How to Ask Smart Questions


October 19, 2007   •   Fact checked by Dumb Little Man

Perhaps this is from my sales background but it has occurred to me that most people ask silly questions. I am not talking about asking questions that a 3rd grader would know the answer to, I am talking about asking questions that do not illicit a favorable response.

Let me give you an example:

YOU: “Boss, what can I do to get a promotion?”
BOSS: “You have to hit your deadlines and the goals we set during your review”

Well, no kidding. That response did indeed answer your question and although YOU asked for it, the response was generic and you are going to walkaway thinking your boss isn’t interested in your development. Right?

Let’s try it my way. Here is another example:

YOU: “Boss, assuming I hit my goals and deadlines, what else can I do to put me in a better position to get promoted?”
BOSS: You really need to get involved more in the strategy of our department as opposed to simply getting projects done. The more you can add to our direction, the more you will be seen as a visionary and a resource to our team.”

As you can see, your wording severely impacts the response you receive. The key is to address the obvious answers within your initial question. You want to make the other person elaborate on what you already know. That’s the entire point of a question isn’t it?

So let’s make a short list of key things you need to do in order to get the response you want:

  • Go to the source: A lot of people ask questions to those that they are most comfortable talking to. This is a huge mistake. It obviously will depend on the situation but using the promotion scenario mentioned above, I don’t see any reason why you can’t accidentally run into your boss’ boss in the hallway and ask, “Oh, hey Mary, I wanted to ask how can advance in the company assuming that I reach all of my objectives.” Why not? If anything, it will tell Mary that you have a ambition. You can then take that information and strategically insert it into a conversation with your boss – remember you now know something your boss doesn’t.
  • Be Specific: Do not generalize. Be as specific as you can in your question, “How to I do X, Y, Z?”


  • Follow-Up: I don’t care what you ask or who answers it. If the question is important, have the answer reiterated. You can do this in one of three ways:


    • The Recap: “So you are saying that if X and Y occur, Z will happen. Is that about right?”


  • The Dummy: “Ok. Can you expand on that a little (I want to make sure I understand)?”



  • In other words: “Ok great, if X and Y happen, I should expect Z because…” Use totally different wording and add a benefit to the end. Even if a benefit was never stated, your adding one will attach something valuable to the conversation.


Asking questions is seriously an art. We can all ask how to do something but only a thinker can ask it in a way that will illicit the desired response. Try it out tomorrow – try asking people questions a little differently and I guarantee you will get more detailed, specific responses.



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