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1-Page PDF Summary of The Coaching Habit

Coaching in the workplace can bring out the best in your team members and increase productivity, while also lightening your workload. But many managers and leaders avoid coaching, thinking that it’s just another task to add to a burgeoning to-do list or that it’s too complicated or awkward to put into practice. Others mistakenly believe that they’re already coaching, when all they’re doing is giving advice.

In this book, you’ll learn how to turn coaching into an informal, effective daily habit by asking team members seven essential questions. Find out how listening instead of speaking for just 10 minutes a day can refresh and revamp your interactions with your team members and ultimately transform the way you and your team work.

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Use “Anything else?” in a variety of scenarios: after your conversation starter, when you’re trying to get to the heart of an issue, when you want to keep a conversation moving forward, or any other situation where you feel like there’s more that is waiting to be said. Be curious and give the person your full attention so that your “Anything else?” comes out as genuine, rather than as an automatic follow-up.

Question 3—The Laser Beam Question: What’s the Central Challenge For You?

As a manager, you’re trained to be the chief troubleshooter in a fast-paced environment. When someone comes to you with a problem, you might come charging in to put out a fire without stopping to figure out what caused it. This then leads to three problems:

  1. You might have to deal with the same fire over and over again, or have other flames crop up from the same source.
  2. You prevent your direct reports from learning how to deal with the fire themselves.
  3. You’re so busy putting out fires, you’re not able to take care of your other responsibilities. This creates a bottleneck and causes work to come to a halt.

The third essential question, “What’s the central challenge for you?” allows you to weed through several issues to find and solve the real issue at hand. Since you’re used to the bad habit of fixing things yourself, stopping to ask questions might feel like inaction. However, any insight you uncover by asking the laser beam question will be much more valuable than the wrong solution to the wrong problem.

Three common situations are great coaching opportunities, but often trigger “fixing mode” if you’re not careful:

  • The other person is dealing with a lot of issues. Some people don’t hold back when you ask them, “What’s on your mind?” and fire off numerous issues. Your brain starts to go into overdrive, trying to figure out which to tackle first. Stop yourself and ask, “If you had to choose only one of these to address, which one is the central challenge for you?”
  • The conversation turns into a gossip session. A team member’s complaints about a colleague or client are within the realm of issues neither of you can control. You can only coach the person in front of you. Switch the focus from a person you’re talking about to the person you’re talking to by asking, “I think I understand what’s going on with Barbara. What’s the central challenge for you?”
  • The issues are too vague. If the team member doesn’t know the exact problem himself, he may talk about abstract big-picture issues or drift between vaguely connected issues. If you’re left feeling confused after a long-winded conversation, narrow the scope by saying, “I can see that this issue comes with a lot of great challenges. What’s the central challenge for you?”

Question 4—The Empowerment Question: What Do You Want?

Every person has wants, but they may not express them due to fear of saying the wrong thing, being rejected, or coming across as demanding. When team members feel afraid to express what they want, the workplace can take on an atmosphere of uncertainty. These underlying negative feelings can make it difficult for team members to perform at their best.

Make a habit of asking the fourth essential question: “What do you want?” This question increases the feeling of safety in the workplace because it makes team members feel that you’re on their side, that they have some control over their future, that they’re valued, and that they’re in a position to make a decision. All these signals encourage team members to lower the defenses that may be blocking them from thinking at their best.

Asking “What do you want?” is especially useful in two situations that can cause friction or uncertainty in the workplace:

  • When a conversation seems to be losing steam. Sometimes a discussion seems to be going around in circles with no solution in sight. It may be a sign that the other person doesn’t feel safe enough to articulate what he wants. Asking, “What do you want?” tells him that he can freely share his desired outcome.
  • When there is conflict. When you and another person reach an impasse, make sure you truly understand what the other person is asking for by asking, “What do you want?” Then clarify your position by telling him what you want as well.

Question 5—The Heavy Lifter Question: How Can I Support You?

When someone comes to you with a question or a problem, you may feel like it’s your duty as a manager to rescue him by finding solutions yourself. It seems like the most efficient way to address a problem, but your good intentions may backfire: Your team members may feel resentful when you step in instead of trusting them to find solutions, and in addition to preventing team members from learning and growing, you’ll needlessly add to your workload.

Replace your old “rescuing” habit with the good habit of asking the fifth essential question: “How can I support you?” This question makes for effective coaching in two ways:

  1. It helps you exercise self-control by slowing you down and preventing you from jumping to finding solutions yourself.
  2. It compels the other person to be clear and direct about what he needs. Often, this question will help him realize that he doesn’t need your help at all—he’s able to learn and grow, and you’re freed from doing unnecessary extra work.

