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  • Writer's pictureShandy Welch

Tips for Asking Great Questions

Updated: Nov 11, 2022



We have been asking questions since the day we could talk but how impactful are these words and are you inadvertently sabotaging yourself along the way?


As a leadership coach, my job is to ask powerful questions without any bias as to where the answer leads us. I try to craft fewer but more powerful questions in an effort to get to the root of the problem rather than dance around the issue. So what is the trick? While I continue to learn and hone my skill, I do want to share some powerful insights.


  1. Powerful questions do not have to be verbose or layered with fancy vocabulary. Most of the time, a simple, well-crafted question is the key to unlocking great wisdom.

  2. You can’t ask a great question if you have not listened to learn. Remember my favorite quote? “Listen to learn rather than listening to respond.” Great questions come when you are present with the other person, consider the context of the conversation, the tone of their voice, and are able to forego emotion and judgment.

  3. Don’t “stack” questions. This is well-known in the coaching world but may be new to you. “Stacking” is when you ask multiple questions at a time in various ways or ask a question and then pontificate and then ask another question (or two) on top of it.


Stacking does two things, it diminishes the power of the question and it confuses the other person since you have strayed from the questions creating a lack of focus. The strategy here is to slow down and pick your words carefully. Craft your one question that specifically asks what you want to learn and then… stop talking! (that is the hardest part) Allow for silence and time for the other to thoughtfully consider the gravity of your question. Once aware, you will notice how often you stack and how little those additional questions add.


Many times we stack because we are nervous or do not have clarity as to what we need. Take time prior to your conversation to organize your thoughts and create questions that clearly express your inquiry.


  1. The last one to highlight is the “why” question. While it makes sense to seek to understand the origin of the thought or action the WAY in which you ask it and the words you choose could elicit different responses. “Why” questions many times invoke a defensive reaction even if that was not your intent. For you linear thinkers out there, this will be tough. You want to get to the point and move on... ”Why did you include Tom in this meeting?” “Why did you send that email?” Simple enough, but the other person may feel you are questioning their authority and conclude that you disagree with their decision. (maybe yes, may no, but either way, the story you just created is not in alignment with your intent)


David Marquet who wrote the great book Turn the Ship Around also wrote a wonderful article in Medium titled 7 Ways a Leader Can Ask Better Questions, check it out!


My Challenge to You:

  • Be mindful of how you craft your questions and if you have a tendency to stack. If so, take a movement to craft one powerful question and then listen to learn.

  • When tempted to ask “Why”, reframe and come from a more curious position. “Could you tell me a bit more about how you decide who should attend the meetings?”

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