A New Way to Listen

This Is a Different Kind of Listening

Listen for Three Components

Follow the Peaks and Valleys

Be Supportive

Be Respectful

Neutralize Your Reactions

Harness Your Emotional Empathy

Practice Your Skills


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.

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 where-fores, 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

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

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.

Simply Absorb and Understand What You Hear

If you’ve conducted interviews in a professional role, you may think of yourself as a good listener. But consider what your brain is doing during those interviews. Often, professionals remain in an “interviewer” frame of mind, continuously analyzing what is being said and comparing it to what they need and what others have said. In certain circumstances, interviewers may be trying to represent an organization or make a good impression. Additionally, professionals may be frantically considering ideas for the next question. All of this brain activity will interfere with the kind of listening you want to do for empathy. You want your mind to be empty, without thought, so that the speaker’s thoughts can fill you up. The only current going through your mind is continuously checking if you are making an assumption about what is being said.

Explore the Intent

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

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.

Toddlers Aren’t Embarrassed

Another aspect of keeping your mind free of assumptions is to ask:

• “Why’s that?”

• “What do you mean by that?”

Get into the toddler frame of mind. Toddlers are really comfortable with letting their brains feel empty. They don’t have the same internal reasoning going on that adults have. Toddlers just absorb what is being said. As they encounter ideas that aren’t clear or are a new use of words, they ask for an explanation. They ask “why?” in succession. They are not embarrassed about not knowing. Mimic a toddler’s empty mind: focus on whether you understand what is being said. Of course, don’t take the toddler why-why-why approach to the point where it becomes annoying. After all, most of the actual toddler-adult conversations end with the adult saying in exasperation, “Because I said so!”

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.

Listen for Three Components

It gets easier after years of experience to recognize the kinds of things being said while listening to the torrent of ideas flowing from a speaker during a session. But for now, all you really need to track is whether you are discovering the speaker’s deeper reasoning.

The things you are looking for are different than in colloquial speech. The things are also different than what you seek in most professional interview and research formats. For example, a job interview might focus on what the other person’s skills are and her problem-solving ability. A talk show host, for instance, will try to elicit stories and secrets that will amuse or provoke the audience. In a usability study, you look for difficulties, complaints, work-arounds, wishes, conjecture, and so on. Empathy is more neutral. To develop empathy, you listen for these three things:

• Reasoning (inner thinking)

• Reactions

• Guiding principles

If you imagine the speaker’s stories are a current flowing past you, you’ll eventually get skilled at watching what flows by in the depths, so to speak. You want to be able to identify these three types of things. There goes an emotional reaction ... That’s some thinking, right there ... Oh, there’s a guiding principle, finally. Let me ask more about that, and skip over that crust of explanation floating on top. (See Figure 4.1.) Recognize what is helpful to developing empathy. This recognition will also help you identify the places where you need to dig behind a statement to understand the reasoning better.

Inner Thinking or Reasoning

Inner thinking is literally what is going through your mind. It’s the reasoning beneath the action you take, every decision you make, and every statement you say. The words “beneath,” “behind,” and “deeper” all convey the idea that you don’t want to stop and accept the first thing a person says. Usually, the way someone starts a story is with an explanation. This happened, and so then I did this. With such a statement, you have to guess why the person did that thing. If you end up with all the facts of a story, but none of the reasoning, then you do not understand the person at all. You’ve only got guesses.


Learn to go deeper than the crust of typical conversation and discover the reasoning, reactions, and guiding principles flowing underneath.


A reaction is a response to a situation or stimulus. In listening sessions, usually the reactions you hear about are emotional, in response to a specific circumstance the person is describing. Reactions are important to identify because they go hand-in-hand with reasoning. Sometimes an emotional reaction to some external event sets off a chain of reasoning. Sometimes an internal thought process causes an emotional reaction. Reactions run underneath a person’s behavior. If you don’t find out what is flowing through someone’s heart, you have missed a chunk of the story.

Contrary to expectation, people have an easy time talking about their emotional reactions. They come out readily, because they are tied in with thinking, and because they are not usually big earth-shaking emotions. They’re ordinary emotions, like frustration, hope, or trust.

Note that an emotional reaction is defined by a specific stimulus. A series of similar stimuli can create a mood, such as elation or disgust. A mood is important to explore so that you can get at the underlying stimuli and reactions. However, if you only know about the overarching mood, it won’t help you understand how that person thinks.