You might be hesitant to ask this question because you’re worried the team member will ask for more help than you’re willing to give. Keep in mind that it’s just a question, not a commitment—asking “How can I support you?” doesn’t mean you’re obligated to say “yes.” You can also say “no,” give a conditional “yes” or “no,” or ask for more time to think about it. When considering your response, let your goal of training your team members to find their own solutions guide you.

Question 6—The Commitment Question: What’s the Cost of Saying ‘Yes’?

Many team members tend to take on any extra tasks someone asks of them—such as sitting in on meetings, joining committees, or participating in social activities—even when their schedules are already overflowing. They tend to say “yes” to these tasks, ignoring their overload, for two reasons: they associate being busy with being successful, and it can be hard or awkward to say “no.”

Seeing team members contemplating an opportunity or additional responsibilities should trigger you to ask the sixth essential question: “What’s the cost of saying ‘yes?” After asking, guide them to the best decision in two ways:

1) Help them reflect on their 3Ps: What projects will they need to give up to take on this new responsibility? Which people will be affected by his decision? What patterns and habits will he need to overcome to accomplish the new task?

2) Give them the tools to say no: You can help them avoid the difficulty of saying “no” with two methods:

  • The “slow yes”: When asked to take on a new task, he can get a better grasp of the commitment required by asking questions such as, “What’s the timeline?” and, “If I can only commit x hours, what would you like me to do?” Such questions will lead to one of four outcomes: He finds out that he doesn’t have a choice and has to do it anyway, he gets some illuminating answers that will better help him make a decision, he buys himself some time to think about it, or he’s left alone and someone else is asked to do the job.
  • The “diplomatic no”: Explain that he can make “no” less awkward by refusing the task and not to the person—for example, saying, “It looks like I have to say no to this” instead of, “It looks like I’ll have to say no to you.”

Question 7—The Insight Question: What Was Most Useful for You?

As a manager, it’s part of your job to help your direct reports learn new skills and become better, more successful team members. Projects and problems provide many valuable teaching moments, but the lessons from those experiences may not always stick.

The best way to help your team members absorb new information is by asking the last essential question: “What insights did you gain?” This question encourages your team members to identify and retain a concrete lesson they learned, as well as making them feel like you care about them. Additionally, knowing what parts of a project or issue taught them the most can clue you in to how to better coach them in the future.

Once the other person tells you what was useful for them, be sure to tell them what insights you gained, in order to reinforce that your coaching conversations aren’t meant to be one-sided.

Refine Your Coaching Skills

It’s not enough to just know and robotically ask the seven essential questions. Take your coaching skills a step further by knowing the most effective way to ask them. There are four elements of “effective asking”: pacing, straightforwardness, engagement, and consistency.

Pacing

  • Mind your pace: With this book’s set of coaching prompts in your toolbox, you might be tempted to fire them off one after the other. However, your direct report may feel overwhelmed if you ask them too many questions at once. Wait for your team member’s response, really listen to it, and consider the best response before launching into your next question.
  • Embrace silence: Be comfortable with silence, and allow the conversation some breathing room. You don’t have to fill every second with conversation. Don’t say anything for a few seconds to give the other person the chance to come up with thoughtful responses.

Straightforwardness

  • Don’t beat around the bush: If you already know what you’re going to ask, just ask. If you feel uncomfortable asking a question or think that your question might sound too blunt, preface it with phrases such as, “Out of curiosity…” or, “To make sure that I understand…”
  • Don’t disguise advice as a question: Sometimes you want the other person to get to the solution you want without making it seem like you want things done your way. So, you ask questions like, “Have you considered…?” to put your ideas in their mind. Whenever you’re tempted to give advice disguised as a question, try asking, “Anything else?” Only after hearing everything the team member has thought of should you offer your own ideas.

Engagement

  • Use “what” questions: While “Why?” is a useful question in many situations, it may sound judgmental and make people feel defensive. Reframe your “why” questions into less intimidating “what” questions. For example, instead of asking, “Why did you do that?” try asking, “What kind of outcome were you hoping for?”
  • Give your full attention: Really listen to the responses to your questions. Turn off distractions such as email or phone notifications, and consciously put aside thoughts like deadlines or what you’re having for lunch. If you catch your mind drifting, just get back in the moment and refocus.
  • Be an active listener: Don’t be a completely passive audience to your team member. Instead, show that you’re listening to them by engaging with what they’re saying. For example, “Great idea” or, “Yes, that sounds like a good solution” are simple ways to acknowledge what they’ve said before you move onto the next question.

Consistency

Keep coaching, even when you’re not face-to-face. These days, much of the interaction between team leaders and team members takes place online via email, text, and messaging apps. This means you have fewer opportunities for face-to-face coaching, but don’t discount the power of remote coaching.

