How To Leverage Sales Roleplay to Train Your Sales Teams

Sujan Patel is the founder of Mailshake, a sales engagement software used by 38,000 sales and marketing professionals. He has over 15 years of marketing experience and has led the digital marketing strategy for companies like Salesforce, Mint, Intuit and many other Fortune 500 caliber companies.
  • February 20, 2024

Most sales teams don’t think very highly of sales role-playing.

It’s hard to blame them – if you’ve been in the industry long enough, then chances are you’ve taken part in some unrealistic, awkward, or embarrassing role-playing situations.

After a while, it starts to feel like a waste of valuable time.

However, that doesn’t mean that you should give up on sales role-playing altogether.

The top sales leaders understand that sales role-playing – when done right – is an effective way to train sales teams and leave reps feeling confident and empowered going into their next call or office visit.

Here’s how to do it:

Do Your Own Discovery Work

In order to successfully implement sales role-play training, you need to start by doing your homework. Little good will come from jumping into role-playing without a game plan or some concrete objectives.

Ideally, your sales training process will help each salesperson boost their confidence, improve their weaknesses, and maximize their results. But in order to achieve this, you need a little background knowledge on what your team needs.

A great starting point is discovering what kind of situations and objections your team regularly encounters. The best way to do this is to have a conversation with your sales team. Bring it up in one-on-ones and team meetings.

From there, you can take it a step further and shadow some of their calls to get a live view of what’s going well and determine where they’re struggling or could use some fine-tuning.

Provide Some Much-Needed Structure

The next step is to determine the structure and content for the exercise. Start by creating a flowchart of your sales process, which will make it easier to visualize each stage of the process and any corresponding situations that your team regularly encounters.

Next, create a breakdown of some common personality types that they encounter day-to-day. Here are some examples:

  • The tech-savvy client who has a lot of questions
  • The tech-challenged client who doesn’t fully understand what you’re selling
  • The runaway client who takes you down extremely unique rabbit holes
  • The fast-talking, no-nonsense client that wants you to cut to the chase

This list may get quite long, so try narrowing it down to a handful of situations that your team would benefit the most from practicing.

Finally, implement an after-action-review (AAR), which is essentially a debriefing process where you analyze what happened, why it happened that way, what to sustain in the future, and what to improve on.

To prepare for the AAR, make a list of questions for the group. Refrain from spoon-feeding the answers to what went right and what went wrong. Let your reps come to their own conclusions and guide them toward the right answers.

Take it Seriously & Make it Realistic

Your team should mirror your enthusiasm for the exercise. If you downplay it and don’t take it seriously, it’s unlikely that they will, and vice versa.

Some simple ways to convey that this training is serious and will provide value to them are:

  • Using real customer personas and situations that they actually encounter
  • Not leaving out important steps in the process
  • Refraining from using filler content or words like “yada yada”
  • Having them practice with someone they genuinely respect
  • Starting with one-on-one role-play and graduating to group role-play
  • Having them put on phone headsets or using real slide decks
  • Practicing putting people on hold when they need assistance

Consider recording the session to give people a better understanding of where they may be rushing certain parts of their pitch, not fully listening to the client, or using certain words as a crutch.

Set The Stage For Role-playing

Now that you’ve done your homework and created some structure, it’s time to jump into the actual role-playing. Here are the steps to follow:

1. Communicate the Rules & Objectives

Start by explaining exactly how the role-playing will work so that everyone understands the rules and goals of the exercise.

It’s also important to note whether you’ll stop the role-playing exercise to address mistakes, or if you’ll circle back to them at the end. One approach is to let each group go through a full dry run before giving feedback or making adjustments.

That way, they can get their lines down and work on making eye contact during the first run-through. The details matter here, and a little rehearsal time can make or break the exercise.

2. Give the Scenario Context

Sales reps rarely head into a call or a customer visit blind, so refrain from having them role-play under such circumstances. Doing so only exacerbates the feeling of awkwardness that role-playing often exudes.

Giving the scene a dose of reality could be as simple as telling them who they’re meeting with and what stage of the sale they’re in.

For example, “The CIO of this mid-market widgets company has agreed to a 5-minute phone call to discuss package options” is a good starting point. It’s up to you how detailed of a background they get, but it’s best to give them something to make the exercise more comfortable and realistic

3. Coach the Acting Customer

Every role contributes to the performance, so make sure that you give ample direction to the salesperson playing the customer. It’s an easy thing to overlook, but it does make a difference.

