I have a confession to make. I actually enjoy role-playing in sales training meetings. I know, I know… that puts me in a very small minority. Most salespeople would rather have a root canal than participate in role-play exercises. And honestly? I don’t blame them.

Here’s the thing most sales managers miss: Salespeople don’t hate role-playing because it doesn’t work. They hate it because we typically do it wrong. So, what did the managers do wrong, and how can role-playing be done correctly?

Do you set your salespeople up to fail?

When I bring up role-play in a training session, I can practically see the energy drain from the room. Top performers will suddenly become reluctant participants, and dreading what feels like an artificial performance in front of their peers.

But role-playing, when done correctly, is one of the most powerful tools in your training arsenal. When done incorrectly, it can be absolutely devastating–not just to performance, but to relationships and careers.

Let me tell you about someone I once knew. She was a national training manager for a company I worked for years ago, and she had a particular approach to role-playing that I’ll never forget. This woman took genuine pleasure in making role-plays as challenging as possible, regardless of how well the participant executed the lessons she’d just taught. If you nailed the technique perfectly, she’d still find ways to grind you down. She seemed to enjoy watching people squirm, stumble, and ultimately fail in front of their colleagues.

I watched her reduce seasoned sales professionals to nervous wrecks. People who could handle the most demanding customers with ease would move to the back of the room when she announced role-play time. She’d keep pushing and pushing until even the most confident salesperson looked incompetent. And she’d do it with a smile, as if the public humiliation was just part of the learning process. She was making the role-play about her, not about learning.

Here’s the thing about role-playing that this training manager never understood: It’s an intensely personal experience. When you force someone to perform in front of their peers and then systematically tear them apart, you’re not just critiquing their sales technique. You’re attacking their professional competence, their confidence, and ultimately their sense of self-worth. People don’t just walk away thinking, “Well, that was tough but educational.” They walk away thinking, “I was just humiliated in front of my colleagues.”

The story doesn’t end there. A few years later, this training manager was reassigned to a different position within the company–one where she needed the cooperation and support of the very people she had once used to grind into dust during those role-play sessions. Guess what happened? They chose not to help her. In fact, some went out of their way to make her job more difficult. She eventually failed in that role and left the company.

You see, this wasn’t just about professional differences. She had made salespeople look bad enough in front of their peers that they had come to severely dislike her. A few even hated her. That’s the power of poorly executed role-playing–it doesn’t just fail as a training tool; it actively damages relationships and creates lasting resentment.

How to administer a sales training role-play

Think of role-playing as resistance training for your sales team. You know how a baseball player in the on-deck circle swings a bat with a weighted donut on it? When he steps up to the plate and removes that weight, the bat feels light as a toothpick. That’s exactly what effective role-play should do–it makes the real sales call feel easier because your people have practiced under more challenging conditions.

The key insight is that role-play is inherently more challenging than actual customer interactions. In real sales calls, your salespeople are confident, comfortable, and building genuine rapport. In role-play, they’re performing in front of colleagues, dealing with contrived scenarios, and too often facing unnecessarily brutal feedback. The last thing they need is a manager who makes it even more difficult than it needs to be.

So how do we fix this? Three fundamental principles will transform role-play from a dreaded interruption into something your team actually values.

Set the stage properly. Before diving into any scenario, I always tell my team that perfection isn’t the objective. This is a safe space for learning and reinforcing essential techniques. When salespeople know they won’t be judged harshly for missteps, they engage authentically and absorb lessons more effectively. Simple concept, but most managers skip this step entirely. They jump straight into the exercise without establishing a sense of psychological safety.

Keep it focused. Here’s where many managers go wrong–they try to role-play entire sales calls. Don’t do that. Instead, isolate specific components. Maybe it’s two strategic questions, a brief product demonstration, or a particular objection-handling technique. This targeted approach allows for deeper practice and more precise feedback without overwhelming participants or eating up your entire meeting. It also reduces the opportunities for public failure.

Run the role-play correctly when you’re playing the “customer.” This is critical. As the sales manager, your job isn’t to be the toughest prospect your salesperson will ever encounter. My philosophy is simple: Make it easy for them to succeed when they’re executing the technique correctly. Only become a challenging customer when they veer off course–and even then, stop quickly before you grind them into powder.

When salespeople nail the technique, reward them with a cooperative “customer” response. When they struggle, provide just enough resistance to highlight the learning opportunity, then course-correct before frustration sets in. The goal is to build confidence and competence, not break spirits or demonstrate your own superiority.

Invest in their success

Remember, the person participating in your role-play isn’t just learning a sales technique–they’re exposing themselves to potential embarrassment in front of their peers. That takes courage. We need to respect that courage. We need to honor it. We need to use it to build them up, not tear them down.

Master these three elements, and you’ll watch your team’s attitude toward role-play completely transform. Instead of groaning when you announce practice time, they’ll start seeing it as valuable preparation that makes their real sales calls feel effortless. More importantly, they’ll see you as someone who invests in their success rather than someone who enjoys their failure.

That’s when role-play becomes what it was always meant to be: A competitive advantage disguised as training, not a weapon disguised as development.

Troy Harrison is the Sales Navigator, a speaker, and the author of “Sell Like You Mean It” and “The Pocket Sales Manager.” He has trained salespeople from 23 different countries who live on three continents and has spoken all over North America and Europe. He helps companies navigate the Elements of Sales on their journey to success. He offers a free 45-minute Sales Strategy Review. To schedule, please visit TroyHarrison.com/ssr.