How to Measure Deal Coaching Effectiveness (According to Our Experts)

When deal coaching is done well, it drives results you can measure—and feel. It sharpens reps’ instincts, builds strategic muscle, and moves real revenue. But you can’t coach blindly. You need structure, tools, and clarity on what “good” looks like.

We asked our expert sales coaches how they measure coaching effectiveness and which tools make it work. Here’s how to do it right—using their insights.

This article is part of Deal Coaching, find out more about why we launched deal coaching from our Founder & CEO Kevin Beales here, and if you're wanting  a step-by-step guide of how to coach your sales team on deals, you can find that here.

1. How to Measure Coaching Effectiveness: Progress, Confidence, and Closure

“Of course, the most tangible [marker] is when they get into situations. Are they able to work their way through it and close it? Because that’s the ultimate.” — Aaron Margolis

Aaron breaks it down: the best indicator of coaching effectiveness is whether the rep can navigate a real deal, solve problems, and close. But the signs show up earlier—when you hear a rep speak with confidence, act with independence, and think more strategically than they used to.

“The difference between day one and two years later should be vast… they’re taking care of things they wouldn’t have earlier.”

What to Track:

• Rep maturity: Are they handling complex scenarios better over time?

• Strategic growth: Do they apply philosophy, not just process?

• Ownership: Are they making smarter, faster decisions?

Alan Duncan adds a practical lens:

“It’s quite simple—closure rates, progression skills of the sellers. Measure what the deal coaching does and really go with the coaching.”

Alan Clark zooms in on post-coaching impact:

“Did the deal progress? Was a blocker removed? Did the individual feel clearer and more confident?”

Questions to Ask:

• What happened after coaching? Did the deal move forward?

• Has the seller improved in progressing blockers or asking better questions?

• Is coaching creating long-term confidence or short-term dependency?

2. Zoom In: Micro and Macro Metrics Matter

“At the micro level: Did we close or qualify out the deal?” — Steve Myers

Steve outlines a tight framework:

Micro = Deal-Level

• Did we progress, close, or qualify out?

• Was value clearly articulated?

• Were decision-makers identified?

Macro = Team-Level

“Leading indicators: better forecast accuracy, clearer value props, actionable next steps. Lagging: win rates, deal size, time wasted on unqualified prospects.”

And don’t forget qualitative signals:

“Are reps asking for more coaching? That’s a sign it’s working. But beware mutual dependency—coaching should help them think, not just fix things.”

Volker Ballueder agrees:

“Ideally: deal progression, win/loss insights, time to close… even client feedback—did the coaching help move the deal faster?”

Do’s and Don’ts:

Do:

• Track both leading and lagging metrics.

• Separate activity from impact.

• Listen for signs of rep growth—not just deal movement.

Don’t:

• Only count wins—look for skill improvement.

• Let coaching turn into hand-holding.

3. Frameworks Build the Foundation for Every Session

“You need a consistent sales framework across the business—MEDDICC is a great example. It gives structure for focusing on the right things.” — Steve Myers

Steve is clear: a sales framework isn’t optional. It’s what makes coaching replicable and scalable. Without it, you’re coaching from memory and opinion.

Use frameworks like:

• MEDDICC / MEDDPICC: Ideal for qualification and deal control.

• SPICED / BANT: Useful depending on deal complexity or buying stage.

“The most important tool? A salesperson who asks the right questions—and a good coach.”

Richard Bounds adds:

“I like MEDDICC because it helps formalise deal analysis… and we pair it with deeper dive questioning and call reviews.”

Volker Ballueder and Alan Duncan both reinforce that frameworks help with testing yourself as a seller:

• Have you really done the work?
• Have you missed anything?
• Are you overestimating the deal?

Build Coaching Structure Around:

• Pre-call checklists (using MEDDICC elements)

• Post-call reflections based on SPICED or BANT

• Live coaching using a shared scorecard

4. Call Intelligence and Real Coaching Work Hand-in-Hand

“We use Gong to listen back to calls, be live on calls, and look at stats… The biggest and best tool? A live coach.” — Kaitlen Kelly

Kaitlen cuts through the noise. Your tools are only as good as the coach using them. She emphasises live coaching—having someone experienced enough to bring alternate views and challenge thinking.

“Someone who’s been in the weeds, has experience, and can bring different lenses to the deal.”

The following tech helps:

• Gong: For async reviews, trend analysis, and stat tracking

• Live observation: For real-time interventions and post-call reflection

But the secret weapon

“Whether it’s a leader, peer, internal or external coach—someone live makes a big difference.”

5. Scorecards, Templates, and Reps’ Notes Drive Precision

“Scorecarding, call recordings, and pre-call information give better insights and make coaching more successful.” — Richard Bounds

Consistency beats brilliance. Scorecards keep coaching focused and reduce subjective feedback.

“Templates from sales methodology—whether it’s MEDIC or BANT—and notes, anything like that…” — Volker Ballueder

Volker highlights the value of a rep’s own perspective too:

“Usually the rep gives you the whole lowdown.”

Build a Coaching Toolkit:

• Pre-call plans: filled out by reps

• Deal review templates: rooted in frameworks

• Scorecards: consistent fields for evaluating calls

• Shared docs: Notion or Google Docs for live collaboration

Steve also recommends deal rooms—spaces to gather context, content, and call recaps in one place.

6. Style, Mindset, and Preparation Are Tools Too

“Some of the tools are basic ones—like the right kind of questioning, the right kind of approach, the right kind of preparation…” — Alan Duncan

Alan redefines “tools”—they’re not just software. They’re habits, mindsets, and methods. Are reps showing up ready? Are they structured in how they run their calls? Are they controlling the tempo?

“There are models we can use together, but also a style thing, which actually is important, and a confidence thing.”

Deal coaching needs to touch all three:

• Process: Are you following the framework?

• Style: Are you in control of the conversation?

• Confidence: Are you playing to win—or playing not to lose?

TL;DR — What Makes Deal Coaching Effective?

 

Struggling to Coach Critical Deals in Real-Time?

When a deal stalls or a key meeting looms, your reps need expert support—fast. Our on-demand Deal Coaching connects them with seasoned sales coaches who’ve navigated and won similar opportunities. Whether it’s risk analysis, objection handling, or stakeholder engagement, we provide actionable strategies to move deals forward.

✔ Choose from 20-minute lightning sessions for urgent challenges or 40-minute deep dives for complex deals.

✔ Sessions are available same-day, often within the hour, ensuring your team gets the support they need when it matters most.

Don’t let another deal slip through the cracks.

👉 Book a meeting with our team to share some ideas around how we can support you, or find out more about Deal Coaching here.