How to Coach Your Sales Team: The Coaching Part.

15 min readJan 7, 2022

Build & Manage a Top-Performing Sales Team — Post #5

Introduction.

Nice, in the past posts we already learned about the first two steps — preparation and discussion — of the Four-Step Coaching Process below as it’s 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.

Let’s now dive deeper into what it means to coach actively and be effective about it!

What Is the Active Coaching All About?

You should be proud of yourself! By now, you prepared for your coaching sessions through observations and reflections, you met with your employee and both of you agreed on what the coaching will be all about. Now it’s time to get to the specifics and start coaching! Time to grow! Exciting!

But first, what’s the purpose of Active Coaching?

The purpose of Active Coaching is to:

1. Guide your employee in overcoming perfomance gaps or acquiring new skills,
2. Achieve real personal and professional development through behavior change and aquisition of knew skills in your employee, and
3. Helping your employee achieve goals that are meaninugful to both you(r company) and your employee personally in a way that are individualized for your employee.

And, Active Coaching is NOT about:

1. Doing the active work for the employee,
2. Simply discussing things without action intentions in mind, and
3. Forcing your view or approach on your employee.

What Should You Consider When Starting to Coach Actively?

As with the preparation and discussion part, there are a few very distinct areas that you should consider when coaching actively. Let’s take a look at them with a bird’s eye view and then dive deeper into them!

Get Mutual Agreement on Goals: Now is the time to move from a mutual understanding of the growth areas to actionable steps to get there.
Create a Specific Plan of Action: Make sure you help your employee to make a specific plan they can follow and that can hold them accountable to achieve those goals.
Coach: Coach! Find ways to help your employee achieve those goals while they’re at it.
Give Feedback: Understand how to formulate feedback that will resonate with your employee
Receive Feedback: During the coaching process, be open to getting feedback from your employee on how helpful you actually are.

Get Mutual Agreement on Goals.

Okay, you surely remember that the main outcome of the initial coaching discussion was a mutual understanding of the areas of growth that would benefit both your employee and you(r company).

And, if you followed the advice correctly, you first left it at that. You allowed for things to sink in. For people to think about what you agreed on before creating premature action plans.

Now that it’s time for the Active Coaching to start, you need to

Transform areas of growth into actionable goals that both your employee and you agree upon.

What are the characteristics of such goals?

Your Employee Fully Understands Them: It seems obvious but this’s one of the most common mistakes: you and your employee are not aligned on the specifics of the goals. So, how do you change that?
1. You both write the goals down as you understand them (succinctly — if you can’t sum it up you haven’t understood it, yet),
2. You both show each other what you’ve written down and read it diligently,
3. You explain to each other what you’ve written down,
4. You both ask questions about it,
5. You both rephrase your understanding of what the other person has said and written down,
6. You discuss and work on a common understanding,
7. You write down a common goal, a succinct one.
Your Employee Can Actually Achieve Them: You need to be realistic about goals. Closing 100% of deals won’t happen. Unless you have a cure for cancer and give it out for free. So, agree on something your employee can achieve.
They’re Challenging (Enough): In his book Atomic Habits (which I can’t recommend enough), James Clear mentions that people need challenges that are approximately 4% above their skill level. Sure, it’s hard to measure this and I don’t encourage you to try this. But, you as a sales manager, do have the experience to understand what is an overcomeable challenge for your employee and what would be too much (or too little). The idea behind this philosophy is easily explained in a short anecdote:
Imagine you’re playing chess against a grandmaster of chess who won three world cups. Chances are that you get frustrated because it’s too hard for you. Their knowledge is just too large, they can anticipate every one of your moves and even they can’t cause you don’t know what you’re doing, they still think five steps into the future. You don’t have a chance to win and you get frustrated.
Now, imagine you’re playing against your six-year-old nephew who has played chess twice in his life. He knows the rules but you’ll most likely beat them every time because you simply have more experience and your brain is more developed. You’ll get bored after a few games because it’s too easy for you.
The sweet spot is somewhere where you can make slight progress.
The Goal Is Meaningful to Your Employee: At the end of your initial discussion, you made sure that your employee understands the causes and implications of why the growth you’re both trying to achieve in them is crucial. The same is important for the goals. Your employee must feel that the goal is meaningful. Just closing more deals might not be enough. Here it’s important to revisit your employee’s intrinsic motivations. Do they wanna achieve them because
- They like growing for the sake of growing,
- They want to achieve a higher bonus,
- They’re competitive and wanna be the best on the team,
- They’re looking after a promotion,
- They wanna prove something to themselves,
or whatever else it might be. You can’t decide that. Have a conversation with your employee about this. Dig deep. Help them understand that they need to know their underlying “why’s.”

Create a Specific Plan of Action.

I used to be the person who hated plans and ventured on from one thing to the next. I had a great life so and I achieved a lot. But, I never achieved what I wanted because I didn’t know what I want. So, in some sense I was lucky, And, I was really lucky because I was always striving for learning and I always worked hard.