Guiding Principles

A guiding principle is a philosophy or belief that someone uses to decide what action to take, what to choose, how to act, etc. It is a philosophy that a person can apply to many events in her life, and she subconsciously relies upon it to help her behave in a manner consistent with her standards. Examples of guiding principles are “avoid disturbing the people around me” and “there should be a place for everything, and everything in its place.” Discovering guiding principles is important to developing empathy because they illustrate the foundation of someone’s perspective. It is much easier to walk in that person’s shoes if you know her guiding principles and how they differ from your own. You will be able to simulate what goes through her mind during a particular experience much more faithfully.

Guiding principles are often acquired in childhood. The principles become automatic—a reflex. Because of this, it’s rare to uncover a guiding principle during a session. They fly by in conversation almost unremarked. Moreover, you’re apt to assume that someone’s guiding principles are similar to your own, so it’s natural to make assumptions about them. This is why you want to be on the lookout for them. Learning that someone’s guiding principle is slightly different than your own sheds a lot of light on her perspective and gives you a handle for thinking along a different pathway than your own.

Follow the Peaks and Valleys

When you are listening to someone, keep all your brainpower focused on that person. You want to follow all the peaks and valleys and branches of the stories that person tells you, and nothing else. You want to show the person how interested you are, so that she is willing to open up. You want to urge the person to go into detail until you satisfy yourself that you understand what she means. You will avoid leading the discussion anywhere other than where she has already indicated. And above all, you will not be problem-solving as you hear what she has to say. Your own mind is only focused on listening. Here are some more details so that you can become competent at this.

Start with a Broad Topic

Begin with a broad description of what you’re interested in, so the speaker selects where to go. Usually, the speaker will jump in to the topic immediately, but often she will be familiar with other types of interviews and wait for your list of specific questions. If this is the case, she will ask something like, “Where do you want me to start, exactly?” Refrain from leading her in a particular direction. A good response is, “What came to mind for you when I mentioned this?” or “What has been on your mind these past few weeks about this?” Through a little negotiation, you can get the speaker off in a direction of her choosing.

Agree with whatever she decides upon, even if it doesn’t seem associated to the topic you asked about, because that is what is top of mind for her. Surprise associations like this expand your internal framework about the topic. Even Sherlock Holmes, the fictional detective, knew that he’d get greater detail and depth from a person’s story if he let them choose the topic. “Just let us hear it all in your own way.”4

Let the Speaker Keep Choosing the Direction

Let the speaker lead the conversation, and follow her closely. She will take you to all the things she wants to tell you. Let her be the tour guide,5 and don’t ask her about anything she hasn’t brought up. She will get to all the things that are relevant to her if you give her time.

You should never have a list of topics to cover, so relax and see what she brings up. If it’s a formal session, it might take a few minutes of encouragement to let her know that she has control. When the speaker realizes she is in charge of the session, you will hear the change in her voice and how she takes over the conversation.

Fill your mind with what the speaker is saying, and it will push aside your worry about what topic to bring up next. Listening sessions are more relaxed and stress-free than interviews. You will never have that panicked feeling of “wondering what to ask next” or “thinking up the next question” during a session. You are the serene, intensely interested, listener. Your simple job is to follow up on some of the last things the speaker said.

There might be a burning topic that you want the speaker to talk about, but nothing she says leads in that direction. Control yourself. Keep your own interests from interfering. There are reasons for this rule.

• If you ask about something you really want to hear about, several things can happen. You become the “owner” of the conversation, and the speaker will gladly relinquish that responsibility to you. The rest of the session will be a struggle to get her to lead the direction of the conversation again.

• The speaker may not have anything to say about the subject you bring up. Maybe it isn’t something she has experience with, or it’s a point of view she doesn’t share. The conversation can falter, and it will take a minute to get it going again.

• The speaker will suspect that the subject is important to you, and might unconsciously engage in conjecture, fabrications, or opinion about it, in an effort to give you the information she thinks you want. None of this will be helpful. You want the speaker to illustrate how her own thinking goes and where she places importance.

Similarly, the speaker may bring up a topic that is of professional interest to you, or that you have a theory about. Resist the urge to ask questions about it that will help support your personal theory. Instead, focus on understanding her points in the most neutral manner you can achieve.

