HBS Managing the Future of Work Reading and riding the AI wave: John Winsor on the value of flexibility
9 snips
Oct 15, 2025 In this engaging discussion, John Winsor, a serial entrepreneur and Harvard Business School executive fellow, dives into the evolving world of work shaped by AI. He highlights how COVID accelerated the shift to freelancing and unbundled traditional jobs into flexible tasks. Winsor provides insights on why many AI initiatives falter and stresses the importance of leadership engagement. He also shares career advice for young graduates, emphasizing the value of curiosity and experimentation. Finally, he envisions a future filled with agile, entrepreneurial ventures enabled by AI.
AI Snips
Chapters
Books
Transcript
Episode notes
Freelancers Fueled Early Ventures
- John Winsor built companies using freelancers because he couldn't staff large full-time teams.
- He sold a magazine to Condé Nast and his agency to Havas after succeeding with flexible talent models.
Pandemic Accelerated Open Talent
- COVID accelerated adoption of digital staffing and made organizations more open to freelancers.
- Companies remain culturally resistant to variable labor despite the productivity and access benefits.
Unbundling Jobs Into Tasks
- Jobs will be unbundled into tasks and then rebundled across employees, projects, gigs, and synthetic labor.
- AI's democratization of expertise will accelerate task-level redistribution and new work arrangements.
