Step 5. Use the Power of Possibility – 10 Steps to Successful Coaching, 2nd Edition

Step 5

Use the Power of Possibility


• Three coaching skills: championing, acknowledging, and visualizing

• How to use questions most effectively

• Details of coach listening and overcoming listening blocks

In my coaching practice, I not only enjoy the privilege of having people share with me their secret (or not-so-secret) dreams; I also have the privilege of helping them see that they can turn these dreams into reality. Granted, this transformation doesn’t always happen, but at every moment of coaching I hold the strong belief that my coachee’s dreams, and even more, are possible.

This step in the coaching process is the one where you help others dream and plan bigger than they think they can. And why do you do this? Certainly it’s not so they can fall flat on their faces. You do it so they can realize their brilliance and their possibilities.

Because of their strengths, people can accomplish far more than they think they can. Coaches let them know that by using the skill of championing. Showing individuals their own brilliance is accomplished by acknowledging who they are—recognizing the wonderful traits that they have and that they are displaying. Sometimes coachees believe in themselves but don’t know how to make their dreams materialize. That’s where the skill of visualizing comes into play. These are three skills that can help the coachee understand a context that is greater than they may experience on a day-to-day basis. It is the context of options, opportunity, and possibility.

The Skill of Championing

A coach must truly believe in her coachee. When the coachee says, “I can’t give a presentation to the senior management team,” the coach says, “You can.” When the coachee says, “I want to start a new business three years or so down the road,” the coach says, “How about next year?”

I remember a fellow participant in my first coaching class saying that this approach seemed very irresponsible. How can a coach encourage someone to do something that he might not be ready or able to do? My course leaders said something then that has stuck with me: People have enough naysayers in their lives—the kind people who simply don’t want them to “get their hopes up,” to get hurt or disappointed, to fail. And coaches can’t just add their voices to that din.

Coaches are not afraid of people failing or getting their hopes dashed. They generally believe that people are capable, powerful, and terrific. They know that their coachees are strong enough to handle hardships in pursuit of their goals. And they know that if not pushed to their highest levels of magnificence, their coachees are robbing the world of their greatness. People do not need another protector; they need someone who will inspire them and expand their possibilities.

Think of a sports coach. Do you think that her players would get anywhere if she was afraid her players would fall down, get injured, or lose a game? In fact, a coach knows her players have to experience these circumstances to learn and improve.

The value of championing has been shown in studies from numerous fields including healthcare, education, and business management. These studies show that when leaders (managers, teachers, doctors) hold the assumption that the others’ (employee, student, patient) capability is high, productivity or performance will tend to be high (Rosenthal and Jacobson 1968; Livingston 1969; King 1971; Eden and Shani 1982; Eden 1992). Key findings from studies on this phenomenon of self-fulfilling prophecies, or the “Pygmalion effect,” show that:

• What managers expect of subordinates is a key determinant of performance.

• Superior managers are able to create and convey higher expectations of their teams than are less effective managers.

• In general, managers are more adept at communicating low expectations than high ones, even when they believe the opposite.

• The phenomenon of self-fulfilling prophecies in business has the largest impact on employees who are relatively young. The reverse also holds true: Employees who are perceived by managers to be mediocre tend to perform at a lower level than their counterparts (Manzoni and Barsoux 1998). This set-up-to-fail syndrome becomes a vicious circle in which poor performance that is influenced by low expectations reinforces the manager’s belief that the performer is weak.

Your coachee knows his own limits only too well. If you ask him to do something he’s not comfortable with, your relationship should be strong enough for him to say “no.” But who knows? He may counter with an offer greater than his original thought. Here’s how that might sound:

Coachee: I need to talk to that employee about her continued lateness, but I just keep getting too busy and it falls off the radar….

Coach: What if you cut out everything you said after “but”? What if we ended our session now—early—and you went out there and got her and spent our remaining 20 minutes having that conversation?

Coachee: Now? But I’m not ready. I really want to have all my facts straight—like how often she’s been late—before we talk.

Coach: You can say “yes” or “no,” or you can make a counteroffer. Are you saying “no”?

Coachee: I guess I am saying “no” to that. But, OK, how about this as a counteroffer? What if we end early and I spend the 20 minutes gathering the data I need?

Coach: Great. What if you do that, and if you also pick up the phone and schedule a meeting with her for the end of this week?

Coachee: I could do that … and then I’d have a real impetus to finish my fact-finding today!

Here are a few ways to stretch your championing muscles. Try the following prompts with your coachee (if you don’t have one yet, enlist a friend, family member, or colleague who wants to live his or her biggest dreams).

“What’s bigger”? Ask your coachee, “What’s your dream?” Let her tell you all about it. Ask “What’s even bigger than that?” Let her answer, and then ask again, “What’s bigger than that?” Ask this four or five times—no kidding. Then ask, “What’s possible for you to do right now to move toward this dream?” Here’s how the conversation might sound:

Coach: What’s your dream?

Coachee: I want to open a senior citizen center.

Coach: Great. Tell me more about it. What’s going on at your senior center?

Coachee: It’s a place where seniors come and remain active in the things they’ve always loved. If they loved to cook, they cook the meals. If they enjoyed playing or listening to music, they can do that with local musicians who drop in. And if they’re near the end of their lives, there’s a hospice wing with counselors to make their final days peaceful.

Coach: That’s a beautiful vision. And I’m curious, what’s bigger than that dream?

Coachee: What do you mean?

Coach: I mean what could your dream hold that’s even bigger than that picture you just gave me?

Coachee: Well, I guess it could also have an organic garden tended by seniors and community volunteers. It could make money when the seniors sell the produce in their own store. It could be a local pet-sitting service. The elderly would have the company of the pets and the pet owners would have a reasonably priced option.

Coach: OK. What’s even bigger?

Coachee: Hmmm. It could be featured on the news and be a model for other centers across the nation.

Coach: And what’s bigger?

Coachee: I guess I could be famous for reforming senior care options.

Coach: So what do you want to do right now in your quest to become famous for reforming senior care?

