Why I love asking “What if I’m wrong?”

It’s no secret that I love questions.

I’ve found it’s more powerful to ask the right question than to offer the right answer.

‘What problem are we trying to solve?’ is among my favorite questions because it is simple to ask, but not always easy to answer. It leads to a lot of excellent discussions that help us deliver value faster.

Often, the first answer to ‘what problem are we trying to solve?’ is not accurate. That’s okay, because it doesn’t need to be.

Done right, this question — and the resulting dialogue — cuts to the core.

Ask and explore just enough to get to the clarity you need to determine the path forward with the confidence of value to allocate resources, communicate intentions, and take directed action.

The key is striking the balance between enough clarity to take action and overconfidence that leads to a bigger mess and the friction that erodes value, destroys trust, and burns people out.

To avoid overconfidence, I reframe the approach and check my thinking — without being negative — by asking, “What if I’m wrong?” and explore the stakes by asking,

“What happens if I’m wrong?”

The consequence — or lack of consequence — is a powerful guide. Lower stakes allow us to move faster, and higher stakes might require more dialogue and exploration before settling on the path and the best next step.

Often these questions lead to more discussions to explore I don’t know (yet), what I can’t see (yet), or to just experience the situation from other perspectives. Once we reach a point of mutual clarity, we move forward with the confidence of value.

Have you tried asking, “What happens if I’m wrong?”



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