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Sales Call Coaching: Kevin Dorsey’s Masterclass

Sales Call Coaching: Kevin Dorsey’s Masterclass

Shruti Kapoor
Shruti Kapoor
August 2, 2021
5 min read

Is sales coaching bullshit?

When I asked this recently on Sales Hacker, I got some interesting responses. Most seemed to echo the sentiment that too many sales managers just get pushed into the deep end when it comes to call coaching for their reps. Ironically enough, they simply haven't received any coaching on how to actually become a better sales coach.

So when KD and I got talking during a recording of the Live Better Sell better podcast, we instantly knew we had to do something about call coaching for managers. And not just talk about it, we had to make it a masterclass for sales managers to be able to create and implement their own call coaching playbook. Taking it a step further, I created this article based on KD’s insights and experiences, as shared during the masterclass. 

If you’re a sales manager who wants to get better at call coaching, this article’s for you.

But first...

What is sales call coaching?

Sales call coaching is NOT the same as sales training or sales managing. Turns out, there is no one definition of what call coaching is because there is a big difference between what sales reps think coaching is and what managers think it is.

Here’s what call coaching is the KD way: 

  • Enhancing knowledge or skill
  • Usually 1:1
  • Usually on the job
  • Usually unstructured and informal

Training is telling, coaching is practicing.

Why is sales call coaching important?

Bottom line. Because it impacts your bottom line.

  • Better business results: Your team (over) achieves their quota.
  • Better employee retention: People stay longer where they are being coached.
  • Amazing recruiting tool: You can recruit great people even with lower budgets and expect them to stay because they know they are going to get coached. 
  • Strategy: Keeps you close to the action so you know where to focus.

“Reps who receive just 3 hours of coaching per month exceed their goals by 7%, boosting revenue by 25% and increasing close rate by 70%.” (CEB)

In our own experience, good call coaching can double revenue. Yet, it doesn't happen enough.

What does good call coaching look like?

Here are some quick tips and tricks to understand what good call coaching looks like.

Good call coaching is immediate, regular, actionable, focuses on one thing at a time, and hinges around practice. 

What call coaching should not look like: 

  • Confusing coaching with telling / teaching
  • Too much feedback
  • Focusing on the wrong things 
  • Haphazard
  • No practice
Focus on what truly matters during call coaching

What is lazy call coaching? 

Focusing on things that do not matter.

  1. Filler words
  2. Speed of speech
  3. Talk/listen ratio
  4. How you did it

What to look for during call coaching?

Here are the 5 things you should be tracking in your reps’ sales calls for call coaching.

  1. Tone: How does your rep sound?
  2. Questions: Are they asking good questions to move the conversation forward? 
  3. Are they asking good follow up questions?
  4. Did they apply what they asked; made it relevant?
  5. Are they asking about problems aka problem-based language?

KD’s call coaching framework and tips

The short version: Observe > Describe > Impact > Prescribe > Absorb > Apply > Measure

KD's call coaching framework

Now buckle up for the long version:


This is incredibly important. Listen but be specific about what you’re listening for. Do you know that some managers coach without actually listening to calls? How can you do call coaching if you aren't listening to calls?

This is why a scorecard is so valuable. It helps you understand and codify what you are trying to observe. Read more about building a call scorecard here.

Take notes as you go. Read vs listen. You need to review at least 2-3 calls per rep per week. That’s mandatory for all my managers. And know what you’re searching for—so search the transcripts for what did or didn't happen.


Let’s try an exercise. Close your eyes real quick and don’t picture a blue elephant. Hard to do it, right? That’s because the brain can’t picture ‘not’ doing something. So describe the problem as you skipped vs you didn’t say. You left out vs you missed.

Share feedback in a 5:1 ratio of positive to bad. This is so incredibly important. 

The sh*t sandwich is BS. “You did this good. But this was bad. You did this good, too.” When that's the ratio, your people don't remember the slices of bread—the good. All they can think about is the filling, the negative feedback. What this also does, by the way, is force you to prioritize your feedback.


Ask your reps—you said, “call you next week.” What's the impact of that? 

By saying, I'll call you next week, we miss the opportunity to schedule those next steps and make sure things are moving forward. We want our reps to tie the action with the impact. So get reps to tell you the impact of what they did, both good and bad. That makes it more meaningful.

