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Sales - 8 min READ

5 sales role play exercises: Close more deals in 2020

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Author photo: Kent Holland

Kent Holland

Vice President of Sales at Copper

Role-playing isn’t just a great way to learn new sales skills or train new sales reps.

It’s also an effective tool you can use to introduce new products and selling strategies, reinforce good habits, and test out new approaches with your sales teams.

As you can imagine, this style of sales training is much more effective than just giving someone a manual with tips, templates, and scripts they have to memorize and work through on their own.

Instead, sales role play becomes a team sport where everyone, including sales leaders, learns how to win together.

Let’s look at five role play exercises you can use to teach your team the essential skills needed to win more business:

  1. Learn the basics
  2. Work out the imperfections
  3. Team (re)education
  4. Navigate technical issues
  5. Master your processes

Exercise #1: Learn the basics

What’s the goal of this exercise?

You (and your sales reps) should have a firm grip on the basics of your "sales motion," or the steps you take to close a sale. For example:

These are the kinds of skills you need to master as a sales professional to effectively engage with prospects one-on-one—and take them from “Who are you again?” to “I can’t believe I waited so long to buy this!”

Who participates?

Because this kind of exercise is meant to help you get better at the basics of selling, this is best handled one-on-one (typically, with one sales manager and one sales rep, or one sales trainer and sales rep, or one senior sales rep and one new sales rep.)

Essentially, you want a seasoned sales pro to lead this role play exercise and help the newest team member strengthen their skills through practice and feedback.

Where will it take place?

To start with the role play scenario, it should be in person. However, many sales activities take place over the phone or video chat (like Google Hangouts), so it's a good idea to run through some of these sales role play scenarios using the platforms where they’re most likely to take place.

That way, everyone on sales teams can get comfortable using your company’s technology, which speeds up the whole process even more.

How does it work?

This is your chance to really cement those basic skills, so design your exercises to be specific as they need to be.

Let’s say you want to teach some salesperson techniques for making cold calls. So, you ask your two newest recruits to work through the exercise together.

You give Mark a cold-calling script and you set Winnie, your sales manager, up in one of the conference rooms with a prompt of her own.

In the role playing exercise, Mark is to play the sales rep and Winnie is to play the small business owner who’s never heard of the software Mark is about to pitch her. She knows that she’s spending too much time on the wrong tasks, but doesn’t have the time or money to hire someone or figure out what kind of software she can offload it to.

You let the two of them work through the salesperson exercise a few times, switching back and forth in the roles. This gives Mark the chance to master the cold-calling script while also being able to see what it feels like in the prospect’s shoes.

Exercise #2: Work out the imperfections

What’s the goal of this exercise?

This exercise can be used to reinforce the basic skills from exercise #1, or it can be used as part of ongoing training.

The overall goal of the role playing exercise, regardless, is to iron out the kinks. It’s perfectly fine to work off of a script when training, but real-world interactions with prospects don’t always go that predictably.

This gives you, as a sales professional, a chance to observe, provide constructive feedback, and show your trainees how to become more agile and flexible when they’re in the thick of it.

Who participates?

This is a one-on-one exercise between two sales reps. This time, though, there is a third person there to observe. It may be a more senior rep, coach, or sales manager.

Where will it take place?

Even though there's a third party observing the interaction, you can still host this role play in person, over the phone, or through video chat.

Just make sure the third party is present, even if it’s virtually.

How does it work?

If you were in memorization mode before, this is where you’ll learn to be more mindful of the conversations you're having. This is what helps you build the confidence to really take control of the conversation and work on relationship-building off-script.

For these exercises, focus on basic skills—but with one complication.

Let’s say that you’ve assigned Stephanie to the role of the sales rep and you’ve given her the standard pitch script. Britt is the small business owner who’s shown interest in Stephanie’s software.

However, this scenario isn’t going to play out smoothly. Stephanie thinks she’s going to deliver her pitch to the interested lead and walk away with a new opportunity to work through her sales pipeline.

