How to Coach Your Sales Team: Prepare to Coach.

Build & Manage a Top-Performing Sales Team — Post #3


So, in the last post, we learned about the Four-Step Coaching Process as recommended by the Harvard Business Review.

To recap, the four steps are:

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.

So, as indicated in the tile, let’s dive a little deeper into preparing for your coaching sessions.

Photo by Jexo on Unsplash

What Should You Consider When Preparing to Coach?

Preparation for coaching from your side as a coach is crucial. You should never go into a coaching meeting without being prepared. That doesn’t mean that you need to know what the coaching outcome will be or what you’ll be working on with your employee. But, it means that you should assess your coachee’s strengths, get data and second opinions, and go into the coaching feeling that you know who you’re coaching. This will help you deliver better as a coach and it’ll make your coachee feel appreciated and like you truly know what you’re doing. When preparing to coach follow these steps.

  1. Begin With Observation: Before you can coach, you need to collect data on your coachee. So, observe them in their behavior with as little bias as possible.
  2. Create & Test Your Hypotheses: Once you observed your coachee, test if your observations are true and can be generalized.
  3. Listen Carefully: With all the objective work done, the subjective part begins: listen to what your coachee tells you, what needs do they have, what topics do they bring up when you speak 1-on-1?
  4. Estimate the Probability of Improvement: You need to be honest with yourself. Some people are resistant to improvement and some other people are not. But, they might have areas where improvement is very unlikely.
  5. Ask Your Employee to Prepare: For coaching to be successful both need to take it seriously and, therefore, both need to be prepared.

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

Photo by Frederick Marschall on Unsplash

Begin With Observation.

You should never ever start coaching based on your gut feeling or anecdotal impressions — or worse — what you heard from others without observing the behavior yourself.

The goal of observation is to begin to understand:

  • The situation,
  • The employee as a person,
  • The employee’s behavior, and
  • The employee’s skill (level).

While you observe your coachee, you can do this in two ways:

  • Formally (during sales pitches or by watching a recording of a sales call), or
  • Informally (during team lunch).

And, while you’re observing focus on two very important aspects:

  • You need to avoid premature judgment: as human beings, we get biased very very quickly. And, we’re lazy. So, we make premature judgments of one or two observations. As you observe your employee make sure to write down your observations incl. concrete examples of the behavior. And then see if it’s one-time behavior or re-occurring. We all make mistakes from time to time. But if you mention something that only happened once your employee will feel mistreated. And, always question if you’re making a judgment based on personal bias. Did your ex-partner behave in a similar way and you just don’t like it because of that personal baggage?
  • You need to observe performance gaps: You can only coach for behavior and skills. If you don’t clearly look for behaviors and skills that are deficient and need improvement, you won’t really make a good coach.
Photo by Chris Liverani on Unsplash

Create and Test Your Hypotheses.

Yes, you should avoid premature judgments but you need to come with something to work with, right? Right!

  1. Conclusions/Write Down Your Observations: You will need to come to conclusions, conclusions based on solid and documented observations. Write them down and make them very succinct and clear. If you can’t write them down on paper, you’re not ready to communicate them to your coachee.
  2. Do a Gut-Feeling Check: Once written down, do a gut-feeling check. Your conclusions should feel to you like they’re objective. Of course, you yourself can’t know. But, if you yourself have doubts, you’ll know that you need to form different conclusions.
  3. Transform Conclusions Into Hypotheses: Whereas a conclusion is the personal synthesis of your observations, it doesn’t necessarily have a testable core. Hypotheses must be testable and they must include some issue that would have benefits when resolved.
  4. Ask Other People to Verify Your Hypotheses: The most important thing first: Only do this with people you absolutely trust. And, always have good intentions in the way you formulate your hypotheses when you share them with others.
    So, what am I talking about? Once you formed your hypotheses you should find trusted people who know your coachee and ask them to do observations on your coachee as well.
    It’s best if you don’t tell them what your observations or hypotheses are to not bias them, but you should still be specific in the task.

Okay, what does this process look like in action? Let’s say you observed a coachee talking over others in meetings. Let’s call him Martin.

  1. Conclusion: Martin repeatedly interrupts people during meetings.
    Check. You wrote down a clear conclusion from your observations.
  2. Gut-Feeling Check: Your rigid notes confirm that Martin interrupted people in all meetings where he was in the position to speak.
    Check. Your observation makes sense.
  3. Hypothesis: Martin and the people around him would benefit from Martin taking a step back. Martin’s behavior undermines others’ views and hinders him from being accepted as a team leader.
    Check. Your hypothesis has a testable core and identified the issues of a behavior. And, it has a hypothesis about what would change for the better if the issue was resolved.
  4. Verification: You asked Linda, your trusted colleague who participates in a few meetings that Martin attends, to take look at him and give your her thoughts. She confirms that Martin repeatedly interrupted others.
  5. Check. You didn’t bias Linda but asked for her subjective observation. And, check. She said the same thing you noted.

