8 Sales Role Play Exercises to Prepare Your Team for the Win

Here’s how most sales role-play exercises go:

The manager gathers the team and exclaims (with just a bit too much excitement) the plan to do some role-playing.

The first exercise covers the most obvious objections that everybody already knows how to handle.

The second exercise is too fake to learn from. The third is worse.

What follows is a poorly structured, incredibly awkward, and minimally effective goof-off session.

Role-play exercises are crucial to developing strong conversational tactics and messaging delivery. It’s mind-blowing how little attention is paid to doing them right.

Medals are given out at the championship, but you earn them in practice. It’s time to take role-play seriously.

I have participated in and run thousands of role-play exercises for sales. Here are the 8 exercises I have found most effective, and tips to execute them right.

8 Highly Effective Sales Role-Play Exercises

  1. Learning is Listening
  2. Objection Island
  3. Persona Mixed Bag
  4. Extreme Conditions (Hot Seat)
  5. Role Reversal
  6. Boardroom Brawl
  7. The Ringer
  8. Pay the Pros

Exercise #1 – Learning is Listening

Before we can help anyone on the other end of our sales efforts, we must become expert listeners. That’s why this exercise needs to be repeated regularly!

It can be performed in a large group, or with as few as 2 people. If in a group, either segment into smaller groups, or play with the whole group, “telephone” style.

  1. One person will begin by making a statement. It can be directly related to your organization or something entirely abstract.
  2. The next person in line will begin their statement using the last three words of the previous person’s statement.
  3. Continue until you have circled the entire group, or for a specified period of time.

This improv comedy technique will help reps learn to pay attention to what others are saying, instead of living within their own agendas and planned responses.

Exercise #2 – Objection Island

This is a great role-play exercise to run anytime your team is together. It not only provides a great field for practicing rapid fire objection response, but allows team members to hear ideas, engage in peer coaching, and shake off some nerves through a shared experience.

Here’s how it works:

  1. Begin by calling out a rep, then hurling a common objection heard during your team’s calls.
  2. The rep has 5 seconds to respond, and do so in a way that will allow the conversation to progress positively, or they are voted off Objection Island.
  3. If the rep is successful, the rep then calls out a person of their choice and repeats the process.

Each time, the objection and response must be unique. Typically the sales leader is the final judgment for timing, response quality, and originality versus other responses.

If you want to vary things a bit, the sales leader can throw out the same objection to every team member sequentially, following the same response guidelines.

RELATED: Four Types of Sales Objections and How to Overcome Them

Exercise #3 – Persona Mixed Bag

This role-play exercise helps a rep sharpen many tools at once –– in particular, the ability to interact successfully with the many personas they’ll work with within your target organizations.

Begin this exercise with a list of personas typically targeted and encountered. Examples of these can be CXO, Director of X, or gatekeeper. Additionally, you can get creative by adding personality traits such as “super direct,” “in a hurry,” “analytical,” or “distracted.”

  1. Write each one down on a small sheet of paper, fold, and place into a bowl or hat.
  2. At the beginning of the role-play (once the goal of the session is defined), the person playing the prospect will draw a piece of paper from the hat and adopt the qualities written on it.
  3. Now perform the role-play, provide the feedback, and start from the top.
  4. After at least 2 passes with that persona and/or trait, grab a new one.

Keep in mind, the goal and tactics for the rep should largely remain the same, save for any tweaks from feedback.

Exercise #4 – Extreme Conditions (Hot Seat)

This exercise isn’t for the faint of heart and should definitely be reserved for those strong teams that can handle a bit of heat. It will add an edge of difficulty that (hopefully) won’t exist in real-world calling.

The idea is exactly the same as warming up before an inning at bat: A batter will swing a weighted bat before stepping up to the plate. Once they drop the weighted bat and pick up the normal one, it feels incredibly light and can be moved through the swing plane at an incredible rate.