The only problem is, Britt doesn’t think she can fit it in her budget anymore nor does she have time to deal with switching vendors.

The third party will observe how this interaction goes and provide feedback when it’s done.

This isn’t about throwing Stephanie under the bus. This is about seeing how well she does under pressure, how well she diagnoses and overcomes potential objections, and how effectively she can pivot through the challenge (which isn’t all too uncommon).

Exercise #3: Team (re)education

What’s the goal of this exercise?

This one-on-one sales role play exercise is going to take place during one of your team meetings, so the goal is to teach a broader lesson to everyone at once.

This would be useful if you have a new sales tactic to introduce or want to reinforce a technique that you think needs some work.

What’s nice about these kinds of exercises is that you can use them to break up the monotony of your meetings. It allows for a more interactive and engaging session where everyone walks away having learned the same new skill.

Who participates?

Because you’re teaching a new skill or reinforcing one that your team is weak on, you’ll want a seasoned pro in one of the roles. They should already understand how this scenario needs to play out, so that you can really drive the lesson home in the end.

While you’ll want your senior reps and managers to observe the role play and provide constructive feedback, everyone should have a chance to share what they think. Open up the floor and give them a chance to relay their own feedback and questions after it’s done.

Where will it take place?

Schedule it ahead of time to take place during one of your team meetings.

How does it work?

It depends on what the role play is teaching. If you’re introducing a brand new skill, you can provide scripts to follow so reps can demonstrate best practices.

On the other hand, if this is for reeducation, you could use a recently recorded phone call in place of the role play.

So, let’s say that your company typically approaches two kinds of cold leads:

  • Ones without a cloud-based voice system.
  • Ones using the cloud-based voice system from your under-priced competitor.

Max recently ran into an objection that you often encounter when calling the competition’s customers. However, he was able to effectively argue against it, which others have reported having a hard time with.

You play the recording of the call between Max and the prospect, who is now one of your new customers.

The prospect’s seen the proposal and says, “Thanks, but [your competitor] promised to give me 30% off next year’s contract if I stay.”

And Max says, “That’s completely understandable. But remember how your phones went down last December during the holiday rush and they weren’t able to send a rep out for two days? That 30% in savings can’t possibly make up for the money you lost in holiday sales.”

This gives your team a chance to hear the way a real prospect responds to this kind of genuine and personal response. It’ll also inspire them now that they know there’s a better way to handle this rejection (rather than to just take it at face value).

Exercise #4: Navigate technical issues

What’s the goal of this exercise?

This kind of sales role play is less about talking to leads and more about navigating the hurdles that may come up during a conversation.

These might be technical issues—like a demo not working—or objections to common practices, like you recording your calls.

By bringing in someone who knows the tech inside and out, you can walk them through a routine sales call or meeting and show them how to get around one of these issues with ease.

Your IT specialist would be a good person to invite along if you’re trying to work through technical issues with your team. If the role play more has to do with using software, bring in a super user (it might be a manager or project lead) who knows your software in and out.

Who participates?

The one-on-one will be played by a sales rep and the specialist. The specialist will play the role of the sales rep in order to demonstrate how the issue can be navigated.

Where will it take place?

Ideally, you can schedule time for a specialist to run through this scenario during one of your meetings.

That way, your specialist doesn’t have to repeat the same session over and over again, which can lead to inconsistencies in how the lesson is delivered to everyone in the company.

How does it work?

Think about all of the ways your sales reps might run into trouble during a meeting.

The product demo stops working. The video conferencing solution won’t play audio. The wi-fi is spotty.

Choose one of the biggest pain points you experience and let the specialist show you how to stay calm when it happens.

For instance, let’s say that you can’t always get audio to work in Zoom—sometimes the lead can hear you talking and sometimes they can’t.