Coachee: I guess I need to start getting famous by speaking about senior care at public events….

It may feel far-fetched to talk about what the coachee can do to become famous, and it’s not that you necessarily do expect her to become a celebrity in the world of senior care; it’s that thinking bigger can tap into actions that are more compelling and that might have a more profound impact than those that she’d focus on initially. In this example, if the coachee is thinking about opening a senior center, she’s thinking about somewhat daunting concerns like finding the funding, securing a property, licensing requirements, and so on. When she thinks more broadly about getting famous, she expands beyond those logistical concerns to what it would mean to do that while also being an advocate and champion for seniors.

“You can do that.” The next time someone tells you his big idea, notice how you’re naturally inclined to respond. Do you start in with the challenges he’ll face, the things you want him to consider, or the reasons it’s not a good time? Don’t judge your response—just notice it. The time after that, don’t just notice where you tend to go, but also take yourself to the “you can do that” frame of mind. Listen and give an unqualified “yes,” and see what’s possible from that place. Where does the conversation go when you’re approaching it from a positive frame of mind?

“Where am I holding back?” List the names of your coachees and employees and the important people in your life. For each person, consider where you might be protecting him or holding him back. When are you thinking small about what he’s capable of doing or becoming?

A coach afraid to champion her coachee, afraid to support him wholeheartedly in whatever he’s doing (provided it’s safe and legal) is thinking too egocentrically about herself. It’s not as if the coachee will do whatever the coach says. But that moment when the coachee has someone believing in him may be just enough time for new doors to open and something he never thought possible to come through those doors.

One tricky part of championing is taking it too far and making it into an agenda. I’ve done this—I’ve really made it “wrong” for a client to do anything other than go for his biggest possible dream. What I learned that the coach needs to remember is that this dream must remain the coachee’s dream for himself. If, for whatever reason, the coachee is choosing to downsize or not to follow his dream, that has to be OK. Championing a coachee’s dream simply lets him know that if he wants it, he can achieve it.


One way to show positivity is through your language. Try an experiment: Notice when you are using negative language versus positive language. Do you talk about what is (“we’ve been talking about this for 30 minutes”) versus what isn’t (“we’re not getting anywhere”)? Do you outline the dos (“To fully focus on our conversation, please put your phone away”) not the don’ts (“Don’t take your phone out during coaching”)? Do you express a belief that your coachee will achieve his desired outcomes with words like when rather than if? Do the words no, not, can’t, and shouldn’t crop up a lot when you’re speaking? Experiment with using only positive language. It’s challenging (note: I said “it’s challenging” rather than “it’s not easy”). The effects of a positive outlook and positive language will be far-reaching: Using positive language tends to reduce conflict, improve communication, reduce defensiveness, and portray you as caring and credible.

In the workplace, coaches are often afraid to think big for their coachees because they think that it means you’re promising the person—or that the person will now expect—a raise, a promotion, or something else. What is the point, they wonder, in coaching someone when there is no chance of a raise and no sure opportunities for promotion? Be transparent that coaching does not promise any of these things and that it will require work outside the coaching relationship to make it happen, when it is even possible to happen.

The Skill of Acknowledging

One of the reasons people can’t see themselves doing great things is that they don’t see their own greatness. The world is pretty good at helping people see their weaknesses or limitations but slow to help them know their strengths and magnificence. Even those enlightened ones who know that they’re special may have a hard time promoting themselves because they’ve been taught that bragging is bad, and they have no healthy ways to “toot their own horns.”

A coach can help her coachee accomplish great things by acknowledging what she sees in the coachee. It’s like holding a mirror in front of a person and helping him see in himself what you see in him. The key in that phrase is “in him.” Acknowledging goes beyond simply recognizing people’s accomplishments or their successes; it reveals what you see at their core—perhaps a good person, a smart person, a thoughtful person, or a powerful person.

I tell my coaching clients that one of the reasons that they don’t see their greatness as well as others do is that we rate ourselves based on our intentions while others rate us based on their perceptions. Because other people can’t see our intentions, they don’t really know where we have—or haven’t—achieved what we set out to do. They are not holding us to that standard. We have to be able to see ourselves as others see us, which is greater than how we favorably or unfavorably measure up to our own high standards.

You might need some practice to get comfortable with this skill of acknowledging, of truly knowing your coachee. Here are some ways to do that:

• Use Tool 5-1 to acknowledge several aspects of people you know well—for example, your employees or friends. Recall and make note of what they’ve accomplished. List their essential characteristics. Then go deeper to consider who they are at the core of their beings. Write a descriptive phrase or analogy that reveals that core. You might even go so far as to share some of this with the people you’ve included.

• When you meet someone for the first time, listen as he tells you about himself. Stay aware of what personal strengths he’s revealing by what he chooses to tell you and how he tells it, by his nonverbal communication, and by the way he stands or sits. Challenge yourself to slip some sort of acknowledgment into the conversation—for example, “I know your proposal will go well because I can see you’re poised and articulate,” or “Your employees really are lucky to have you as their boss—I can see you’re fair and open,” or “You’re clearly a caring parent.”

• Try an acknowledgment in every conversation this week. This is similar to the last exercise but instead of just trying out acknowledgments in situations with strangers, see what happens when you intentionally do it with each person you speak with.

Acknowledgments usually start with the words “you are” because they are about seeing who a person is. The most effective acknowledgments are extremely brief and follow this formula: “You are” + adjectives, then stop! Let what you’ve said sink in. Don’t dilute the power of your acknowledgement by continuing to talk and explain. Just, “You are inspiring,” and that’s it.

Even if you don’t know a person well, you can acknowledge what you see right in front of you, such as:

• “You’ve been really open and honest in this meeting. Thank you.”

• “You are really confident and motivated. What a great place to start from!”

• “From what I hear, this will come easily to you because you have such great self-awareness.”

• “You’re really guiding yourself to a great answer—that’s being powerful!”

TOOL 5-1

Instructions: List your coachees, employees, or friends. Then consider what they’ve accomplished and what characteristics they possess. Finally, write an analogy to describe who each one is at her or his core. An example is provided.

