How to tell if you’re asking a stupid question

A common cliché I often hear leaders say is, “Feel free to speak up! Remember, there are no stupid questions.”

By Cy Wakeman3 min readUpdated July 20, 2022

A common cliché I often hear leaders say is, “Feel free to speak up! Remember, there are no stupid questions.”

I can think of a time when that statement was true. My second-grade teacher would remind us of this to build our confidence with adults, who at that time could be a bit scary to us. But in the workplace, everyone is an adult. There should be an expectation that everybody will participate and select questions wisely. In the workplace, there really are stupid questions.

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In my experience, these are really unhelpful and expensive questions and here’s why:

There is no answer to these questions—really.
Even if you could speculate an answer, it would add no value to the situation.
They all imply blame.
They fly in the face of personal accountability as a concept, let alone a core expectation.
They are focused on other people who are outside of the control of the employee.

To spend a single second of thought or action on such questions is a complete waste of resources, period.

Questions that begin with “Why,” “Who,” or “When” often fall into this category, especially if they concern human behaviors. The words “Why,” “Who,” or “When” are only valuable when beginning questions that seek information on a process or logistical detail of a plan. Human behavior is simply not rational, which means there are often no answers to these questions.

A single “stupid” question can commission hours of resources in the form of meetings, research, analysis and discussions that are a total waste of time, talent, and focus. In my research, almost 2.5 hours per day per employee are wasted seeking an answer that doesn’t exist, doesn’t matter, or reinforces the erroneous belief that others are the source of our problems.

When you hear yourself or someone else asking one of these stupid questions, for the love of resources, move quickly to help steer their efforts into asking smarter questions that have actual answers, and that, if found, lead to actions that deliver results.

Help to re-write stupid questions. Here’s how:

Change every “Why,” Who” or “When” to either a “How” or “What.”
Follow with the words “can I.”
End the question with some action word such as “do” or “help.”

Here’s what helpful and accountable questions sound like:

“Why do things keep changing?” becomes “What can I do to get skilled up for change so I am unfazed by it?” or, “How can I help drive the change?” or even, “How can I quickly align with the change?”
“Why doesn’t anyone tell me anything?” transforms into “What can I do to get the information I need?” or “How can I actively stay informed?”
“Who thought of this?” will become “How can I best support this?” or the even more proactive, “How can I provide better information to my decision makers?”

These powerful, rewritten questions are filled with personal accountability. Plus, these smarter questions empower the employee and encourage the team’s energy toward results. As teams pull together to answer these questions, they’ll focus their energy on what matters.

As leaders, work with your employees to specifically create a list of possible answers to these smart questions. Teaching our teams to ask more accountable questions relieves the impossible burden on the leader to be the only problem solver. Leaders can move from over-managing and rushing in to fix problems to leading first by calling teams up to solve any problems that arise. The answers generate an instant list of simple instructions of where the employee can use their time and talent to create results and add value in spite of challenging circumstances.