How fast can you upskill in AI? We did a sprint to find out.

How fast can you upskill in AI? We did a sprint to find out.

From Possible by Reid Hoffman

May 20, 2026 · 38 min

About this episode

The episode explores the urgency of learning AI and the experience of conducting an AI Sprint to implement new tools across an organization.

We all feel the urgency: learn to use AI, or risk falling behind at work. And we all know there’s upside: AI can reduce tedious tasks, streamline operations, and boost output. But knowing is half the battle (maybe even less) and implementing AI needs to happen across an entire organization. So what does it take to start? Well, here at WaitWhat (the company behind this podcast!) we paused all operations for three days to find out. From editorial curation to visual design to event planning, we split into teams for an “AI Sprint.” And this Pioneers of AI episode takes you to the starting blocks on the track with us, as we test new tools, discover their limitations, and find where AI can deliver on its promise. Learn more about Pioneers of AI: http://pioneersof.ai/ Follow Pioneers of AI on all channels: https://linktr.ee/pioneersofai At the center of AI is people, so we want to hear from you! Share your experiences with AI — or ask us a burning question — by leaving a voicemail at 601-633-2424. Your voice could be featured in a future episode!

People in this episode

Host: Reid Hoffman

Topics covered

  • AI
  • upskilling
  • organizational change
  • technology implementation
  • productivity

Keywords

  • AI
  • upskill
  • sprint
  • productivity
  • implementation
  • technology
  • operations

Mentioned in this episode

Organizations: WaitWhat, Pioneers of AI

Places: AI

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