People get noticed for their awards, speeches, and promotions, for their tangible successes. How much more would they be capable of if we also noticed them just for being who they are? How much more could they accomplish if they saw themselves in the positive light in which you see them?

The Skill of Visualizing

You can do two things to increase the likelihood of acting on an intention, goal, or desire. One is publicly stating your intention or goal aloud. The other is painting a vivid picture of your vision so that you can recognize it when it actually happens.

Painting a vivid picture of the vision is also useful when your coachee shares it with others in his life. Then he has not merely one person working to make his dream happen but his whole support system looking out for him as well. Finally, having a clear picture helps propel the coachee forward on days when his dream seems way out of reach.


Many of my clients have created vision boards. A vision board is a collage or other visual representation of what you want at a given time. The idea is that keeping in front of you an image of what you want to have or to do in your life will keep you connected to your dream, stimulate you to action, and help you recognize it when it manifests itself. It’s not enough simply to make a vision board, sit back, and wait for everything on it to materialize, but it is a tool that’s meaningful and helpful to some people.

It’s very simple to make a vision board, even if your coachee doesn’t consider himself artistic or creative. Have him cut out pictures, scribble words, or sketch images of where he wants to live, what he wants to do, how he wants to look, what he wants to acquire, and so forth. Paste all of these images and words together on a large poster or gather them into whatever format he prefers. He should post his vision board in a prominent place. Check in frequently see how it helps him move toward his goals and dreams.

When a coachee tells you his goal—whether for a project, a team, a career change, or whatever—probe deeply to make it as tangible as you can. Who’s around when he reaches this goal? What does he hear, see, taste, smell at that point? What’s the predominant color or setting? When he pictures it clearly, what’s happening, and what’s going to happen after that?

For a coachee who likes visual reminders of what he’s moving toward, ask him to find pictures of what he’s described to you and to post them around his office. A simple visual cue sometimes is all it takes to keep a person tuned in to his vision. That’s why it helps to ask about the sensory details. For example, if his vision of a dream home has a lot of yellow in it, carrying around a yellow file folder will help him stay in touch with that vision every day.

Aligning Dreams With Values

Whether we’re faced with a task we really want to do—or one we’d really like to avoid—it’s important to know why we’re doing it. We often do things without questioning or because we “should.” We do things to reach a particular outcome without considering the other potential outcomes we’ll encounter. We may continue working toward a dream without realizing it isn’t still the one we want.

What’s going to hold a coachee to her dreams is how closely her actions and dreams fit with what’s important to her. You already learned your coachee’s values in your earlier work with her. How does her dream tie in with those values?

For example, one of my clients dreamed of starting her own website and eventually publishing a book comprising the columns she’d included on her blog. When she tried to make time to write her columns, however, she grew discouraged. She started questioning all parts of her dream. “Who am I kidding?” she said. “It’s impossible to get a book deal. I’ll never get enough done to fill a book. This could take me another 10 years.” What did compel her to write some columns for the blog was realizing that each column she wrote helped her honor her values of connecting with others and repairing the world.

Transformative Power of Questions

What can break people out of a rut? What can jump-start their thinking about possibilities? What’s the ultimate coaching tool for helping coachees turn their dreams into reality? Questions. The power of questions to get people thinking deeply and creatively is truly amazing. Questions get past people’s defenses and prompt them to devise answers that work for them.

Peter Ingram was the public works director when I was director of employee development for Redwood City. One afternoon, he sat down with one of his division’s supervisors to talk about staffing in his division. The meeting wasn’t going especially well. There was lots of blaming and frustration on the part of the supervisor who wasn’t certain that existing staff members had the capacity or passion to create success. He also was annoyed with the amount of time he had to spend on operational tasks and issues. After a moment’s thought, Ingram popped in a powerful question that changed the future of the department: “Where are your passions?” The supervisor visibly relaxed and began to talk about water conservation and how much he really wanted to take that program to a whole new level. Ingram reports, “I was so clear on what he felt he could do if given the chance that we began to explore the ultimate organizational change we made—to create a new water conservation program for the city.”

Not all questions have that much power. The kinds of questions that do have it are curious, open-ended, bold, and often naïve. They’re the questions that are hanging out in the room but no one’s asking; the questions the coachee is forgetting to ask himself. They’re the questions that really want to get at the heart of the matter or at the heart of the person being asked.

Where do you find the questions? Everywhere (or you can use the question generator in Tool 5-2). Here are some suggestions:

Build off what the coachee says, as in this example:

Coach: What do you want to talk about today?

Coachee: I don’t know. I feel confused.

Coach: What’s the confusion about?

Coachee: I don’t know how I feel about the new employee.

Coach: It sounds like you do know, but aren’t saying it. How do you feel about him?

Coachee: Well, he’s not motivated, and I’m not sure I can motivate him.

Coach: How might you motivate him?

Coachee: I tried the same things that have worked withww other employees, but they didn’t work with him. I’m not sure what to do next.

Coach: So, what might you try next?

Ask the dumb questions, the ones that only a naïve person would ask. These are the questions that you’d often think to preface with “Pardon my stupidity, but …” These are questions like, “Why do you think that?” “Why do you have to?” “Who told you that you had to?” “Is [fill in] true?” and “Isn’t [fill in] also true?”

Read up. I keep several books on my shelf that are loaded with thought-provoking questions. Here are some examples:

• Marilee G. Adams’ Change Your Questions, Change Your Life: 12 Powerful Tools for Leadership, Coaching, and Life, 3rd edition (Berrett-Koehler 2016)

• Michael J. Marquardt’s Leading with Questions: How Leaders Find the Right Solutions by Knowing What to Ask, 2nd edition (Jossey-Bass 2014)

• Warren Berger’s The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead (Bloomsbury 2019).

Not only are these books full of tried and truly powerful questions, but they’re also fascinating reading. Gallup’s Q12 questions are especially relevant when doing workplace coaching.