However, I would’ve achieved way more had I understood earlier that to achieve something, you need to

Understand what it is that you want to achieve (as we’ve seen in the chapter above),
Make a plan on how you can get there (we’ll talk about this here), and then
Continuously measure and check if you’re on the right track (we’ll talk about this in the next post on “Continuous Follow-Ups”.

So, knowing why an action plan is important, how do you create one that your employee can actually commit to?

You Don’t; They Do: Your employee most likely things differently than you do. And, they need to take responsibility for their own growth. You can give them guidance on how to create the action plan. But, they need to create it. If they can’t take action here, they won’t achieve their coaching goals. I guarantee it.
KISS: This stands for Keep It Simple, Stupid. This is just a reminder that everything should be succinct. Looking at the plan, you shouldn’t need to invest a lot of brain effort into understanding it. One look, a few seconds, and you should get it. In fact, everybody who looks at it should get it. I wrote an article on the topic if you wanna learn more about this powerful concept every great sales professional needs to internalize.
Include a Statement of the Situation that Needs to be Changed: This should be easy by now. In your initial discussion meeting, your employee did a lot of reflection work, you agreed on growth areas, and you even know what goals you have. They should be able to write down clearly what it is they want to change. In the long run, this serves as a reminder of what needs to be avoided in the future.
Include the Specific Achievable Goals that You Came Up with Above: This should be a no-brainer. Your employee wrote down what the situation is that needs to change in the future, you reflected on the goals associated with this. Now, they need to write it down.
Include a Timeline: It’s nice to have specific and achievable goals. But, in the business world time is crucial. If you don’t act in time, other companies will outcompete you. So, progress needs to happen in time. I’m not pushing for unrealistic goals. I’m a huge fan of the theory that if you achieve 1 % of improvement every day, you’ll be 37 x better at the end of the year. But, the 1 % needs to happen every day to get to the 37 x performance increase after 365 days. So, make sure your employee includes realistic dates by which progress will be achieved and where you can check in. Your employee might not hit them. That doesn’t need to mean that they performed poorly. In a first step, it’ll mean that you both will need to evaluate what you need to do differently: do you need to adjust the process, or does your employee need to put in more work?
Include Tasks and Actions: Okay, you both know where your employee wants to get, but what does this mean? What do they need to do? This is crucial and oftentimes forgotten. If your employee doesn’t know what things need to be done specifically, they’ll be lost in figuring it out.
This is kinda like a to-do list, you break down goals into a roadmap.
You can help your employee here so so so much with your experience and help them understand how you acquired this useful skill they’re trying to acquire right now.
In addition, this is a very important metric for you as a coach. Here. you’ll see what resources your employee will need that you’ll most likely need to provide to achieve their goals.
Include a Statement About the Admired Future Situation: This is about expected outcomes. It’s the pendant to the description of the current situation. In a perfect world, what is your employee capable of when they achieve their goals?
Include Your Responsibilities as a Coach: Yes, your employee is the owner of their progress but you’re also involved for a reason. And, your employee will surely need your help. You might need to
- Open doors,
- Provide protection,
- Provide financial resources,
- Provide training/advice,
- Connect them with the right people,
- Review their progress,
or whatever else it is.
Write it down together with your employee! And be very clear about it. Include it in your schedule and in your to-dos. You cannot fail here. If you don’t deliver on your end, the entire coaching process might be at risk. Don’t forget that your employee looks up to you. You are their role model. You are the help they need. You bear huge responsibility in their growth and for your company.

Coach.

So, when it comes to Active Coaching, the last column of the coaching plan becomes super important: Your Responsibilities as a Coach. So, do the following things to be sure you actually coach well!

Be Clear About What Your Employee Expects of You:
Understand the Coaching Style They Need: This will vary from person to person and maybe even from task to task for the same person. It’s important to understand if you need to:
- Explain things,
- Provide formal training,
- Provide examples of how to do it,
- Throw them into a task,
- Team them up with others,
- Guide them to written/visual/audio/… resources,
- Just listen,
or whatever else it is they need. People learn in different ways. I learn by slowly reading books, watching videos, and having endless discussions until I finally get it. My co-founder Sebastian would die in such an environment. He uses apps that help him to read through books as quickly as possible (I can’t pick up info that fast). He reads scientific articles (they would bore me to death). He wants to quickly figure out what to do and get to it (I can’t do things before I’m clear about why I do them).
So, different people learn differently. Therefore, different people need different coaching styles.
The easiest way is to ask your coachee how they learn best, what they expect of you, how you can help them best. And, the answer might be that you need to get in other experts if a specific style is just not for you.
Set Boundaries: Again, you shouldn’t do the work for them. They need to be able to stand on their own feet and do the work. You’re just there to provide what they can’t get themselves or to accelerate the process but you’re never there to do their work. You can show them how you’d do it at an example but you should rewrite something they’ve worked on. Instead, comment on it, give them examples, help them be better. Don’t be better for them.
Write Down Your Responsibilities: Write them down in your to-do lists, include them in your calendar, make sure that you proactively get the things done that you need to get done.
When You Give Advice, Use a Dialogue Approach: You’re not the godfather or godmother of wisdom. And even if you know more about the thing you’re trying to help your employee with (which I hope you do), you need to treat your employee like someone who wants to learn and will contribute important perspectives to their own learning.
So, when you give advice, don’t just throw it at them and tell them that “this is the truth.”
A more sustainable and effective approach is to
- Describe observations, situations, or problems in a neutral way,
- Make your employee aware that this is your perspective and you’re open to hearing theirs,
- State your opinion, and make sure they know it’s your opinion,
- Provide explicit examples,
- Share your experience with these types of observations, situations, or problems (to establish ethos and see if you’re talking about the same problem).

