Why Most Sales Managers Fail at Coaching
I was working with a B2B company last week. About $40 million in revenue. Strong market position. Good products.
The CRO pulls me aside after our session.
“We’ve got underperformance on the team. I think it’s the territory plan and comp structure.”
I ask her a few questions about the person who’s underperforming. How long have they been there? What’s their background? What does good look like for that role?
She gives me decent answers. Then I ask: “When’s the last time you listened to one of their sales calls?”
Long pause.
“I don’t really have time for that. I’ve got 8 direct reports and board meetings and strategic planning.”
This is a person making six figures to lead revenue for a $40M company. She hasn’t listened to a single call from the rep she’s worried about firing.
That’s not a territory problem. That’s not a comp problem.
That’s a coaching problem.
The Myth of “Available for Questions”
Most sales managers think they’re coaching when they say “my door is always open” or “call me if you need help.”
That’s not coaching. That’s being reactive.
Real coaching is proactive. It happens before the call and after the call. It’s structured. It’s intentional. It requires you to actually pay attention to what your people are doing.
I learned this the hard way early in my career. I worked with a guy who sought me out for coaching. We’d sell training packages and I’d tell clients “just call me when you need me.”
Most people never called.
This guy called me three to five times a week. “I’m paying for it. I might as well get the help.”
He was in his mid to late thirties, had never sold software before, and took a job with one of the worst products in the company’s portfolio.
Eight months later, he was number one in the company selling that product.
They gave him a team of nine. He turned them profitable for the first time.
Then a team of eighteen. Then forty.
His approach with every rep was simple: “This is your craft. Not a job. Something you commit to getting really good at.”
But here’s what made the difference. He didn’t just tell them to get better. He showed them how. He was in their calls. He was reviewing their approach. He was giving them specific feedback on specific moments.
That’s coaching.
What Actual Coaching Looks Like
I was training a group of SDRs recently. Young team. Hungry.
We’re role-playing a conversation about setting expectations with prospects. Basic stuff about communication, timelines and access to decision makers.
One of the reps stops mid-roleplay. “I can’t say that. It sounds too pushy.”
This is the gap most managers miss.
Your people aren’t failing because they don’t know what to do. They’re failing because they’re scared to do it.
They’re scared of sounding pushy. Scared of losing the deal. Scared of looking unprofessional. Scared of being rejected.
No amount of “my door is always open” fixes that.
You have to get in there with them. Before the call. After the call. In the moments where fear is making decisions instead of strategy.
Here’s what that actually looks like:
Pre-call planning. Before any significant call, sit down with your rep for 10-15 minutes. What’s the objective for this call? Not “close the deal” but what specific milestone needs to happen? What questions do they need to ask? What information do they need to get? What might go wrong and how will they handle it?
Post-call debriefing. Immediately after the call, spend another 10-15 minutes. What went well? What didn’t? What did they learn? What would they do differently next time? This isn’t about beating them up. It’s about helping them see what they can’t see on their own.
Most managers will read that and think “I don’t have time to do that for every call.”
You’re right. You don’t.
But you have time to do it for your new reps until they develop the muscle. You have time to do it for your underperformers who are about to get fired anyway. You have time to do it for your top performers who want to get even better.
And if you truly don’t have time because you’re managing too many people, that’s a different problem. You’re managing the wrong ratio.
The $40M Example
Back to that CRO.
After our conversation, something shifted. She started listening to calls.
Not every call from every rep. But enough to understand what was actually happening versus what people were telling him was happening.
She discovered his underperformer wasn’t lazy. Wasn’t incompetent. Wasn’t a bad culture fit.
The rep was having the same conversation twenty different ways and getting the same poor result. Nobody had ever shown him a better way.
Three months of actual coaching. Pre-call planning on big opportunities. Post-call debriefing on the ones that went sideways. Role-playing the tough conversations before they happened.
The rep’s performance improved by over 40%.
Not because of territory changes. Not because of comp adjustments.
Because someone finally coached him.
The CRO told me later: “I was so focused on board decks and strategy that I forgot my actual job is developing people.”
Here’s the thing that hit me about this story.
This executive was willing to listen to strategy presentations from his team about $2M deals. But she wasn’t willing to listen to actual sales calls where those deals were won or lost.
He was managing the appearance of sales instead of the reality of it.
Most sales managers are doing the same thing.
Why Managers Avoid Coaching
I’ve asked hundreds of sales managers over the years why they don’t do more pre-call planning and post-call debriefing.
The answers are always some version of these:
“I don’t have time.” You have time for what you prioritize. If coaching isn’t happening, it’s because you don’t actually believe it matters more than whatever else you’re doing.
“My reps are experienced. They don’t need that level of hand holding.” Experience doesn’t equal effectiveness. I’ve seen twenty-year veterans making the same mistakes they made in year two. Nobody ever showed them a better way.
“I don’t want to micromanage.” Coaching isn’t micromanaging. Micromanaging is controlling how someone does every task. Coaching is helping someone get better at their craft.
“I trust them to figure it out.” That’s abdication, not delegation. Your job isn’t to hope they figure it out. Your job is to help them get there faster.
But here’s the real reason most managers avoid coaching: it’s uncomfortable.
It requires you to have direct conversations about what’s not working. It requires you to sit in someone’s struggle with them instead of just telling them to try harder. It requires you to actually know what good looks like so you can help someone get there.
