Role-Playing for Skill Development

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?

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.

Speaking lessons built around escape rooms and imaginative role play are some of the most effective ways I develop oracy in both native and ESL learners. These tasks require sustained talk, collaboration, and thinking aloud, which is why my students are deeply engaged and regularly ask when the next lesson will be. A simple example is asking them to take on the role of an inanimate object, such as the ocean, a pencil case, or a chair, and speak one sentence about what it feels like to be that object. I then extend this through teacher-led questioning, asking prompts such as: Tell me about your typical day, What is your biggest worry for the future? or What do humans do that affects you most?* Students must remain in role, selecting language carefully and responding thoughtfully. Then reverse. Students step into the role of humans, and I continue questioning with prompts like: What else could you do to solve this issue?, Is a compromise possible? or What responsibility do humans have here? This role reversal deepens perspective-taking and requires students to evaluate ideas from more than one viewpoint. Through such activities is how students use talk to think. As they speak, they plan what they want to say, monitor whether their message makes sense to others, and adapt their language in response to new ideas. In problem-solving tasks, they draw on what they already know, identify gaps in understanding, test ideas aloud, and revise their thinking as the task unfolds. Spoken language becomes a working space for thought rather than a finished performance. Critical thinking is embedded as students analyse causes and consequences, justify opinions, challenge assumptions, and explain reasoning. Questioning sits at the centre of this process, yet not all learners arrive with the ability to ask productive questions. Some require explicit modelling and scaffolding, while others benefit from being pushed to refine and extend their thinking. During these lessons, I do not interrupt, avoid correcting language in the moment and instead focus on listening for reasoning, vocabulary choice, and interactional strategies. This allows students to take risks, think aloud, and use language as a tool for problem solving. Feedback is then planned and delivered intentionally, based on observed needs. Careful planning for individual students remains essential. Some learners excel at empathy and perspective-taking in role play, while others are stronger at logical reasoning or leadership. Differentiated questioning and targeted prompts ensure that each student is supported and appropriately challenged, allowing different strengths to contribute meaningfully to the task. When speaking tasks are cognitively demanding, socially purposeful, and thoughtfully structured, oracy develops alongside metacognitive awareness and critical thinking skills that extend well beyond the classroom. #Oracy #ESLTeaching #CriticalThinking #Metacognition #StudentVoice #SpeakingSkills

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

Aspiring to lead? Make role-playing a regular part of your development journey—it’s one of the most effective ways to prepare for the real thing. 💡 In my Succession-Ready Leader Mastermind, for instance, we use role-playing exercises to simulate real-world challenges leaders face. Why? Because there's no substitute for practice. Role-playing allows leaders to: 😎 Test and refine their skills in a safe environment. 😀 Experiment with new approaches to challenging situations. 😊 Build confidence to handle the unexpected with grace. Whether it’s navigating tough conversations, influencing stakeholders, or making high-pressure decisions, these exercises sharpen both emerging and seasoned leaders alike. After all, leadership isn't just about knowing what to do—it's about doing it with confidence and skill when it matters most. What’s a skill you’d like to practice in your leadership toolkit? Share below! 👇

ROI in talent development is a white whale. You know how valuable training is, but translating that into a sellable narrative to your CFO is the tough part. Quantifying soft skills has historically been near impossible. The way most companies try to track ROI – if they try at all – is through self-reported participant surveys. You gather a bunch of high scores, share them with your executive team, and bam — there's your proof that the training was effective. 5s across the board! But deep down we all know that this is really not ROI. The trainees could rate the program a 5/5 based on anything—they enjoyed themselves or the environment was fun and interactive. The CFO and CEO are not optimizing for how the trainees felt. They care about the ROI for the organization. They care about going way deeper to quantify the value of talent development by tying it back to sales pipeline and retention. There is good news, though. At Exec, we can actually quantify performance by looking at how a trainee performed before and after the training. Take our AI Roleplay tool, for example. Brief summary: AI Roleplays is a tool that allows team members to practice high-stakes conversations with hyperrealistic AI characters, providing immediate feedback, scoring, and skill certification. We score your team members' development as they complete assigned simulations. Once they reach a score you've labeled as an improvement marker, they're ready to get back in the field. Now, in every call afterwards, you'll immediately see results. Recently, we ran a customer through a communications training program. Their original scores were in the low 60's (failing by U.S. education standards). At the end of the month-long program, they were scoring in the mid-90's. That's over a 30-point increase. They went from objectively failing to concretely winning. And the practice environment makes it possible. They got the reps in a simulation that very closely mirrored their ultimate performance environment. And look, you don't have to stop doing participant surveys. You can use those surveys to adjust the program for future cohorts and to give some warm-and-fuzzies to the program. That's valuable, but it's not ROI! My DMs are open if you want similar results.

