Chi Nguyen -

Apr 21, 2024

How to Ask Meaningful Questions with Jeff Wetzler

communities gathering and building

The following interview has been edited and condensed. You can learn more about the Ask Approach and pre-order the book here.

Your new book is about the superpower of asking questions in ways that tap into people’s wisdom and turn talk into action. What are the secret ingredients behind this superpower?

We are all much worse at reading other people’s minds than we think. Research by Nick Epley, a professor of behavioral science at the University of Chicago, has consistently shown that we overestimate our ability to make accurate inferences about what other people are really feeling or thinking at a given moment – even those closest to us. And common advice, like reading body language or trying to take someone else’s perspective, just doesn’t work. In fact, research shows that there is only one way to reliably get access to what’s really going on in other people’s heads: you have to ask them.

The Ask Approach is a concrete set of five practices that anyone can use to discover what those around them think, feel, and know.

  1. Choose curiosity by asking yourself, “How can I awaken my curiosity to make new discoveries and unexpected connections?”
  2. Make it as safe, easy, and appealing for people to tell you hard things.
  3. Pose quality questions, determining which questions will maximize your chances of learning something from another person.
  4. Listen in a way that allows you to hear what someone is really trying to tell you.
  5. Take the time to reflect on what you have heard and reconnect with the other person to share your reflections back with them.

While each practice on its own is powerful, when combined, they give us the greatest possible chance of learning from – and connecting more deeply with – the people around us.  

The single most powerful way to read people’s minds is to get genuinely curious about what you don’t know. Train yourself to constantly be asking, “What am I missing, and what can I learn from them?”  

What do you see as the main challenges preventing people from asking meaningful questions and sharing honest answers?

When it comes to people withholding what they think, feel, and know, my experience and research on this topic reveal four main barriers. Some of these barriers are about what people are experiencing – maybe they are too busy or tired to share, or maybe they just can’t find the words to express what they have to say. Other times, their reasons may have to do more with who we are and our relationship with them. They may fear hurting us or worry that what they say will lead to judgment, shaming, and punishment. All of this can be exacerbated across lines of difference and when power dynamics are at play.  

However, one of the main reasons people withhold is that they don’t think we are interested in what they have to say — in large part because we don’t ask them questions.  

Our reasons for not asking as often as we should are both psychological and cultural. We are wired to see things from our perspective, which means we often forget to get curious about how our experiences may differ from others. What’s more, research shows that we tend to underestimate how much people want to be asked questions, while overestimating how rude or invasive we would be perceived for asking.  

This creates a self-perpetuating cycle. People hold back from sharing the full extent of what they think, feel, and know because we don’t ask, and while they stay quiet, we assume we have already heard everything there is to know.   

But if we can start to ask questions, the well of information begins to flow, opening our eyes to just how much we can learn from others and motivating us to ask even more questions.    

Early in the book, you wrote about your childhood in which you associated staying safe with staying quiet, listening, and observing others. At what point did you find the shared rewards of asking quality questions and listening? How did that experience change you?

The real lightbulb moment arrived for me during my first job out of college, at the consulting firm Monitor Group. It was there, under the mentorship of experts like Chris Argyris and Diana Smith, that I realized there was a whole set of tools and methods designed to unlock exactly this kind of information. Over the next decade, I witnessed and personally experienced the power of these methods to unlock unexpected insights and open up whole new levels of learning.   

I consistently observed three patterns in the leaders I worked with, regardless of the kind of organization and where it is located around the world. First, people again and again reported with amazement that this was the most powerful material they’d ever learned professionally. Deceptively hard, but worth every drop of effort. Second, they became aware, often for the first time, of how their actions blocked the results they most wanted, stunted their relationships, and cut off learning. But the most important pattern I observed was the third: once they started working with these concepts, they got better very quickly and immediately opened new possibilities for themselves and those around them. These experiences convinced me that I had stumbled upon pure gold – a simple set of concepts and experiences that could unlock learning, better decisions, and stronger relationships for anyone willing to try them. 

Can you explain the safety cycle, and why is it important to create the appropriate conditions for people to share openly?

