How to Coach Your Sales Team: The Initial Coaching Discussion.

Build & Manage a Top-Performing Sales Team — Post #4


Again, let’s recap the Four-Step Coaching Process as recommended by the Harvard Business Review:

Preparation: Preparation is oftentimes neglected but super crucial to successful coaching. Both coaches and coachees need to be clear about development goals, limitations of coaching, and their personal relationship. To do so:

Discussion: After both have prepared, both need to have an open and brutally honest conversation to ensure that they’re on the same page. Goals and needs and limitations need to be addressed and aligned. The outcome of the discussion should be a mutually agreed-upon plan that assures systematic attention to performance improvement.

Active Coaching: Only when both the coach and coachee are very clear about the desired coaching outcome, the active coaching can begin. The most crucial part of the active coaching process is to find a systematic approach that ensures that the coachee can improve, the coach can evaluate, the coach can provide feedback, and the coachee is truly heard.

Follow-Up: All effective coaching needs follow-ups to ensure that the coachee stays on track. Just analyzing the situation once and providing feedback on how to deal with it won’t do much. Without any follow-ups the coachee won’t have the necessary guidance and feedback to stay on track with their development.

In the last post, we discussed in detail how to prepare for your coaching sessions. Now, that you know how to get yourself and your sales team started, let’s take a look at how you should approach the first real coaching meeting: the discussion.

Photo by Mimi Thian on Unsplash

What Is the Discussion Meeting All About?

You are prepared, you observed your employee, you formed and tested hypotheses, you had informal conversations with your employee and listened carefully, you came to the conclusion that coaching makes sense, and you asked your employee to prepare for the first coaching session: the discussion.

With you being so prepared and your employee hopefully, too, it’s time to schedule the meeting and get to it!

But first, what’s the purpose of the discussion meeting?

The purpose of the discussion meeting is to:

1. Align your and your employee’s understanding of areas of growth,

2. Have your employee to commit to areas of growth, and

3. Have your employee understand underlying causes.

And, the discussion meeting is NOT about:

1. Starting to coach,

2. Seeking concrete strategies to achieve growth, and

3. You making jugments about your coachee.

Photo by Tachina Lee on Unsplash

What Should You Consider When Going Into the Initial Discussion?

Knowing what the discussion meeting is about and what it’s not about, let’s take a look at the four most important things for the discussion meeting.

  1. Discuss Your Observations: First, you need to communicate to your employee what you observed and discuss with them if your observations are right. Only if you can find common ground, you can move on to improving on growth areas.
  2. Practice Active Listening: Without paying close attention to your employee, you can’t coach them. You need to be an undistracted listener.
  3. Listen for Emotions Behind the Words: And it’s not only what your employee says but also what they don’t say, what say between the lines, and how they say things.
  4. Move Discussions to Causes: You initiate great coaching, your employee needs to understand why the improvement is important or what the consequences of not improving might be for them or for others.

Okay, let’s dive into them in more detail!

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Discuss Your Observations.

The key here is that you can’t know if you’re right with your observations. So, treat your employee as a crucial part of discovering and understanding if your observations are valid. To do so:

  1. Start with Praise: You might be a little nervous if this is your first coaching session as a coach. But imagine how nervous your employee most likely is. No matter how well they’ve been performing, they’re most likely terrified to hear that they’re a poor performer and you wanna fire them. So, to make sure that they’re in the right space of mind, start with something positive. Tell them what you appreciate about them before you get into your observations about areas of improvement. While discussing your observations make sure to start with praise and balance it with an area of improvement.
  2. Focus on a Few Things: If you give your employee more than three things to work on, they’ll get cognitive overload and won’t know what to focus on anything. Part of your job as a coach is to help your employee identify what they should focus on.
  3. Stick to Observations of Actual Behaviors: Don’t include the personal motives you might have derived from the behavior. This is crucial! Remember that behavior can be situational or expressions of character. The same goes for how you phrase your observations. If you phrase something the right way you address a situational behavior. If you phrase it wrong, your employee will feel like you attack them. Another benefit is that behaviors can be described and oftentimes even measured (You did X Y times). Personal traits cannot not. In a concrete example it might look like this:
    No: You seem a little lazy compared to Jim and Rajesh.
    Yes: In comparison to others on the team, you close 30 % fewer deals.
  4. Don’t Take Your Observations for the Truth; Ask Probing Questions: Ask good as your observations might be and as great as your hypotheses were and even as much as you tested them, you might be wrong. You can only really know what’s going on if you discuss things with your employee and hear their understanding of things. And even if you’re right, if you don’t carefully start asking questions but bluntly state your observations and try to sell them as the truth, your employee could easily shut down.
    Another interesting fact is that people learn the most in dialogue. And dialogue is the exchange of thoughts, hypotheses, questions, and opinions between two people. So, starting with questions to build understanding is crucial.
    Another great benefit of probing questions is that they allow you to help your employee get closer and closer to the real issue. This is why they’re called probing questions. You very diligently and carefully test if a thought of yours might be right but you do it by asking a very open question that gets your employee talking. Then, you listen carefully and ask follow-up questions based on your new finding.
  5. Ask Open-Ended Questions to Create Understanding: Again, everything you found during your preparation needs to be tested while talking to your employee. But, don’t ask them if your understanding is right or wrong. Ask them questions that get them talking.
  6. Ask Closed Questions to Confirm Understanding: Once you listened to your employee for a bit and you heard them say things, use closed questions (usually yes/no questions or questions with simple/short answers) to confirm your understanding is right. An example might be: “Do I understand correctly that you struggle with…” And, make sure that you use your employee’s words. Don’t say struggle if they said that “they’re figuring it out right now.”
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Practice Active Listening.

