Most sales managers run coaching sessions. Most of those sessions aren't coaching.
They feel like coaching. You're meeting with a rep, talking about their performance, offering advice. But there's a difference between a conversation and coaching, and it comes down to what you're doing in the room.
If you recognise yourself in a few of these, you're in good company. Every sales manager does.
Sales coaching sessions fail when managers come to deliver rather than listen. The most common traps include preparing answers before the session, judging reps against your own standard, jumping in during live calls, and cancelling when the week gets busy. All of them produce conversations that feel productive but change nothing. According to MySalesCoach research, 41% of reps say they are never or rarely coached despite near-universal belief in coaching's importance.
Seven specific patterns explain why sessions happen but coaching doesn't.
Why Sales Coaching Sessions Stop Working
75% of SaaS sales reps say they don't receive adequate or useful coaching from their manager.
That's not because sessions don't happen. For most teams, they do. It's because what happens in those sessions isn't coaching.
There's a clean line between the two. Training is the giving of ideas: product knowledge, methodology, process.
Coaching is making sure those ideas get executed. Coaching holds reps accountable by encouraging them to find their own answers.
If you're giving away the answers, you're not coaching.
As Mark Ackers, Co-Founder and Head of Sales at MySalesCoach, who has spent over a decade building and coaching sales teams, puts it:
"Pipeline reviews are really important. But it's not coaching. It's ticking boxes."
Knowing the difference is the first step. Knowing which patterns are killing your sessions is the second.
If you want to go deeper on the techniques that separate coaching from telling, the sales coaching techniques guide covers the practical moves in detail.
The MySalesCoach Coaching Session Traps Framework: 7 Patterns Killing Your Coaching
These aren't character flaws. They're patterns, and every sales manager falls into at least a couple of them.
The point isn't to feel bad about it. It's to recognise them when they happen.
Trap 1: The Delivery Trap
You came prepared. You have three things you want to cover, a piece of feedback ready to give, and a suggestion for how the rep should handle their next discovery call.
That's not a coaching session. That's training.
Coaching doesn't have an agenda you bring in. It has questions you ask and a conversation you follow. The moment you walked in knowing what you were going to say, the session stopped being coaching.
The fix is simple, though not always easy: walk in with questions and no answers.
Trap 2: The Mirror Trap
Not every rep wants what you want.
Just because you set out to be a top performer doesn't mean your coachee does. They may be happy in their role, performing consistently, and not interested in promotion. That's a legitimate position.
A coach doesn't get to decide what the coachee should want. Their job is to listen to what the rep wants and help them get there. If you find yourself thinking "they should be pushing harder" or "at their stage I was already going for management," you've moved out of coaching and into projection.
Trap 3: The Judge Trap
Be very wary of the following phrases. If you hear them in your head during a session, it's a signal you've stopped coaching:
- They should be further along
- They should set bigger goals
- I remember when I was selling and I...
- They should have closed this deal by now
- That's not how I would have done it
These phrases mean you've brought your own ego into the room. A good coach takes their ego out of the equation and works from the coachee's values, not their own.
Trap 4: The Hero Trap
This one happens most on live calls.
You're shadowing a rep. The prospect asks a hard question, the rep hesitates, and you jump in. It feels helpful. You've saved the call. But the rep didn't learn anything, and you've just told them they can't be trusted in a difficult moment.
If the prospect wants to talk to you, push it back to the rep. A line that works: "[Rep's name], we were talking about this just now. You had some great ideas, didn't you?"
Even if you know a better answer, keep quiet. The rep will learn more from working through it than from watching you rescue it.
Trap 5: The Answer Trap
As a manager, you have real influence over how your reps think. When you share your idea first, you close down the conversation, even without meaning to.
If you suggest something and the rep agrees, you don't know whether it's because they genuinely agree or because disagreeing feels risky. Coaching is about tapping into the rep's inner critic: the voice that already knows what's right and wrong. It works by making them listen to that voice rather than seeking your reassurance.
Ask first. Let them work through it. Your perspective has more value after they've run out of their own thinking.
