October 11, 2025 | Read online

Why Most Sales Coaching Fails, And What To Do Instead

by Kevin 'KD' Dorsey

Let me paint a picture you’ve probably seen a hundred times.

A rep is behind on quota. You ask their manager what's going on.

And the answer comes back like this:

“They need to improve their discovery.”
“They should generate more pipeline.”
“They gotta close better.”

Cool. And how exactly are they supposed to do that?

That’s not coaching. That’s a weather report. Tells you what’s happening — but not how to fix it. Welcome to the epidemic of lazy sales leadership.

Sales Isn’t About Big Moves. It’s About Millimeters.

Most reps aren’t struggling because they’re bad at everything.

They’re struggling because they’re missing one thing.

It’s easy to overlook. But in sales, one inch off target is the difference between:

Scheduled and no-show
Curious and confused
Demo and ghost
Almost and closed-lost

I once had a rep who was scoring 95% on their calls.

Rapport? 🔥
Discovery? Textbook.
Urgency? Check.
Objections? Controlled.

And yet… they hadn’t closed a single deal in months.

They weren’t bad at sales. They were just bad at closing.

More specifically: the last 3 minutes of a call.
They’d freeze. Rush. Overspeak. Ask a weak question like “Does that make sense?” and kill the momentum.

One micro-miss. Whole deal dead. Sales is ruthless like that.

You Don’t Need Motivation. You Need a Microscope.

The fix wasn’t “get better at closing.”

It was specific.
Four tiny changes:

Stop rushing when you sense hesitation. Let tension breathe.
Ask “What questions haven’t I answered yet?” before you close.
Use silence after pricing. Count to 5 in your head.
Never end with “Does that make sense?” Try “What do you think about moving forward with this?”

That’s it.

And with just those adjustments, their close rate jumped from 12% to 31% in 6 weeks.

Not from grinding harder. Not from rah-rah hype.

From coaching the inches.

Broad Advice is a Death Sentence

Here’s what most leaders say:

❌ “Improve your discovery”
❌ “Handle objections better”
❌ “Close more deals”
❌ “Build more pipeline”

Cool, thanks.
Let me just go… manifest more pipeline real quick.

These are too vague to be useful. If your “coaching” can be printed on a bumper sticker, it’s probably not helping.

Your job as a leader is to zoom in.

Get so granular the rep knows exactly what to change.

So what does that look like?

From Vague to Valuable: How to Translate Coaching That Lands

Let’s bring it down to eye level.

You’ve heard advice like this before:

“Improve your discovery.”
“Handle objections better.”
“You need more pipeline.”
“Be more confident on calls.”

Sounds helpful. Isn’t.

Now let’s translate each one into coaching your reps can actually apply tomorrow:

❌ “Improve your discovery”
✅ “Ask a second-layer question after every pain point they share.”

❌ “Handle objections better”
✅ “When they say ‘too expensive,’ ask: ‘Compared to what?’”

❌ “Build more pipeline”
✅ “Add 10 new LinkedIn connects before your first call block every day.”

❌ “Be more confident”
✅ “Stand up and smile during your cold calls. It shifts your tone and energy.”

Spot the shift?
One is abstract. The other is actionable.
One puts pressure on the rep. The other gives them precision.

That’s real coaching.
That’s how you fix the micro-miss that’s costing your team macro results.

Coaching Isn't Correction. It’s Calibration.

Think of your team like athletes.
You’re not yelling “run faster” from the sidelines.

You’re tweaking mechanics:

“Tuck your elbow in on the release.”
“Shift your weight before you pivot.”
“Watch the defender’s hips, not the ball.”

Sales is the same.
Coaching is about seeing what they can’t, and helping them adjust in real-time.

And sometimes? That means being quiet and just watching.
Call reviews. Call shadows. BIPSY-style behavior audits.

Because if you’re guessing, you’re gambling.
Great leaders don’t guess. They observe, diagnose, prescribe.

The BIPSY Layer (How You Coach the Why)

Once you know what’s off, you can ask: why is it off?

That’s where BIPSY kicks in.
If you’re new here — BIPSY is how we break down performance issues beyond just the metric.

Behavior – Are they doing the right actions?
Individual – Are they burned out, blocked, or disengaged?
Process – Are the systems and scripts actually working?
Skill – Can they do what we’re asking?
You – Are you as the leader coaching, guiding, and setting the standard?

Example:
Rep’s demo-to-close rate is low. You spot they’re rushing at the end.

→ Behavior? They’re skipping pricing questions.
→ Skill? They don’t know how to handle hesitation.
→ You? Have you coached that moment directly?

See how deep this can go?

Good coaching is never just “more reps.”
It’s reps with better form.

TL;DR — How to Coach Like a Surgeon

Here’s your cheat code for world-class coaching:

✅ Stop giving “weather report” feedback
✅ Identify the single weakest moment in the sales motion
✅ Write one specific behavior to change
✅ Pair it with a BIPSY-level diagnosis
✅ Practice it deliberately for 1–2 weeks
✅ Track the result (don’t guess — measure)

Rinse. Repeat. Scale.