My most reliable coaching question is “What do you want?” Why that question? This question implies that the power is in the coachee’s hands; that she gets to decide how a situation resolves itself. It gives the coachee a blank slate to work from, and it focuses her on what she wants at that moment from the situation, or from the coaching conversation (“What do you want from me as your coach today?”). She may just be going down a path but isn’t sure it’s what she wants. It’s more than being able to ask for something tangible and getting it; it demands first that you know the objectives of your communication or the outcome you want for a situation. For example, a client was talking to me about an argument she’d been having with her boss. She talked about wanting to write a letter to explain her side of the story. “That’s nice,” I said, “but what do you want him to do as a result of reading it—agree with you? That might not be realistic. Repair your relationship? If so, do you need to explain your side (again)? Perhaps it would be better to write the following in a letter: ‘I want to have a good working relationship with you, as we once had. I want to sit down and talk about what we can do to recreate that.’”

Ask questions from your gut. Many questions live in your gut, but you’ve been taught to hold them there, not to be nosy or inappropriate. Be curious. If you have a question burning inside you, blurt it out.

Ask your coachee for questions. The coachee drives the coaching process, so ask him, “What’s the question you need to ask yourself about this situation?” My clients come up with brilliant questions for themselves all the time.

Have one or two “go-to” questions. There are some questions that just work in any coaching situation. Keep one or two of these in your back pocket at all times. When you or your coachee get stuck, pull out these questions. Trust that you have these questions to fall back on at any time. These questions sound like: “What do you want?” “How is that working for you?” “Where have you seen that to be true?” or “What’s behind that [desire, question, statement]?”


Another coaching question I like is “What if that were true?” When a client says, “I’ll never achieve that thing,” I ask, “What if that were true?” When he says, “She’s trying to manipulate me,” I ask, “What if that were true?” Same with “My colleague hates me” or “I’ll never get this done in time.” Asking “What if that were true?” allows them to face their fear in a theoretical context. It can help them see that what they are fearing may not actually have such dire consequences.

At each of the 10 steps in the coaching process, there are questions it’s appropriate and helpful to ask. Tool 5-3 presents a list of them, arranged by step. These aren’t the only questions that work at each step—they aren’t even necessarily the best questions. But they are questions that will help you achieve what’s meant to be achieved at each step. As you add your own favorites to the list, keep it in front of you as a tickler when you work with your first few coachees.

TOOL 5-2

Coach instructions: Pick one word or phrase from columns 1, 2, and 3 to create more than 125 questions.

Column 1 Column 2 Column 3

• happening

• possible

• working

• needed

• your wish

• your role

• the sticking place

• not being said

• your choice

• important

• fun

• next

• or you?

• right now?

• from this perspective?

• when you get/do that?

• in the big picture?

• for/in that meeting/

• interaction?

• for/in your team?

• as a leader?

• in five years?


• is responsible

• do you need to be


• will you do/get that

• will this work

• do you feel

• can you be [insert adjective here]


TOOL 5-3

Step Questions
Step 1: Prepare Yourself for the Coaching Role Ask yourself:

• What’s my definition of coaching?

• What do I need to have in place to be a good coach?

• What do I want from coaching?

• What excites me about coaching?

• What gremlins are present for me around coaching? What do I want to do with them?

• At what other time have I overcome obstacles to do what I wanted to do?

Step 2: Create Your Coaching Relationship Ask your coachee:

• What expectations do you have of yourself or me, your coach?

• What kind of meeting schedule would work for you?

• Where would you like to meet?

• To what amount of time shall we commit?

• What kinds of information would you be open to sharing (for example, personnel file, 360-degree evaluations, and the like)?

• How will we know if this relationship is working?

• How will we know when it’s time to stop?

• What’s the best way to deal with you when you’re resistant to coaching?

Step 3: Facilitate Discovery Ask your coachee:

• What’s your favorite childhood memory?

• What is your idea of fun?

• Who is someone who inspires you, and why?

• Will you describe a perfect day?

• What is one of your greatest accomplishments, and why?

• What is your favorite book, movie, or song? What memories are associated with it?

• Which assignments or role in the past provided you with the greatest challenge? The least? Why?

• What makes you unique?

• What lessons have you learned from your successes or failures?

• What part of your education or work experience has been the most valuable to you over the years?

Step 4: Agree on What You Want to Accomplish Ask your coachee:

• What is it to be a leader/boss?

• How does this goal fit in with your plans, way of life, and values?

• Why are you here?

• What in your life do you want to change?

• What obstacles are in your way?

• What can you do now and in the long term to get you there?

• What tools or resources do you require?

• How will you know you’ve changed?

• What does success look like for this goal?

• By when will you achieve it?

• Why is this goal important to you?

Step 5: Use the Power of Possibility Ask your coachee:

• What excites you?

• What’s next?

• What do you want?

• What’s your dream?

• What’s bigger?

• How would you like this situation to resolve itself?

• Where do you see yourself in five years?

• How would you like to be remembered?

• What would you want others to say about you when you’re not listening?

• What do you want your contribution to be?

• What if that were true?

Step 6: Partner to Enhance Growth Between Sessions Ask your coachee:

• How can you carry that perspective with you this week?

• What would remind you of that aha until we talk again?

• Can you try [fill in] this week?

• What assignment do you need to do to move you toward that goal this week?

• Will you take on this assignment? [yes, no, or counteroffer]

Step 7: Realign When Things Go Bad Ask your coachee:

• What’s stopping you?

• What are you avoiding? What aren’t you saying?

• What do you feel is a roadblock to your success?

• Is this a perceived roadblock or a real one?

• What would you say if you did know?

• If you had unlimited resources and power, and there were no repercussions, how would you overcome this roadblock?

• What would be your next step?

• What do you want to tell your gremlin?

• What value are you stomping on right now?

Step 8: Maintain Positive Changes Ask your coachee:

• Where are you feeling satisfied or accomplished?

• What will keep this feeling alive for you?

• What is working?

• What’s possible for you right now?

Step 9: Complete the Coaching Cycle Ask your coachee:

• Is it time to complete our coaching relationship?

