April 14, 2020  |  David R. Novak

Asking Better Questions

Asking Better Questions

Being able to ask good questions is essential to being a good communicator. Why is asking good questions important? Hey, good question! And how can we ask good questions? Look at that, another one! How are question-asking and listening related? What’s important to keep in mind when we want to ask questions?

First, you should know that people like people who ask questions. Asking many questions improves bonds and connections. Questions demonstrate interest in someone. Questions extend and lift conversations. They keep the ball rolling. They allow you to explore and open up space where people can learn from one another.

Questions aren’t merely an act of transmission. Good questions encourage and lead to relational breakthroughs and insights, new places where conversations would not have gone, had a question not been asked.

The first step to becoming a better questioner is quite simply to ask more questions. This much is basic. Humans like to be asked about themselves. This is an exploitable feature in our programming. It’s good to ask questions about others — provided that you’re genuinely curious and hopefully respectful of their radical individualism.

The number of questions is not the only thing that influences the quality of a conversation, but more questions is a good start.

Ok, so we have to ask better questions, but how? Here’s 6 principles to keep in mind about asking questions. Follow these to better communication.

1. Asking questions demonstrates your interest in the other person.

This is basic, but your questions show your interest in the other person: their perspective, what they know and feel. So show interest! Be excited and enthusiastic. Be inquisitive. It’s how we learn. A simple question that demonstrates you’re interested in what the other person is talking about goes really far to developing bonds and forming connections.

2. Don’t ask yes/no questions.

This is one of the worst mistakes you can make. This? Or that? Yes? Or no? Any question that is easily answerable with a surface-level yes or no, or this or that, is probably not a very good question. They don’t lead anywhere. They don’t open up any possibilities for conversation, exploration, or explanation. Along those lines…

3. Ask open ended questions that invite the other person to talk.***

When you narrow potential responses through how your question is phrased, you introduce your biases into the conversation. You want to phrase questions in a way that invites people to talk. “Can you tell more about…?” “Would you explain more about…?” “What happened?” All easy open-ended questions. Now, if someone answers you with one word or gives you a short answer, that’s on them. But you should try not to limit potential responses in how you ask. Leave the possibilities open. Use questions to probe your conversational partner’s experience and learn their perspective.

Sometimes you need to be more pointed with your questions, for example if there are only two viable or potential answers. However, always be mindful of cutting off alternatives through how you ask your questions. We do this often, almost with a naturalness in our abilities to see things in binary terms. There are almost always more than two options.

4. Use Follow-Up Questions.

Follow-up questions have special powers. Use them. They show even more interest in what the other person is saying than you did by asking your initial question. They allow you to further mine for depth and build deeper connections. The best part is that you can follow up on whatever you (the asker) finds most interesting!

Follow-up questions signal to your partner that you’re listening, that you’re interested, and that you want to know more. Follow-up questions make your conversation partner feel respected and heard.

Best perhaps, is the fact that follow-up questions don’t require a whole lot of thought, effort, or preparation. All you need is something like “Ooh, interesting. Can you explain more about that?” or “Tell me more!” (Not technically a question.)

It all has to be authentic though. People will sniff through the fake enthusiasm of inauthenticity in milliseconds.

5. Ask your question and be quiet.

Use silence to your advantage. We don’t think much about the role of silence in communicating (because we tend to think about communication as ‘sending messages’), but the two are connected. Staying quiet is key to listening, which is one of the most important parts of communication. Once you ask your question, use the time immediately following to concentrate on listening.

A trick I learned when I was learning how to teach was to ask your question and then wait. You have to wait. Someone will respond eventually. Ask your question and be quiet. Whether you’re teaching or not, the lesson is the same. Let the other person think, don’t interrupt. Leave space for your question to work its magic.

Once the other person is talking, stay quiet. Listen to them and their answer. Find places to follow up and probe.

In many situations, such as on a job interview or a date, it’s to your advantage to sit quietly and look interested while the other person is talking. It’s scientifically proven that people who leave conversations and feel like they were listened to feel better about the interaction and the person across from them. Ask questions, listen intently, and people will find you likable. That’s science! [1]

6.  Order matters.

There are optimal ways to order your questions, but much is dependent on the circumstances. How you open up conversational space is always a concern with initial questions and the order of asking. There are not perfect answers here. When it comes to building a relationship, opening with less-sensitive, even benign questions and then slowly ratcheting up question depth and personalness can be successful.

In some situations, going to the serious questions first can fail miserably. As a part of some fieldwork as a young researcher, I once naively asked a guy named Lonnie how it was he came to be homeless. Lonnie gruffly replied, “I’m not telling you that!” And I realized how insensitive and profoundly personal it was to lead with such a question. I managed to salvage the conversation and actually became friendly with Lonnie at the time. But, je taught me a real lesson that question order matters.

Questions foster smoother and more enjoyable interactions. Good questions result in trust, rapport, and meaningful connection. Good questions come from a place of wonder and curiosity, with a capacity for us to delight and discover each other.

Questions show a willing belief that a conversation produces a whole greater than the sum of its parts, as if almost by magic.

Questions let us learn. You get to hear and consider other people’s perspective, inquire for their insight, and learn from their experience.

These principles can help you ask better questions. And better questions build better connections, better relationships — better communication.


[1] Huang, K., Yeomans, M., Brooks, A. W., Minson, J., & Gino, F. (2017). It doesn’t hurt to ask: Question-asking increases liking. Journal of Personality and Social Psychology, 113(3), 430–452. https://doi.org/10.1037/pspi0000097

***Disclaimer: Does not apply to all circumstances, especially negotiations and legal proceedings. In a negotiation for example, open ended questions can leave far too much wiggle room, which invites people to dodge or lie by omission. In certain situations, closed questions work better especially if they are framed correctly. Question-askers assume all liability.

Skills | Listening | Good Communication