Keeping Questions Casual

Here in the US, it’s the spookiest time of year. No, not Halloween… Election season! I wonder if you too have been receiving emails (or texts) with calls for immediate action, and questions like “Why haven’t you [donated/called/supported]?!” The uptick in demands – from both sides of the political spectrum – is always alarming during election season, and it’s in stark contrast to the kinds of questions I hear from people in real life as we gradually embrace ‘normal life’ in a post(?)-pandemic world, like bears emerging from hibernation. Conscious of different people’s level of comfort, these questions are much more relaxed and breezy – “I was just wondering how that project you mentioned before is going?”, “How would you feel about getting together for a meal?”, or simple check-ins like “What are you up to these days?”

In recent coaching sessions with groups of executives from a variety of companies, I have been struck by the importance of tone in asking questions. When practicing high-stakes conversations, most people focus on using “correct” wording – i.e. wording that is non-judgmental and seeks understanding. What’s much harder is to speak those words in a tone that does the same thing, especially if you’re feeling frustrated or challenged yourself. I worked with two executives just yesterday on rehearsing a conversation that one of them needed to have, and it turned out that the other would need to be quite involved in that conversation too, on the other side – the realization of which meant that it was a perfect hands-on learning experience! They were both adept at using a framework that we provided to ask powerful questions, but the tone they both carried shone through in undeniable ways. Over the course of the session, though, they were able to ask (and answer) questions in a much more relaxed way, that led to significant breathroughs and actionable next steps to resolve their challenges.

In a 2018 article in the Harvard Business Review, business professors Alison Wood Brooks and Leslie K. John explore “the surprising power of questions,” much of which would not be a surprise to regular readers of ours; we have written extensively about using open-ended questions, and the value of wondering and asking (it does, however, talk about asking tough questions first to allow people to open up, and the value of closed questions in some cases; so it is certainly worth reading if you haven’t before). The article also speaks extensively on the use of a casual tone in asking questions, both in an online format (participants were twice as likely to reveal sensitive information on a casual-looking website than a formal one), and in person. “People also tend to be more forthcoming when given an escape hatch or “out” in a conversation. For example, if they are told that they can change their answers at any point, they tend to open up more—even though they rarely end up making changes. This might explain why teams and groups find brainstorming sessions so productive. In a whiteboard setting, where anything can be erased and judgment is suspended, people are more likely to answer questions honestly and say things they otherwise might not.”

This Week’s Tip:

Keep questions casual. This may take a lot of practice, but good news! You’ll be asking questions for the rest of your life! Lots of time to practice.

  • In writing: When drafting emails, take a pause before hitting send. Read back over your email – sometimes it can be helpful to read it backwards – from the last sentence to the first – to pick up on anything you missed while writing. You could also scan your email for question marks, and look at how those questions are asked. How would you feel if you were asked these questions in the context you used? Are there ways you could ask these more casually to get more useful responses? Is there anything else you can change in your email to make the tone more collaborative?
  • In speaking: If you know you have a high-stakes conversation coming up, take a few minutes to draft some questions, and use the notes above to help you think through them. If you’re in a conversation you haven’t been able to prepare for, but you find yourself wanting to ask a question, take a breath first. If you feel relaxed, your tone is more likely to be one of curiosity than accusation. After the conversation is over, reflect on how it went – perhaps with a trusted colleague or other observer who was there, to get another perspective. If you find you could have asked in a more inviting tone, no worries! Just use that as a reflection before you go into your next conversation. You’ll have plenty more opportunities to practice!

Try this out this week, and let us know how it goes in our Facebook group! We’d love to hear from you. As always, you can subscribe to our feed here, or sign up for our weekly newsletter to get these articles directly in your inbox.

Published by Ian Jackson

Ian Jackson is the founder of Building Bridges Leadership, which works with individuals, teams, and organizations to create authentic community in the workplace. He also writes children's fiction and teaches creative writing.

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