• What did you learn?

• What’s next?

• What do you want to celebrate about our work together?

• Is there anything else you need to say right now before we part?

• How should our relationship continue after the coaching is over?

Ask yourself:

• What did I learn by coaching this person?

• Where did I grow as coach?

• What questions do I have about coaching, and who can answer them?

• What’s next?

Step 10: Prepare Your Organization Ask yourself:

• Who in my organization would benefit from coaching?

• Who am I the best coach for?

• How can I make my organization more supportive of coaching (or of development in general)?

Questions You’re Not Asking

Not all questions are created equal. Just as some questions can work better for getting your coachee to think about a situation differently, other questions can do the opposite and cause harm to the relationship. These are the types of questions you should avoid in coaching.

“Why” Questions

Coaching has as its focus the present moment and how the coachee can get from the present moment to the desired future. This is not the place for analyzing how a person got into his present circumstance or situation. We don’t ask, “Why are you in this predicament?” or “Why do you think you feel that way?” Leave it to therapists to determine why someone believes as he does or what happened in his past to create the situation he’s in now. Why questions (Why did you do that? Why didn’t you do this?) also can put coachees on the defensive.

That said, there are exceptions to this “don’t.” If there is learning that can be immediately applied from asking a why (or how) question, you should go with it. For example, if asking “How did you get so far behind in your work?” would lead to identifying some best practices the coachee could use right away to avoid getting behind, it’s worth asking. You just don’t want to go too far down the analysis road. Coaching is less about how you got where you are today than it is how you will move to where you want to be tomorrow.

“Why Don’t You …” Questions

Coaches want coachees to come up with solutions themselves. Asking, “Why don’t you call that person today?” or “Why don’t you look for a new job?” implies that the coach has the correct answer and, indeed, will judge the coachee if she chooses another approach. Also, because a “why don’t you …?” question is phrased in the negative, people tend to give a negative answer (for example, “Why don’t you make that call?” “Because I don’t want to!”). If instead you ask, “What would you do to remedy this situation?” people are guided to think positively.

Questions About Details

This step is about greatness. Greatness doesn’t spring from the stories coachees tell; it resides in what they’re capable of doing or becoming. You can do a lot of coaching without knowing all the particulars when it’s only your own curiosity that wants to know all the minute details. Sometimes you seek the details because you want to build rapport and show an interest in the coachee’s life. Remember that a little of that is fine, but manage yourself and your questions so that you’re not bringing the conversation to a mundane level of detail. Here’s what happens when you don’t manage yourself:

Coachee: I think I need to move out of this city.

Coach: Really? How long have you been here?

Coachee: About 10 years. But it’s just too expensive to raise a family here.

Coach: I know. How many children do you have?

Coachee: I have three.

Coach: That’s nice. How old are they?

Coachee: Five, seven, and 10.

Coach: Great ages. So, why do you think you have to move out of the city?

Although the coach might be interested in how long this coachee has lived here, or the number of children the coachee has and their ages, those details really aren’t going to move this conversation forward and asking such questions is distracting the coachee from the situation. The coach is right to bring the conversation back around to the original issue—moving out of the city. The client knows the answers to these detail questions already, so these questions aren’t helping him. That’s the litmus test: Who benefits from the answer to a question? If it’s just the coach, avoid the question. If the coachee can learn something from the response, it’s a good question. You’d be surprised by how many questions we think we need to ask to get a handle on the situation that we really don’t, especially if we are helping them come up with their own answers. If you do ask a factual question, tell why you are. For example, instead of asking, “How many presentations do you deliver?” just elaborate, like, “You’re feeling your presentations are not effective. How many a week do you have? The reason I ask is that maybe the content is getting stale for you as you’ve delivered it so many times.” Just offering this explanation can get you to an even better question, like, “So, what can you do to keep the content fresh even when it’s your ninth time presenting it?”

Here’s how the conversation could have gone:

Coachee: I think I need to move out of this city.

Coach: What is it you’re looking for that you don’t have here?

Coachee: Well, it’s really expensive to raise a family here.

Coach: So, you’re looking for a place to live that’s more affordable. What would that do for you?

Coachee: My wife and I wouldn’t have to work as hard. We could relax more with our kids.

Coach: So you’d have more family time. What else would living in another area do for you?

Coachee: If we lived closer to the ocean, as I’d like to, we could be outside more and I could do more sailing, which I once loved to do. Haven’t done it in a really long time.

Coach: OK. How about if we talk about what moving would involve, and also about how you can get those things you’re after—the family time, the sailing—right here and now without moving anywhere.

Close-Ended Questions

You already know that open-ended questions are those that open the door for more talking, and close-ended questions require only a couple of words in response. But you may be surprised how often you use close-ended questions or sometimes yes-no questions. When I started looking at this more closely, I was amazed how often I was shutting the door on valuable conversation. Here’s where I got caught: As a trainer, I’d ask, “Do you have any questions?” rather than the more encouraging open-ended inquiry, “What questions do you have?” As a coach, I’d ask, “By when will you do that?” rather than “What’s involved in getting that done?” As a parent, I’d ask “How was school today?” rather than “What was the funniest thing that happened at school today?” If people tend to respond to your questions with few words, consider how you’re phrasing those questions and try again.

Leading Questions

In reality, these aren’t really questions at all; they’re statements posing as questions. They sound like this: “Don’t you think you deserve a raise?” or “Are you a manager who frequently communicates with his employees?” or even, “That sounds pretty doable, right?” Try not to manipulate questions to steer your coachee toward a certain belief or action.

Multiple Questions

I also call these run-on questions. Like run-on sentences, these questions just don’t end. We heap on more and more questions because we’re afraid we didn’t ask it right the first time. Or our first question results in silence (and we all have a fear of silence), so we throw in another question to fill the space. People need time to consider their responses to your questions. They need to know what question they are being asked. Throw one out there and let it sit. If you do decide it was a bomb, break into the silence after several moments and just say, “I think that wasn’t the right question. What question do you want to be asked about this right now?” Usually, however, simply sitting with the silence long enough will produce some real nuggets from the coachee. Remember that he’s as uncomfortable with silence as you are, and to break the silence he’s likely to contribute something he wasn’t planning to talk about. At a minimum, he might say something like this: “That’s not really the big question for me.” That’s your perfect opening for this response: “Great. What is the big question?”

