Coaching That Sticks: How to Level-Up Reps Every Week

Azeem Sadiq
April 30, 2025
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2
min read

Quarterly trainings fade fast. Weekly coaching embeds skills and turns average reps into consistent performers. Here’s the playbook.

Anchor Coaching to Pipeline Events

Forget role-playing hypothetical scenarios. The best classroom is your real pipeline. Every live opportunity is a hands-on lesson waiting to happen.

When a deal stalls at the Discovery stage, it’s a perfect moment to coach questioning techniques. If a prospect ghosts after a demo, it’s time to sharpen closing skills. Coaching becomes more meaningful when it’s tied to real revenue movement—or the lack of it. Reps feel the urgency and relevance when it’s tied to their actual deals, not theory. Plus, coaching in the context of live deals sharpens skills that stick because the emotional investment is already there.

Follow the 70-20-10 Rule

A winning coaching model leans on the 70-20-10 rule: 70% doing, 20% feedback, 10% theory.

This model is backed by adult learning research. Adults retain skills better when they actively apply them rather than just listening or reading. In sales, that means most of a rep’s growth happens on live calls. They need to do the work to learn it.

Coaching feedback should focus on immediate application: what went right, what could improve. Playbooks and training materials (the 10%) support the process, but they can't replace live reps doing the job. The key is balance. Skew too much toward theory, and your reps nod along—but change nothing.

Record, Reflect, Reinforce

Memory is fallible. That’s where call recording comes in.

Modern sales intelligence tools let you record conversations effortlessly. But it’s not just about recording—it’s about using those recordings the right way. After coaching sessions, have reps re-listen to their calls and jot down two specific improvements they will apply in their next conversation.

This reflection step is crucial. It moves feedback from "I heard it" to "I own it." According to learning science, reflection after practice dramatically improves skill transfer. It turns every coaching moment into a compounding advantage over time.

Measure Coaching ROI

Coaching without measurement is like steering blindfolded.

You must track the performance of coached vs. uncoached reps—specifically looking at win-rate lift. Data-backed metrics like average deal size, sales cycle length, and quota attainment give a clear picture of coaching effectiveness.

Tools like Gong, Chorus, and sales CRMs can help surface these insights. If coached reps are consistently outperforming, you’ve built a proof point for leadership—and for scaling your program. If not, the data reveals where your coaching content or method needs refinement.

Tracking ROI turns coaching from a "nice-to-have" into a strategic revenue lever.

Wrap-Up: Build Skills That Stick and Deals That Close

Weekly coaching focused on live deals isn’t just a productivity booster—it’s a culture builder.

Here’s how to make it work: ✅ Tie coaching to real pipeline events, not hypotheticals
✅ Follow the 70-20-10 rule to balance action, feedback, and theory
✅ Record calls, encourage reps to reflect, and reinforce learnings
✅ Measure the impact with hard data like win-rate lift

By weaving coaching into the fabric of daily selling, you don’t just improve reps—you transform your entire sales motion. Skills stop fading. Revenue starts compounding.

Invest in opportunity-driven, weekly coaching now—or watch skills (and pipeline) atrophy later.

Try it for free zero commitment

If you're looking to improve your win rate
Free your reps up from boring admin
And get unprecedented visibility into winning behaviours
You can start moving the needle with Velocity AI today!

Book a Demo

Try it for free zero commitment

If you're looking to improve your win rate
Free your reps up from boring admin
And get unprecedented visibility into winning behaviours
You can start moving the needle with Velocity AI today!

Book a Demo