This one is harder than it sounds. But it’s also more crucial than many people know. It is absolutely necessary that you pay close attention to every word your employee says. But, as a sales manager, you know this. So, let’s get into the “how to do it.”

  1. Maintain Eye Contact With Your Lead: Okay, don’t be creepy about this one. Don’t overdo it. But, especially when they’re speaking, look into their eyes, follow their hands while they’re making gestures in their explanations. If they write something down or draw something, take a look at it and really consider what they’re showing you. And, it’s totally normal to look away here and there, but make mental notes and catch yourself if you’re looking away from them too long because this usually means that you’re drifting off or that you’re forming questions or responses and not paying attention to all the other things they’re saying.
  2. Pay Attention to Your Internal Judgments: Ask your mentor, a colleague, or a friend if they can help you with figuring out your tell tails of judgment. Do you make certain faces or do say certain words? And constantly be on the lookout for these. Because, once you start judging, you stop listening. But, there might be so much more to learn from your lead that you’re depriving yourself of by getting into a state of judgment.
  3. Don’t Interrupt: This is hard for many people, including all of my co-founders and me. But, always resist it, unless your employee is talking on end for 10 minutes or so. A good strategy is writing down thoughts rather than verbalizing them immediately. On top, most people have some kind of outcome in mind while they’re speaking. If you interrupt them before they get there, they’ll immediately feel unheard and they’ll just feel the urge to get back to their storyline. Let them finish, your time to speak will come. And, if your employee doesn’t know the outcome of what they wanna say, they might just need some time talking to figure it out.
  4. Ask Questions Rather Than Stating Views: And when it’s your time to speak, ask questions, real questions. Questions that are based on the notes you were taking. Questions that only somebody would ask who really listened to them.
  5. Let Yourself Be Drawn Into Their Stories: People can sense it when you’re multitasking. Every human being is a master of picking up subtleties of communication. Some of us are better than others, but we all understand the basics to an insanely high level. This is how we survived as human beings. Seeing somebody’s face turn angry before they tried to kill us. Seeing somebody get scared while a tiger was approaching you from behind. Differentiating a real smile from somebody who loves you from a fake one from somebody who wants to take advantage of you. We might not all understand the science, but we’re very good at executing on this. So, it’s no surprise that your leads will be able to tell if you’re really listening or just pretending. So, look for the things in their stories that really interest you and allow yourself to be drawn into the conversion.
  6. Avoid Distractions: This is a follow-up to #5, so you can really execute on it. Put your phone away, seriously. Put your computer into do-not-disturb mode. Turn on the noise cancellation mode of your earphones. Close everything on your computer that doesn’t absolutely need to be open. And if this is really hard for you, you might want to use something to fidget with so you don’t end up doing other things. If it’s a virtual meeting, my co-founder Sebastian always says, “move a few feet away from your keyboard and monitor to make sure you don’t get drawn to distractions.” And, it works!
  7. Visualize Their Word in Your Head: This might not be for everyone, but creating mental images helps you with two things: understanding what your employee is saying and remembering it. Mental images are so much stronger than words. Make sure you don’t drift off or you don’t add too many of your own elements to the mental image.
  8. Ask Clarifying Questions: Although you shouldn’t interrupt, it’s important that you ask clarifying questions to make sure you understand things right. Even if you listen to every word, you might interpret it incorrectly or your employee might not find the right words to express their thoughts.
  9. Don’t Evaluate in the Moment: Try to resist in-the-moment evaluations for three reasons. One, when you start evaluating, you’ll stop listening. Your brain will be busy with other things. Two, you might miss out on important information that you need to make a conclusion and instead make premature judgments. Three, your employee will notice that you’re not listening anymore.
  10. Don’t Be A Listening Robot: Yes, be yourself. Make a short comment, smile, laugh. Make sure both of you are engaged in the conversations. Don’t be too busy with taking notes and trying to understand everything. Be a human being while listening.
Photo by Tengyart on Unsplash

Listen for Emotions Behind the Words.

