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Sales Coaching Done Right: Game Footage, Role Plays, and the Mindset of a Great Coach With Chris Duprey

Let me ask you a simple but powerful question. Do you spend enough time coaching inside your organization? Not just telling your sales team to “sell more,” but actually rolling up your sleeves to guide them, develop them, and help them flourish?

If the answer feels like a shaky “maybe,” you’re not alone. Most leaders underestimate the importance of coaching. They assume performance problems mean their team just needs to “work harder” or “make more calls.” But the real issue usually lives somewhere deeper, hidden in the way we listen, observe, and coach.

That’s where game footage, role plays, and true sales coaching come in. And to unpack this the right way, we’re drawing insights from Chris Duprey, a U.S. Army veteran, leader, and sales coach with two decades of experience inspiring people to grow.

So let’s get into it.

What Is Sales Coaching and Why Does It Matter?

Here’s the reality. Too many organizations confuse leadership with pressure. They push sales teams to perform but never pause to actually look at what’s happening on the front lines.

Sales coaching is about shifting from assumption to observation. It’s not just about telling your reps to sell more. It’s about:

  • Watching sales calls like game footage.

  • Identifying real challenges.

  • Providing training and guidance that address the root problem.

Without this, leaders end up shouting instructions from the sidelines without ever seeing the play. Coaching makes sure you know what’s actually happening before you try to fix it.

Why Game Footage Is a Sales Leader’s Secret Weapon

Think about sports for a second. Can you imagine a football team refusing to watch film from their last game? Of course not. Yet in sales, so many companies skip this step entirely.

Recording and reviewing sales calls — your team’s game footage — unlocks three big wins:

  1. You see the difference between what you think is happening and what’s actually happening.

  2. You can provide specific, actionable feedback instead of vague “good job” or “that was bad” comments.

  3. You create a shared library of real-world moments your whole team can learn from.

Tools like Gong, Chorus, or even HubSpot Playbooks make this easy. And if budget is tight? A spreadsheet and a Zoom recording button still get the job done. The important thing is to start watching.

Role Plays: Turning Cringe Into Confidence

Let’s be honest. The word “role play” makes most salespeople break out in hives. We’ve all seen it go sideways — awkward, unrealistic, even downright goofy.

But when done right, role plays can transform your sales culture. Here’s how to make them work:

  • Use real scenarios. Don’t make things up just for fun. Practice real upcoming calls or replay a tough one from last week.

  • Prep the “buyer.” Give the role player the same background info a real buyer would have.

  • Pause for learning moments. Stop in the middle, give feedback, and keep going.

  • Define good feedback. “That stunk” isn’t helpful. Specific and actionable comments are the goal.

When role plays follow these rules, they stop being dreaded exercises and become training sessions your team actually looks forward to.

Reviewing Calls Without Falling Into the “That Sucked” Trap

Most of us watch a sports game and sum it up in two sentences: “That was great” or “That was terrible.” But a coach doesn’t stop there. They break it down play by play.

The same is true in sales. Reviewing a call means looking for specifics:

  • Did the rep pitch before understanding the buyer?

  • Did they ask follow-up questions that dug deeper?

  • Did they uncover a real problem worth solving?

  • Did they earn a clear next step?

Whether you use a formal scorecard or a simple checklist, the goal is to move past surface-level reactions. Good feedback isn’t about judgment. It’s about growth.

What Makes Someone an Effective Sales Coach?

Not everyone is built to be a coach. A true sales coach needs curiosity, empathy, and the ability to communicate with clarity. They aren’t dictators barking orders. They’re guides helping others sharpen their skills.

The best coaches:

  • Stay curious about buyers, the business, and their team.

  • Blend different sales methods into what works for the organization.

  • Lead with empathy, building trust before pushing for improvement.

  • Inspire confidence, reminding the team they’re already good and capable of becoming even better.

Think Top Gun. The pilots were already the best of the best, but they showed up to flight school to become even sharper. That’s the energy a great coach brings to sales.

Strategies and Tactics You Can Use Right Away

If you’re ready to put sales coaching into practice, here are a few immediate steps:

  • Redesign your sales process to be buyer-centric, not just internal box-checking.

  • End every call with the next meeting booked, not just “I’ll send you an email.”

  • Train reps to ask second smart questions that go deeper than surface-level answers.

  • Build role play sessions into your regular schedule, using real-world scenarios.

  • Record and review calls every week. Even an hour of footage makes a big difference.

These aren’t theory. They’re practical habits that create lasting results.

The Common Pitfalls to Avoid

Here’s what derails sales coaching faster than anything else:

  • Believing top performers don’t need coaching. They do. Even Tiger Woods has a swing coach.

  • Avoiding recording because “buyers won’t like it.” They will, especially if you explain why.

  • Giving generic feedback instead of actionable coaching. Vague comments don’t move the needle.

If you can avoid these traps, your coaching will make a lasting impact.

The Role of AI in Sales Coaching

One of the biggest excuses leaders give is, “I don’t have time.” That’s where AI comes in.

With tools like ChatGPT, you can:

  • Generate role play scenarios tailored to your team.

  • Create buyer personas instantly for practice.

  • Analyze calls for patterns and missed opportunities.

AI won’t replace the human element of coaching, but it can save you hours of prep and give you sharper insights faster.

One Big Takeaway

Sales coaching isn’t about shouting “sell more” from the sidelines. It’s about watching the game, breaking down the plays, and guiding your team to grow as world-class communicators.

If you don’t know what the real problem is, you can’t fix it. Coaching reveals the truth, builds trust, and equips your team to flourish.

So here’s the question for you: are you ready to stop assuming and start coaching?

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