Author "Product Management in Practice"; career coach
AUG 14 2025
The Question
Ask This Before Every Product Decision
"The question is: 'What would need to be true for this to be the right decision?' That question saves careers. Most PMs never ask it."
The right question reveals your assumptions — which is where most decisions fail
PM failure: making decisions based on confident assumptions that were never validated
The question forces hypothesis-testing rather than advocacy
It works in any direction: what needs to be true for you to be right AND for you to be wrong
Framework
The One Question Framework
80%
of PM decisions fail at assumption level
3×
better outcomes with assumption-testing
1
question that unlocks all the others
"What would need to be true for this to work?" — reveals the hidden bet
Once you name the bet, you can test it — a prototype, an interview, an analysis
If the bet is untestable, it's not a decision — it's a guess
The career-saving move: say "I'm making a bet that X is true. Let's verify before we build."
Matt's observationThe best PMs say "here's what I'm assuming" before they say "here's what we should build." The worst PMs say the second without the first.
Product Career Survival
Why PM Careers Derail
Advocacy over inquiry: Defending decisions instead of testing assumptions
Losing the forest: Optimizing features while the strategy is wrong
Stakeholder management theater: Managing optics instead of managing outcomes
Impact measurement avoidance: Shipping without defining success first
The advocacy trap
PMs who advocate for their ideas and test their competitors' ideas are operating backwards. Test your own ideas hardest.
The impact definition test
Before every project: "How will we know in 90 days if this was the right thing to build?" If you can't answer it, don't start.
Playbook
Ask the Right Questions
For every major product decision: "What would need to be true for this to be right?"
Define your success metric before you start building — never after
Document your assumptions explicitly and assign each a confidence level
Revisit your assumptions monthly: which ones changed? What does that mean for the decision?
The book insightMatt's "Product Management in Practice" is required reading for every PM. The advice is annoyingly simple and consistently ignored.
Contrarian
PM Wisdom Myths
✗Data-driven decisions are always rightINSTEAD →✓ Data without good questions produces confident wrong decisions faster than gut instinct.
✗Great PMs advocate for usersINSTEAD →✓ Great PMs advocate for outcomes. Users ask for features; they need solutions to problems.
✗Stakeholder management is about managing upINSTEAD →✓ Stakeholder management is about aligning incentives. "Managing up" is a symptom of misaligned incentives.
✗Shipping is the measure of PM successINSTEAD →✓ Learning is the measure of PM success. Shipping without learning is expensive activity with no value.