Decades of research by Harvard Business School Professor Amy Edmondson and others have demonstrated that for people to speak up, they need to feel psychologically safe doing so. In other words, they need to believe that you will not judge, shame, or punish them for sharing openly with you. Like I mentioned earlier, this is all the more important when there is any kind of power dynamic at play or when you are interacting across lines of difference, such as age, race, and gender, all of which can intensify the risks (real or perceived) of speaking candidly.  

The Safety Cycle incorporates the three key elements of making it safe for people to share openly: creating connection, opening up, and radiating resilience. It starts by creating a connection. When people feel genuinely connected to you, and you to them, you both can relax in each other’s company and feel safer.  

One of the most effective ways to foster a connection is to enrich and deepen your stories about one another. A question like “What’s the story behind how you ended up where you are today?” can prompt people to share a part of themselves you don’t already know, while also allowing them to share only as much as they feel comfortable.   

But you have to share, too. People are far more likely to share what matters to them if you open up about your intentions to learn—and if they perceive you as truly open to learning from them. That starts with explaining why you’re asking a question, so they don’t have to guess at your agenda. This way, they know up front that they’re not being tricked or misled into sharing something that you could use against them.   

It’s also important to radiate resilience by demonstrating that you can handle whatever they have to say and that you won’t hold them responsible for any emotional reactions you have. The fear of hurting, upsetting, or angering you is the number one reason people don’t tell you what they think or feel. Identifying and assuaging this fear upfront is often the permission slip people need to start sharing. But remember – once you make this promise, you have to keep it. This step takes vulnerability – something I and so many people can struggle with – but it’s a risk you have to take if you want others to open up to you so that you can truly learn from them. 

I have a three-year-old who is very good at asking why. What message do you have for parents who want their kids to be more curious about other people and the world?

Kids are born with an incredible desire to learn and connect, and questions are the primary tool they use to do this. Unfortunately, children receive messages in school and from the broader culture that discourage this natural curiosity, and over time their question-asking declines to near-zero. If we want all kids to stay curious and keep asking questions, we can’t be passive about it. We need to do so through a combination of nurturing and modeling.  

On the nurturing side, you can kindle the flame of your child’s natural curiosity by exposing them to a diversity of people, perspectives, and experiences and giving them the time and space to explore what they feel drawn to. When they ask you a question, do your best to give an honest, thoughtful response. When they make a discovery, help them trace it back to the questions they initially asked.  

It’s also essential to model the behavior you want to encourage. Ask them questions about themselves and really listen. Model vulnerability by being honest when you don’t know something.  

What’s the most memorable question someone has asked you?

One of the most powerful – and most overlooked – questions is simply, “Who are you?” When this question is asked from a place of genuine curiosity, in a way that makes the other person feel safe to share authentically, it opens the door to whole new levels of insight and connection. 

This is a question we sometimes ask as part of an identity-deepener exercise at Transcend. I learned it originally from Thaly Germain, an amazing leader and facilitator. In the exercise, each person repeatedly asks the question to a partner, over and over again for 2 minutes (and then they switch roles for another 2 minutes). What you learn from the other person gets deeper and more interesting each time the question is repeated. 

When I was on the receiving end of the question, I even found myself surprised by some of the answers I gave after the fourth or fifth time I was asked, which shows how questions can reveal new insights for both the asker and the person being asked. This kind of repeat question-asking – basically asking some form of “what else?” each time the person finishes speaking  – is an incredibly effective way to surface thoughts, feelings, and knowledge the other person would likely not share otherwise, in part because they themselves don’t even realize what’s within them.  


Jeff Wetzler has been on a quarter-century quest to transform learning opportunities. Blending a unique set of leadership experiences in the fields of business and education, he’s pursued this quest as a management consultant to the world’s top corporations, as a learning facilitator for leaders around the world, as Chief Learning Officer at Teach For America, and most recently, as co-CEO of Transcend, a nationally recognized innovation organization.

Jeff earned a Doctorate in Adult Learning and Leadership from Columbia University and a Bachelor’s in Psychology from Brown University. He is a member of the Aspen Global Leadership Network and is an Edmund Hillary Fellow. He lives in New York with his wife, two children, and their puppy.

Chi Nguyen leads Einhorn Collaborative’s communications and Belonging Strategy. Learn more about Chi. Sign up to receive our monthly newsletter and be the first to read Chi's blog posts.