Dig into the Last Few Remarks

When faced with a session without a list of questions, most people feel a little nervous. What do you ask when the speaker finishes what she was saying? There are two directions to go:

• Ask about a topic the speaker mentioned earlier.

• Ask for more detail about a part of a speaker’s story that you might have made an assumption about.

When neither of these directions is viable, then you know the session is over—don’t try to push it into new territory.

Usually, the speaker will tell you a part of what was on her mind, and you’ll notice that details are missing or too superficial. So it will be useful for you to make queries to get a deeper level of explanation. Often, there will be a few things to follow up on after she finishes saying something—little hooks you can use to expand the story.

You can remember most of these remarks without having to jot them down. Sometimes, however, you might need to jot one or two of them down because you suspect she won’t be finished with the current topic for quite some time, and you may forget. At the start of a session, the speaker will introduce several topics. Often, she’ll get to more detail about each of these topics on her own, but if you think you’ll want to remind her of it later, and you can’t remember all of them, jot them down. Keep these notations to just a word or two to represent the subject (see Figure 4.2).


Here’s everything that was jotted down as a reminder to get back to during a 55-minute listening session.

Sometimes before the session really gets going, the speaker doesn’t comprehend what level of detail you want. If this is the case, don’t be surprised to find yourself asking for more information about every little thing the speaker says. You’ll help her unfold her thoughts, and demonstrate, through your interest in details, that you want her inner monologue. The speaker usually catches on and starts providing more detail on her own.

As the session unfurls, the speaker will jump from one idea to the next. Certain details she brings up will remind her of other things, so she’ll branch off into a description of those. Eventually, she’ll get back to concluding her description of the original topic. You’ve experienced the circuitousness of a conversation like this. It’s nothing new. Let it keep unfolding. Furthermore, if the speaker switches to third person, using “you” instead of “I,” usually it means she is talking about her own thoughts and emotions.

Do Not Take Notes

A session can be informal: for example, you might run into someone in the hallway or the café. Or it can be a scheduled time to sit down and talk. And if it’s scheduled, you can decide to record it.

In all cases, you will not take notes.

During the listening session, all your attention is on the speaker and the winding, wandering threads of her exposition. If you take notes, it will distract you from this focus. Your mind is not supposed to be doing anything but listening and trying to understand. Writing takes up valuable focus in your mind.

If you are recording the session, everything is already being captured. If you are not recording, your mind will soak up the important stuff, and you can write down what you heard later. Because of the level of concentration you achieve while listening, important things the speaker says will leave unforgettable impressions.

Most people’s notes consist of observations that are the beginnings of pattern synthesis—the session is not the time for doing synthesis. For developing empathy, break yourself of that habit. You only get a little time with the speaker, so use all your brainpower to pay attention.

Also, don’t worry—asking about details will not lead you out of scope. Think of it like mining for a certain kind of gemstone. It’s okay to spend time exploring around to see where a vein leads. More than half the time, it will lead to something rich.

Use the Fewest Number of Words Possible

Use the fewest number of words that you can throughout the session. The questions you’ll ask are simple and informal, like:

• “Why’s that?”

• “What were you thinking?”

• “What’s your reasoning?”

• “Tell me more about <her phrase>.”

You don’t even have to form full sentences. You can simply say:

• “Because?”

As a question, “because” allows the speaker go into more detail without you getting too specific. Let the speaker take the interview where she wants. Save yourself the effort of making a formal, well-worded question during the intensity of a session.

You’ll want to make sure that your tone of voice is curious and light, rather than hard and demanding. Asking “why?” in a demanding way can sound as if you are judging the person and that you don’t think she did the right thing. “So I decided to buy the cardamom ice cream for dessert.” “Why?!” This type of tone makes it sound like deciding on ice cream is bad, or that the chosen flavor is disgusting. To temper your meaning, use a curious tone. Or, try saying, “What was your thinking there?”

Sometimes, you will say things in an inelegant way. It’s so tempting to reword your own question so that it is clearer. Don’t use the time to do this unless the speaker asks for a clarification of what you’re after. Generally, the first way you say it, although not perfect, is good enough for the speaker to understand and respond. If you take the time to correct yourself, you run the risk that the speaker will get distracted while waiting for you to form your question. Instead of starting with the initial response she had to your original question, she might give a shallower answer.

