Role-Playing Training Techniques

Here's why most reps (and I'll even say most managers) hate role plays. It's because they've been done the wrong way for so long. How most role play sessions go. 1. There is no prep. Rep doesn't know what they are working on. 2. It's not a real account/name/situation they are practicing (I messed this up for YEARS my teams pitched to superbizz for like a decade) 3. It's the full call which not only doesn't full count as practice but even worse... 4. Only 1 repetition. They only get to do it once. 5. Then there is a TON of feedback given, like waaaaaay to much feedback given. Most of it negative or areas to improve. 6. They never actually get to apply that feedback in practice, they are sent out into the game again. 7. BONUS - It's done in front of a large group peers (hot seats anyone) - that is not practice, that's a performance. -- So yeah... No wonder reps and managers dont like practice. What's funny is a very large (not all mind you) but very large % of sales people played a sport or instrument going up. Think about how THOSE practices were run and you can improve your sales practice immenselye. Structured - Set time. Set place. Scenario Based - Pick real scenarios and situtations. SKILL Based - What skill are you working on (the call is not the skill) For UPCOMING games/performances - Pick a a call coming up/an account they are targeting. Chunked - Skills and Drills - Just the disco questions, JUST 2 objections. Short Punchy Feedback - More doing, less talking. - That was good! Do it again, try this! High Energy - This is key! HIGH Repetition - When chunking you can get 4-5 (often times more) repetitions in that same session. THAT is how you practice. That is how you actually can improve skills quickly. Implement that and not only does practice get better... But so do your people!

Founders, role playing feels awkward. But so does losing a deal your team could’ve won. Role playing is probably the single most effective exercise you can do as a salesperson. It feels a bit awkward at first, but that disappears quickly as your teammates join in and you start to see the results. Sales role playing is like a baseball player taking batting practice, an actor going through dress rehearsal or a winner practicing their acceptance speech. Role playing gives you the opportunity to make (and eliminate) mistakes before the “live event.” You never want to be in front of, or on the telephone with, a prospect or customer and not be prepared. You can role play any sales situation. Role playing is particularly effective when going through select deals with your peers and/or your sales manager. Pick an account you want to close or where you want to help move the buying process along. Discuss the strategy and then have someone else play the role of your prospect. Go through the meeting just like you would with your prospect. If you stumble just keep going. One of the benefits of role playing in a group is that you can have multiple prospects firing questions at you from multiple points of view. It always amazes me how two people can be presented with the same information and come up with different interpretations and/or questions. Take advantage of that phenomenon. Another benefit (mostly for the sales manager) of role playing in groups is that it keeps your sales presentations consistent. You may have multi-call deals where the prospect ends up talking to multiple people in the sales organization. It always gives the prospect confidence when they hear a consistent message. At the end of the role play discuss how the “call” went, make any corrections as needed and do it again. You will be amazed how this simple exercise will give you additional insight into your deal, put you more at ease and fill you with confidence. 📌Tip: Record your role-playing sessions. Reviewing these really helps accelerate the learning and acceptance process. 📍Role playing is just one step in building a great sales team. If you're ready to discuss strategy on building your dream team, schedule an introductory call. My scheduling link is in my About section.

There’s no question that AI is transforming the training landscape. From AI’s ability to tailor an employee’s learning journey based on their existing or required skills, learning preferences, and previous courses to virtual training that uses AI chatbots to answer employee questions and provide on-demand microlearning support, AI has opened up lots of developmental possibilities. While some speakers and trainers, understandably, are worried about being rendered irrelevant, here’s some context (and potentially good news) about what I’m seeing when it comes to skills-based communication and leadership training. Organizations are not seeking external training for purely knowledge-based issues, since AI can put together training on just about anything. Good information is not a differentiator. But with more technology comes more miscommunication. Employees may have instant access to information, but retention of that information and the emotional intelligence and ability to navigate high-stakes conversations—these are still deeply human skills and require real-time coaching and training to build. Skills-based trainers and coaches can make the most impact by using role play to help people practice the communication and aligned leadership skills for learning transfer to happen. The L&D initiatives that drive real change aren’t about knowledge acquisition—they’re about skill embodiment. And the best way to ensure that learning sticks? Live, immersive role-play training. A lot of trainers say they use role-play for skill development, but in reality, it’s often a surface-level exercise—scripted, predictable, and failing to replicate the real-world pressures of high-stakes communication. What True Role-Play Training Looks Like -Learners experience the tension and unpredictability of real conversations. -Scenarios are customized to specific challenges. -Participants get live coaching and feedback to adjust in the moment and get to retry critical communication. -There's psychological safety and trust for high-stakes practice—before it counts in real life. Role-play training isn’t just a nice-to-have; it’s becoming a business imperative! As AI reshapes the learning landscape, the ability to embody skills—especially in high-stakes communication—is what sets impactful training, like what we do at Step into Your Moxie, apart. The most effective L&D initiatives aren’t just about acquiring knowledge; they’re about building the confidence and competence to use it when it matters most. How are you seeing AI impact leadership and communication training in your organization or consulting practice?

