The Importance of Role-Playing in Customer Experience Training

When your CSM freezes on a tough call, do you blame them? I’ve heard many Customer Success leaders hesitate to use role-playing. Some feel it comes across as awkward. Others believe their teams will learn through exposure to real calls over time. But here’s the truth: observing a tough conversation is very different from being the one responsible for navigating it. Especially when a renewal is at stake or a customer clearly feels frustrated. Most teams struggle less with understanding the product and more with staying composed when a customer pushes back, questions the value, or speaks in a way that throws the team off balance. In those moments, confidence does not appear on its own. It comes from preparation. That’s why we practice regularly. It begins in onboarding and continues as part of our rhythm. We walk through real scenarios that actually show up in the day-to-day. We focus on tone, pacing, phrasing, and staying grounded when conversations get uncomfortable. When a high-pressure call comes up, I join. I stay present without taking over. If the dynamic shifts and the customer starts to dominate, I step in briefly to help reset the tone and bring the focus back to a shared direction. Then I hand the conversation back to my rep. The goal is to build capability, not dependency. After the call, we reflect together. We talk through what worked and where we can fine-tune the approach. That space, where someone can try, miss, and improve, is where real learning happens. If your team struggles when conversations get tough, ask yourself whether they’ve been given the space and structure to train for those moments or if they’ve been left to figure it out while under pressure.

You spend a week training new hires. Product knowledge, sales process, CRM basics. Friday arrives. How do you know if any of it stuck? Most companies end training with a survey: "How would you rate this experience? Any feedback?" That tells you if they liked the donuts. Not if they can sell. Give the ol' "Friday Test" a shot: Every new hire presents on Friday. AEs give a customized demo. SDRs do a cold call role play. CSMs walk through an onboarding scenario. You get the idea. Their direct manager watches. Either live or recorded. No exceptions. Here's a few reasons why this works: 1. It forces real application. You can't fake your way through a live demo. Either you understand the product or you don't. 2. It sets expectations immediately. Come Monday, their manager knows exactly what they're getting. No surprises in month two when the rep can't handle basic discovery. 3. It identifies problems early. By Tuesday of training week, you know who's going to struggle. The Friday test confirms it. 4. It creates accountability for training. When managers see the output, they care about the input. Suddenly training quality matters to them. Naturally, switch the format up by role: - AEs: 15-minute demo to a "prospect" (other new hire or trainer). Must include discovery, demo, and next steps. - SDRs: Live cold call to a real prospect or detailed role play with objection handling. - CSMs: Onboarding walkthrough with a mock customer scenario including potential roadblocks. Some things to inspect for: - Not perfection. Competence. - Can they handle the basics without falling apart? - Do they understand the process, even if execution needs work? - Are they coachable when they make mistakes? As with anything else related to development, the follow-up is critical. The manager gives feedback IMMEDIATELY. Not in a week. Not in their first one-on-one. Right after the presentation. "Here's what you did well. Here's what needs work. Here's what we'll focus on in your first month." Some people won't make it through the Friday test. They'll bomb the demo, freeze during the role play, or clearly demonstrate they're not ready. Good! Better to find out now than six months into their ramp. Regardless, the Friday test forces everyone to prove they can do the job, not just sit through the training. Your managers get a real preview of what they're working with, and your new hires get immediate feedback on where they stand. And you get to sleep better knowing that everyone who "graduated" can actually function in their role. Remember that the goal isn't to complete training, but it's actually to produce functional reps. And the only way to know if you've done that is to make them prove it.

One team I worked with increased their discovery to demo conversion by 40% in just 30 days with consistent role playing. But… Before I started working with them, they used to HATE it! Here’s what their sales leader said: "Marcus, my team hates it. It feels awkward and forced. Plus, my top performers don't need it." Here's the exact framework I implemented that transformed their performance (and changed their minds): 1️⃣ Make it unexpected Don't announce who's going next in your meetings This keeps EVERYONE engaged and prepared Your reps should be slightly uncomfortable (that's where growth happens) 2️⃣ Include your stars: Make sure to also pick your top performers This shows the team that EVERYONE needs practice It creates psychological safety for less experienced reps It prevents the "I'm-too-good-for-this" mentality 3️⃣ Make it specific: Don't use generic scenarios ("sell me this pen") Focus on REAL objections your team faces daily Target specific stages of your sales process Address actual deals they're working on 4️⃣ Keep it brief: 3-5 minutes per role-play Immediate, actionable feedback Recognize what they did well and then.. One or two specific improvements to focus on 5️⃣ Create a feedback culture: Have peers provide feedback too Focus on what could be improved, not what was "wrong" Document common challenges for future training Celebrate improvement openly This worked so well that even their top performer came to me and said: "I honestly thought I was too good for this, but you caught me off guard in that role-play and I realized I was leaving money on the table." The reality is simple: every professional athlete still practices fundamentals daily. Every world class musician still practices scales. Your sales team needs the same discipline. One sales leader told me: "I was shocked at how quickly our conversations improved. My team went from dreading role-plays to actually requesting them before big meetings." — Hey sales leaders… want to top this off with a 3 step blueprint to running the PERFECT sales meeting? Go here: https://lnkd.in/gtkFi9CK