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A New Way to Listen

A note from the editors: In Practical Empathy, Indi Young underscores the importance of developing empathy—and helps us improve our listening, gain perspective, and balance our business practices in the process. We're pleased to bring you this excerpt from Chapter 4 of Practical Empathy. Buy the book from Rosenfeld using the code "empathy" and save 20 percent.

To develop empathy, you need to understand a person’s mind at a deeper level than is usual in your work. Since there are no telepathy servers yet, the only way to explore a person’s mind is to hear about it. Words are required. A person’s inner thoughts must be communicated, either spoken aloud or written down. You can achieve this in a number of formats and scenarios.

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Whether it is written or spoken, you are after the inner monologue. A recounting of a few example scenarios or experiences will work fine. You can get right down to the details, not of the events, but of what ran through this person’s mind during the events. In both written and spoken formats, you can ask questions about parts of the story that aren’t clear yet. Certainly, the person might forget some parts of her thinking process from these events, but she will remember the parts that are important to her.

A person’s inner thought process consists of the whys and wherefores, decision-making and indecision, reactions and causation. These are the deeper currents that guide a person’s behavior. The surface level explanations of how things work, and the surface opinions and preferences, are created by the environment in which the person operates—like the waves on the surface of a lake. You’re not after these explanations, nor preferences or opinions. You’re interested in plumbing the depths to understand the currents flowing in her mind.

To develop empathy, you’re also not after how a person would change the tools and services she uses if she had the chance. You’re not looking for feedback about your organization or your work. You’re not letting yourself ponder how something the person said can improve the way you achieve goals—yet. That comes later. For developing empathy, you are only interested in the driving forces of this other human. These driving forces are the evergreen things that have been driving humans for millennia. These underlying forces are what enable you to develop empathy with this person—to be able to think like her and see from her perspective.

This chapter is about learning how to listen intently. While the word “listen” does not strictly apply to the written word, all the advice in this chapter applies to both spoken and written formats.

This is a different kind of listening#section2

In everyday interactions with people, typical conversation does not go deep enough for empathy. You generally stay at the level where meanings are inferred and preferences and opinions are taken at face value. In some cultures, opinions aren’t even considered polite. So, in everyday conversation, there’s not a lot to go on to understand another person deeply. To develop empathy, you need additional listening skills. Primarily, you need to be able to keep your attention on what the person is saying and not get distracted by your own thoughts or responses. Additionally, you want to help the speaker feel safe enough to trust you with her inner thoughts and reasoning.

There’s virtually no preparation you can do to understand this person in advance. There are no prewritten questions. You have no idea where a person will lead you in conversation—and this is good. You want to be shown new and interesting perspectives.

You start off the listening session with a statement about an intention or purpose the person has been involved with. In formal listening sessions, you define a scope for the session—something broader than your organization’s offerings, defined by the purpose a person has. For example, if you’re an insurance company, you don’t define the scope to be about life insurance. Instead, you make it about life events, such as a death in the family.1 Your initial statement would be something like, “I’m interested in everything that went through your mind during this recent event.” For listening sessions that are not premeditated, you can ask about something you notice about the person. If it’s a colleague, you can ask about what’s on her mind about a current project.

Fall into the Mindset#section3

How often do you give the person you’re listening to your complete attention? According to Kevin Brooks, normally you listen for an opening in the conversation, so you can tell the other person what came up for you, or you listen for points in the other person’s story that you can match, add to, joke about, or trump.2

It feels different to be a true listener. You fall into a different brain state—calmer, because you have no stray thoughts blooming in your head—but intensely alert to what the other person is saying. You lose track of time because you are actively following the point the other person has brought up, trying to comprehend what she means and if it relates to other points she’s brought up. Your brain may jump to conclusions, but you’re continually recognizing when that happens, letting it go, and getting a better grip on what the speaker really intends to communicate. You’re in “flow,” the state of mind described by Mihaly Csikszentmihalyi.3 You are completely engaged in a demanding and satisfying pursuit.

It’s a different frame of mind. You don’t want to be this focused on someone else all the time—you have to do your own thinking and problem-solving most of the time. But when needed, when helpful, you can drop into this focused mindset.