What if learners could practice tough conversations and get a realistic response back from a video? I’m exploring a DIY concept using Colossyan avatars, OpenAI, and n8n to create responsive roleplay scenarios. The idea is a learner watches a video prompt, responds in writing (voice or camera would be ideal but starting here), and then gets a new avatar reply, generated based on their input. It’s a lightweight flow, but the potential is big for soft skills practice. Like, performance reviews, compensation convos, feedback, stakeholder alignment. These moments are high-impact and hard to rehearse in traditional formats. There are tools that do pieces of this. But by building it yourself, you get full control of the experience, from how realistic the responses feel to how feedback is delivered. You’re not limited by someone else’s UX or roadmap. Of course, this isn’t meant to replace coaching or live training. But it could fill the gap between content and real-world practice, especially when time, access, or psychological safety are challenges. Right now, this is just an experiment. Curious to hear, where do you think something like this could work well? #InstructionalDesign #LearningDesign #eLearning #WorkingOutLoud #EdTech #DigitalLearning #AIInLearning

Stop practicing on your prospects. You're throwing away opportunities. Don't get me wrong, the best way to learn is by doing. But you shouldn't try out a new talk track for the first time in a live situation. You would never apply this logic in any sport. In most sports, you practice far more than you play. By a factor of 5 or even 10:1. Here's how you can leverage ChatGPT to practice cold calling: ✅ Prompt "You are a [persona] who works at a company like [typical target account]. You're busy, hard to get a hold of, and you're not going to like that I'm cold calling you. I've attached my cold call talk track, along with how I should be handling objections. Please follow the Outbound Squad framework. I've also uploaded a few transcripts from recent cold calls with this persona. Use that as a guideline for how these calls usually go. Here's my company [website URL] so you have a better idea of what I do. I want to role-play a cold call with you. Here's exactly what you should be critiquing: 1. Intro I will be using a permission-based intro. Listen to see if I stumble over my words, don't sound confident, or hesitate. If I do any of those things, give me an objection. Or hang up. I will then use a Reverse Pitch. The idea here is NOT to pitch my product. But to pitch the problems we hear from your peers. Again, if you hear me start to pitch the product—give me an objection or hang up. 2. Hook During this call, we should get to a problem you might have that our solution could solve. I should be engaging you with great questions to find problems. Feel free to throw out more objections as well. If I don't do a great job of handling those objections, hang up. 3. Close Lastly, I should be making an explicit ask for the meeting. When I set the meeting, you should be listening for a triple confirmation. I should confirm the day/time with you and ask you to accept the calendar invite on the call. I should be confirming the agenda with you. Lastly, I should let you know the confirmation process. After I complete the call, I would like feedback on two things I did well and two areas for improvement. Got it? Let me know and I'll speak with via voice." ✅ Practice Send that promp. Then start talking back and forth with ChatGPT. This works best on the premium version. I like to do this for about 10 min before a cold calling block. Or anytime I'm trying to work out new messaging. ~~~ Leslie Venetz joined the Outbound Squad podcast to talk about practice and much more. Check out the full interview here: https://lnkd.in/edH7_vV8 How are you leveraging AI to practice your cold calls?