Similarly, refrain from filling in silent gaps after you’ve asked something but while the speaker is thinking of her answer. Respect that she has to think about it and wait.6

Reiterate a Topic

After the speaker has finished a description, take a tiny amount of time to demonstrate that you’re intensely alert to her story. Briefly reiterate what she just said, in one very short phrase—not even a whole sentence. Reflect back to her a tidbit of the content that was just revealed. Something short like, “The gate!” will work just fine. Use a word she used. “Terrifying!” Mirror her way of talking just a little bit to build rapport and show that you’re on her side.

You can also use a very short reiteration to test whether you have understood her correctly. She will respond if you’ve made a mistake comprehending her meaning. Additionally, you can use reiteration as a way to prompt the speaker to tell you a little more about the subject. “Somebody official ....” If there’s something more to be said, the speaker will launch into it at that point. This sort of reiteration is not supposed to be a summary of what you just heard; instead, it is just a few words or a phrase that you use to elicit a response.

Avoid Introducing Words the Speaker Hasn’t Used

As a rule, stick to the speaker’s vocabulary. Try not to introduce terms she has not used. If you introduce vocabulary, she is likely to change the way she normally speaks about the topic and adopt your terminology. The biggest challenge you might face is stopping yourself from unconsciously saying words that are jargon from your industry.

On a related note, you’re probably already aware that leading questions are dangerous. They cue the speaker to answer in a way that she thinks you want to hear. Any question that hints at what you expect as an answer is a leading question. Usually, leading questions begin with “Do you ...” or “Have you ...?” Because they’re so common in our everyday speech and in our media, you won’t be able to completely eliminate leading questions. Don’t let it make you feel anxious. If you hear yourself saying “Do you ...” or “Have you ...,” stop mid-sentence or as soon as you can get control of your mouth. If the whole leading question comes out anyway, don’t try to make it worse by taking it back. Just listen to the answer and move back into a more neutral style the next time you say something.

Try Not to Say “I”

Saying that personal pronoun “I” puts too much emphasis on your part in the listening session. You want to minimize your presence so that the session belongs to the speaker. “I want to know ....” “I want you to tell me ....” If you tell the speaker you want something, it’s implied that you have control of the conversation. The speaker will be less likely to take the initiative to dive into a story; she will wait for you to tell her what to talk about.

Speakers are familiar with the customary interview format, and they might think you want to adhere to that call-and-response arrangement. Instead, use the pronoun “you.” “You said something about ...?” “What did you mean by ...?”

Be Supportive

During the listening session, you will want to develop rapport with the speaker. You will want to encourage her to open up, and to do this she will need to trust you. By demonstrating that you are not judging any of her reasoning, and that you’re paying rapt attention, you can earn that trust.

You’re already paying rapt attention to the speaker. That devotion earns you half of what you need for a strong connection. Your support—your authentic sincerity—can earn the other half. Make this person feel comfortable; make her feel valued. When someone realizes she has your full attention, she is likely to respond to your questions gladly.

Remember a past boss you liked or a professor who was great? Even though she was in a position of power over you, you felt respected for the ideas you could contribute. You felt like you mattered to her. Chances are it was because this person knew how to listen. She knew that, because so few people really listen, it is a very powerful way to collaborate and forge a team. And, as a manager, it is a great way to encourage an individual to try her hardest to be clear and intentional in her work.

Don’t Fake It—React, Be Present

Lose yourself in the speaker’s view of the world. Like Yoda would say, don’t try to be interested, be interested. Really, truly let yourself go—get excited by what excites the speaker. This session is not just part of “practice” or “work.” It’s you, building a new understanding of another human. Channel all your intensity toward finding out who this person really is (see Figure 4.3). Be sincere. Be present.7


Lose yourself in the person’s view of the world.

Act human during the session; don’t be a robot. React, laugh—be in the moment with the speaker. Use a reassuring tone of voice and vocal cues. “Wow!” “That’s amazing!” “Huh!” Let your smile be heard in your voice. The more the speaker hears your support, the more comfortable she will be to delve into her own thought processes.

But don’t overdo it. You don’t want to take up the speaker’s talking time during the session. Moreover, you run a slight risk of misinterpreting the emotion and offending the speaker with your response. So keep it kind of neutral. And don’t start talking about yourself. Something like, “You’re giving me goose bumps,” is as far as you should take it in terms of referencing yourself.