  1. To begin, the sales leader will outline the rules.
  2. Pitches must be perfect. Any deviation to the ideal will result in a “buzzer” or “gong” sounding, and the rep will be moved to the back of the line.
  3. If the rep nails it, the role-play continues, leading to objections and other opportunities for the rep to get it just right or get out of the hot seat.
  4. This can continue for many cycles if the sales leader really wants to turn the heat up.

A variation on this is to require the next rep in line to pick up exactly where the last rep left off.

Exercise #5 – Role Reversal

This should be an obvious one: Turn the role-play around for the rep, allowing them to assume the position of the prospect.

  1. The sales leader conducts the ideal role-play, objection responses, conversational tactics, and closing techniques.
  2. Allow the rep to provide feedback, or comment on what they thought worked well or not at all.
  3. After a round or two, compile the items that worked well and switch seats again.
  4. Using the list of winning tactics, help the rep develop their own comfort level with them. Work on wordsmithing and delivery until the rep has a strong grasp of the skills.

This also works very well with top sellers demonstrating as the sales leader would.

Exercise #6 – Boardroom Brawl

This is another exercise best left to culturally strong, performance-oriented teams.

  1. Gather the team in your boardroom. Come prepared with some recorded calls that could have gone better. Make sure you have at least one for all reps present so the field is level, and they all experience this together.
  2. If you have a large team, break them up into manageable chunks, letting everyone know that their time will come.
  3. Now, play the call for all to hear.
  4. Once it is over, immediately adopt the persona from the prospect on the exposed call (make sure you have studied the call, and prepared a transcript to work from).
  5. Have the rep begin a role-play based on the exact scenario just played for the team. The goal here is to help the rep correct their own mistakes. It gives them a mulligan of sorts and also applies a bit of pressure as the entire team is witnessing the process.


  • Encourage peer coaching during these brawls, and even to add a competitive twist by rewarding points and prizes to reps who can successfully correct the call.
  • Have a different rep take over after the call is played and handle it in their way.

NOTE: A great side effect of “Boardroom Brawl” and “Extreme Conditions (Hot Seat)” is the softening of Ego that can wreck a salesperson’s ability to improve their skills and natural talents.

RELATED: Sales Call Script for SDRs: 5 Questions You Absolutely Must Ask Your Prospect

Exercise #7 – The Ringer

It is one thing to act out a persona during a role-play. It’s an entirely different thing to seek out the exact persona within your organization and invite them to participate.

If your team targets C-Level prospects regularly, go grab your C-Suite (they probably aren’t very busy anyway…) and bring them into your sales training!

  • Have them simply be who they are, and treat your sales team as they would the numerous salespeople who are attempting to connect with them every single day.
  • Solicit their feedback on the tactics and have them detail what is important to them with respect to their position, demands, goals, and motivators.

If you can draw on this wealth of experience and knowledge within your own organization, you can bet it will pay dividends as you target these folks in other orgs.

Yes, everyone is different. But never forget the Normal Curve. The majority of C-Level executives face similar challenges and demands, have similar thought processes and certainly similar motivators. There are always outliers, but you’ll be far better prepared if you focus your improvement efforts on the majority.

Exercise #8 – Pay the Pros

Anytime a leader has to consider implementing a new idea, they come to the “build vs. buy” conundrum. If you are at this crossroad and tend to follow the “buy” approach, reach out to the guys over at Roleplay.co.

At Roleplay’s “sales gym,” your team can participate in real-world-based sales role-play training led by industry experts and receive feedback from the best in the game today. They can also help you build out your own programs to maximize your time and effort spent training your teams.

RELATED: Winning Sales Training Advice from a Long-Time Test Prep Instructor

Tips for Better Sales Role Play

Set a Practice Schedule

Proper sales practice is not a once-a-week or once-a-month activity. It is at least a 2–3 times-per-week directed effort to improve highly specific parts of your sales attack.

It not only works out the “what” you say but the “how” and “why” as well.

Set your team up for maximum success by planning practice time in advance. You should front-load your practice time and stretch it out as you improve your targets.

For example, if your company launches a new product line, role-play every day for 2 weeks. As reps improve, reduce role-plays to 3 times per week, then 2, then 1 if they are really getting dialed in.