  • For example, when someone sends you a lengthy email about a dilemma at work, use it as an opportunity to ask a question, rather than replying with detailed advice. You can say something like, “Before I send a more detailed reply, can you tell me what the central challenge is for you?

Commit to your habit of being curious and regularly coaching your team by asking the seven essential questions and making use of the conversational tips above. If you think of new coaching questions that would fit into your team environment, work them into your conversations as you would the seven essential questions. By building up these good habits, you’ll greatly improve your coaching skills and be better able to help your team members become more valuable players.

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PDF Summary Introduction: Why You Need a Coaching Habit

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  • It allows you to refocus. You can lose sight of your goals when you keep getting pulled in several directions at once. Coaching can help you and your team remember what’s important.
  • It clarifies your purpose. Having coaching sessions can help both you and your direct reports see the meaning behind the work you’re doing, motivating you to perform at your best.

In short, coaching helps your team members grow and develop while making your work easier, more focused, more meaningful, and more enjoyable.

In order to be effective and sustainable, your coaching should cover seven essential questions:

  • The Conversation Starter Question: What’s on your mind?
  • The Follow-Through Question: Anything else?
  • The Laser Beam Question: What’s the central challenge for you?
  • The Empowerment Question: What do you want?
  • The Heavy Lifter Question: How can I support you?
  • The Commitment Question: What’s the cost of saying ‘yes’?
  • The Insight Question: What insights did you gain?

In the following chapters, we’ll discuss each of these questions and why they’re important to effective coaching, and explore ways to make them habitual. Asking these questions is...

PDF Summary Chapter 1: The Conversation Starter Question: “What’s on Your Mind?”

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First, recognize your bad habit—when someone comes to talk to you, do you get caught in small talk, jump to giving advice right away, or talk about some other work topic that isn’t really the issue? All these habits prevent the other person from effectively releasing their cluttered thoughts.

Then, determine what usually prompts you to jump into these bad habits. Often, this trigger looks like a team member or colleague popping in to ask if you’ve “got a minute” or instant messaging you to ask if you’re busy—in other words, when someone approaches you with an issue, you react by doing what feels the most helpful or least awkward.

Once you’re aware of the different ways team members approach you, you can consciously respond by performing the good habit of asking the right question: “What’s on your mind?”

Make sure you really understand what they’re saying, instead of steering the conversation towards what you think they’re saying. It helps to keep in mind that every issue involves one of the “3Ps”:

  • People: Relationships that may be causing friction or tension
  • Patterns: Repeated behaviors that may be detrimental to a person’s growth. Talking about...

PDF Summary Chapter 2: The Follow-Through Question: “Anything Else?”

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3) More Time

As a manager, you want to show that you’re always on top of things—but sometimes, you may not know the answer to a question your team member is asking you or aren’t sure of the correct way to proceed. When you ask, “Anything else?” and let your team member continue hashing out the problem, you give yourself more time to think.

How to Make It a Habit

You can use this question in a variety of scenarios: after your conversation starter, when you’re trying to get to the heart of an issue, when you want to keep a conversation moving forward, or in any other situation where you feel like there’s more that’s waiting to be said. Be curious and give the person your full attention so that your “Anything else?” comes out as a genuine inquiry, rather than as an automatic follow-up.

Follow Through Enough, But Not Too Much

To keep the conversation productive, keep a balance between asking enough and too much. Ask the question more than once: Some people need time to warm up and get comfortable before saying what’s really on their minds. Asking them the question three to five times gives them the chance to open up and provide you with better...

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PDF Summary Chapter 3: The Laser Beam Question: “What’s the Central Challenge for You?”

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You don’t have to stop giving advice altogether—in fact, it’s bound to get annoying if you answer every question with another question. You just have to learn to differentiate between a problem that needs your immediate attention and problem-solving prowess and one that is a golden coaching opportunity.

Three common situations are great coaching opportunities, but often trigger “fixing mode” if you’re not careful:

Trigger 1: The Team Member’s Dealing With Many Issues

Some people don’t hold back when you ask them “What’s on your mind?”

  • For example, the supplier is late giving estimates, the internet connection has been slow, the art director is waiting for creativity to strike, her landlord has been giving her grief, and so on.

Your brain, oriented towards problem-solving, will go into overdrive, trying to figure out which issue to tackle first. Stop yourself from going into fix-it mode—take a deep breath, and ask, “If you had to choose only one of these issues, which would you say is the central challenge for you?”

Trigger 2: The Conversation Turns to Gossip

When the other person complains about another team member, customer, or client, the...

PDF Summary Chapter 4: The Empowerment Question: “What Do You Want?”

