The Art of Asking Good Questions

It has been said that assumption is the mother of all f**k-ups (or failures, in more polite company). This statement, ironically, is an assumption itself. However, it is true that it is easy for us to assume we know something. Unfortunately, this kind of thinking leads to all sorts of biases in action – confirmation bias, recency bias, and others enable us to fool ourselves. And while it is easy for us to fall into this trap, it can be simple to avoid as well – by using the right questions to check ourselves.

I’ve written before that I believe that good questions are like a “free” and often overlooked superpower. It is incredible what people will tell you if you ask them open questions and listen to their answers. There are some prerequisites to getting the right answers, though.

  • There has to be a level of trust in the conversation
  • You must be genuinely interested in listening to the other person
  • Your questions must be open – not geared towards yes/no answers

On the first point, it can take time to build trust with other people, but even a basic level of trust in a first conversation can be established by how you interact with the person from the start. There are entire books written on the subject, so I’m not going to attempt to summarise that whole field here.

Listening is a skill in itself – and it’s one that most of us think we’re better at than we are. “Listening to reply” is different to listening to the other person without judging what they’re saying or preparing your response. It takes a lot more patience and practice than we routinely put in. I’ve gotten better at listening openly in my coaching work, but I still make mistakes when listening to people in my personal life. I’m particularly guilty of this when I’m having a chat with my wife, and I think I’m helping her by finishing her sentences – in reality, I’m just being impatient by assuming I know the point she’s going to make.

Then, to the point of this piece, the questions themselves. Asking questions that help others clarify their thinking is a core parting of coaching. For example:

“What would make you more likely to want to complete this?” is very different from “Why didn’t you get this done?”.

“What do you need from me?” is a very different question from “What don’t you have?”

Simply asking “What else?” at the end of a conversation can prompt additional thoughts or insights, which is a different question than “Is there anything else?” which is a yes/no question and can signify that you are done with the conversation.

There’s another question that can be very helpful in sparking insight, and it is one we don’t often ask in a work context. “How do you feel about this?” can bring up emotionally-driven concerns from the person you’re speaking with. Helping them identify and label the emotions attached to their thinking can help them move forward productively with the work.

Given the topic of this post, I’m going to finish with a question – what are your favourite open-ended, insight-generating questions to ask?

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