An interesting coaching tool is the Daily Question Process, a coaching exercise that was suggested to me at a conference I attended with executive coach and author Marshall Goldsmith. Goldsmith and a friend simply ask each other a series of questions every day that help them live life more fully—and happily. Questions like:

• Did you do your best to increase your own happiness yesterday?

• Did you do something to make your wife happy?

• How many sit-ups did you do?

• How many pages of creative writing did you write?

They each came up with their own list of questions based on things that they wanted to make time for or that have meaning for them. Goldsmith identified some of the major stakeholders in his life—like his wife and children—and asked them what they would like him to focus on on a daily basis.

Goldsmith has found that the repetitive nature of the questioning eventually leads to action. For example, he says, when you get sick of being asked every day how many sit-ups you’ve done and answering, “none,” you start doing some. When you are asked if you helped out someone less fortunate every day, that activity remains in the forefront of your thinking. And active questions—questions that focus on what you can do to make a positive difference for yourself and the world, questions like, “Did I do my best to maximize my performance yesterday?”—are especially effective.

If you want to use this tool, make sure you remember to check in with your coachee not just on the questions themselves but on this tool you are using. When it is no longer adding value for him, or when it starts to feel like you are nagging him, it is time to retire the tool. Also, as a coach is not a daily presence in the coachee’s life, it’s a better idea to teach him the tool and have him find someone else in his life who he wants to go over the questions with him each day.

How to Hear the Responses: Coach Listening

Coaching means you’re asking some big questions. How do you need to listen to the responses? How do you need to listen when your coachee is telling you her biggest hopes and dreams? How do you need to listen to hear the greatness within her? This is going to require a higher order of listening than just mechanically hearing another person speak, which we do automatically. How you listen to your coachee has a profound impact on her sense of self-worth and her ability to achieve.

So, how do you have to listen? The answer will be based partly on your designed relationship with your coachee. He may have told you he prefers positive input rather than being told what’s going wrong. He may have said he needs time to vent and wants to know you’re there to listen rather than having you ask any questions. If you didn’t have this conversation initially, you can ask at your next meeting, “How am I as a listener to you? What do you want more of or less of in my listening?” If you’re not ready to have that discussion with your coachee, have it with your children or your siblings. They’ll tell you. I hear it all the time: “Mom, I didn’t want you to tell me what to do. I just wanted you to listen.”

Make asking how you are expected to respond part of your everyday interactions. Try it at your next coaching session. Before you get under way, ask “What kind of response do you want from me after you share this?” Similarly, make it a practice to tell people what kind of listening and reaction you want from them. Doing so can circumvent a lot of difficult situations. For example, I asked a project team to do a practice presentation in front of my boss. I forgot to tell the boss that we really just wanted her overall opinion of how the senior management team might react to it. What we got was a critique that ripped the presentation apart piece by piece. I should have explained to her that although I was used to her feedback and could take it, this presentation was being made by a group of volunteers who’d worked really hard and who needed a little sugar-coating. I should have explained the purpose of her listening in on the practice session.

Beyond that, here’s how I define the kind of listening you have to do as a coach. Coach listening is brief and in your own words reflecting the essence of the content and emotion the coachee is sharing. Let’s deconstruct that. We’ll work with the following two examples:

• “My boss actually called me when I was on vacation last week. It made me so angry. She could have found what she was looking for herself. She tried to make it sound like she just needed me so much, that I’m indispensable, but really I felt she was just, once again, invading my private life.”

• “My team members are so unmotivated, and I don’t know what to do about it. I don’t think you can teach work ethics or desire to do well. They either have it or they don’t. What am I supposed to do with unmotivated people?”

Briefly means just that. If the coachee gives you a paragraph, you give him a sentence in a listening response. If he gives you a sentence, you give him a word. Here is a sentence for each of the examples above: “You’re angry you had to work on your vacation,” and, “You don’t think a boss can change the way people feel.” Don’t worry if you don’t capture everything the person has said. If you’ve focused on the wrong part of their message, they’ll let you know, and this is good data.

Reflecting what’s been said in your own words is the best way to show that you’ve heard what your coachee has told you. Rephrasing shows you’ve internalized his message and made it your own.

Reflecting the essence means you’re mirroring the most significant aspect of what the coachee has said, that which is at the heart of her statement. What’s the essence in each of the two examples above?

After listening to the first speaker’s message, I’d say she felt her personal time and space had been invaded, she’d been taken advantage of, or she was trapped. In the second example I notice feelings of being trapped again and of being inadequate and unable to perform. One thing to remember here: It’s OK if you don’t correctly identify your coachee’s core message—she’ll let you know if you’re way off base. But simply by trying to capture the essence, you avoid unnecessary details and get more deeply into the real message.

Both content and emotion are important. Thinkers or analysts among us (rather than feelers or emotional types) tend to focus on the content. They can be deaf to the emotion that’s present in what someone is telling them. Even us feelers can overlook emotional content. I learned this lesson the hard way while conducting a seminar for parents. I asked a parent for her impression of a book we’d just read. She gave a quick summary that was right on target. I said, “Thank you,” and moved on. My co-leader said, “Wait, Sophie, I think Joan is really upset about what she read.” I asked Joan if that was true. She nodded and began to cry. We ended up talking about the sadness that book created for her for quite some time. Many of the other participants had had similar reactions. A very rich conversation occurred because my co-leader noticed the emotion I missed in what Joan had been saying in her summary. I’ve carried that experience with me ever since that seminar and go out of my way to check for emotional responses while listening.

