David R. Longnecker

Ever notice how the most powerful question in product management is also the favorite of three-year-olds, philosophy professors, and 90s boy bands?

That deceptively simple word—"why"—might just be the most underutilized tool in your product toolkit.

The “Why” Intersection

Product managers live at this peculiar intersection of curiosity, persistence, and sometimes annoying repetition. But there’s profound power in embracing your inner three-year-old’s relentless questioning.

Beyond the 5 Whys

Toyota’s famous “5 Whys” technique—asking why repeatedly to get to the root cause—has become product management gospel. But the real magic happens when “why” becomes a mindset rather than just a methodology.

When we stop asking “why,” we start making assumptions. And assumptions are the silent killers of great products.

The Why Toolkit

Three powerful moments to deploy your “why” superpower:

1. Feature requests: “Why do you need this feature?” often reveals the actual problem needing solving.
2. Strategic decisions: “Why are we prioritizing this now?” cuts through organizational inertia.
3. User behavior: “Why did users do this instead of that?” uncovers invaluable insights that data alone misses.

Embracing the Awkward Silence

The most valuable “whys” are often followed by uncomfortable silence. That’s your signal to wait, not rescue. The best insights emerge after the practiced answers run out.

So next time your at a planning session or a Zoom call, channel your inner Backstreet Boy. Keep asking them to “tell you why” until you reach understanding that transforms your product decisions from guesswork into insight.

Your users might not “want it that way,” but they’ll thank you for taking the time to understand why they want anything at all.