Misunderstanding the emotions a speaker is trying to describe will happen. Even people who have 20 years of experience with listening sessions misunderstand what someone means. On the other hand, pretending to be interested is inexcusable. Asking for understanding and then dismissing the story and emotions that come up does nothing for developing trust. “When you ask people to open up, be prepared to listen.”8

There is a fine line you’ll need to watch for when you’re developing trust from a coworker or a direct-report. If you lead that person to believe that you agree with her, but you really don’t, she could feel betrayed later when she finds out. In a situation like this, you’ll want to work on expressing your curiosity and understanding about this other person’s point of view, instead of reflecting back a perspective that you don’t truly hold. If your curiosity is genuine, if you prove that you care, she will be able to tell, and that alone will be your foundation for developing trust.

Never Switch Abruptly

Refrain from switching back to a detail a person mentioned earlier until you are absolutely certain you have explored and understood the current subject completely, from the perspective of the speaker. And never say, “Okay, great” when she finishes up a topic, so that you can ask about another detail. “That’s great” smacks of your hurry to get through the session, or your need to pack in as many topics as possible. It can also sound as if you’re bored or belittling what she just told you, or that you didn’t pay emotional attention. Maybe what she described wasn’t “great” at all, but distressing.

Now that you’re aware of the “okay, great” phrase, you’ll notice it everywhere. You’ll hear conference hosts say it when one speaker finishes her presentation and another is introduced. You’ll hear talk show hosts say it when they are trying to fit all of their questions into a defined period of time.

By the same token, do not telegraph the change in direction with phrases like “Let’s switch gears,” or “Now I want to ask you about ....” Using these kinds of direction change phrases implies that you’re in control of the session. You’re not supposed to be; the speaker should be in charge of the direction of the story. Since you are only after more detail, just dive into what you want to hear about by saying, “You mentioned ...” or “What was that about ...” with a few of the words she mentioned. You don’t even need a question after that.

Adapt Yourself to the Mood

Musicians say they can feel the mood of the audience and play differently according to that mood. Make yourself aware of your speaker so you can adapt to her a little bit. Try not to impose your own mood on your speaker.

Pick up on how the speaker is perceiving the experience of the listening session. Tune into whether she seems to think you only want to hear certain things, like only positive emotions or only logical reasoning. Encourage her to tell you the other kinds of things that looped through her mind at the time. Encourage her to relate her complete thinking process. A good listener knows that a sentence like, “It was a great experience” hides all sorts of thinking and reactions, which you will need to dig up.

A part of the mood includes the speech patterns the speaker uses. If you can, try to fall into a similar speech pattern. Mirror her style and some of her vocabulary—but not too much. Don’t make her feel uncomfortable about being copied or think that she’s being made fun of. For example, don’t mimic poor grammar if your own grammar sticks to the rules. Just pick a few vocabulary words and phrases, and use them with a similar cadence and level of humor. Demonstrating your interest in what she has to say by copying a bit of her speech style helps establish a connection between you.

Don’t Cause Doubt or Worry

Avoid saying things in a way that might make the speaker worry, doubt, or become uncomfortable. You’re not saying much during the session, so it should be easy to avoid this.

“The human interaction in the interview affects the interviewees ... Consequently, interview research is saturated with moral and ethical issues.”9 You not only want to observe confidentiality with the transcripts and the results that you report, but you also want to be sensitive to what unfolds during a session, and whether the speaker is comfortable with it. You do not want to cause stress, and any changes in the way she understands herself should be self-revelations, not judgments on your part.

Be Respectful

Let the person be who she is. She needs to trust that you will not trample her sense of self, especially if she thinks you have a different way of thinking. Demonstrate that she is in charge, and that you respect her worldview. Your goal is to find out why she thinks the way she does—through lucid descriptions that you truly understand, including how she swerves around problems and slides her thinking, depending on the scenario and all the nuances of her experiences that have built up over the years. Be an expert at curiosity about other people—open curiosity, without analysis or assumptions. Put off analysis until you are ready to apply your understanding to design or strategy, namely, when you are trying to see patterns and make decisions for your organization.

Be the Undermind, Not the Overmind

You are not “the researcher” in the session. You have no expert role to play and no agenda to pursue. It’s not about you. Your only goal is to generate trust and encourage deeper descriptions and understanding.