Trap 6: The Cancellation Trap
Mark Ackers is direct on this one: "We all know the stats of how frequent coaching improves performance and revenue more than any other action. But it's the first thing we drop. That's a sin."
MySalesCoach research shows teams coached weekly hit 76% quota attainment versus 47% for those coached quarterly or less, a 29-percentage-point gap driven by frequency alone. Neither outcome happens from sessions that get rescheduled whenever something more urgent comes up.
Your reps read cancellations clearly: when it gets busy, coaching is optional. Don't let that be the message.
Trap 7: The Sandwich Trap
Positive feedback. Critical feedback. Positive feedback. It's a familiar structure, and it doesn't work.
The rep hears the first positive, braces for the criticism, and stops processing either piece properly. The feedback sandwich is well-intentioned, but it muddies the message.
Instead: work out what's most important to address at that moment. Look for genuine opportunities to praise, even if it seems small. Remember that your coachee may be proud of something you don't think is praiseworthy. That pride is worth acknowledging.
What a Sales Coaching Session That Works Looks Like
It doesn't look dramatic.
You sit down with a rep. You don't have an agenda. You start with: "What's been happening since we last spoke?"
You listen. You follow the thread. If they mention something they're struggling with, you ask more about it rather than solving it. You resist the urge to fill the silence with your own experience.
At the end, if it feels natural, you ask whether there's one thing they'd like to try before you speak again. You let them name it.
Nothing is fixed in the room. But the rep leaves with one clear thing to think about and the sense that someone actually heard them.
As John Richardson, Head of Coaching at MySalesCoach, puts it:
"Ask yourself how you can understand better, how you can help them understand, and how you can be a resource and a support to that person. That's the whole job."
For the broader picture of how coaching fits into sales team management, including how to balance development with hitting short-term targets, that's worth reading alongside this.
The One Change That Moves the Needle
Fix the Delivery Trap first.
Stop preparing what you're going to say. Walk in with three questions and nothing else. The rep will fill the silence, and what they say will tell you more than anything you planned to cover.
Three questions that work in any session:
- "What's been on your mind since we last spoke?"
- "What are you most stuck on right now?"
- "What have you tried?"
Ask the first. Listen. Follow where it goes.
If your team's sessions feel like they've hit a ceiling, MySalesCoach matches sales teams with expert 1:1 coaches. Find out how it works.
Frequently Asked Questions About Sales Coaching Sessions
How long should a sales coaching session be?
Length matters less than frequency. A 20-minute weekly session done consistently produces better results than a monthly hour-long review. MySalesCoach research shows weekly coached teams hit 76% quota attainment versus 47% for those coached quarterly. The cadence drives the outcome, not the duration.
What's the difference between a pipeline review and a coaching session?
A pipeline review focuses on deals: what's progressing, what's stuck, what's next. A coaching session focuses on the rep: their skills, thinking, and development. Running them back-to-back blurs the line. Keep them separate, or pipeline will colonise the whole conversation every time.
How do I know if my coaching sessions are actually working?
The rep starts coming with their own questions rather than waiting for yours. They bring updates on what they tried. They think out loud rather than looking to you for the answer. If you're doing most of the talking, the session isn't working.
What should I do if the rep isn't engaging in sessions?
Ask them directly whether the coaching is adding value. Low engagement usually means one of two things: the session doesn't feel safe, or the agenda feels like yours rather than theirs. Adjust before assuming it's a coachability problem.
Why do managers struggle to coach their own team?
Because the two roles pull in opposite directions. A manager is tied to outcomes: targets, pipeline, headcount. A coach is focused entirely on the individual in front of them. When those roles sit in the same person, the manager agenda tends to win. It's one of the main reasons companies bring in external coaches: the separation makes better coaching possible.
The reason most managers fall into these traps isn't lack of effort. It's that coaching your own team is genuinely hard when you're also responsible for their numbers. MySalesCoach pairs each rep with a dedicated external coach, so the coaching relationship sits outside the manager dynamic entirely. Talk to us about your team.
