators execute, adapt, and connect across functions. As AI reshapes work, Britt argues the future belongs to flexible, problem-centered teams, and to organizations designed to move as fast as the challenges they face.
#28
April 16 · 36 min
The Capability Stack
In a world where skills expire faster than ever, how do you stay relevant? Veronika Kryuchkova explores the idea of the “capability stack", a dynamic mix of core, human, and future skills, and why thriving in today’s workplace requires continuous reinvention, high agency, and the ability to learn, unlearn, and evolve faster than the market.
#27
April 1 · 37 min
Rethinking Compensation
What if we stopped paying for time and started paying for outcomes? Matt Seiler, founder and CEO of Excelerators Inc., explores why traditional compensation models are breaking down in an AI-driven world, and how performance-based pay, better incentives, and a renewed focus on human value can reshape how we work, measure success, and reward impact.
#26
March 19 · 39 min
The Orchestration Era
As AI accelerates and traditional corporate structures strain under pressure, what does leadership look like in the next era of work? Justin Billingsley, co-founder of Simbioniq and former Global CMO of Publicis Groupe, explores why the age of heroic managers is giving way to orchestrators who design systems that think, adapt, and coordinate at scale.
#25
March 4 · 36 min
Work Enabling Learning
Are we preparing students for the world of work or a world that no longer exists? Authors Alexandra Levit and Stephanie Loeck explore how work-based learning can close the gap between education and employment, and why real-world experience, not just classroom instruction, may be the key to building adaptable, future-ready talent.
#24
February 18 · 42 min
Beyond The Resume
What if the future of careers isn’t about résumés or job titles but about fit? Avi Steinlauf and Tomas Chamorro-Premuzic, co-founders of myTrudy, explore how personality science and AI are reshaping career decisions, helping people move from static search to dynamic, human-centered reinvention in a rapidly changing world of work.
#23
February 4 · 39 min
Turbocharge Human Talent
As AI reshapes the marketing landscape, what makes human talent more essential not less? Jeff Levick, CEO of We Are Rosie, shares why performance-based compensation, flexible teams, and the right culture are key to unlocking the full power of people in a tech-driven world.
#22
January 21 · 36 min
The Shift Work Revolution
How do we bring dignity, flexibility, and innovation to the millions of hourly workers who keep our world running? Jarah Euston, President and Co-founder of WorkWhile, shares how behavioral data and community-driven design can reshape frontline work and why the future of labor starts on the warehouse floor.
#21
Dec 11, 2025 · 43 min
How Small Teams Do Big Work
How can small teams now match, and even outperform, the output of much larger organizations? The team at Fourth Wall Advisors shares how AI-driven workflows, intentional design, and diverse, non-overlapping expertise are reshaping how work gets done. From reducing friction to unlocking deeper creativity and faster iteration, they explore why the future of high performance belongs to small teams built for curiosity, adaptability, and human connection.
#20
Nov 26, 2025 · 30 min
The Future of Workforce Mobility
What if where people live became a core part of how they work? Gary Brown, president and co-founder of Furnished Quarters, shares how workforce mobility is changing in a hybrid world, and why companies are shifting from hotels to flexible housing, what employees need to thrive on remote assignments, and how thoughtful living solutions can strengthen culture, retention, and performance.
#19
Nov 5, 2025 · 36 min
Reinventing How Companies Access Talent
What if companies could access top creative and marketing talent as easily as opening an app? Lara Vandenberg, founder and CEO of Publicist, shares how she built a platform that connects global brands with premium freelance talent, and why the future of work depends on flexible, trusted systems that empower both companies and creators.
#18
Oct 22, 2025 · 36 min
Death of the Corporate Job
What if the corporate job is no longer the default path to a meaningful career? Alex McCann, founder of TrueNorth, explains why so many young professionals feel lost at work, how Gen Z is redefining success, and why the future may belong to those who start with self-discovery instead of job titles.

Showing 1–20 of 21 episodes