From Executive Hackathons to Shadow IT: Making AI Normal at Work + Is Notion Mail replacing Superhuman?

From Executive Hackathons to Shadow IT: Making AI Normal at Work + Is Notion Mail replacing Superhuman?

From Work Less: AI at Work by Work Less

August 25, 2025 · 27 min

About this episode

Justin and Tom discuss bridging the AI gap in executive teams and the implications of new tools like Notion Mail and Airbook.

Justin and Tom dig into the growing exec–team AI gap, and what actually works to close it. From exec hackathons (yes, that's a thing now) and weekly “show your prompts” rituals, to putting bumpers on shadow IT before someone wires a weekend AI toy to your codebase, it’s a playbook for making AI normal at work. We also side‑eye Apple’s latest Siri/Gemini rumor, explain why Notion Mail finally pried Justin off Superhuman, and kick the tires on Airbook, aka “cursor for analytics.” W...

People in this episode

Hosts: Justin, Tom

Topics covered

  • AI in the workplace
  • executive teams
  • shadow IT
  • Notion Mail
  • Superhuman
  • Apple rumors
  • analytics tools

Keywords

  • AI
  • executive hackathons
  • shadow IT
  • Notion Mail
  • Superhuman
  • Apple
  • Siri
  • Gemini
  • Airbook

Mentioned in this episode

Organizations: Apple

Products: Siri, Gemini, Notion Mail, Superhuman, Airbook, cursor for analytics

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