For Insightful Conversations, Learn How to Ask Great Questions

Judging from the nodding heads, you see that a deep state of ennui has settled in around the table. (And this is just 15 minutes after break!) You have three hours left of this interminable day, with lots of  ground still to cover.  You know that the usual tedious process of asking everyone to take a turn around the table won’t do anything to inject energy into the room.

Luckily, you’ve prepared a set of “just in case” questions – just in case people aren’t speaking, or speaking too much, have become disengaged, are falling asleep or begin digressing. (Asking questions off-the-cuff doesn’t come easily to you. You envy people who have the kind of natural inquisitiveness and sense of timing that allows them to conjure up brilliant questions on the fly.)

You zero in on the perfect question and once you ask it, everyone starts inching up to the table, puts down their devices, and dives into an animated conversation. You breathe a sigh of relief.  If asking the perfect question at the right time isn’t exactly magic, it’s pretty close to it.

In their article The Surprising Power of Questions (May/June 2018 issue of Harvard Business Review), authors Alison Wood Brooks and Leslie K. John share the results of extensive research on the role questions play in spurring conversations, building trusting relationships, fostering learning and mitigating business risks.

Here are some of their observations and tips, combined with some of my own. The bottom line: It’s never too late to learn how to craft and pose great questions. And if you want to amp up the quality of your conversations, there’s no time like the present.


  • Ask a lot of questions. Most of us ask far too few, for many reasons. The biggest inhibitor, say the authors:  Most people have no idea how beneficial asking really good questions can be. In fact, we can improve our emotional intelligence with the simple act of asking questions, which in turn makes us better questioners, creating a virtuous cycle. The people we’re conversing with benefit, too. By expressing real curiosity, you show people you care (assuming, of course, that you actually listen to what they have to say in return). One of the chief reasons that so many job interviews and first dates fall flat is the fact that the other person failed to ask questions of the other.
  • The secret to creating great questions: Ask questions others will enjoy answering. Consider what kind of question will make them think deeply, spark their creativity, give them energy.  If you’re in a group, what can you ask that will foster conversation and prompt the sharing of ideas?  Think about the goal of each conversation, and the individuals who are participating.   Chances are, some questions will resonate more with some than others. The key is to create a set of questions which, taken together, can energize the group as a whole.
  • The wisdom of follow-up questions. The authors list four distinct types of questions: Introductory questions (“How are you?”), mirror questions (“I’m fine. How are you?”), full-switch questions, which completely change the topic, and follow-up questions to solicit more information. Of the four, follow-up questions are the most powerful, for they show you’re paying attention, and that you want to know more. For example, when I write interview questions, I create a set of probing questions for each. This way, I don’t have to think up a follow-up question in the moment, though, I do ad lib frequently. For some of us, the ability to ask follow-up questions comes naturally; others may need to plan out such questions ahead of time. The more you practice, the more naturally it will come.
  • Know when to ask open-ended questions. Well-worded open-ended questions help stimulate conversation, generate new ideas and elevate energy. Ask questions in a way that can be answered easily and fairly succinctly; beware of questions that require a lengthy response. Even in the unlikely event that you have unlimited time, it can be tedious for everyone to have to wait his/her turn while waiting for many long-winded participants to speak. Calculate how much time is needed for everyone to respond, and make sure your agenda allows for it. It might be that not every person needs to weigh in, and that a few responses will be sufficient.
  • Closed questions have their place, with qualifications. Asking a closed-ended question (“On a scale of 1-10…..” or “Provide just one adjective to describe…”) can be a quick way to obtain a lot of information in a short time. I often use close-ended questions when people are disengaging from the conversation, when a few people are dominating, or conversely, when some are not speaking up. Answering a close-ended question early on can make even the most reticent person more likely to jump into the conversation. On the flip side, beware of closed questions that limit thinking, force false choices (“Do you care about our future, or do you want to stick with the status quo?”) or constrain conversion.
  • Sequence matters, depending on the situation. During contentious conversations, asking the tough questions first can persuade people to open up more easily. People are more willing to reveal sensitive information, say the authors, when questions are asked in a decreasing order of intrusiveness. (If, however, the initial question is too intrusive, you risk offending or alienating others.) To build relationships, it’s usually best to open with less sensitive questions, working your way up to more sensitive ones.  Cultural differences matter, too. In some cultures, asking highly personal questions of someone you don’t know well can be highly offensive; other cultures tend to “overshare” and relish answering questions that others might find invasive. (If you’re looking for love, try 36 Questions in the exact order given, which were designed to bring people closer together, in just 45 minutes!)
  • Using the right tone makes all the difference. People are more likely to respond freely when a casual tone is used, versus a more clinical, formal delivery. The authors found that people are more likely to reveal sensitive information in an online survey when the user interface was “fun and frivolous,” contrasted to less revealing respondents who were directed to an “official-looking” site. People tend to be more forthcoming when they’re given an “out,” such as the option to take a pass or change their answers later. This can help explain why brainstorming sessions with erasable white boards and removable sticky notes can be especially effective in generating freewheeling ideas.
  • Watch out for group dynamics. The willingness to answer questions can be greatly affected by the mere presence of others. What’s more, group members often follow one another’s lead, whether due to the perceived power of certain people, laziness, lack of confidence, or other factors. (This is especially true for some cultures, notably where hierarchy is important.)  Sometimes it takes just one person to answer openly for everyone else to follow suit. Conversely, if everyone else is staying mum, it will be harder for those who want to respond to find the courage. Consider having people write down and post, or type in, their responses before opening up a group dialogue. Gauge the situation constantly to determine how, when or if to pose a question.
  • Treat your introverts with sensitivity. Most introverts need time to reflect and are more comfortable if the question-and-response process is predictable and safe.  So, instead of asking everyone to shout out responses, try giving everyone a moment or two for silent reflection and ask them to write their answers on paper before seeking verbal responses. Then, try going around the room, rather than asking for random shout-outs. Introverts are reluctant to interrupt others, and often need a gentle prodding to volunteer ideas. Instead of asking something like: “John, do you have something to add?” personalize your question: “John, you’ve had some relevant experience that others here have not. Would you mind sharing an example or two of how these two environments are different?”
If asking questions doesn’t come naturally to you, jot down great questions you notice. Search for resources (articles, books, etc.) that explain the art and science of asking great questions and offer examples you can modify.  Even seasoned interlocutors can’t always pluck that perfect question from memory; write down questions ahead of time so you have them handy when you need them. Pay attention to how dramatically the energy can shift or a face can light up when a thoughtful question is posed. Err on the side of asking too many questions rather than too few. By posing carefully-worded questions at the right time, we can build stronger relationships, establish trust, awaken minds and hearts, cultivate greater shared wisdom and sustain engagement and motivation.


Facilitation Skills Training by Guided Insights – including a significant component about how, when and where to pose the right questions, whether working virtually or face-to-face

The Surprising Power of Questions by Alison Wood Brooks and Leslie K. John (May/June 2018 Harvard Business Review – paywall)

Better Brainstorming (with questions) by Hal Gregersen (March/April 2018 Harvard Business Review)

36 Questionspublished in Psychology Today

Making Questions Work – book by Dorothy Strachan (fabulous resource!)

Previous Communiques:

Wait, What? and 4 Other Essential Questions that Expand Thinking and Spark Conversations

To Get People Talking, Try Asking the Right Questions   

How to Create Opportunities for More Aha! Moments


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