That brings up this fact: In coach listening, you do name the emotion. You don’t ask, “How are you feeling?” You say, “You’re angry that …” or “You’re hurt that …” Participants in my listening skills workshops often ask, “Aren’t you just creating anger that way? Might he not get over it if you just moved on? Wouldn’t your conversation in that group have been quicker and easier if you hadn’t stopped him?” My answers? No—maybe—and yes. No, I’m not creating anger—just naming it. The feeling already exists. When you name it, you validate the emotion, and the person experiencing it. When you don’t, the person can feel like you’re ignoring him. Even as a volunteer crisis response counselor I was told to say, “You’re depressed,” or “You’re devastated.” That doesn’t cause someone to feel that way; it validates how they are feeling.

If you’re wrong, they’ll tell you, and this is good data. Maybe he would have gotten over it and moved on, but is that what you want? To have him carry those sad feelings with him for the rest of the discussion? To have him think you didn’t care? And then again, maybe he wouldn’t have gotten over it. Then he wouldn’t remain a productive member of your conversation; I’d have lost him and possibly others who felt as he did.

Finally, yes, it would have been quicker and easier just to gloss over his emotions, but that’s not the goal in coaching. The goal is to peel the leaves off the artichoke to get at the heart inside, to remove all the layers your coachee has wrapped around himself that make him unable to access his solutions and magnificence. Naming the emotion and getting to the heart of an issue don’t always mean taking lots of extra time. It only takes a moment to acknowledge that the coachee seems to feel sad or angry or discouraged.

When reflecting a speaker’s feelings, you need a vocabulary of emotions. Repeatedly using the same words to describe someone’s feelings grows stale and disingenuous over time. One way to develop a more comprehensive and accurate vocabulary to describe feelings is to read and reread a list of feeling words, like the one presented in Tool 5-4. Add your own words to make this list more personally authentic.

TOOL 5-4

Now, taking another look at the two examples above, how would your coach listening responses sound?

Here are several responses that meet all the criteria—briefly and in your own words, reflecting the essence of the content and emotion the coachee is sharing:

• “It’s annoying when you can’t get away from your boss!”

• “You’re fed up with having your privacy repeatedly invaded.”

• “It’s disappointing when your work ethic isn’t shared.”

• “You’re stuck and confused about what to do with your team member.”

You can give an active listening response even when nothing has been said or when the person’s words don’t match their nonverbal reactions, like these: “You were chuckling a bit. Does that mean you recognize that behavior?” “You just agreed to do that, but you don’t sound like you really want to,” or “That was a long sigh. What was that about?”

Having covered what coach listening is, let’s consider what it is not:

Parroting—How annoying it would be if you simply repeated what the coachee said. Do you hear the difference? The coachee says, “I’m tired of being micromanaged. She wants a list of steps, and I don’t work that way.” A parroting response would be this: “So, you’re tired of being micromanaged and want to do things your own way.” A coach-listening response would sound more like this: “You want the trust of your boss to manage the way you know you can.”

Advising or problem solving—It’s in our nature to want to help people. That’s not a bad intention, but it is bad in coaching where you want people to access their own answers. You may also jump in with your solution before you’ve heard the entire issue, and the conversation will go down the wrong path.

Turning the spotlight on you—Coaching focuses on the coachee. Saying things like, “I know how you feel. I once had a boss who did this and that, and it always made me feel small” intrudes on that focus and makes it all about you.

Being overly supportive—It is also a natural instinct to try to make people feel better, but doing this discounts how the coachee is actually feeling in the moment. We say things like, “This will get better,” “That’s nothing; some people have made much worse mistakes,” or “Oh, the person who said that doesn’t know what they’re talking about.” We have the best of intentions when we’re smoothing over people’s feelings, but this isn’t an effective way to show that you understand how they’re feeling and have heard them.

Contradicting—You don’t have to play devil’s advocate to contradict someone. Sometimes, it’s much more subtle. For example, we may want the coachee to give someone the benefit of the doubt; to consider a situation from another perspective. That’s a sound coaching strategy, but it’s not the same as listening. People need to know you’ve heard them and their perspective before you ask them to take on another one. So, before you say, “Maybe your boss didn’t mean it that way. Have you ever thought about what’s going on for her?” first acknowledge what they experienced.

Grading—Whatever the coachee says has to be OK. Watch your facial reactions and your nonverbal communication. Do you display a poker face, or do you smile when they’re “right” and frown when they’re “wrong”? Do you sigh when they say something that disappoints you? Do you sit up straighter when they’re talking about the stuff you like to hear? Even when I coach people on the phone, I try to keep myself from doing these things, and I pay attention to the tone of my voice and the message it may convey. Of course, you want to refrain from verbal grading. That’s when some of the things your coachee says get a response from you like “good” “great” or “aha,” while others get a “tsk,” a grunt, or no response at all. This isn’t to say that a coach can’t have a human response! It’s just that there are some moments when the coach must be listening and not reacting. It is OK, however, to note your or the coachee’s energy with a statement like, “When you talk about that, there’s an electricity in the room. It got me sitting up straighter in my chair. How about you?”

Only after the coachee has been heard and he’s sorted out his feelings about the situation will he be open to working on solutions. This is true even when he plainly asks for a solution, saying, “I’m so stuck. What should I do?”

Let’s look at two possible conversations starting from the same place. In this first one, the coach makes a number of mistakes:

Coachee: I’m so stuck. What should I do?

Coach: Well, it seems like a talk with your manager is in order. [giving solutions]

Coachee: I’ve tried that over and over. Each time she seems to get it, but then it only lasts a week or so.

Coach: When was the last time you had one of these conversations? [question about details; close-ended]

Coachee: About a month ago. But it’s hopeless. She’s that way with everybody.

Coach: Has your whole team had a retreat lately? [problem solving; close-ended]

Coachee: Not for a couple of years.

Coach: I think a retreat is a great idea. I once worked for a manager like yours and a team retreat really turned things around. It’s also a good way to bond outside the office, which you should be doing periodically anyway. [spotlight on the coach; problem solving]

Coachee: Well, OK.

Coach: Fantastic! [grading]. Can you make that happen? [close-ended question; leading question]

Coachee: Yeah….

