Aristotle said, "We are what we repeatedly do. Excellence, then, is not an act, but a habit."
That ancient wisdom applies to improving our question skills just as anything else in our life.
That being said, I want to clarify that our goal isn't really to get better at asking questions – our goal is maybe to be more persuasive, empathetic, judicious, or accurate – and we find that one of the most effective tools in pursuing those things – happens to be question skills.
Here are some things you can do on a regular basis to strengthen your question muscles.
First is to watch for great questions and capture them for yourself. The reality is that you aren't likely to invent a question that's never before been asked – your library of great questions will grow faster if you find and collect them.
You may hear them from friends, mentors, books, or even listening to thoughtful people in a podcast interview.
A question that has stuck with me is from the late business thinker Clayton Christensen. He asks organizations, "What job is your customer hiring your product to do?" I've always thought it's a fascinating take on a question that may more commonly be asked as "Why do customers buy your product?" On the surface, they are similar, but how I apply the first question yields very different thinking than the second. I'm focused on the problem my customer has that they are willing to pay money to have something like my product to solve. Whereas the latter version may get me thinking about the promotion I offered or word-of-mouth referral.
When you hear questions that give you a different experience – capture them! It's like playing Pokemon, only with questions!
Next. Experiment. When you're going for coffee with someone, in a business meeting, or interview – try out a question that you haven't normally used to see how they respond.
You might hear – "Ooh… that's a good question." Or "Hmm. I'll need to think about that." But there's a chance you also hear, "I'm not sure what you mean" "I don't know how to answer that."
Your first thought if they struggle with answering, maybe "Oh, I didn't ask a good question," but rather than thinking about it being a failure – look at it as feedback in your question development. You're testing out questions that work for you.
Which means, before you show up at the meeting or for the coffee appointment – taking some time to prepare will be another powerful habit. I'm not talking about an hour of prep for a 45-minute meeting. It could be just taking 5 minutes to answer for yourself some primer questions like:
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How can I be most helpful in this conversation?
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What do I need to be mindful of?
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What's being assumed, but not talked about?
Find for yourself questions you can ask on your own that will help to get your mind oriented.
Here's another one – comfort with discomfort. For many, that means being ok with silence. I've seen it so often that a great question gets asked – but while one person is reflecting it, the asker jumps in and says or asks something else. When you ask a question – give it space! If I ask someone what the implication is of not addressing an employee's bad behavior, I need to give space to the other person to wrestle with it. I can't jump in with ideas to save them from the silence.
Another form of discomfort is asking questions about bad things that could happen in the future. In the previous example – finding out what may happen if the behavior isn't addressed may be uncomfortable because I'm asking the other person to experience an uncomfortable future.
The power of that is there is something they can do today to avoid that future. But I have to be ok with introducing that experience.
Here's a final habit for you – asking, "What else?" This might sound just like, "Is there anything else?" But it is radically different.
Let's keep on the employee behavior topic. Their first response is: "It might hurt team morale."
If I ask – "Is there anything else?" they can easily stop their thinking and say, "Nope."
But by asking "What else?" they feel compelled to keep searching for things. They start finding things like productivity, customer satisfaction, employee retention, and the list goes on. I keep on what else until they say, "I think that's it!"
I'm telling you – the discipline to ask what else is a superpower. I had a student tell me two days after training that he had a sales presentation with a client in Brazil. He asked what they wanted to cover – they named a topic. Then, rather than his usual "OK, let's get started," he instead asked, "What else?" What came after was five minutes of the prospect pouring out frustrations and problems they've been experiencing with their current approach. Because of that little question – he was able to completely shift his message and hit exactly what the prospect was really needing.
Your assignment, identifying the one habit that you can put in place for the next two weeks. Be intentional, incorporate it into your routines, then monitor for results.
In our next session, we pull all the pieces together.