Most managers would rather review dashboards than do that work.
The Role Play Problem
I was working with a tech company recently. Team of about 20 sellers. Good training program. Solid onboarding.
I asked the sales manager: “When’s the last time you role-played with your team?”
He laughed. “We don’t really do that. These are professionals.”
This is like a football coach who never runs practice plays because “these are professionals.”
Even elite performers practice.
Olympic athletes have coaches. PGA tour golfers work with swing coaches. Top trial attorneys do mock trials before the real thing.
But sales managers think their reps should just figure it out on live calls with real prospects.
The best sales managers I’ve seen treat role-play like a non-negotiable part of development. Not once during onboarding, but regularly. Weekly team role-plays where everyone practices the hard conversations.
What do you say when a prospect ghosts you? Let’s practice that.
How do you handle price objections? Let’s practice that.
How do you ask for access to the economic buyer when your contact says “just send me the information”? Let’s practice that.
Most reps are terrible at these moments because they’ve never practiced them in a safe environment. So they practice on your prospects instead.
What Changes When You Actually Coach
I worked with a services firm that was stuck at about $3 million in revenue. Owner was frustrated because his team “knew what to do but weren’t doing it.”
We started implementing real coaching. Pre-call planning before significant opportunities. Post-call debriefing within an hour of the call ending. Weekly role-play sessions for the whole team.
The owner pushed back initially. “This feels like a lot of time investment for maybe incremental improvement.”
Six months later, they were trending toward $5 million.
Not because the market changed. Not because they hired better people. Not because they got better leads.
Because the people they had got better at executing.
Here’s what shifted:
Reps started asking better questions in discovery because they’d practiced asking them. Fewer deals stalled out because reps were setting clearer expectations upfront. Close rates improved because reps were having better conversations about value instead of just price.
The owner told me: “I thought my job was to set strategy and get out of the way. I didn’t realize my job was to make my people better at executing the strategy.”
That’s the shift most sales leaders need to make.
The Daily Discipline
Real coaching isn’t a program you run once a quarter. It’s a daily discipline.
Every significant call should have a pre-call planning conversation and a post-call debrief. Not just for underperformers. For everyone.
Your top performers want this. They want to get better. They want feedback. They want to know what they’re missing.
I have one client who closes over 60% of qualified opportunities. Well above industry average. Still asks for pre-call planning on deals that matter.
Because he knows no matter how good you are, you can always be better. And you get better through deliberate practice with someone who can see what you can’t see.
That’s what coaching actually is.
The Leadership Standard
I learned something important about leadership from watching that CRO make changes.
When he started listening to calls and coaching his team, something else happened. His managers started doing the same thing.
Not because he mandated it. Because he modeled it.
If you’re a VP or CRO and you’re not coaching your managers, don’t expect your managers to coach their teams.
If you’re not listening to calls, don’t expect your managers to listen to calls.
If you’re not doing pre-call planning and post-call debriefs with your direct reports, don’t expect them to do it with their teams.
Leadership standards cascade down.
The CRO of that manufacturing company now blocks time every week specifically for listening to calls and coaching her team. She treats it like board meetings. Non-negotiable. On the calendar.}She told me recently: “This is the highest leverage activity I do. Everything else is just keeping score.”
I learned something important about leadership from watching that CRO make changes.
When he started listening to calls and coaching his team, something else happened. His managers started doing the same thing.
Not because he mandated it. Because he modeled it.
If you’re a VP or CRO and you’re not coaching your managers, don’t expect your managers to coach their teams.
If you’re not listening to calls, don’t expect your managers to listen to calls.
If you’re not doing pre-call planning and post-call debriefs with your direct reports, don’t expect them to do it with their teams.
Leadership standards cascade down.
The CRO of that manufacturing company now blocks time every week specifically for listening to calls and coaching her team. She treats it like board meetings. Non-negotiable. On the calendar.}She told me recently: “This is the highest leverage activity I do. Everything else is just keeping score.”
What This Means For You
If you’re managing a sales team and this feels convincing, good. That means you’re paying attention.
Here’s what to do:
Start with one rep. Your newest person or your biggest underperformer. Commit to pre-call planning and post-call debriefing with them for 30 days.
Before their next significant call, sit down for 15 minutes. Help them think through objectives, questions, and potential obstacles.
After the call, spend another 10-15 minutes debriefing. What worked? What didn’t? What did they learn?
Do this consistently for a month and watch what happens.
You’ll probably see their performance improve. But you’ll also see something else. They’ll start asking for more coaching. Because people who get real coaching want more of it.
Then expand to the rest of your team.
Build role-play into your weekly rhythm. Make it normal to practice hard conversations in a safe environment before trying them on prospects.
Most importantly, examine your own calendar. How much time are you spending on activities that feel productive but don’t actually develop your people?
Dashboards don’t make your team better. Coaching does.
Strategy decks don’t make your team better. Coaching does.
Compensation plans don’t make your team better. Coaching does.
Your job as a sales manager isn’t to be the smartest person in the room or the best closer on the team. Your job is to make everyone on your team better at their craft.
That only happens through coaching.
Real coaching. The uncomfortable, time-intensive, daily discipline of helping people see what they can’t see on their own and practice what they need to practice until it becomes natural.
Everything else is just keeping score.
Questions our sales training programs? Email me at adam@thenorthwoodgrp.com.