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

Role Plays ... We both love them and hate them. At their best, they're a great way to build new muscles. At worst, just a chance for people to goof off in a breakout room. Now you can do them with AI, which is great for more at bats, or when you need to role play a first meeting with an industry SME or a specific ICP. But there's great value in having your team do these live to build shared experience and get them coaching eachother. How have you made them productive and useful for your team? Some things I've been incorporating: 1. Kick it off by creating a safe space for learning together 2. Ideally a role play should be done on a real, current Opportunity. If that's not possible, on a current Lead for a real Account. If that's not possible, on a fictional scenario, but it better be very realistic. Otherwise it's too contrived. 3. Role plays should be short. Ideally you're practicing just one behavior (how to open a call, a common objection, or introducing one differentiator) If they go on longer than a few minutes, you lose people. 4. Your best coaches are more experienced sellers currently or recently in the same role. So create your breakout room groupings with intention. 5. After the role play, start the feedback portion by having the person self assess on how they did and what they would change. Then ask for feedback from their peers. 6. Remove friction that keeps people from focusing on what you want them to practice, by: * Having them write possible questions, proof points, examples, etc. in a conversation planner before they start * If you're trying to change a behavior, and a sales scenario is too complex, can they practice in a different context? (i.e. "Tell me about your pet." as a prompt to practice listening and keeping the focus on the prospect) * Giving the "prospect" and "seller" a set of questions and answers they can use, if what you're doing is completely new to the team. Just let them go back and forth with those the first time to build muscle memory. * Providing an "out" - by letting them phone a friend if they have no idea what comes next * Have a couple people do an example role play before you go into breakout rooms. (Let them prep for it ahead of time, so you can be sure it will be a good example) 7. Finish by having the team share their key takeaways Role plays don't have to be painful. And ideally they make the real thing easier and more fun. #roleplay #saassales #enablement #salesenablement

RSP: A Realistic Preview of Campus Placements, Beyond Role Play! When we hear the term Recruitment Simulation Process (RSP), many may assume it is just another classroom activity or role play. But RSP is far more than that. It is a comprehensive and immersive experience that mirrors the realities of campus recruitment while engaging students meaningfully on both sides of the hiring process. In this initiative, selected students act as recruiters. This is not a performance based on assumption but a role that demands preparation and analysis. The student recruiters begin by researching actual companies that have visited the campus. Their preparation involves: 1. Studying profiles of past recruiters and understanding industry domains, roles offered, and compensation details. 2. Analyzing real recruitment processes including the sequence of tests and interviews. 3. Understanding the difficulty levels of online aptitude or domain-specific tests. 4. Exploring commonly asked group discussion topics based on real trends. 5. Identifying interview patterns, commonly asked technical and HR questions, and the kind of traits companies value in candidates. Meanwhile, the rest of the class participates as job applicants. Each student receives a realistic Job Description (JD) created by the student recruiters. Based on this, the students: 1. Tailor their resumes to match the job requirements. 2. Attempt an online test to assess their current skill levels. 3. Participate in a group discussion to test clarity of thought and communication. 4. Attend mock interviews, receiving valuable feedback on presence, articulation, and domain knowledge. This process gives students a complete picture of what to expect during placement season. It helps them identify areas they need to work on and how to present themselves more effectively. RSP is not just a simulation. It is a powerful tool to shift students from simply preparing for interviews to truly becoming placement ready. #RecruitmentSimulation #CampusToCorporate #SoftSkillsTraining #PlacementPreparation #HigherEducation #ExperientialLearning

What is a training activity people don't like but nearly all agree is super effective? Sitting in a training session what is one activity most people hope isn't on the agenda but deep down inside agree is very helpful? Role Plays. Back in my sales & sales manager days, role plays were a powerful way to apply skills in a dynamic setting while challenging your recall of information in real time. We didn't like them at all but agreed they helped us improve. They can be used for training of all sorts of disciplines, not just sales people. Role plays are outstanding to apply information in real time and have to adjust based off what the other person. And (assuming you built a safe environment) the "pressure" of performing really shows what they did or didn't retain from the session. Tips to make role plays more effective: ✅ Prepare scenario ahead of time focused on practicing specific skills ✅ Build scenario around real situations for the industry ✅ Build scenario that guides participant to practice specific skills ✅ Consider what is great/good/needs improvement outcomes ✅ Give the audience a job - ex: observe and listen for ____________ ✅ Prompt them to self evaluate: what was good & you want to repeat, what is ONE thing you'd improve for next time What one question can I answer about using role plays to improve your training programs?

When Pursuit was a smaller company, living or dying by each client, we were constantly working to get better at our craft so that we didn't get left in the dust by more experienced players. Sales role play, shadowing, advanced training, etc. We still do a lot of this, but I realized the need to lean heavier into sales role playing for our Account Management team! Afterall, "Practice should be harder than the actual game". So we did 15 min. of role play at the end of our weekly Account Management meeting yesterday and it brought so much life to the room! Sales role playing is uncomfortable, and we admitted that, but then we leaned into the uncomfortable in order to get better. Here's how we structured our role play: 1️⃣ A volunteer role-played a real-world scenario. 2️⃣ The team provided constructive feedback on what worked, what could be improved, and alternative approaches. 3️⃣ We ran it back giving that person a second opportunity to adjust and improve based on the feedback. The third step is the most important. Give the salesperson the opportunity to be coachable and "fix" any mistakes they think they made. Everyone leaves feeling more confident.