Project Management Happy Hour

126: "What's your AI Strategy?" Handling the Executive who wants AI in everything

Jun 3, 2026
Executives pushing AI into every project and how to respond when they ask for it without a plan. How to speak AI buzzwords credibly while avoiding hype. When AI makes good prototypes versus when it creates production or governance risks. Practical tactics to say yes in principle, ask the right how/what questions, and keep projects grounded amid the AI gold rush.
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ADVICE

Ask How AI Will Solve A Specific Problem

  • Ask "How?" not just "Can we?" — require a clear vision for AI's role (automation, insights, etc.) before adding it.
  • Kate recommends probing whether the sponsor means chatbots, analytics, or something else.
INSIGHT

AI Feature Value Depends On Real Pain

  • AI features can be either vitamins or painkillers depending on customer pain.
  • Kate contrasts PM tool chat summaries (nice-to-have) with Monday.com's AI onboarding (real cost-saving painkiller).
ADVICE

Say Yes In Principle Then Define Options

  • Say yes without committing: acknowledge interest, then return options and success criteria.
  • Kate suggests agreeing in principle so sponsors feel heard, then present quantified options later.
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