TSW - Performance Coaching & 1:1 Improvement Plans: How to Turn Good Reps into Great Ones

Welcome back to The Sales Wagon — today we’re diving into the secret weapon of every elite sales organization: coaching that actually develops people, not just checks in on them.

Here’s a hard truth about sales teams: most managers think they’re coaching… but most reps feel like they’re just being checked up on.

Real coaching isn’t about asking for pipeline updates or reminding people about quota. It’s about developing skills, sharpening habits, and unlocking potential — even in reps who are already performing well.

The best sales orgs thrive because they invest in their people consistently, not just when someone is struggling. Let’s break down how performance coaching really works, and how a structured 1:1 system can turn good reps into absolute killers.

Managing is about accountability.
Coaching is about capability.

Managers ask: “What’s in your pipeline this week?”

Coaches ask: “What’s holding this deal back?”
“What skill do you want to get better at this month?”

Managing keeps reps on track.
Coaching makes reps unstoppable.

And according to Gartner, companies with strong coaching cultures see higher quota attainment and 20% faster ramp times for new reps.

Because great coaching builds confidence, consistency, and clarity — the three ingredients every top performer needs.

Here’s where most leaders go wrong: they cram pipeline review, strategy talk, and skill coaching into one 30-minute meeting.

That’s a recipe for chaos.

A proper 1:1 coaching session should focus on development, not just deals. Keep pipeline reviews separate.

Your weekly rhythm should look like this:

This simple separation makes reps feel supported instead of interrogated.

Elite coaches don’t “wing it.” They follow a system.
Use this simple yet powerful framework:

Start by asking the rep to self-assess.

This builds ownership and eliminates defensiveness.

Pick ONE specific skill to develop — not ten.
Examples:

The biggest mistake leaders make is trying to fix everything at once. Improvement comes from focus.

Share guidance, examples, or best practices.
Show them what “good” looks like.
Play real call recordings or analyze messages together.

Role-play.
Rewrite an email.
Rebuild a talk track.
Redesign a follow-up sequence.

Reps get better by doing, not just hearing.

Set a micro-goal for the next week.
Examples:

Small commitments → big long-term improvements.

The best coaching relationships feel like a partnership, not a performance review.

Here’s how great leaders create a safe coaching environment:

When a rep knows coaching isn’t punishment, they lean in instead of shutting down.

Coaching shouldn’t be based on “vibes” or personal bias. Use data.
Look at:

Patterns don’t lie.
If a rep struggles at the same stage repeatedly, that’s your coaching target.

Data tells you where to coach.
Calls and conversations tell you how to coach.

Every rep is different — strengths, weaknesses, personality, learning style.
Your coaching should reflect that.

A great 1:1 improvement plan includes:

And most importantly…
🎯 Reps should co-create the plan.
People commit to what they help build.

Avoid these traps:
❌ Turning coaching into criticism
❌ Focusing only on low performers
❌ Making every session about deals instead of development
❌ Giving vague feedback (“just be more confident”)
❌ Skipping practice and expecting improvement

Coaching must be actionable, specific, and ongoing.

Your team will rise or fall to the level of your coaching.
When reps feel guided, supported, and challenged, they push harder, learn faster, and stay longer.

And the best part?
Great coaching turns managers into leaders — and reps into top performers.

Because in sales, skills pay the bills…
but coaching builds the skills.

“You don’t build a great team by hiring great people.
You build a great team by developing them.”

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That’s All For Today

I hope you enjoyed today’s issue of The Wealth Wagon. If you have any questions regarding today’s issue or future issues feel free to reply to this email and we will get back to you as soon as possible. Come back tomorrow for another great post. I hope to see you. 🤙

— Ryan Rincon, CEO and Founder at The Wealth Wagon Inc.

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