Do You Ask Dumb Questions?


My boss, Nick, recently taught me one of my favorite leadership lessons. He said, “Sometimes you just have to ask dumb questions”. I think by “dumb”, he meant “blatantly obvious”.

It is surprising what you can uncover from your team by asking blatantly obvious questions to which you already know the answers. He also gave me a powerful phrase to preface the question: “Help me understand…”

For example, you might have an employee who is under-performing and it is clearly because he or she is prone to wasting time on the clock. A dumb question conversation might sound like this:

“Bob, help me understand why you have only sold 2 widgets so far this month. The minimum goal is 10 and we are 3 weeks in. What’s going on?”

Bob: “Um… well, I have just been really busy with the paperwork. You know, there’s been a lot of customer service issues I’ve had to deal with… uh, I don’t know. I mean… I’m trying…”

“Great. I’m glad to hear you’re trying,” (following up with more dumb questions) “but let me ask you this… your teammates seem to have the same challenges and time frame to work with. Why do you suppose they are able to reach their goals while you are struggling?”

Bob (getting a little defensive): “I don’t know. Maybe they are just better at selling…”

“Do you really think so?” (Dumb question.)

Bob: “No. I mean, I guess… I don’t know; maybe they are just better at time management or something…”

“I see. Well, I really need you to pick up the pace on your numbers. Do you think you can sell 5 widgets by the end of this week? Would you agree that one a day is a reasonable goal?”

Bob: “Yes. That’s reasonable. I will make it my top priority.”

“Great! What can I do to help?”


That last question–“What can I do to help?”–is not a dumb question (though I suppose there are times when it could be). It is, according to Nick, ┬áthe proper follow-up to the phrase, “Help me understand…”. When you are trying to discover the root cause of performance (good or bad), or if you are trying to remove excuses from an under-performer, or even just seeking a way to fill the holes in your team’s game, try Nick’s method.

Start with, “Help me understand…” then ask dumb questions to discover or uncover information, and finish by asking, “What can I do to help?”

By the way, there may be times when you can legitimately provide a new tool, resource, training, or perspective to help, but the most common answer to “What can I do to help?” is “Nothing I can think of right now…”. Turns out if you are asking what else you can do to help, it is usually because you have already done all you can think of, and the sub-text of the conversation is that the employee is quickly running out of options to avoid being successful.

Remember: “Help me understand…” Ask dumb questions… “What can I do to help?”

Try having a dumb question conversation and let me know what results you get. This has quickly become one of my favorite management tools.


(Thanks Nick.)



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Michael Salamey

People are made of many things, but only a few things define a person. For me, those things are Philosophy, Leadership, and Health. I help independently owned and ethically run businesses break through communication obstacles and challenge conventional thinking. Sometimes that means delivering insightful marketing content; sometimes it means having tough but compassionate conversations. All the time, it means communicating and building relationships with honesty and integrity. I am a vegan, an individualist, and occasionally a man willing to risk everything to reach a goal. I am known for being uncompromising in my values, and for being someone who dares to own his own life.

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