Here’s the thing, as coaches we tend to only focus on the negative. So when you hear something good—“Oh, your tone here is perfect!”—focus on that impact too by asking ”How do you think that makes the prospect feel?” 

Again, reinforcing the good is so important because if all you do is talk about the bad, your reps will stop paying attention. So do focus on the impact of what your reps are doing well.


Look at the best coaches in music or sports. The way they deliver coaching is direct and focussed. Choose your battles aka points to improve and focus on those.

Remember, the best feedback is short, punchy and tactical.


Make sure there is understanding. How do you know if someone has absorbed what you're teaching? How do you know they've absorbed it? This is important, coaches. They need to explain it back to you. Repeat the what and why. “Again, why is this important? Why do we need to schedule those next steps on the call?” Then they're less likely to skip those steps next time. BTW, training skips the absorption part.

Make sure they are taking notes and this is key—have them enter feedback on the call into your tool, Wingman or something else. Why? Muscle memory, they internalize the feedback, and retain it. Your reps should be sending you coaching recap notes.


In the moment practice: DO IT! Just make them repeat a few times. Prompts and reminders are big.

As KD says,” I’ve realized that the amount of stuff we expect our reps to remember is pretty ridiculous. They have to remember all the product information. They have to remember all the competitor information. They have to remember all the objections… the script… the pricing, who is involved… the impact of the problem… the problem… all the personas they are dealing with, and all the individual problems of their personas… AND social proof and testimonials. Your reps have to remember everything and apply it at the right time on the call, on every call.” 

This is where tool-based prompts are useful - so many great ones to choose from, including Wingman.

Scheduled role plays are also really important. Work on just the key points for 10-15 mins before the next demo. Short, punchy feedback only.

The other thing is to run call reviews. Have your reps submit calls where they implemented a good thing/new tactic. Do not wait a week in between to check on progress. Ask them to send you calls every single day and share positive reinforcement.

If you have a tool like Wingman, set up trackers to check whether your feedback is being implemented. Application is everything when it comes to improving your sales coaching.  

If your reps are not applying your feedback, you're not coaching.

Lastly, reward the behavior. Don’t wait for the deal to close, for the next call, or the contract. Ask and check if your feedback was implemented in the last call and reward that behavior. Don’t wait for lagging indicators like deal closing. You could be waiting awhile. Instead, celebrate the process.


You cannot manage results, only behaviors and skills. And coaching needs to be measured. So pick a metric, any metric, and then define the behaviors and skills associated with that metric. 

And this is key—if you're only paying attention to the results, that could take months if you have a long sales cycle. But if you're managing the behaviors and skills, you can see if your reps are getting better tomorrow. Identity what’s missing or low and then create a game plan for those sales skills.

Your coaching plans need to be specific, frequent, delivered in chunks, come with a definite start and end, be agreed upon and see participation from both sides, and results need to be tracked.

You don’t have to sell people on coaching if it actually works.

You owe your reps call coaching

Leverage sales call coaching tools and technology

Thanks to technology, you can do call coaching much more efficiently. How?

  1. Download call transcripts, search through them, and read them. You can cover so many more calls by reading and skipping to the parts you want to focus on.
  2. Set up alerts and trackers on tools like Wingman. So you know when your reps use a particular phrase, set next steps, or ask certain sales discovery questions.
  3. Most tools allow you to listen to calls at faster playback speeds. So just listen to more calls at 2X the speed.
  4. Study your calls at scale. Listen to your best calls and the worst ones, find the commonalities, and add to your call coaching scorecard.
  5. Win with in-the-moment coaching. Wingman shows your reps sales battlecards and prompts triggered by what the customer says. As good as being with your reps on call.

Smart call coaching is powered by people, processes and technology.

And that’s, well, almost, it. You deserve 3 bonus points if you made it to the end.

Bonus call coaching tips

  1. What do you do if you have a rep who has very little room for improvement? You use them to coach your other reps, reinforce the good things, and study them. Simple. 
  2. Everybody practices. “The best do it on purpose, the rest do it on prospects,” as KD says.
  3. If you’re not listening to calls, you’re losing money. PERIOD.

A big thank you to KD for being so generous with sharing his experiences and tactical tips for improving sales call coaching.

You can watch KD’s entire 60-minute masterclass on sales call coaching here.

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