Here’s the second conversation, which shows a better coaching approach to the same opening statement:

Coachee: I’m so stuck. What should I do?

Coach: You seem at a loss for ideas.

Coachee: Yeah. [After a few moments of silence] I’ve tried everything I can think of, but it’s hopeless.

Coach: It’s very unmotivating to be scrutinized so closely all the time.

Coachee: Yeah, it’s like I’m a kid and she’s my disapproving mom!

Coach: It’s a dynamic that really makes you feel small.

Coachee: Yeah. And I’ve been doing this job for 12 years. I don’t need to be told how to fill out a planning sheet.

Coach: It really irks you that your professionalism is continually called into question.

Coachee: Exactly.

Coach: You seem tired when you talk about this.

Coachee: I’m just bored. I feel like I’ve had this conversation again and again. I’m just tired of it.

Coach: It’s probably disappointing to be back at this stage again.

Coachee: Yeah. Maybe I should start looking for a new job. But I love this job—or I did before she came along.

Coach: So, you want to fall in love with this job all over again.

Coachee: Yeah.

Coach: What can you do to fall back in love with your job, despite this boss?

Rather than leading the coachee, the coach has waited until she sensed that the coachee knew he’d been heard and was ready to move on. Then she shifted from listening to moving the discussion forward. Those two conversations came from the same situation, but they have very different energy and very different outcomes—all because of one used coach listening while the other did not.


Some people use the expressions “I hear what you’re saying” or “I understand” to convey that they’ve been listening. However, this feels like a canned response and doesn’t actually demonstrate that you were listening. Instead, say, “I hear you saying that you don’t think your staff is engaged” or “I understand you’re feeling overwhelmed.” The sentence stems alone are not enough to convey you’re listening.

Coach listening isn’t just about the things you say in response to a speaker. It’s also about what’s going on in your brain while the coachee is talking. To be a good listener, you need to be aware of some of the common internal blocks to listening and start noticing when you are using these so you can begin to manage them. If you were to do a Google search for “listening blocks,” you would likely encounter lists of 10-12 common blocks, including those Matthew McKay shares in his book, Messages: The Communications Skills Book. I’ve extracted the following from multiple searches I’ve conducted on those words:

Rehearsing—You cannot be fully engaged in listening if your mind is racing because you’re thinking about what you want to say when the coachee finishes speaking. Instead of being present and focused on your coachee, your attention is on the preparation and crafting of your next comment. When you find yourself worried, “I don’t know how I’ll respond to this” or thinking, “I know what to say next. I’ve heard this concern before, I’ll start with …” this is the time to notice you are not being present and to bring your focus back to the coachee. When he stops talking, you can always say something like, “Wow. You’ve just said a lot. Give me a moment to process all of that.”

Filtering—When you filter, you listen to some things and not to others. You pay only enough attention to ascertain whether your coachee is happy or upset or angry; then you let your mind wander. Another way we filter is simply to avoid hearing things we don’t want to hear, like if your coachee mentioned that the assignment he tried this week didn’t work at all, or that he failed at something.

Comparing—Comparing makes it hard to listen because you are busy thinking about yourself and how you are in relation to how your coachee is; for example, asking yourself “Is he better at adjusting to change than I am?” Or, while someone is talking, you think something along the lines of, “He thinks he has a hard time with that. I had it much harder and you didn’t see me complaining.” Comparing is similar to identifying, another listening block, where everything you hear reminds you of something that you have felt, done, or suffered. Instead of listening, you are busy thinking about your own experience.

Mind reading—Instead of listening to what your coachee is telling you, you are searching for hidden meaning, trying to figure out what he’s really feeling or even guessing how he’s reacting to you (“Did he just notice the new photo on my desk? Is that why he paused?”). Instead of listening as he provides context, you’re jumping ahead to, “What is he going to ask me to do?” Instead of focusing on hunches, assumptions, or wild guesses, listen to what the person is actually saying. Ask directly if you think that might not be the full picture; for example, “You’re saying you are okay that your boss didn’t ask you to be on this committee, but I imagine that could be disappointing. Was it?”

Engaging with your coaching gremlin—Another thing that gets in the way of listening to a coaching client is when those negative voices pop up in our minds in the middle of coaching. When this happens, remember the steps for responding to the beliefs that limit you as a coach and, in the moment, be transparent: “You know, when you said that, it made me think that I don’t have the experience to guide you through this, but I know that that’s OK. You have the resources to get through this and I will help you reconnect with those.”

If you think your coachee is displaying any of these listening blocks, you need to call him out on them too. Educate him about what good listening is, and point out when he is—or isn’t—using it.

The Next Step

One of my favorite parts of coaching is helping people see their own greatness. The world is big on pointing out our faults, but how often do we get to see how powerful we are? The days when coaching is most rewarding for me are those days when people realize something they saw as a far-off dream can happen—or start to happen—now. There is magic in this step for coach and coachee alike. It’s not always true, however, that this magic happens in the moment when you are doing the coaching. Much of the coachee’s growth and discovery happens between coaching sessions, and that is the focus of the next step.

Applying the Learning

“A good coach will make his players see what they can be rather than what they are.”

—Ara Parasheghian, Former head coach of the Notre Dame Fighting Irish

• Who is your coachee at her core? Think about it and share it with her. No coachees? Try it on a family member.

• Do you believe enough in your coachees, employees, loved ones? Is there any area in which your opinion of what they’re capable of doing is holding them back?

• Can you create more questions in your life? Ask four questions in every interaction this week, especially when someone asks you for advice. Notice if you’re wedded to a certain response. What does that dynamic do for you?

• How do you want to listen? How does your coachee want you to listen? What parts of coach listening will be easiest for you? Which parts will be most difficult? What is your most prevalent listening block? First notice it. Then start managing it.

• As an argument is starting this week, pause and engage your coach listening skills. Instead of arguing your point, just reflect the essence of what the other person has said. Keep doing that until the tide of the conversation appears to turn. When it has de-escalated, you can return to your side of the situation at hand.