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3) You Improve Communication

Asking “What do you want?” also makes the path forward more concrete. Expressed wants focus on outcomes and therefore prevent you from getting bogged down in the details of how to get there.

How to Make It a Habit

Unless you’re a mind reader, you shouldn’t assume to know what another person wants; neither should you assume that they know what you want if you haven’t expressly told them. Asking, “What do you want?” instead of making assumptions is especially useful in response to the following triggers:

Trigger 1: The Conversation Seems to Be Losing Steam

Sometimes a discussion seems to be going around in circles. If you’ve cycled through one solution after another, but nothing feels right, it may be a sign that the other person doesn’t feel safe enough to articulate what he wants. Directly asking, “What do you want?” expresses that he can freely share his desired outcome.

Trigger 2: Conflict

Sometimes you and another person might reach an impasse, whether it’s with a colleague, a boss, or a client. When neither of you wants to budge and you can’t come to an agreement, make sure you...

PDF Summary Chapter 5: The Heavy Lifter: “How Can I Support You?”

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Don’t let your discomfort trigger you to shy away from asking about your team members’ needs. Keep in mind that it’s just a question, not a commitment—asking, “How can I support you?” doesn’t mean you’re obligated to say “yes.”

There are four acceptable responses, based on the situation:

  • “Yes”—when the requested help is necessary and something only you can do
  • “No”—when the help they’re asking for isn’t something you can give
  • “No, but”—when you want to compromise by giving them other choices
  • “Maybe”—which you can phrase as, “Let me think this over.” This gives you more time to determine the best course of action.

When considering your response, let your goal of coaching your team members’ ability to find good solutions on their own guide you.

PDF Summary Chapter 6: The Commitment Question: “What’s The Cost of Saying ‘Yes’?”

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How to Make It a Habit

A team member who’s considering taking on additional tasks should trigger you to ask, “What’s the cost of saying ‘yes’?” Then, you can guide him to make an informed decision with two further steps:

1) Ask Him to Reflect On the 3Ps

Have him outline the projects he’ll need to give up to take on this new responsibility, the people who will be affected by his decision, and the patterns and behaviors he’ll need to overcome to accomplish the new task.

2) Give Him the Tools to Say No

Explain that there are two ways to turn down new opportunities that make the process a bit easier.

1) The “slow yes”: In response to the offer of a new task, he should ask questions that give a clearer picture of the commitment required, such as, “What’s the timetable?” and, “If I can only commit x hours, what would you like me to do?” Such questions will lead to one of four outcomes:

  • He finds out that he doesn’t have a choice and has to do it anyway
  • He gets some illuminating answers that will better help him make a decision
  • He buys himself some time to think about it
  • He’s left alone and someone else is asked to do the job....

PDF Summary Chapter 7: The Insight Question: “What Insights Did You Gain?”

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3) The Peak-End Rule

The peak-end rule states that when people recall an event, they tend to remember the emotional peaks and the end. Therefore, if an experience ends on a high note, people will recall it more positively.

  • For example, you organize a meeting that’s overall very dull. However, during the last five minutes, you do a fun, informal “awards ceremony.” The attendees recall the meeting as an overall fun experience.

Asking, “What was most useful for you?” at the end of a conversation means that the experience will end with the team member thinking about the most useful parts of the conversation. According to the peak-end rule, this will cause him to recall the entire conversation as a useful and positive experience.

How to Make It a Habit

Instead of rushing your team member off at the end of a coaching session, finish strong by asking, “What insights did you gain?” This gives your team members the chance to reflect on the important information they picked up and is an elegant way to signal the end of the conversation.

Additionally, share what insights you gained. Being a manager doesn’t mean your learning has stopped. Sharing your...

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PDF Summary Chapter 8: Refine Your Coaching Skills

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Don’t Disguise Advice as a Question

Sometimes you want the other person to get to the solution you want without making it seem like you want things done your way. So, you ask questions like, “Have you considered…?” to put your ideas and solutions in their mind.

Whenever you’re tempted to give advice disguised as a question, resist your bad habit—instead try asking, “Anything else?” Only after hearing everything the team member has thought of should you offer your own ideas.

Element 3: Engagement

Make sure that, in addition to asking the seven essential questions, you’re paying attention to both their attitudes and their responses.

Use “What” Questions

While “Why?” is a useful question in many situations, it may sound judgmental when it comes to coaching and make people feel defensive. Reframe your “why” questions into less intimidating “what” questions.

  • For example, instead of asking, “Why did you do that?” try asking, “What kind of outcome were you hoping for?”

Give Your Full Attention

While this book focuses on the seven essential questions, they only contribute to half of your coaching success. The other half is really listening...