Thinking With Mitch Joel

Navigating Strategy In The Age Of AI With Roger Martin - TWMJ #1021

40 snips
Feb 1, 2026
Roger Martin, retired Rotman dean and strategy advisor known for Playing To Win, joins to unpack strategy in an AI era. He contrasts AI as a questioning thought partner vs an answer engine. They explore AI’s tendency toward modal answers, how to use it to reach rare insights, the promise and limits of diversity, and why rigorous strategy is really persuasive argumentation.
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INSIGHT

AI Gives The Mode, Not The Edge

  • Roger Martin warns AI as an answer engine gives the modal (most frequent) response, not the novel tail answers strategy often needs.
  • Use AI as a Socratic thought partner to surface questions and challenge your own assumptions rather than a decision oracle.
ADVICE

Treat AI As A Socratic Thought Partner

  • Build AI tools that act as dialogue partners to provoke better thinking, not to hand you answers.
  • Structure prompts to question definitions, assumptions, and inferences so you discover answers yourself.
INSIGHT

Diversity Helps Only With Proper Dialogue

  • Diversity only helps if people know how to mine opposing views productively instead of crushing them.
  • Teach teams to surface inferences and evidence so differing perspectives combine into better ideas.
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