This part may be the single most difficult thing for people to adopt. It’s hard to stop yourself from jumping to solutions. It’s hard to turn off the frame of mind where you are a professional, skilled at finding themes and ideas to dive into. If you don this “research” frame of mind in a listening session, you’ve missed the mark. It’s just the opposite.


Take off the metaphorical white lab coat; put aside the notepad. When you’re actively listening to someone, you’re just a person, a human, trying to understand another human. The session is not the time for doing your own thinking or synthesis.

Make the speaker feel confident—an expert about herself. If you act like you’re an expert at deriving meanings and generalizations about people, you’ll miss the chance to ask about the deeper parts of her story. If you make a comment or nod your head as if confirming a guess you’d made about the speaker, you will sound officious and kill the rapport between you. Don’t let a researcher frame of mind get in the way.

Resist the Urge to Demonstrate How Smart You Are

When you meet someone new, you have a natural tendency to want to demonstrate something of your talents to that person. Circumvent your reflex to demonstrate how smart you are—to talk about your knowledge or experience. Competition will destroy the relationship you are trying to build with the speaker.

Squash your inclination to tell a speaker how things really work, as opposed to how she thinks they work. Never explain that the speaker is wrong. The speaker is always right—because this is her mind you’re exploring, not her understanding of your offering, nor her knowledge of how things work in general. Whatever she thinks, it’s true in her mind. This guideline assumes that you believe the speaker is being truthful. If you strongly suspect she is making things up, then just wind down the session.


For formal sessions, do not advertise for participants on social media or public bulletin boards. These places are flooded with people trying to earn money by participating in any study they can. A participant is likely to lie and invent stories to meet your expectations to earn the stipend. Worse, it’s difficult to tell when that person is being deceitful.10

Here’s another way to think about this. You’re not to trespass upon the structures of her mind. If the speaker says something that’s not quite correct about the service you offer, it’s true for her. Squash your impulse to correct her. It’s not important that she learns the difference.

Additionally, don’t imply that there’s another, better way of approaching things than what the speaker just told you. You’ll only make the speaker feel like her reasoning is inferior.

Moreover, refrain from asking, “Are you sure?” This phrase implies that you know a better answer. Even if you don’t mean it that way, it sounds too much like the way you talk to a child, encouraging him to correct himself about the deductions he made from some observation. Instead,believe the speaker. Ask her to tell you about the details when she first learned about the subject. Find out the reasoning underneath.

Also, if you want to share a tip or trick with the speaker that you think will make her life easier, don’t. Avoid offering advice. The session is about the speaker, not about you or your organization. It’s about her world, not yours. If you give her advice, then you’re belittling her worldview. A listening session is about developing empathy. It’s person-focused, not solution-focused.

Neutralize Your Reactions

Your emotional reactions can’t be prevented. They’re like weather, coming inexorably. At some point, you will react to something a speaker tells you. But if an emotion blows in on you like a rain squall, let it blow right on past you. Don’t let it monopolize your attention, because then you won’t be paying attention to the speaker.

Notice Your Emotional Reactions

Through your practice sessions, you can elevate your emotional literacy. If you are self-aware, then you understand when you are having emotions, what they are, and why they occurred. Recognizing your own emotions can give you emotional maturity, which allows you to realize that others can have different reactions than you do. It leads to a more open mind when trying to gain empathy with a person. Recognizing your own reactions and assumptions—before they distract you—leaves your mind open to considering foreign possibilities. You will be able to recognize when you condemn an idea or a reaction, be able to stop yourself, and then be able to spend some time investigating it instead.

Embrace Your Emotions

Meditation teacher Stephanie Noble describes a way for you to practice dealing with your reactions in her blog post, “Emotions as Honored Guests.”11 Stephanie writes, “Anger arrives at the door. Instead of saying ‘Oh, God, what kind of awful person am I that I’m always so angry?’ ... If instead you ... say, ‘Hello, Anger. What brings you here today?’ right at the door, the emotion may not even feel it has to come in. But never bar the door to an emotion. That kind of denial only results in emotions breaking in the back way.”


You can’t realize an emotional reaction has happened until it actually happens. Don’t feel embarrassed that you actually felt the emotion for a while first. You can’t prevent emotions from occurring, but you can recognize and then ignore them.

Some people say that learning to meditate—spending time with your own brain learning its process and its habits of circumventing your intentions—helps them notice their reactions before they act. Other people learn to notice their emotions in other ways. You might need to try out different ways to learn this skill before you find a method that works for you.

