Sales Call Coaching Best Practices: A Playbook for Sales Leaders and Enablement Teams

Most sales managers were never taught how to coach. Only 34% say they have ever received any training on it.¹ Meanwhile, 91% believe coaching is what drives rep performance.

That gap is the starting point for almost every conversation I have with sales leaders at Kennett Advisory.

I have spent more than twenty years coaching B2B sales reps. Before Kennett Advisory, I worked as a sales leader at several B2B companies, and in 2019, I built Replayz, a sales call coaching company acquired by Highspot in November 2024. My team reviewed thousands of discovery and demo calls across 60+ SaaS companies.

Sales leaders who actually move the needle are not the ones with the most clever frameworks. They are the ones who have figured out a handful of basic things and do them consistently, every week.

Below are 10 best practices for sales call coaching, framed as the traps that keep good sales leaders from becoming great coaches.

1. Frequency: Coach weekly, not sporadically

This is the one that matters most. If you get this wrong, the other nine will not save you.

The performance data is unambiguous. Teams where reps are coached weekly hit quota at 76%. Drop to monthly, and that falls to 56%. Drop to quarterly or less, and it sinks to 47%.² Yet 73% of sales managers spend less than 5% of their time coaching, because the calendar eats everything.³

Why does frequency matter so much? Two reasons, and neither is about the rep.

First, the leader forgets. Coach once a month, and you cannot remember what you covered last time. You flag three new things, but the rep has not resolved the last three yet. No continuity. No through-line. You are running in place.

Second, the rep stops feeling accountable. Six weeks is long enough for a rep to assume nobody is checking. The thing they were asked to work on quietly falls off the list.

Weekly is the answer. One call per rep, every week, in the calendar as a non-negotiable. If you cannot hit weekly, every other week, protected like payroll. Hitting that rhythm 30 weeks out of 52 is enough to transform a team.

2. Know both the strengths and the blind spots

A lot of coaching conversations are only about what the rep is doing wrong. That is a mistake.

Sales is a tough enough profession. If the only time reps hear from their leader is when there is something to fix, coaching starts to feel like a tax, and not a gift. The best coaches also name exactly what a rep’s superpower is, and most reps have no idea what they are actually good at.

They might be the calmest person on the team when a prospect pushes back on price. They might be the only rep who consistently gets the next meeting on the calendar before hanging up. Those are not accidents. Those are strengths. If you do not name them out loud, the rep assumes everyone does it and stops leaning into what makes them different.

At Kennett Advisory, I always start with what went well, not as a compliment sandwich trick, but as a genuine data point. The rep should walk away knowing their superpower with precision, so they can double down on it.

Then we talk about the blind spot.

3. Keep feedback to no more than three things, often just one

Smart, well-intentioned sales leaders pack coaching sessions with every observation from the call. Twelve things. Fifteen things. A whole document of edits.

The rep walks away with none of it.

The brain can only work on one or two new behaviours at a time. Give a rep fifteen, and they pick the two that feel easiest and ignore the rest. Or they feel overwhelmed and end up working on none of them.

The rule: no more than three things per session, and most weeks just one is plenty.

Most reps in your industry get six or seven coaching touchpoints a year, crammed with fifteen things that never stick. Your team is building 30 habits while theirs is building zero.

As James Clear puts it in Atomic Habits, “habits are the compound interest of self-improvement.”⁴ The returns on one good habit in one week are invisible. The returns on 30 good habits over a year are transformational. That is the entire argument for weekly coaching in one sentence.

4. Create a safe environment

Reps will not tell you what is hard if they do not feel safe. And if they will not tell you what is hard, you are coaching the rep you wish they were instead of the rep who actually got on that call.

In practice, safety means the rep knows they will not be judged in performance reviews for what they admit in a coaching conversation. It means asking a dumb question is not a mark against them. It means they believe you are on their side even when the feedback is direct.

One of the scariest things for a sales rep is pitching in front of peers. If you are going to run team role-plays, and you should, build up to it. Start small. Normalise it. Make the first one something everyone does badly together, so the fear of being the one who looks silly disappears.

Safety is a prerequisite for everything else in this post. Without it, none of the mechanics land.

5. Direct, productive feedback that keeps the rep’s dignity intact

The best feedback is direct and kind at the same time. Those things are not in conflict.

Not this: “Yeah, so overall not bad, a few things, nothing major.”

Not this either: “You completely missed the discovery. You didn’t ask a single good question.”

This: “At minute 12, the prospect said ‘we’re worried about onboarding,’ and you moved on. That was the moment to go one layer deeper. You do this well on other calls. On this one, you missed it. That’s the one thing I want you to work on this week.”

Specific. Timestamped. Rooted in what the rep already does well. Clearly actionable. Not a personality attack.

Direct plus dignity. Both. Every time.

6. The accountability loop: review the next call for evidence

This is the step almost everyone skips, and the step that makes everything else work.

When you give a rep one thing to work on in week one, the coaching is not finished in week one. It is finished in week two, when you review the next recorded call looking specifically for evidence that the rep did the thing.

The follow-up opens with: “How did it go with what we talked about last week?” And then you actually watch the next call to see whether the behaviour showed up.

Without it, coaching is just advice. I have been the leader who gave great advice and never followed up, and I have been the rep who quietly let it slide because nobody was going to check. Both are the same failure of accountability.

If you do nothing else on this list, do this one.

7. Document everything

Every coaching conversation needs to leave an artifact.