Rather than freak out and cancel the meeting, the tech specialist shows you how to use the chat function to notify the lead that they’re about to restart the session and to hold tight. They then return to Zoom, relaunch the session, and make sure to enable audio from the get-go.

Exercise #5: Master the backend workflow

What’s the goal of this exercise?

You won't always be in the presence of leads, physically or virtually. So, your sales role playing needs to address this.

With this kind of role play, you'll learn how to use email as well as your CRM to communicate with leads.

Who participates?

There are a couple of ways to do this.

The first is similar to the one-on-one setup in basic training. However, the trainee will be communicating with a fake client email address and account set-up for this scenario.

You or another senior member of the sales team will need to manage and monitor the fake account.

The second way to do this is to host it during a team meeting. You’ll set up screen mirroring so that other people who are being trained can observe as one of you walks through a simple communication on the computer.

Where will it take place?

If this is a one-on-one training, the trainee should handle all of these exchanges from their own computer and desk.

If it’s during a meeting, it’ll be in one of your conference rooms with screen-sharing capabilities.

How does it work?

Now, the purpose of this is not to teach your team how to do basic tasks like writing a email or using a CRM to add contacts or manage their pipeline. They should already have these essential skills.

The purpose of this is to show them how to work more efficiently by incorporating these platforms into their day-to-day work. (Think of it as building muscle memory.)

For instance, let’s say you’ve decided to do a one-on-one scenario with Mason. He’s expecting something to come in from you today—but he doesn’t know when or from where.

You know that Mason is out on a sales call at 2 p.m, so you call his desk phone just after this time and leave a voicemail from Daisy Duck:

“Hi Mason, I think you emailed me about a property I’m trying to sell. My name is Daisy Duck and I live at 123 Main St., Disney World, FL. Can you please call me back?”

When Mason gets back and checks his voicemail, he should know that this message is part of the role play, and that it's from a prospect who's following up on a cold pitch he sent by email.

Will he know to go into the CRM to track down Daisy Duck’s lead and contact information? How quickly will he follow up?

You can play out the rest of the role play scenario for as long as you want. It just depends on what specific lesson you want to teach.

In this case, Mason should reach out via phone to reconnect with Daisy Duck and find time to discuss the potential property sale. If Mason can’t reach Daisy Duck on the phone, following up via email is a great second step:

Once you receive the reply from Mason, you might even schedule a mock face-to-face meeting between Mason and this potential seller.

This exercise allows you to observe more than just the conversations your reps have with leads. You’ll get to see what goes on behind the scenes, how your reps perform outside of conversational settings, and whether their tactics are effective at getting prospects to the table.

One of the nice things sales leaders about using a CRM for this is that once the scenario is done, you’ll also have a record in the CRM that you can review with your reps. Here's how it looks in Copper:

You can show them where they did well during their convos with the lead, where they can improve, and give them pointers on how to use your company tools to simplify these sales tasks.

Sales role play tips to keep in mind as you design your exercises:

In order to make sales role plays an effective part of your sales training strategy, keep these points in mind as you build out the exercises:

  • Always set a goal for each session—start and end the sales role-play scenarios sessions with a focus on achieving that goal.
  • Plan ahead, and provide advanced notice to your trainees when it makes sense to do so. There’s no need to make them feel like they’re being put on the spot every time. (In real life, they have time to prepare!)
  • Give everyone an equal chance to sit in the hot seat.
  • Make it collaborative and positive. Feedback should always be constructive.
  • Listen to your team. If there’s something they’re struggling with, use role playing as a way to help them work through the specific problem.
  • Set up your CRM for training. Create demo accounts so that the role play doesn’t end when the phone call or meeting ends; let them practice their skills continuously.

By putting your sales reps into the driver’s seat, they’ll gain hands-on experience with the tools and techniques they need to close more business. Whether a first time rep or one of your most seasoned pros, everyone should be focused on growth.

So, don’t take this lightly. If you do your due diligence in crafting these exercises, your team and company stand to gain a lot from role plays.

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