10 Proven Ways to Make Sales Role-Plays Feel Natural (and Actually Helpful!)

Want to hear your sales team groan? Tell them it’s time for sales role-plays. It’s the activity sales professionals love to hate because it feels awkward and uncomfortable. Role-playing combines two of the most dreaded soft skills—public speaking and acting—with a public test of career competence. It’s no wonder sales teams cringe at the mere mention of it.

But here’s the thing: sales role-plays are incredibly effective. They are a form of deliberate practice, a method proven to improve performance. As researcher Anders Ericsson explains, “Deliberate practice involves stepping outside your comfort zone and trying activities beyond your current abilities. Simply wanting to improve isn’t enough—people also need well-defined goals and the help of a teacher who makes a plan for achieving them.”

While sales role-plays might never be your team’s favorite activity, they don’t have to be awkward or dreaded. With some thoughtful planning and structure, role-plays can become a powerful—and enjoyable—tool for building sales skills. The statistic reinforces this, “Sales reps who participate in regular role-playing and practice sessions improve their performance by 24%.” (Sales Readiness Group​.)

Here are 10 ways to make sales role-plays less awkward and more effective:

1. Set Structure and Lead by Example

You can’t expect your team to embrace role-plays if you’re unwilling to participate.

One of the most effective approaches involves a two-part structure:

• Start with a Showcase Role-Play: Have two leaders (e.g., a sales manager and a top-performing rep) conduct a pre-planned role-play in front of the team. This demonstrates the skill or behavior you want the team to focus on while setting the tone for the exercise.
• Break into Small Groups: Divide the team into groups of three, where each person rotates through three roles: the Customer, the Salesperson, and the Evaluator. This allows everyone to observe and practice multiple scenarios while eliminating the pressure of performing in front of the whole team.

This structure not only reduces the fear of public speaking but also creates more opportunities for learning and growth by exposing reps to multiple role-play scenarios.

2. Set Specific Goals

Don’t try to tackle everything in one role-play. Instead, focus on one or two skills at a time.

For example:

• One session might center on smoothly incorporating a value proposition into a conversation.
• Another might focus on effectively handling a specific objection.

By narrowing the focus, you reduce the pressure on reps to “get everything right” and allow them to hone specific skills. Provide feedback on those targeted areas rather than critiquing the entire performance.

3. Clearly Define the Scenario

Set your reps up for success by providing a detailed and realistic scenario. Clearly outline the circumstances they’ll encounter, including:

• The prospect’s title and role.
• The company type and industry.
• Specific solution interests or pain points.

This clarity eliminates the need for improvisation and helps reps focus on the behavioral improvements you’re targeting. When role-plays mirror real-life situations, they become more relatable and effective.

4. Prepare the Customer Too

The person playing the customer often wings it, which can derail the exercise. Sometimes, they play hardball for laughs; other times, they make it too easy on the rep. Neither approach is productive.

Instead, provide the customer with a detailed persona to emulate. This could include:

• Specific pain points.
• Buying motivations.
• Common objections they might raise.

A prepared customer makes the role-play more realistic and gives reps a better opportunity to practice their skills.

5. Allow Time for Preparation

Would you send your reps into a real customer meeting without preparation? Of course not. Role-plays should follow the same principle.

Once you’ve provided the scenario details, give reps a few minutes to prepare. This not only reduces anxiety but also ensures they approach the exercise with a clear plan. Preparation time sets the stage for success.

6. Develop a Safe Environment

Role-plays should be a safe space for practice and growth, not a forum for criticism or embarrassment. Encourage reps to treat the exercise like a rehearsal for the real thing.

Here’s how to foster a constructive environment:

• Provide feedback that is constructive, not destructive.
• Establish clear guidelines for group feedback to ensure it remains positive and actionable.
• Emphasize that mistakes are part of the learning process.

When reps feel supported, they’re more likely to engage fully and learn from the experience.

7. Rotate Roles

Having everyone take turns as the Salesperson, the Customer, and the Evaluator offers multiple perspectives.

For example:

• The Salesperson practices their pitch.
• The Customer experiences what it’s like to be on the receiving end of the pitch.
• The Evaluator develops critical listening skills by providing feedback.

This rotation ensures everyone understands the sales process and fosters empathy for both sides of the conversation.

8. Practice the Way You Actually Sell

Role-plays are most effective when they replicate real-life conditions. If your team sells primarily over the phone, have them practice role-plays over the phone as well.

One technique is to have reps sit back-to-back while role-playing, so they focus solely on the conversation rather than body language. This mirrors the actual sales call experience and makes the practice more authentic.

9. Make Role-Plays a Habit

The more frequently your team practices, the less awkward role-plays will feel. Over time, they’ll become second nature.

Here’s how to build these into your team’s routine:

• Schedule weekly or biweekly sessions.
• Pair off reps for daily role-plays. Encourage them to record these and submit them for feedback.

Regular practice not only boosts confidence but also reinforces skills, making reps more effective in real-world situations.

10. Record and Review

If possible, record sessions so reps can review their performance. This allows them to identify areas for improvement that they might overlook in the moment.

Use the recordings to:

• Highlight strengths and celebrate improvements.
• Provide specific, actionable feedback.
• Create a library of top-notch role-plays for new reps to learn from.

Reviewing recordings helps reps self-coach and accelerates skill development.

