Outthinkers

#149 — Adam Brotman: Building the Mindset of an AI‑First CEO

Oct 7, 2025
Adam Brotman, former Chief Digital Officer of Starbucks and co-CEO of J.Crew, dives into the mindset needed for AI-first leadership. He shares insights from his conversations with tech visionary Bill Gates, emphasizing AI as a tool for enhancing decision quality rather than just productivity. Brotman discusses the challenging 'middle era' of AI and how leaders must adapt their strategies. He stresses that authentic inspiration, not technical know-how, is vital for CEOs to drive meaningful AI transformation across their organizations.
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INSIGHT

CEO Aha Drives AI Strategy

  • An AI-first CEO needs an authentic personal ‘aha’ about AI’s strategic importance.
  • They should mandate adoption and empower teams rather than become technical experts.
INSIGHT

AI Delivers Qualitative Uplift

  • Bill Gates views generative AI as qualitatively different from past deterministic software.
  • Gates felt AI could uplift the quality of work like a smart advisor, not just speed it up.
ADVICE

Act In The Middle Era

  • Treat the current period as the 'middle era' and act despite messiness and risks.
  • Begin integrating AI across functions now to avoid competitive disadvantage later.
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