Explore the Intent#section4

Developing empathy is about understanding another human, not understanding how well something or someone at work supports that person. Set aside this second goal for a bit later. For the time being, shift your approach to include a farther horizon—one that examines the larger purposes a person is attempting to fulfill.

The key is to find out the point of what the person is doing—why, the reason, not the steps of how she does it. Not the tools or service she uses. You’re after the direction she is heading and all her inner reasoning about that direction. You’re after overarching intentions, internal debates, indecision, emotion, trade-offs, etc. You want the deeper level processes going through her mind and heart—the things that all humans think and feel, no matter if they are old or young, or you are conducting the session 500 years ago or 500 years in the future. These are the details that will allow you to develop empathy. Collecting a shallow layer of explanation or preferences does not reveal much about how this person reasons.

To remind the speaker that you’re interested in answers explaining what is going on in her mind and heart, ask questions like:

  • “What were you thinking when you made that decision?”
  • “Tell me your thinking there.”
  • “What was going through your head?”
  • “What was on your mind?”

If you suspect there might be an emotional reaction involved in her story that she hasn’t mentioned yet, ask: “How did you react?” Some people ask, “How did that make you feel,” but this question can introduce some awkwardness because it can sound too much like a therapist. Additionally, some people or industries eschew talking about “feelings.” Choose the word that seems appropriate for your context.

Avoid asking about any solutions. A listening session is not the place for contemplating how to change something. Don’t ask, “Can you think of any suggestions…?” If the speaker brings up your organization’s offering, that’s fine—because it’s her session. It’s her time to speak, not yours. But don’t expand upon this vein. When she is finished, guide her back to describing her thinking during a past occurrence.

Make Sure You Understand#section5

It is all too easy to make assumptions about what the speaker means. You have your own life experience and point of view that constantly influence the way you make sense of things. You have to consciously check yourself and be ready to automatically ask the speaker:

  • “What do you mean?”
  • “I don’t understand. Can you explain your thinking to me?”

Keep in mind that you don’t have the speaker’s context or life experience. You can’t know what something means to her, so ask. It takes practice to recognize when your understanding is based on something personal or on a convention.

Sometimes, you will probe for more detail about the scene, but there’s nothing more to say, really. These kinds of dead-ends will come up, but they’re not a problem. Go ahead and ask this kind of “please explain what you mean” question a lot, because more often than not, this kind of question results in some rich detail.

You don’t need to hurry through a listening session. There’s no time limit. It ends when you think you’ve gotten the deeper reasoning behind each of the things the speaker said. All the things the speaker thinks are important will surface. You don’t need to “move the conversation along.” Instead, your purpose is to dwell on the details. Find out as much as you can about what’s being said. Ignore the impulse to change topics. That’s not your job.

Alternatively, you might suspect the speaker is heading in a certain direction in the conversation, and that direction is something you’re excited about and have been hoping she’d bring up. If you keep your mind open, if you ask her to explain herself, you might be surprised that she says something different than what you expected.

It’s often hard to concede you don’t understand something basic. You’ve spent your life proving yourself to your teachers, parents, coworkers, friends, and bosses. You might also be used to an interviewer portraying the role of an expert with brilliant questions. An empathy listening session is completely different. You don’t want to overshadow the speaker at all. You want to do the opposite: demonstrate to her that you don’t know anything about her thinking. It’s her mind, and you’re the tourist.

Sometimes it’s not a matter of assumptions, but that the speaker has said something truly mystifying. Don’t skip over it. Reflect the mystifying phrase back to the speaker. Ask until it becomes clearer. Don’t stop at your assumption. Teach yourself to recognize when you’ve imagined what the speaker meant. Train a reflexive response in yourself to dig deeper. You can’t really stop yourself from having assumptions, but you can identify them and then remember to explore further.

Another way to explain this is that you don’t want to read between the lines. Your keen sense of intuition about what the speaker is saying will tempt you to leave certain things unexplored. Resist doing that. Instead, practice recognizing when the speaker has alluded to something with a common, casual phrase, such as “I knew he meant business” or “I looked them up.” You have a notion what these common phrases mean, but that’s just where you will run into trouble.

If you don’t ask about the phrases, you will miss the actual thinking that was going through that person’s mind when it occurred. Your preconceived notions are good road signs indicating that you should dwell on the phrase a little longer, to let the speaker explain her thought process behind it.


