Episode 10: How Might We?
S1 E10 January 31, 2026

Episode 10: How Might We?

What if the question you're asking is killing your best ideas before they're born? "We should redesign the dashboard." "We need to fix onboarding." "We have to implement AI features." Thes...

What if the question you're asking is killing your best ideas before they're born?


"We should redesign the dashboard." "We need to fix onboarding." "We have to implement AI features."


These statements sound decisive and action-oriented. But they're creativity killers—because they skip exploration and jump straight to solutions. The answer is already embedded in the question.


In Episode 10, Bill introduces "How Might We"—three words representing 50 years of cognitive science research and the single most powerful reframe in innovation.


You'll learn:
- The linguistics: Why each word matters—"How" (optimistic), "Might" (opens possibility), "We" (collaborative)
- The Goldilocks problem: How to scope questions that aren't too broad ("make customers happy") or too narrow ("add a blue button")
- Classic transformations: Airbnb's shift from "get more bookings" to "make guests belong anywhere" (the billion-dollar difference), P&G's Coast soap beating Colgate
- The 5-minute Complaint Converter: Turn raw frustration into innovation opportunities through structured reframing
- Common failures: Solution disguise ("How might we implement chatbots?"), blame game, impossibility constraints
- The evidence: IBM research showing 301% ROI from design thinking practices centered on HMW
- AI age evolution: Using AI to generate variations, async HMW for distributed teams, pairing research insights with questions


Real impact stories:
- Startup that avoided 6 months and hundreds of thousands in AI development by reframing one question
- Team that dropped churn 40% in two months by asking about "essential" instead of "retention"
- Checkout redesign that generated 23 ideas (vs. 8) just by changing the question framing


The core insight? "The question is the strategy. Get the question right, and solutions follow. Get it wrong, and you'll execute brilliantly toward irrelevance."


Resources: Download the Complaint Converter template, Goldilocks checklist, and real company examples at workshopr.io/hmw