None of this emotional-awareness advice is new. The founders of many of the world’s religions—and some fictional religions, too—hoped to teach people to recognize and consider their own emotional reactions. Emotions are part of the human makeup, and because many humans go right ahead and speak or act based on those emotions, all sorts of excitement results. Sometimes, it can be damaging or catastrophic. It’s no surprise that spiritual leaders encourage emotional literacy so that people can short the emotional circuit and use both emotional and cognitive empathy to consider other options as shown in Table 4.1.


Spiritual Quote


“Don’t give in to hate. It leads to the Dark Side.”


(Yoda, The Empire Strikes Back)

“There is no offense where none is taken.”


(Surak, Star Trek)

“Fear is the mind killer.”

Bene Gesserit


“When anger rises, think of the consequences.”


“If one becomes angry, let him keep silent.”


“A meaningful silence is always better than meaningless words.”


“Anger deprives the sage of his wisdom.”


“Turn the other cheek.”


“Holding on to anger is like grasping a hot coal with the intent of throwing it at someone—you are the one who gets burned.”


Dissipate Your Reactions and Judgments

If you are in your own neutral emotional space, you’re able to understand another person’s thinking and reactions better. When you have a reaction during a listening session, you don’t want to betray the fact to the speaker, because you do not want to cause her to have a reaction of her own, or let your reaction influence what she is telling you.

Don’t let your negative emotional reaction get control of your thoughts or your mouth. Instead, guide any spark of condescension, disgust, shock, or anger right out of your mind. Ground it in the earth, like a lightning rod grounds lightning (see Figure 4.4).


Without a way to ground the lightning strike of emotion, your head might explode!

If you have trouble guiding the emotion out, make yourself take on that person’s viewpoint for a moment. What would make them say or believe something? Dissipating reactions is hard to do when the speaker’s reasoning gets into uncomfortable territory for you. Imagine a scenario where it makes sense from her viewpoint.12 It’s surprising how instantly free of the emotional reaction your mind will be. Practice this mechanism so that it becomes a reflex.13

Mistakes to Avoid

It’s all too easy to let the wrong examples guide your approach to a listening session. You hear plenty of “interviews” on radio programs and television shows. It’s hard not to let them influence you. Here are a few quick pointers.

• Reporters are not good role models.

• Don’t display your point of view.

• Opinions are not empathy (nor are they news).

• When developing empathy, you are not after “the facts” of how something happened.

• Professional researchers are not good role models.

• Analysis leads to brainstorming, distracting you from the person.

• Don’t think too hard.

• Avoid demographic profiling.

• Don’t tell this speaker about other speakers.

• Quell your excitement about an epiphany.

Harness Your Emotional Empathy

You cannot really apply emotional empathy. Emotional empathy is your own emotional resonance with someone, which happens during a particular instant. But you can capitalize on your ability to notice that you are emotionally reflecting someone else and use that connection to listen to that person and get deeper understanding.

Emotional empathy tends to strike suddenly. The other person has an emotional reaction or tells you about one he had previously, and suddenly you can feel it, too. In this situation, your awareness will help. You’ll want to free yourself from the emotion itself so that you can return to understanding the other person’s thinking. First, quickly recognize that you are experiencing a reaction, identify the source, and mentally step away from it—even if it’s a positive emotion.

Then return to your curiosity about what underlies the other person’s behavior. This curiosity is difficult to maintain if you’re distracted by your own emotions.

Should you let the other person know you are sharing their emotion? Probably not. You can say something like, “Wow, I understand.” The more important goal is to disentangle yourself from the emotion. Move beyond its grasp so you can focus clearly on the other person’s mind again and dig deeper.


It’s easy to assume that since you can identify with someone’s reaction, you also share the same principles, decision-making, and thinking style. If you fall into this trap, you will stop being curious about the other person’s underlying reasoning. You will lose the opportunity to develop rich cognitive empathy.

To develop empathy, you don’t have to identify with any emotions. You might experience emotional empathy, but it isn’t necessary. When emotional empathy happens, move past it and get back to your focused mind, so that you can use the opportunity to develop an assumption-free understanding of the person.

Practice Your Skills

Glue yourself to the topics the speaker brings up. It’s easy to do, but your conversational and professional habits may make it a challenge. It will require practice. Practice means incorporating it into your everyday life and trying it out with people for a few minutes every few days or so. You’ll need months of practice before these guidelines become a part of your subconscious.

