Great questions inspire better conversations. My book club recently read Basketball (and Other Things) by Shea Serrano, which seeks to ask and answer approximately 33 questions about, you guessed it, basketball and other topics, such as action movies and anthropomorphism.  While reading this book and reflecting on how to lead the conversation, I participated in coaching workshops and deep, challenging practice as part of a foundational coaching experience at Vancity. I am learning a lot about how to construct incredible, discussion-enriching questions. Here are five more tips for asking great questions.

Make them relevant and personal

“What do you need from this conversation?”

Great connectors can make someone in a crowded room feel like they’re the only one who matters. Focusing on the person in front of you and deeply listening to what they needis critical for experiencing a great conversation. Whether you’re meeting an in-law or getting to know your new direct reports, it’s crucial to take a step back from the work or the goal and get to know the people. Great questions reveal how you can begin to understand another human, not just advance your agenda.

Be ridiculous provocative

“If 1997 Karl Malone and a Bear Swapped Places for a Season, Who Would be More Successful?”

This question is literally asked and answered by the great Shea Serrano in his book. If you know anything about basketball and/or wrestling and/or noted outdoorsman Karl Malone then this very unique question probably intrigues you. Especially since Serrano runs right into the ridiculousness of the question with clarifying points like, “once the bear is placed on the team nobody finds it weird or strange” and “the bear is anthropomorphic like a Ninja Turtle” and “if the bear acts aggressively, it’s only in a very human manner”. When you ask a big, bold, possibly-bonkers question be ready to dig into the idea and flesh out the criteria for responding because doing so will light up your conversation partners as co-creators, debaters and enthusiastic observers.

Keep an open mind

“What is the opposite point of view of My Gut?”

If you have a brain then you have a bias. Being able to question your instincts, perspectives and decisions is essential for asking the kinds of questions that unlock the potential of a conversation (as opposed to just taking it where you think it should go). One of the things that I do to mitigate my bias is think about people with very different perspectives and/or styles than me and ask what they would do if presented with the same facts.

Shift perspective

“How might we enhance curiosity in our organization?”

I love this question. Specifically, the how might we…?beginning. How it’s phrased emphasizes openness (how), potential (might) and collaboration (we). We should expect this sort of beautiful simplicity from the innovative geniuses at IDEO.According to HBR’s Warren Berger, “Proponents of this increasingly popular practice say it’s surprisingly effective — and that it can be seen as a testament to the power of language in helping to spark creative thinking and freewheeling collaboration.”

Seek to understand, not to reply

“What would it look like to seek their perspective on this issue?”

My former boss and current friend, Kim, and I were recently at the same conference. After reflecting on several really great indigenous learning experiences she expressed the problem about taking someone’s perspective as opposed to seeking it. Taking things – even a perspective – sounds like colonialism and taking a perspective isn’t really possible. Stephen Covey, of course, would probably enthusiastically agree. When we’re chatting with people we so often ask and listen in order to reply to the question, which doesn’t make your conversation partner feel great. Remember, saying “tell me more” is always better than, “yeah, something similar happened to me!”

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