  • 1. If you’re a researcher, it helps to know that listening sessions are a form of generative research that is person-focused rather than solution-focused. Thus, it’s easy to remember to keep them from dwelling on how solutions might work for people.
  • 2. This was my epiphany from the UX Week 2008 workshop (PDF) by Kevin Brooks, PhD. Sadly, Kevin passed away from pancreatic cancer in 2014.
  • 3. Mihaly Csikszentmihalyi, widely referenced psychologist and author, Flow: The Psychology of Optimal Experience, New York: Harper Collins, 1991, and Finding Flow: The Psychology of Engagement with Everyday Life, New York: Harper Collins, 1997, plus four other book titles on Flow. Also see his TED Talk and YouTube presentations.

About the Author

Indi Young

When not coaching clients on empathy research and application, teaching workshops, and writing, you can find Indi Young eating chocolate, growing veggies, and making her home greener. She was a co-founder of Adaptive Path and writes a blog at

10 Reader Comments

  1. A very thoughtful piece on how to be more empathic. The keeper line for me: “A person’s inner though process consists of the whys and wherefores, decision-making an indecision, reactions and causation.” Asking questions such as “How did you react?” “What were you thinking when you made that decision?” are quite helpful in being able to emotionally appreciate what the other person is experiencing.
    Using Indi Young’s techniques just some of the time will make me a better listener all of the time.

  2. Thank you, Susan. I practice this kind of listening every chance I get, because it was a challenge to stop thinking about what I wanted to say or a problem I wanted to solve. I practice whenever I’m in a line (grocery store, cafe, etc.), sometimes on the bus, at lunch with friends, etc.

  3. “Teach yourself to recognize when you’ve imagined what the speaker meant.” Great line and an important skill. It’s incredible how we can trick ourselves into thinking we understand what others are talking about when we are actually just projecting our beliefs onto their words.

  4. Thanks, Ben. It’s so true that we’re usually caught up in our own perspective. But when you intend it, you can sort of do an inverse of your thinking when you’re listening to someone for work. Continually wonder, “What are the ways I could fail to understand what this person is saying?” Paired with a beginner’s mindset, this trick usually works.

  5. Great article! I’ve experienced how tough it is to just listen to the other person when interviewing them about their experience. I usually want to “move the conversation along” when the interviewee stops talking and I can’t think about any follow-up questions. I’ll try not to skip to the next topic so often now.

  6. So true, Jorge! A good way to get better is to comb through your transcripts, picking out the repeats of concepts the participant is trying to communicate, and seeing how your own questions are hemming him in at times. Everyone tells me they learn so much about listening by spending time with the transcripts this way.

  7. I love this article, thanks for writing it!

    It’s especially important in these fast moving times to try to understand core human motivations and behaviours that don’t go out of date, as you say.

    I find that almost all internal stakeholders want to ask users for ‘feedback’, ‘what they want’ and ‘how we could improve’ and also start any interview with a long explanation of what we think would be a good solution.

    This can be difficult to manage and when I have raised it they say they completely understand but still, they don’t act like UX researchers in practice because they aren’t.

    Do you tend to allow/invite business stakeholders to listening sessions or not?

    Also, you imply that you don’t have a script at all? or do you have a few bullet points you want to ask about or that business stakeholders have requested you ask about. I find it takes a bit of thought up front to plan how to frame questions in the right way so am inclined to write some bullet point questions guides when I next try this…thoughts?

  8. Much appreciated Indi, thank you for sharing your valuable advice. Being a real learner and avoid making assumptions aren’t habits easy to switch by applying empathy principles, but worth to try them every day and continue practicing. -Fabiola Martinez.

  9. Completely agree with what you say about the experience of being a ‘true listener’ and falling into a different brain state. I suspect this state of calm attention while listening has a lot in common with how a psychotherapist listens to a patient.

    You mention that words are required: a person’s inner thoughts must be communicated, either spoken aloud or written down. I think perhaps it’s also worth considering the role of non-verbal communication in empathy during user research. In the same way that a great actor can communicate a depth of emotion before they speak a single word, we pick up a huge amount from minute facial movements as well as tone of voice. If I only had access to written transcripts of interviews, rather than actually seeing or hearing the participants themselves, I’m sure my ability to empathise with the potential users of a product would be greatly diminished.

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