Give Feedback.

Oh, the one thing we always ask for and we so badly want to hear; in theory. But once, somebody is about to tell us we get that uncomfortable feeling of “please don’t kill me.” Well, good thing that you’re primary work as a coach is to give feedback.

So, but how do you give feedback, and what do you need to understand before you do this?

The Difference Between Praise and Positive Feedback: Yes, you can praise people by telling them “great job,” but it won’t really help them because it’s not specific enough.
Positive feedback goes a step further and tells people exactly with examples what they did right and how they can repeat this behavior, e.g, “ you did a tremendous job when explaining the product to the customer. You explained it within less than thirty seconds and you immediately asked a follow-up question to allow them to deepen the understanding.”
The Difference Between Criticism and Negative Feedback: As you can guess, it’s similar to the one above. But criticism is way worse than praise. Because criticism is like telling somebody that they did something wrong and, then, just leave them with it. Criticism can feel like a punch in the face. It’s like, “You really didn’t know what you were doing in the sales meeting.” What can your employee learn from that other than that you’re not capable of communicating like a real leader?
Negative feedback tells somebody in a careful and acceptable way that somebody behaved in a non-optimal way, explains why it was non-optimal, and leads into a direction that can help resolve it, e.g. “during the customer meeting you regularly seem to lose your leads after 5 minutes. I believe the reason is that you don’t give your leads an opportunity to speak during the first 10 minutes of the sales call. I believe, you should consider adding a little small talk at the beginning and check in with your leads every two minutes. Do you see how this would help you engage better with them?”
Focus on Improving Performance: Feedback should always help somebody take action towards improving their performance. Saying something that was done wrong without being able to guide somebody out of that behavior isn’t helpful.
Feedback Should Be Immediate: “I noticed that last year, you did…” You can already see that this isn’t helpful. If you notice something, go through the preparation process, and address it immediately. Like this, your employee will understand what you mean as it’ll be fresh in their mind and they’ll like your immediately helpful.
Always Focus on Behavior, Never Character: Remember that you can’t change character with short-term coaching. Everything that criticizes character will feel like an attack to your employee. Never address something that’ll sound to them like “you’re a terrible person. You need to change.” Rather focus on things that can be phrased like “your behavior in the context of […] could be optimized by […].” Be careful tho. Something that seems like behavior to you might be a deeply entrenched character trait. A good tell tail is how often the behavior occurs. The more often it occurs, the more likely it is a character trait.
Be Specific: Even better, give multiple examples. Make things tangible. Don’t generalize. “You talk too much” immediately leads to follow-up questions: “When, why, how, where?” Instead say: “At the beginning of sales calls you tend to talk for up to 10 minutes. I noticed this in the calls with Company A and B. Do you remember it?”
Always Be Sincere: If you notice that you don’t wish somebody well, immediately stop coaching them and figure it out first. You need to sincerely want to help them.
Be Realistic: Advice that your employee can’t implement won’t be helpful. So, always focus on the things that are achievable for your employee. If you’re unsure if something is feasible, talk openly about it with your employee.

Photo by Franco Antonio Giovanella on Unsplash

Receive Feedback.

This is just a quick reminder that coaching is a mutual process. You’ll never be the perfect coach. You might say things that won’t be helpful to your employee and you need to hold yourself accountable. Because if you’re not helpful, you both are wasting your time.

So, make sure that you also receive feedback from your employee. There are multiple things to consider here:

Tell Your Employee That You Need Their Feedback, Too: It starts with letting your employee know that you’re approachable and that they need to tell you their honest opinion.
Ensure There’s Someone Else Your Employee Can Talk to: There might be things your employee doesn’t wanna tell you. Make sure that they have somebody else to turn to if they want to discuss something they don’t wanna raise with you. HR is a great place to start. Tell your employee that it’s totally fine if they want to speak to others in confidence.
Be Ready to Receive Negative Feedback: If your employee tells you something you don’t wanna hear, be ready to deal with it in the correct way:
- Take it in,
- Thank your employee,
- Ask clarification questions,
- Don’t react/respond immediately,
- Don’t explain yourself,
- Reflect on it,
-Bring it up in a productive way in the next meeting.

Conclusion.

So, now you know how to coach actively. To not overload you with more information, let’s save the follow-up and ensuring long-term progress for the next post!

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 teddy@resonaid.co.