Role-playing isn't just for athletes; it's for sales pros too. Here's how practice builds confidence. Sales calls can feel like stepping onto an unfamiliar field. You face objections, rejections, and even moments where someone tells you exactly where you can go (you know what I mean). But here's what separates sales pros from salespeople: preparation. Before any call, I focus on these steps: 1️⃣ Mindset Work ↳ Detach from outcomes. Rejection isn’t personal—it’s about timing, not you. ↳ Get your energy right. If athletes warm up before games, why shouldn’t you? 2️⃣ Framework Development ↳ Every call needs structure: intro, body, conclusion. ↳ Anticipation is key. Think about objections before they arise. During Locomote days, we flipped objections like “no one’s traveling” and turned them *into* reasons for engagement. 3️⃣ Research ↳ Spend one minute on LinkedIn. Find three things about your prospect. ↳ Earn your spot on their calendar by showing you understand their business. 4️⃣ Role-Play ↳ Practice objections with colleagues or on Zoom. ↳ Test your tone, language, and approach. Adjust based on feedback. Role-playing isn’t about memorizing scripts. It's about refining your framework so you’re ready for anything. (𝘠𝘦𝘴, 𝘦𝘷𝘦𝘯 𝘵𝘩𝘰𝘴𝘦 “𝘣𝘢𝘥 𝘵𝘪𝘮𝘦” 𝘤𝘢𝘭𝘭𝘴.) 𝗛𝗲𝗿𝗲’𝘀 𝘄𝗵𝗮𝘁 𝘄𝗼𝗿𝗸𝘀 𝗳𝗼𝗿 𝗺𝗲: → If I catch someone at an off moment, I acknowledge their position. “Sounds like I’ve caught you at an inconvenient time—can we reschedule?” → I lower my tone, slow my pace, and *never* argue. Empathy turns tension down. And sometimes, even after all this, you'll get pushback. That's okay. Not every call leads somewhere. But every practice session builds confidence for your next one. What’s your favorite objection-handling strategy? Have you tried role-playing before? Would love your thoughts!

Most sales organisations don’t underperform because reps “lack motivation”. They underperform because they lack clarity, practice, and structure. And when those three pillars are missing, everything becomes noisy: • hiring becomes guesswork, • coaching becomes inconsistent, • onboarding becomes slow, • training never sticks, • and performance issues repeat. I’ve seen this pattern again and again – in the teams I’ve supported directly, and in the stories leaders share with me every week. But something powerful happens when you connect three elements together: 1️⃣ Role-specific competencies 2️⃣ Clear use cases for AI roleplay 3️⃣ High-quality, realistic practice scenarios Suddenly, reps know what good looks like… They know how to practice it… And they have the tools to practice it on demand, without waiting for a manager or a workshop. That’s when enablement stops being a “set of events” and becomes an operating system. --- Over the past months, in partnership with Hyperbound, I’ve been building a combined framework that ties all three pieces together. The result is a new, expanded one-pager that includes: 🧩 1. Sales competencies (SDR, AE, AM, CSM) A full role-specific breakdown of the skills, behaviours, and knowledge areas that are key for all major IC GTM roles. 🤖 2. 31 AI roleplay use cases A practical map of how AI can be used to sharpen skills, improve coaching, accelerate onboarding, enhance messaging, and scale practice. 🎭 3. Ready-to-use AI roleplay scenarios Cold calls, discovery, renewal conversations, objection handling, competitive selling, negotiation – all designed with clear objectives, buyer profiles, and criteria for success. Put together, they create a complete skill-building system: • Clarity → what great looks like • Practice → realistic, repeatable scenarios • Scalability → AI that adapts to every rep, every skill, every moment This is the kind of structure I wish I had years ago – not as theory, but as a practical spine to build high-performance teams. --- 💬 Where do you see the biggest gap between what your team knows, what they practice, and what they can actually do in live conversations? If you’d like the high-res one-pager + the full combined guides, drop “master roleplay system” below and I’ll share it with you. ✌️ #sales #salesenablement #salestraining #ai

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.

