When Leaders Ask the Wrong Question

Why the real crisis isn’t bias—it’s misframing power itself.

Executives love to talk about “answers.” Metrics, dashboards, AI-powered analytics—every boardroom is filled with confidence about answers. But here’s the uncomfortable truth: most failures don’t happen because the answer was wrong. They happen because the question itself was broken from the start.

The Challenger disaster wasn’t caused by faulty math. It was caused by NASA asking, “Can you prove it’s unsafe to launch?” instead of, “Can you prove it’s safe?” One framing made risk invisible; the other would have made it unavoidable. The result? Catastrophe.

That pattern plays out every day in corporate decision rooms.

The Wrong Questions That Sink Companies

Take the e-commerce example: executives noticed a decline in average order value and immediately asked, “Which promotions will lift AOV the fastest?”

The framing assumed price was the lever. So they pulled it. Promotions went out. Discounts flowed. The charts looked healthy for a quarter. And then the bottom fell out—customer trust collapsed because the real issue was quality and delivery reliability.

The executives didn’t make a “bad decision.” They made a “bad question.” And by doing so, they made the problem worse.

Why This Keeps Happening

Traditional strategy work is still trapped in the myth that the job of leaders is to find answers faster. But answers are cheap. Generative AI will produce endless ones at the push of a button. The real test of leadership is whether you have the discipline—and the power—to ask the uncomfortable questions that expose root systems, not surface optics.

And this is where the so-called “framing effect” isn’t just a bias. It’s a structural failure. Organizations punish people for reframing. Middle managers learn to answer the boss’s question, not challenge it. Analysts optimize what’s asked, not what’s missing. HR packages dissent into “engagement feedback,” not strategic correction.

The bias isn’t cognitive. It’s political.

The Power to Reframe

Let’s stop pretending the remedy is just “invite devil’s advocates” or “use red teams.” Those are window dressings. The real fix is to shift organizational power so reframing isn’t optional—it’s enforced.

Here’s what that looks like:

• Reverse accountability: Before approving a decision, executives must document the assumptions embedded in the framing. If those assumptions fail, accountability flows back to the framers—not the implementers.

• Systematic dissent: Reframing questions isn’t a brainstorm exercise; it’s a formal checkpoint. If no one has challenged the question, the decision cannot proceed.

• Outcome-back design: Start from the enterprise outcome (profitable growth, resilience, trust) and trace backward until you surface the real question. Anything less is activity theater.

The Cost of Speed

Executives often defend poor framing with urgency: “We don’t have time to step back.” But speed doesn’t save you if you’re running in the wrong direction. A perfect answer to the wrong question is just acceleration toward irrelevance.

Patience in framing is not indulgence—it’s the cheapest insurance policy an organization can buy.

The Insurgent Mandate

The real insurgent insight is this: organizations don’t fail because they lack answers. They fail because the system protects bad questions.

If leaders want resilience, they must hardwire reframing into the enterprise. Not as a workshop. Not as a leadership competency. As infrastructure.

Because until reframing becomes enforceable, every “answer” is just a gamble disguised as strategy.