Specific Role-Play Exercises for Account Executives and CSMs

When it comes to role-plays, how you format the exercise is just as important as what you practice. A properly formatted role-play increases the effectiveness of the material that you present during it and introduces your reps to more relevant scenarios that they can draw from in the future.

As you structure your training it’s important to consider that different types of teams will benefit from certain role play structures while other may not be as effective. For instance, inbound sales reps or those who make cold calls will benefit more from a high pressure, on-the-spot format that recreates some of the pressure of cold calling a contact. On the other hand, account executives or customer success roles that deal with warm leads or nurture existing accounts may be a better fit for lower pressure role-play formats that allow team members with specialized knowledge to share it with their colleagues in small groups.

Here’s some of the most effective role play formats, and how to use them:

The Dyad Sales Role-Play: One-on-One

Structure: Basic format where two people each take one role. Typically one is the sales rep and the other is the contact. This can be done as needed to practice or reinforce material that was just introduced.

Use with: Anyone, in sales coaching one-on-ones, can be done with the coach and rep.

Use for: Sales coaching one-on-ones or ad-hoc peer-to-peer prep and training. Difficulty can be reduced by providing parties with more information surrounding the scenario

Best practices: Perform two rounds to ensure that both players swap and get experience as the rep and the contact.

The Triad Sales Role-Play: Small Group Sales Coaching

Structure: Similar to the Dyad but includes a third player. The additional player functions as an observer or coach to watch the exercise and provide extra input to the other participants. The roles of rep, contact, and observer should rotate between each person.

Use with: Anyone

Use for: Ad-hoc peer-to-peer prep and training, sales meetings, or when introducing new techniques, products, and materials.

Best practices: Play at least three rounds so each player gets a turn in each role. Additional rounds allow players to apply the advice that they received in the first round. Difficulty and can be increased or decreased depending on the amount of information that is provided to the participants.

The Pop-Quiz Role-Play Exercise: On the Spot

Structure: With little to no notice, choose two participants to perform a role-play exercise in front of group. This structure works best with cold call or inbound lead situations.

Use with: Inbound reps, SDR/BDR’s, and reps who make cold calls.

Use for: Sales trainings, meetings, sales kickoffs

Best practices: Perform two rounds so each rep gets time in both roles. Although the purpose of this structure is a surprise, ensure it is conducted in comfortable environment where reps don’t feel like they’ve been put on the spot.

The Fishbowl Sales Role-Play

Structure: Two or more reps run through a scenario in front of rest of team This differs from the pop since they will have notice beforehand and time to prepare. The entire team is then asked to provide feedback and input.

Use with: Anyone

Use for: Team trainings, sales kickoffs

Best practices: Run the scenario multiple times. You can either run it so each person gets time in each role, or so that the participants remain in the same role but can apply feedback from the audience to see how it impacts outcomes.

The Audience Sales Role-Play

Structure: Similar to fishbowl, except with a single person providing input while the rest of the team observe or step in to participate on a rotating basis. This allows everyone to learn through observation and actively apply the knowledge. Whoever is providing input should be a subject matter expert on the situations that reps are being put in.

Use with: Anyone, but the person providing feedback should be an expert.

Use for: Larger and more formal trainings, or when bringing in an external consultant

Best practices: Center role role-play around the knowledge of the observer and focus on practicing a specific problem area.

The Rotating Group Sales Role-Play

Structure: Each participant has a specific role to play: salesperson, prospect, customer, etc. You provide further roles such as the VP of Sales at a prospect company, a sales rep at the prospect company, and so on. Form groups that all contain one of each role. The groups then rotate to different stations within the room that each have a specific scenario assigned to them. At each location, the participants role-play that scenario as their role.

In another version, players are assigned specific stations to stay at, while others rotate to them. You can assign prospects to remain at the stations, with varying degrees of sales difficulty and have reps rotate to each prospect.

Use with: Anyone

Use for: Formal, larger trainings

Best Practices: Provide a short break between each scenario to allow reps to record their thoughts and feedback. At the end, review each situation as a team. You can also bring in observers to walk the room and provide feedback as the scenarios play out.

Process Simulations

Structure: Process simulations are a highly involved, lengthy role-plays can last hours or even days. They allow you to bring reps through an entire sales process, from the initial cold call, through the discovery process, the demo, negotiation, and close. Each player is assigned a role with an extensive amount of background information. Whomever plays the role of the rep will have to uncover the needs of their prospect and properly sell to them.

Use for: New reps or sales kickoffs

Use for: formal, larger trainings with lots of time.

Best Practices: The more information you can provide the players about their roles, the better.

Modifications

To help reps with highly specific use cases, product knowledge, or problem solving, involve your company’s other teams. Have members from product or support play as prospects who have atypical use cases or very technical questions so reps aren’t blindsided when the encounter the problem in real life.

If reps require extra motivation, or you need to lighten the environment and make participants more comfortable, turn role-plays into a game with prizes. For example, in the pop-quiz role-play, observers can vote on who did the best pitch or cold call, and the winner will receive a prize. To make role-plays part of your team over time, make it an into a RPG with a leaderboard. Every week, work on a specific scenario where and whoever handles it best wins a point. At the end of the quarter, whoever has the most points wins!

Try These Tactics to Transform Role-Plays

By implementing these 10 strategies, you can turn sales role-plays from dreaded exercises into valuable learning experiences. Your team will not only become more comfortable with role-plays but also see a direct impact on their sales productivity and confidence.

What have you done to make sales role-plays less awkward and more effective?

Read more about the seven best sales role-play exercises.