𝗧𝗛𝗢𝗨𝗚𝗛𝗧𝗦 𝗢𝗡 𝗔𝗜-𝗘𝗡𝗔𝗕𝗟𝗘𝗗 𝗥𝗢𝗟𝗘 𝗣𝗟𝗔𝗬 (𝗔𝗡𝗗 𝗥𝗢𝗟𝗘 𝗣𝗟𝗔𝗬 𝗜𝗡 𝗚𝗘𝗡𝗘𝗥𝗔𝗟) I'm bombarded with InMail about AI-enabled role play and all the tools that support it. They share stats about improved win rates, bigger pipelines, and higher quota attainment. 𝗠𝘆 𝗧𝗵𝗼𝘂𝗴𝗵𝘁𝘀: 🔹First, I love the idea of AI-enabled role play. It allows reps to practice more than they do, which is usually zero. I'm a fan. 🔹I've seen daily role play take a sales team from last place in their division to second place in under a year. It works. 🔹Because I've seen the positive impacts of regular role play, I have no trouble believing the impact statements and stats from these vendors. 🔹Thinking managers are too busy to role play is ludicrous. If you think that, you don't understand what frontline sales managers (FSMs) should be doing with their time. Their most important job is to improve the performance of their team. Field training, coaching, counseling, and providing feedback should be a major part of their role. FSMs should hire, train, coach, motivate, manage, and lead—all to improve sales performance and develop a high-performing team. Get this right and watch your sales results improve steadily. 🔹Role Play Reruns (role play, get feedback, role play again to incorporate it; rinse, repeat) are the single fastest way to improve skills and increase confidence in the shortest time possible. 🔹In studies, a lack of confidence correlates to lack of transfer (not using the skills). High confidence correlates to using the newly learned, coached, and/or practiced skills (improved transfer). Role plays done well improve confidence. 🔹Psychological safety during feedback improves the likelihood suggestions will be used. Understanding someone's personal motivators and couching feedback accordingly further improves that likelihood. (Remember: PAM Orders Power BARS = Purpose, Autonomy, Mastery, Order, Power, Belonging, Achievement, Recognition, and Safety.) So, please, CEOs, sales leaders, FSMs, and enablers of all flavors, use AI-enabled role play. Maximize it. But do not let the humans off the hook, especially your frontline sales managers. 𝗦𝗼𝗺𝗲 𝗥𝗲𝗮𝗱𝗶𝗻𝗴/𝗩𝗶𝗱𝗲𝗼𝘀: 🔹𝘚𝘢𝘭𝘦𝘴 𝘓𝘦𝘢𝘥𝘦𝘳𝘴: 𝘐𝘵’𝘴 𝘛𝘪𝘮𝘦 𝘵𝘰 𝘎𝘦𝘵 𝘚𝘦𝘳𝘪𝘰𝘶𝘴 𝘈𝘣𝘰𝘶𝘵 𝘗𝘶𝘳𝘱𝘰𝘴𝘦𝘧𝘶𝘭 𝘗𝘳𝘢𝘤𝘵𝘪𝘤𝘦 & 𝘚𝘬𝘪𝘭𝘭 𝘔𝘢𝘴𝘵𝘦𝘳𝘺: https://lnkd.in/eP8-PP_E 🔹𝘔𝘢𝘹𝘪𝘮𝘪𝘻𝘪𝘯𝘨 𝘵𝘩𝘦 𝘗𝘰𝘸𝘦𝘳 𝘰𝘧 𝘙𝘰𝘭𝘦 𝘗𝘭𝘢𝘺 𝘢𝘯𝘥 𝘚𝘢𝘭𝘦𝘴 𝘚𝘪𝘮𝘶𝘭𝘢𝘵𝘪𝘰𝘯𝘴:  https://lnkd.in/eU_HhPMW 🔹𝘛𝘩𝘦 𝘗𝘰𝘸𝘦𝘳 𝘰𝘧 𝘙𝘰𝘭𝘦 𝘗𝘭𝘢𝘺 𝘙𝘦𝘳𝘶𝘯𝘴: https://lnkd.in/eJR7YQjg 🔹𝘏𝘰𝘸 𝘵𝘰 𝘗𝘳𝘰𝘱𝘦𝘳𝘭𝘺 𝘋𝘦𝘣𝘳𝘪𝘦𝘧 𝘢 𝘚𝘢𝘭𝘦𝘴 𝘙𝘰𝘭𝘦 𝘗𝘭𝘢𝘺:  https://lnkd.in/erDmReD8