Playing the customer’s part is often difficult for the salesperson because they have the “curse of knowledge.” They’ve been on countless discovery and closing calls to know the product like the back of their hand, so it’s often challenging to “play dumb,” act uninformed, or ask elementary level questions in a serious way.

Here are a few tips to help them get into character:

  • Have them listen to a sales recording of real customers in challenging situations.
  • Ask them to be unruly, ask for outrageous discounts, or act distrusting of everything the sales rep says.
  • Give the client actor a backstory and a goal, so they have something to work toward. It will help make the dialogue flow more naturally.

4. Set Aside Time to “Get Into Character”

This is a small step that is often forgotten but is very useful. Even five minutes or so to take down notes, come up with some lines, or expand on their backstory is helpful.

The customer can write down questions they need answering, or features they desire, while the sales rep can write down their discovery questions or jot down some “research” that they can cite throughout the call.

5. Make the Stage a Safe Zone

Remind everyone that the goal is to hone their skill set. The exercise should feel serious but lighthearted. Encourage them to take risks, try new things, and open themselves up to constructive criticism.

As the leader, don’t avoid judgment entirely but avoid labels like “right” or “wrong” in the beginning. Opt instead to guide them toward certain behaviors and talk tracks. Use phrases like, “I see what you were going for there, but what about trying X next time?”

Arguably the best thing you can do for them is to stay silent and let them act the situation out from front to back. As they perform, take detailed notes and provide them with a list of items to practice or work on for later sessions.

Role-playing Exercise Examples

You’ll naturally have some specific role-playing scenarios that fit your unique sales team, but it’s also a good idea to toss in some other ideas from time to time as well. Here are a few examples to get you started:

1. The Isle of Objections

This exercise is great for teams of all sizes. It helps salespeople think on their feet by practicing some rapid-fire objection handling techniques while simultaneously allowing team members to engage in peer-to-peer coaching. It’s also fast-paced enough to help them shake off some nerves through a lighthearted shared experience.

Here’s how it begins:

  1. Start by calling out a rep’s name and simultaneously toss an objection you hear regularly.
  2. The receiving rep now has five or six seconds to respond in a way that naturally progresses the conversation in a positive way.
  3. If they fail, the rep gets voted off The Isle of Objections. If they succeed, they call out another person’s name with a new common objection to keep the game going.

It’s best to set some ground rules, such as enforcing unique objections each time and not allowing reps to be called more than once. It’s also good to appoint a judge for response quality, timing, and originality, so you’re not wasting time arguing over the score.

2. The Uncommitted Customer Call

This one is a battle of wits and relentlessness. The scenario itself is simple because it involves one customer and one sales rep on a closing call. However, it can get tricky because the acting customer is ruthlessly indecisive to the point of exhaustion and frustration.

Here’s a common exchange:

Customer: “I’m definitely interested in the premium package, but I’m caught up on the annual pricing. What if we’re not in business six months from now? Or what if you’re not in business?”

Salesperson: “I’m in the business of betting on myself. I believe in this company, which is why I’m here, and I like to think you feel the same. Otherwise, you wouldn’t be talking to me about software to improve your odds of success.”

Customer: “Well, I saw that you had three 1-star reviews out of 1,000 on this review website. One person said they were put on hold for 3 hours one time. That makes me nervous. What if I’m in need of assistance and can’t get a hold of someone?”

As you can see, a customer like that is relentless about unique one-off scenarios because they’re risk-averse and indecisive. It’s a fun exercise for sales reps because they get to think of creative talk tracks to get people to stick with the sale, and the actor gets to dream up all sorts of ways to seem uninterested.

3. The Ole’ Sales Leader Switcharoo

In this exercise, the sales rep gets to play the prospect while the leader plays the salesperson.

  1. The sales leader provides a presentation and goes back and forth with the prospect.
  2. The rep playing the prospect gets to provide feedback to the sales leader on what they thought worked and what may have fallen flat.
  3. After a few rounds of different scenarios, you switch seats again and repeat.

An exercise like this helps your sales rep practice empathy, which is a critical component of the sales process these days. They’ll also find patterns of what talk tracks or sales techniques tend to work the best and slowly build confidence using them.

Sales role-playing is a worthy endeavor when you put in the effort to make it realistic and value-rich for your sales team. Poor planning is usually to blame for lackluster results, but these tips will help you turn your next role-play training session around.

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