Practice also helps you gain confidence. It helps you realize that people love to tell you their innermost reasoning. If you practice every time you recognize an opportunity in tiny listening sessions, it means approaching people and asking won’t be as daunting as it once might have been.

The tricky part is that you do not want to think about these guidelines while you’re listening to someone. You want your mind to be empty and open to that person’s thoughts, rather than full of rules to follow. So until these rules become second nature, just forget about them. It’s more important to focus your brainpower on the other person than on the rules. For the time being, approach it more like a conversation. If you force yourself to empty your mind, you will eventually fall easily into the mindset for developing empathy. Becoming aware of your capacity of empathy is an idea that can permeate your mind quite suddenly and powerfully.

Just like practicing a sport, practicing a musical instrument, or practicing meditation, you can build your empathy skills. Little by little, you can make it a reflex. You can train yourself to reframe your thinking as situations present themselves each day. Developing empathy is not a switch that you throw.

Practice 1: Where Will You Practice Listening?

Think about your past week. Where did you go? Who was around you? In the future, which of these opportunities can you harness for impromptu, informal listening sessions? By listing these places, next time you’ll recognize the opportunity to engage another person.

1. List the places you went the past week (or typically go) where there are other people around. You can list any place, as long as there are people around whom you don’t constantly interact with: work, meetings, conference, grocery store, gym, bus, train, lunch line, restaurant, coffee line, even home or friends’ homes, etc.

2. Scratch out the places you listed where it’s usually not socially acceptable to speak to a stranger or semi-stranger, like in the elevator or the subway or a doctor’s waiting room.

Practice 2: Identify Your Reaction/Assumption

Another everyday practice involves noticing when you have a reaction, when you make an assumption, when you judge, or when you classify someone. For this practice, you don’t have to speak to anyone. You do have to be around real, live people, though. (Actually, TV and movies work for this exercise, also.)

As you drive, or walk through a crowd, or encounter people in a gym, or on public transit, or wherever, the game is to recognize when you have had an emotional reaction to someone’s behavior or speech. Give yourself a point every time you notice your reaction. Likewise, give yourself a point when you notice you have made an assumption about what a person is doing or thinking. Also, if you realize you’ve judged or classified someone, give yourself a point. The points represent your awareness that you’re doing it. The goal is to become aware of it, not to stop doing it.

Similar to walking 10,000 steps a day, try for 2–3 points a day for this exercise.

Practice 3: Classify What’s Being Presented

You probably remember a news item or two where you were shaking your head at how “the facts” were presented. The next time you encounter such a news story, try to classify what is putting you off about the presentation. Did the reporter concentrate on opinions? Did his point of view skew the tone of the piece?

Additionally, try to identify when a report includes demographic profiling. For example, if you read something like, “Millennials who use social media become addicted and become unable to put down their phones, even late at night,” rephrase it in your head in a way that neutralizes the demographic profiling. Focus on the root behavior. “People who have become addicted to social media may have a tendency to check updates late into the night.”


To develop empathy, you must get past the surface level of what people tell you. This requires more attention when you listen, the ability to let go of your responses, and the presence of mind to help the speaker feel confident and understood. It requires you to let go of your need to do something, in order to demonstrate your worth. Absorb everything the other person is saying. Be passive and neutral.

This skill of listening will help you in other aspects of your life, besides work. It will help you know your mind and recognize your own emotional reactions.



Reasoning: Thinking, decision-making, motivations, thought processes, rationalization.

Reaction: Responses to something—mostly emotional, some behavioral.

Guiding Principle: Belief that guides decisions.



• Start with a broad topic.

• Let the speaker keep choosing the direction.

• Dig into the last few remarks.

• Use the fewest number of words possible.

• Reiterate a topic to show attention, verify your understanding, and ask for more.

• Avoid introducing words the speaker hasn’t used.

• Try not to say “I.”



• Don’t fake it—react, be present.

• Never switch abruptly.

• Adapt yourself to the mood.

• Don’t cause doubt or worry.



• Be the undermind, not the overmind.

• Resist the urge to demonstrate how smart you are.

• Avoid implying or telling the speaker she is wrong.



• Learn how to notice your emotional reactions.

• Dissipate your reactions and judgments.


It’s almost magical how much better you understand someone when you spend time in review.