First, let’s be honest. This is hard. I’m not gonna tell you how to do this theoretically, and you just venture into implementing it perfectly. You’ll need to commit to coaching and listening carefully. You’ll need to hone this skill. But, how do you do this? Glad you asked.

  1. You Need to Show Real Interest in Your Employee: You can only spot the real intent behind the words of your employees if you really care about their development. It takes another level of active listening, which I call “interested listening.” You need to want to listen to your employee and figure out what’s going on to really find out what’s going on.
  2. Create an Environment Where People Can Share: Don’t expect that you create a positive environment and people just start sharing things with you. They’re still your employees and you could fire them. That’s very much at the top of their head. But, creating a positive environment is crucial as it might allow your employee to be a little more open and for you to read between the lines. To achieve this:
  3. Build Up Confidence Through Praise: Make sure they see that you appreciate them, so they can be confident enough to open up about performance gaps.
  4. Reduce Fear of Failure: Say things that make “trying out” and “it’s okay to fail” seem okay and desired. Maybe even share how you made mistakes that helped you grow.
  5. Embrace the Benefit of Conflict: You’re a sales manager, you made mistakes, you had conflicts. Make sure your employee understands that we can only achieve real growth by allowing conflict with ourselves.
    Ask Continous Why Question: You might have heard about continuous why cadences. At its core, it helps you to get to the real reason behind something. You spot a behavior, you ask: why do you behave like this. And you continue asking the same question until you are at the core. However, there is more nuance to this in a coaching session.
    Real Why Questions: This one is easy. If your employee is okay with it, continue asking “why do you say this?” until you get to the core. But, the obvious downside is that your employee might not be open to sharing.
    Masked Why Questions: This is basically the same as real why questions, but you mask it up a bit. Rather than asking “why do you say this?”, you ask “when did you first notice this behavior?” or “why do you do this?” “do you behave similarly in your private life?” The intention here is that you get to the core through anecdotal stories rather than through straight digging. It’s more like driving down serpentines.
  6. Hypothetical Why Questions: This one is dangerous because the conclusions might not be reliable. But, if your employee doesn’t wanna share a lot, you need to take in the information you have and try to get as close to the core as you can, based on your observations. Ask yourself the why questions and assume what your employees most likely answer would be. Write them down and test your conclusions when appropriate during another meeting. Don’t ever accept them as the truth.
  7. Know When Not to Comment or Move On: Equally important, if your employee had a real breakthrough and understood something about themselves, they might just need the time to accept it. If it was hard to get to where you are, you might suggest a break. Again, real growth is achieved through conflict. And, conflict is exhausting. If your employee is too exhausted, they won’t be able to focus on the next steps.
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Move Discussions to Causes.

Okay, most people like to talk. But, during the coaching discussion, we don’t talk for the sake of talking. We want to kickstart and guide true and important development in our employees.

For this, our employees need to understand why the development is important to move from talking to acting. For this, it is helpful to understand the d

  1. Your Employee Needs to Affirm That You Have Common Ground: Before you can move on, you both need to agree that you have the same understanding of the areas of your improvement. To do this ask questions like the ones below. But, don’t force your employee to say “yes.” Be ready for a “no” and further discussion if necessary.
    Do I understand correctly that […]?
    Do we agree that it would be valuable to work on […]?
    Do we have common ground when I say […]?
  2. Your Employee Needs to Understand the Necessity for Action: Most of us are driven by reason. So, make sure that your employee understands why the improvement or change is important. This usually comes in one of two ways:
    External: It’s crucial within their current responsibilities or for the greater team or company. Understanding that the improvement is necessary for people and causes beyond their own can be very motivational.
    Internal: Your employee sees an intrinsic and personal benefit to the change. They want to become an account executive. They will be intrinsically motivated to get the necessary skills.
  3. Your Employee Needs to Understand the Consequences of No Action: This is the reverse of the point above. Understanding that not acting will put the entire team at risk or might cost them their job are truly motivational. I’m no advocate of using fear to lead. But, understanding consequences if they’re real is important might be truly effective to change behavior. In the end, nobody wants to lose their job or let others down.
Photo by Mimi Thian on Unsplash


So, if you follow this advice, your initial coaching discussion will certainly be successful as you’ll be able to really understand your employee and verify areas of growth. Your employee will feel understood and know what’s at stake.

In the next post, we’ll finally get to the gist of it and dive into Active Coaching.

About the Author.

Teddy Lange is a co-founder at Resonaid and is responsible for business development and customer experience. Before joining Resonaid, he’s been a negotiation coach at the Harvard Negotiation and Conflict Resolution Collaboratory, a Sales Rep and Junior Sales Manager, and co-founded various companies. He has just finished his graduate degree in Public Policy with a focus on communication at Harvard University. Feel free to reach out to him at



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