It does not matter whether it lives in Gong, Chorus, Salesforce, a Google Doc, or a Notion database. What matters is that the rep and the leader can both look back at what was asked, when it was asked, and what happened next.

Documentation does three things. It makes the rep clear on what was asked of them, because verbal feedback evaporates and written feedback stays. It gives the leader a reference point for the follow-up. And it feeds performance evaluations: a coaching log shows not just whether a rep closed deals, but whether they were willing to work on themselves when asked. That willingness is a core part of the assessment.

Documentation turns a coaching moment into a coaching program. Without it, you are having conversations. With it, you are building a system.

8. Role-play in pods of three: seller, customer, observer

The best way to build a coaching culture inside a team is structured role-play in groups of three.

Pick a specific skill: agenda setting, handling a pricing objection, a 30-second customer story. Break the team into pods. Each pod runs the drill three times, rotating through three roles:

• Seller, practises the skill
• Customer, plays the prospect and pushes back realistically
• Observer, watches and gives specific, timestamped feedback afterwards

By the end, every person has been in every seat.

This works for three reasons. The rep practises the skill, and sports teams practise far more than they play while sales teams almost never do. The rep learns how hard it is to be the customer, which builds empathy for real prospects. And the rep learns to give good feedback, which is arguably the most valuable skill in the room. Reps who can coach each other become the foundation of a real coaching culture, and take the whole thing off the leader’s single set of shoulders.

Run it in 20 to 30 minutes of your weekly team meeting. Do it for a quarter and you will see live call behaviours change.⁵

9. Tie the coaching to the rep’s “why”

“You need to do X” lands differently than “you need to do X because it gets you to the promotion you told me you were going after.”

The first is an instruction. The second is a partnership.

Every rep has a why. The money, the promotion, proving something, the lifestyle they are building. The specific why does not matter. What matters is that you know it and tie your coaching to it.

Ask directly in the first few weeks: “What are you trying to get out of this role over the next two years?” Take notes. Revisit quarterly. Reference it every chance you get.

This is the human part of the playbook. Do not skip it.

10. Authentically want the rep to win

This is the one I cannot teach.

I can teach cadence, feedback frameworks, role-play formats, documentation, and accountability loops. I cannot teach a leader to genuinely want the rep in front of them to succeed.

But the reps can feel it. Every time.

When a coach authentically wants the rep to win, the rep feels supported even when the feedback is hard. When a coach has already written the rep off, the rep feels that too, and no amount of technique will get them to work on the things you are asking them to work on.

Coaching is built on the belief that the rep can get better. If you do not believe that, the coaching will not work. If you do believe it, almost any coaching system will.

Putting it all together

Less than 5% of sales teams have a real coaching process.⁶ Which means that just by committing to a weekly rhythm, a documentation habit, and the accountability loop, you can separate your organisation from 95% of competitors.

You do not need a fancy framework or a new tech stack. What you need is one call per rep per week, one thing to work on, written down, checked the following week. Repeat for a quarter and you will see behaviours change. Repeat for a year and you will see a different sales team.

The hardest part is usually not the system. It is holding the line on weekly cadence when the calendar fights back. That is exactly where a second set of ears helps: an outside coach who reviews calls alongside you, models the feedback, and keeps the rhythm honest until it becomes habit.

If you want help building a coaching rhythm that actually sticks, I would love to talk. At Kennett Advisory, this is the work we do with sales leaders at early-stage and growth-stage B2B SaaS companies.

A note on what “coaching” means here

In the broader coaching world, the textbook definition is a facilitated conversation where the coach asks open questions and helps the person find their own answers. That is real coaching. I am not arguing with it.

In the context of sales call coaching, I am personally more directive. I am an experienced sales leader reviewing a specific call. I can see where the rep is strong and where the gaps are, and I see my job as naming those things and giving the rep something specific to work on. I still bring the rep along. I still ask questions. But I do not pretend I cannot see what I can see.

Notes

1. The 34% and 91% figures come from MySalesCoach’s annual State of Sales Coaching report, which surveys sales leaders across industries on coaching habits, training, and outcomes. Worth reading in full if this topic is your focus: mysalescoach.com/state-of-sales-coaching-2025-report. ↩
2. The quota attainment numbers, 76% weekly, 56% monthly, 47% quarterly, are pulled from MySalesCoach’s coaching statistics research. The gap between weekly and quarterly is bigger than most leaders expect until they see it in writing: mysalescoach.com/blog/sales-coaching-statistics-2025. ↩
3. The 73% figure is from Hyperbound’s sales coaching research, which aggregates data across manager behaviour and time allocation studies: hyperbound.ai/blog/sales-coaching-statistics. ↩
4. James Clear, Atomic Habits (Avery, 2018). The full line is “Habits are the compound interest of self-improvement. The effects of your habits multiply as you repeat them. They seem to make little difference on any given day and yet the impact they deliver over the months and years can be enormous.” More of his writing on habit compounding is at jamesclear.com/atomic-habits. ↩
5. I talked through the pods-of-three format in detail on episode 130 of Make It Happen Mondays with John Barrows. One of the better conversations I have had on what world-class coaching actually looks like in practice: blog.jbarrows.com/blog/sales-coaching-dave-kennett. ↩
6. The less-than-5% figure came up in a conversation I had with Rob Jeppsen on the Sales Leadership Podcast, episode 77, focused on building a real coaching culture rather than just a coaching philosophy: salesleaderpodcast.fireside.fm/77. ↩