If you follow this process, you will successfully create and test hypotheses.

Photo by Brett Jordan on Unsplash

Listen Carefully.

It’s very unlikely that your coaching meeting will be your first meeting with your employee. You most likely already have some kind of relationship with them and you speak with them on some regular basis.

Use these conversations to get cues from your employee about how you should approach the coaching at hand.

Especially now that you have your hypotheses, you can have great conversations that’ll prepare you for the official coaching meetings.

Okay, what do you do specifically?

  1. Never Ever State Your Hypotheses or Any Critique Outside of the Coaching Meetings: Your employee might not be ready for it. And, even if they are. This is not the time. This is the time to understand where they’re at and figure out important information around the “why” your hypotheses might be true.
  2. Ask Questions: This can be as easy as: “Hey, I’ve been preparing for the coaching meeting next week. I wanted to check in if there is anything you’d like to talk about so I can prepare to help you better?” People highly appreciate a check-in and genuine intent to help them.
  3. Ask Follow-Up Questions: People rarely tell you what really bothers them or where they really need to help. In the end, you’re still their superior and they don’t wanna appear like they have weaknesses. So, ask follow-up questions to dig deeper. “What makes you say that?” “Do you have examples of that behavior?” “Why do you think that’s something you need to improve on?” The purpose is not necessarily to get the answer to that question but to get people talking. The more comfortable they feel, the more they’ll open up and tell you what’s really on their minds.
  4. Don’t Always Accept Statements at Face Value: Read between the lines. Oftentimes people don’t wanna share certain things or don’t even know what the core issue is. And, it’s your job to help them be honest with themselves or guide them towards things they themselves might not see.
Photo by Naser Tamimi on Unsplash

Estimate the Probability of Improvement.

Coaching is only valuable if you can close a performance gap and develop a skill. But, in the real world, some people can’t be helped through coaching or some goals are too far away for someone to be achieved in a reasonable time. The reasons for this are manifold, but the fact is: coaching is not always the solution.

So, now that you have made your observations, formed your hypotheses, and talked to your coachee informally, it’s time to make up your mind if coaching for certain gaps or skills makes sense. The two core questions to ask here are:

  1. How Frequent Is the Behavior? Did Martin interrupt people every 2 minutes or once or twice over the duration of 3 meetings? The more frequent behavior is the less likely it is that you’ll be able to change it. It’s not impossible, just way harder. And in the business world where resources are scarce, make sure you use your coaching resources in the most efficient way. Maybe Martin is not the right choice for the job you’re thinking about.
  2. How Deeply Entrenched Is the Behavior? The scale here goals between “responses to particular behavior” and “expression of character.” Other than in the frequency part, the sad truth is that changing expression of character is oftentimes virtually impossible if your coachee isn’t open to it themselves. Bringing it up might already cause severe issues because — from their perspective — you’re not helping them develop a skill, you’re attacking who they are.

So, you might wanna create a 2x2 matrix like the one above to figure out if the behavior is gonna be changeable with the limited resources at hand.

Photo by Brett Jordan on Unsplash

Ask the Employee to Prepare.

In the end, all coaching is a mutual and reciprocal relationship. If your coachee doesn’t take it as seriously as you do, coaching won’t be very effective. So, make sure both of you are committed.

On top of this, most personal change only happens if we ourselves realize that we’re doing something in a way that could be improved. We undergo the most significant change if we ourselves realize it’s necessary and find a way to improve. You as a coach are simply a facilitator of that thought process.

So, to do this, your coachee must be prepared. And, this starts with simply asking your coachee to prepare for your first coaching session.

You can use this as guidance for self-perp for your coachees:

  1. “You should really think for yourself what you want to get out of this meeting. The most useful coaching is based on you realizing what change would benefit you, our team, and our company. I’d encourage you to think about what you want out of it.”
  2. “Think about what you’re really good at and how you could become even better at it.”
  3. “Think about what tasks make you uncomfortable, which ones you avoid, and why.”
  4. “Ask some people you trust for feedback about your strengths and areas of improvement.”
  5. “Think about your idols and what exactly you admire in them.”
  6. “What skills do you think you lack to get a promotion tomorrow.”
Photo by Marija Zaric on Unsplash


So, I hope that you feel prepared to prepare for your coaching sessions. Rember to

  • Observe,
  • Form Hypotheses and Test Them,
  • Listen Carefully,
  • Evaluate If Coaching Makes Sense, and
  • Ask Your Employee to Prepare.

If you follow this plan, I’ll assure you, you’re first coaching discussion will go great. And how you approach this, you’ll learn in my next post. Go crush it!

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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