How to Ask Better Questions

Why do you want to learn how to ask better questions? Walk me through the next steps of how that might help you? What else will have to be true for that to work out for you? Who will help you? Who is going to resist and prefer the status quo or some alternative?

Questions like these will help you to find the best insights, which will help you to develop the best plans. Because if you want better answers, you should start asking better questions

Fortunately, there are people who can help us to learn how to ask better questions. For instance, the questions above were found in part by trying to learn how a great interviewer works, what techniques an FBI hostage negotiator uses, and how innovators and disruptors think. These people are trained, or have trained themselves, how to think more clearly, how to dig deep for truths, how to question things, and what makes people tick. You can do the same.

The secret is to be curious. If you relentlessly seek to understand the world around you, you will make progress. Good questioning technique will help you go further and it will help you go faster.

A great interviewer will make the person being interviewed feel comfortable. That’s helpful to keep in mind as you manage a conversation. David Letterman was interviewing Kanye West on an episode of Letterman’s Netflix show My Next Guest Needs No Introduction. I remember how Kanye looked a bit nervous and uptight as they came out on stage in front of a large audience and sat under the lights on a start set that had just two chairs. What did Letterman do? He asked Kanye what he had for breakfast. It immediately changed the mood and allowed Kanye to get into the interview where later on they delved into deeper discussion topics. 

How you phrase a question matters too. FBI hostage negotiator Chris Voss has found that questions like “What are the next steps?” throw people into analytical mode. They want to come up with a thoughtful, perfect answer, so many tend to defer a response. Instead, he suggests phrasing like “It seems like you might have some next steps in mind…” that allows a person to more comfortably roll ideas off the top of their head.

I’ve noticed also that one of my favorite podcast interviewers will phrase a question multiple ways at once in order to give the interviewee options in how to respond. It’s another way to make a question less pointed and allow a person to choose a comfortable path and also give them an opportunity to shift the direction more easily. That can help uncover information and insights you wouldn’t otherwise know to ask about.

If you are looking for more pointed and direct answers, I like to ask a lot of “why” questions. It always surprises me how much useful information can be learned by asking about someone’s motivations and what they think the motivations of others might be by asking “why” questions. But “why” questions can go further. They can help you to understand what people perceive as limitations. Understanding and perhaps testing those limitations can help to reset parameters for possible solutions. “Why” questions can also help you to understand how things work, especially when you string together a series of questions aimed at understanding how something works. 

As you practice all of these techniques, and whatever other techniques you pick up on your own, you will also be learning how to be a better listener. You will naturally boost your emotional intelligence. After all, you will be thoughtful in questioning, you will be considering the reaction of others, and you will be responding in real time to all of the dynamics of a good discussion again and again. People may also like you more, because you will be interesting. But also because you will be showing interest in them. We all like to be asked about things we know, the work we do, and our opinion on things. 

Perhaps one of the most important techniques to build in your quest to ask better questions is one of the simplest, but often overlooked. The follow up question. This can be as simple as asking for an example of whatever the person just described. “Can you give me an example?” This question can quickly take a high concept down into a concrete example where you can get a much clearer understanding of something. Another great follow up is simply, “What do you mean by that?”It can really take you inside someone’s thinking. Rather than accept the conclusion, it’s often more interesting—and more helpful—to understand the thought process that got them there.

Great insights don’t just pop out of nowhere. But they are sometimes hiding in plain sight, if you simply ask better questions. It takes some time to build this skill, but it is very much worth doing. If you are curious and persistent, you will find better answers. You will develop better solutions, uncover keen insights, and see more possibilities.