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How to ask a great question

by | Jul 25, 2021 | Open Leadership

great question

In my career as a coach, one of the best compliments I can ever be given is to ask a question of someone, then, after they pause, to hear back “that’s a great question”.

Two recent occurrences come to mind which, together, have set me to musing on “how to ask a great question.

First, I’m a huge fan of John Amaechi and have not only often enjoyed learning so much from him over recent years, but also many exchanges with him over Twitter. Last week he afforded me a great compliment (in the screenshot) above, around my ability to ask a great question.

Second, and also in the last, someone I hadn’t spoken to for some time messaged me with: “this is going to sound weird, but I have thought of you several times in the last few weeks. Somehow I was trying to picture what your questions and your advice would be in some situation.” For that person, I encouraged them to set up a zoom with me, which they did, where I listened, asked questions, reflected (could be thought of as advice, and sometimes more as a reflection to help the other person work out their own thoughts).

So, “how to ask a great question?”

For sure, sometimes asking a great question will involve having width and depth of relevant knowledge of the topic at hand.

That said, to me, a key to asking a great question, particularly when you are in a coaching space and there to support the other person in finding their own answers, my absolute key lies here:

“hold your thoughts lightly”

This begins with active listening, or, using a famous adage from Stephen Covey, “listening with the intent to understand, not to reply”.

However, it goes beyond that. For me, the absolute best questions always come when I have totally cleared my mind of any last remnants of my mind holding the thought “what is my next question?”. Now, as with meditation, we cannot stop thoughts from appearing, unbidden, in our mind. However, we can choose to hold them lightly, to allow them to pass, so as to keep our mind clear for what emerges.

In my experience, my best questions come forth when my mind is absolutely NOT thinking about what the question could or even should be. I’ve even had experiences where I’ve heard words come out of my mouth and felt as if it was a disembodied voice, as if “where did THAT come from”. You know what, though? For whatever reason, they are often the very best questions.

Those are some thoughts. What helps you ask a great question?