Prepare Your Scouting Report

Build your role-play routine based on real-world interactions. Leveraging technology is your best play here.

Tools such as Gong.io and Chorus.ai can provide insights into trouble spots in your reps’ talk tracks, tactics, and delivery. It can also line up some fantastic objections to practice against.

  • Begin collecting popular objections while reviewing call recordings.
  • Then use them to test your reps rapid-response abilities and train their skills in overcoming them.

Expand Your Training Focus

Positioning statements and objection responses are definitely important parts of role-plays, but far from the only parts. Crank up the effectiveness of practice sessions by keying on other important parts of successful sales conversations.

Intonation, energy and articulation are vital to successful talk tracks, as well as pace and vocabulary. Even the best messages and objection responses can be done in by a lack of enthusiasm, speaking too fast/slow, and using words that are insider-speak or used to boost the perceived intelligence of the rep.

An excellent way to ensure you are listening closely for these characteristics is to create a scorecard for each session.

  • Use a scale of 1-10 for each category.
  • As you work through your role-play schedule, look for a pattern of positive improvement (or negative). Trust me, it will emerge.
  • You can also aggregate these scores and create an overall performance matrix to classify capabilities. This also provides opportunities for competitions and incentives tied to intentional improvement.

No Surprises

Provide your reps (or have your reps provide you) with the framework and intended goals for each practice session. This produces more creative thinking for the reps, helping them to develop quality delivery in their own voice.

As you grow your practice routine, reps will begin identifying their own areas in need of improvement, and set goals they want you to help them with.

Since keeping your sales role-play exercises as close to the real-world as possible is key to its success, having a rep prepare for the role-play as they would a real sales call is in line with this directive.

Be the Buyer

It’s time to role-play! Typically, role-plays are conducted between rep and rep, or rep and manager. In either scenario, the player in the buyer’s seat has to lay down the team-member hat and put on the buyer hat.

Even the most accomplished salesperson or sales leader has been a customer at some point. Use this experience to become the customer for your training partner.

  • Truly consider the persona and scenario you are working within.
  • Think of the daily challenges faced by the persona/role, what is important to their business, and how they may react to this particular call.
  • It can be difficult, especially in the rep-to-rep role-play exercises, but try to keep the wild and crazy responses to a minimum to maximize the effectiveness of the training session.

If you provide feedback, they will come

This is gold: the secret sauce where the rep finally steps into the cage for batting practice.

Feedback is how role-plays create behavioral change in reps, and there is a “right way” to do it.

ALWAYS keep your feedback kind and encouraging. Sales is difficult. We all know that. Practice is for improving, so let the prospects dish out the beatings.

Provide real-time coaching. Don’t allow a rep to continue past a real hiccup. Stop the role-play, provide the feedback, then begin the role-play again. This will ensure the rep develops along the correct pathways and with proper timing.

If the rep is progressing nicely with the role-play, provide positive reinforcement by allowing the session to progress towards a win for the rep. Don’t be afraid to pepper in some objections as necessary, but again, reinforce positively by allowing progression if the rep deftly overcomes them.

Finally, debrief the session with the rep. Provide the rep with their scores, discuss goal attainment, and follow up for effectiveness of sales objectives.

Wrap up

There has never been a championship team, gold medal Olympian, or Greatest Of All Time that achieved winning status without practice and training.

In fact, a case could be made that far more of their time was spent in practice and training than actually competing.

If your goal is to equip your sales teams with the highest ability to convert calls and close deals, there is no better way to achieve this than regular, reality-based, and highly structured practice.

Make the time for it, build your practice facilities, and transform your teams into a well-oiled closing machine!

Director of Sales at REPAY. Adam is a proud father of 4 wild and wonderful children, Husband to an incredible saint of a wife, and passionate about all things sales! His goal is to help salespeople improve their win rates through a focus on intentional improvement, coaching, and tactics that drive results far beyond quotas! When not helping teams ramp up production, Adam can be found fishing the gulf coast of Southwest Florida and keeping up with his young and growing family.

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