Sales is a competition that requires practice. Just like how a professional sports team trains regularly, having your sales team practice role-playing can increase their success.
“You want to practice in a controlled environment where you can pause, you can go back, you can rewind, you can fail, and it’s not going to affect the outcome of the game,” says Justin White, owner of K&D Landscaping, Inc., based in Watsonville, California. “I think practicing is exactly that. It’s just being in an environment where you can fail and be okay with failing. Then when you’re in the game, you’re in the moment, the pressure’s on, you’re going to just have those instincts that you built to make yourself more successful.”
The Benefits of Sales Role-Playing
Duane Cashin, owner of Cashin Sales, says the main benefit of role-playing is how it helps your sales team develop methods to establish trust and credibility with clients early on.
“Practice before performance,” Cashin says. “If it’s a football team and we’re running a play over and over and over, if they’re not comfortable doing it there, they sure as heck aren’t going to be comfortable in front of 70,000 people when the lights are on.”
Role-playing can be especially beneficial for newer employees on your sales team.
“I think those with less experience need more practice,” White says. “They just don’t have as much reps in the field. Giving them more reps in the office definitely helps them work through issues before they go live.”
Cashin adds that role-playing can still be of value even to your top performers. He suggests asking them to mentor others who may be struggling in a certain area.
White notes that practicing regularly can also create smoother communication and conversational flow with the client.
“Whether they talk to Jamie or Tony or Kendel, whoever on the sales team, they’re going to hear a similar message,” White says. “I think our close rate and sales performance has improved.”
Addressing Challenges
When implementing sales role-playing, you can encounter some resistance from your salespeople or your sales manager. The first step is to explain to your team why you are adding sales role-playing.
If you have employees expressing discomfort or reluctance in role-playing, have a one-on-one conversation with them about how these sessions provide a safe environment to address common client objections and you just want them to get better.
In the case of experienced sales reps who feel they already do a good job, White says even the best quarterback in the world still practices every single day so they can always do better as well.
“I think the answer to them is, ‘Look, there’s a lot of other people that actually are watching you and learning from you, so when you do a role-play, yeah, maybe you don’t need it, but everyone else watching it is going to learn from you, and that sets a good example for the team,’” White says.
For sales managers who are hesitant to lead their team through these role-playing exercises, Cashin says it is on the sales manager’s boss to make them feel comfortable with the concept with guidance and support.
Moving forward, make it clear to new sales employees that role-playing is a regular practice at your organization so there are no misunderstandings or pushback.
“It’s got to be part of the culture,” Cashin says. “Leadership has to buy into that and know that that’s the way it is. When you interview new reps, you explain to them there will be role-playing on a regular basis.”
Role-playing can be extremely beneficial for your team, but they also run the risk of backfiring if they are poorly managed. Cashin says without structure and clarity about what you’re trying to achieve, role-playing can reinforce bad habits and poor execution with your sales reps.
It’s also important to strike the right balance when role-playing. You don’t want to make the session so easy it is practically useless, but you also don’t want it to be so difficult the salesperson becomes demoralized and loses confidence in their skills.
“It’s like teaching a child to ride a bike and you’re throwing nails and rocks in the road in front you go, ‘Let’s see if you can ride over the rocks and the nails,’” Cashin says. “How’s that going to work out? The kid’s going to fall down, have a nail in her arm and never want to get on a bike again.”
White agrees you need to be compassionate and supportive when a sales rep performs poorly in a role-playing session, instead of chastising them for everything they did wrong.
“It’s important to if you haven’t done it before, hire a professional or a coach to help you,” White says. “I also think it’s important to have good data on your current sales and sales performance so you can measure the improvement.”

