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Business Management

Good Leaders Ask Dumb Questions

6 leadership traits in defense of asking the obvious

Walt Grassl

Paul and Trudy work in a medium size company. Trudy was having lunch with Paul after a particularly grueling meeting.

“Paul, I can’t believe what just happened in the budget meeting. None of the supervisors had the guts to point out an error the manager kept repeating. Everyone looked at each other, but no one spoke up. I wanted to say something but I was afraid if I was wrong, I would look stupid. As we were leaving, I asked Jim (her supervisor) privately if I was wrong and he said no, the manager was."

Paul said, “I believe good leaders ask dumb questions. It is not only OK, but one must question the obvious and call out the elephant in the room.”

He went on to share a quote from his mentor, Sam, who said, “If you ask a question, you may look stupid for five minutes. But, if you don't ask, you stay stupid forever.”

People may be afraid to ask dumb questions because of peer pressure. They may lack self-confidence. Whatever the cause, not asking dumb questions diminishes your value to your employer.

Here are six benefits of questioning the obvious:


Asking dumb questions allows you to develop courage. Courage is the ability to do something that scares you. Like facing most fears, the more we face them, the smaller they become.

Asking a dumb question is often a tough decision. Demonstrating the courage to ask also demonstrates decisiveness—an important trait for leaders.

Asking dumb questions indicates a lot about you. It indicates you are not intimidated by the situation. It indicates you add value as a participant in the meeting. It indicates you represent the silent majority in the audience. The silent majority who had the same question but lacked the courage to bring it up.


When you ask dumb questions, you acknowledge that you don’t have all the answers. You show that you don’t know everything. You are seen as more open to being questioned. 

You don’t appear to be superior. You are approachable, relatable, and authentic.

Ask dumb questions to ensure you have all the facts, data, and opinions you need to make higher percentage choices. You will be a trustworthy leader. You will instill confidence.

People are likely to use you as a sounding board. They know you will thoughtfully consider what they say. They know you will honestly question them and offer suggestions. Good leaders value those open and honest people.


When you have vision, you imagine what might be. Asking dumb questions can help determine creative, out-of-the-box solutions to problems. Your wild idea/question may be totally nuts, but may inspire someone else. They may see a solution not quite as whacky as yours. That solution solves the problem, saves money, and/or greatly improves performance.

Another part of vision is contingency planning. What is your plan B?

If your company is awaiting a widget from a notoriously dependable supplier, questioning their reliability may initially seem to be a dumb question. But, the answer may be, “You’re right, we should explore some contingency plans in case they are late. Thanks for reminding us.”


Many have left meetings comfortable with the decisions that were made, only to suddenly have those decisions change.

At the end of every meeting it may seem dumb to ask, "What have we agreed to?" You get agreement on what decisions were made, who is doing what, and by when. It may often seem dumb. But one day, answering that question will uncover misunderstandings. Clarifying misunderstandings takes minutes, and it can save weeks of lost time and money.


When a new process is being deployed, asking questions may be seen as dumb. It may be seen as a sign of resisting change or a questioning authority. But, blindly following a new direction can lead to problems. The organization may not get the intended results—not because the change was bad, but because the people implementing the change didn’t understand why.

Avoiding asking the obvious can lead to companywide groupthink. When members of the team blindly accept a new initiative or the direction of a project, there can be a crippling lack of clarity and cohesion.

The path of least resistance often leads to peril. By stepping up and daring to ask the dumb questions you ensure that everyone is focused and on the same page. 

Teaching Moments

Good leaders learn to delegate. Delegation requires follow-up. It also requires confidence that the right things are being done right. One way to be confident that things are being done right is to ask questions. If they know the answer and assume you are dumb for asking, so what. If the answer you get indicates that they aren’t on track, you have an opportunity to correct the course of action.

You will learn whether they grasp the concept. You may be surprised to learn that what you meant is not what they understood. When that occurs, try to explain it another way.

That evening, Trudy thought about Paul’s words. She remembered that she had seen others ask dumb questions and nothing bad happened. She remembered an instance when a dumb question turned out to be not so dumb, after all. She realized that she could handle feeling dumb for five minutes, if it meant speaking up. She felt she could maximize her value at work.

Her work life got a lot easier. She felt less stressed in meetings. She got relieved looks from her colleagues when she had the courage to ask the obvious.

About the Author

Walt Grassl is a speaker, author, and performer. He hosts the radio show, “Stand Up and Speak Up,” on the RockStar Worldwide network. Walt has performed standup comedy at the Hollywood Improv and the Flamingo in Las Vegas and is studying improv at the Groundlings School in Hollywood. For more information on bringing Walt Grassl to your next event, please visit