Stop Practicing on Real Prospects
There’s a story I tell whenever someone tells me they hate roleplay.
I was in business school. A professor was in the middle of selling his company. Offers ranging from $40 to $75 million on the table. Before he went into any negotiation, his investment bankers ran him through every scenario they could think of. Every question a buyer might ask. Every objection. Every pressure tactic. They rehearsed it all.
Because the stakes were too high to find out what you don’t know when you’re sitting across from the buyer.
When I tell that story, I ask one question: if it’s worth roleplaying to handle a $75 million transaction, why wouldn’t you do it for a $7,500 one?
Most people go quiet.
The Real Objection
When salespeople say they hate roleplay, that’s usually not what they mean.
What they mean is: it feels awkward. It feels artificial. They don’t want to look bad in front of a manager or a peer. They’d rather handle it live, with a real prospect, where the stakes feel lower because it’s just one deal.
Except it’s not lower stakes. It’s higher. Because now you’re practicing on someone who might actually give you money.
The best athletes in the world don’t show up on game day hoping instinct carries them. They’ve already run the play so many times it doesn’t require thought. The execution is automatic. What you see on the field on Saturday is the product of everything that happened Monday through Friday.
Sales works the same way. The difference is most sales teams never really practice. They debrief after the fact if a deal dies. They might do a training once a quarter. And then they wonder why the same mistakes keep showing up in deal after deal.
What Actually Happens Without It
I worked with a company a while back. High volume, transactional environment. I pulled a sample of six calls and the pattern was obvious within the first few minutes.
Reps were rushing. They were in their heads about time. They’d get to the end of a call without ever really connecting with the person on the other end, and instead of asking for the business, they’d say something like “here’s a link if you want to do something.”
Nobody had ever told them that wasn’t working. Nobody had sat with them beforehand and walked through what a good call actually looks like. Nobody had made them do it until it felt natural.
We restructured the call flow. Trained them on it. Made them run it repeatedly before they ran it live. Five months later, close rate went from 18% to 32%. Then they raised prices. The number held.
The skill was always there. What was missing was the repetition.
The Specifics
If you’re a sales manager and you’re not doing pre-call planning and post-call debriefs consistently, you’re leaving your team to figure it out on their own. Most of them won’t. Not because they’re lazy. Because without structure, people default to what’s comfortable, and what’s comfortable is usually what they’ve always done.
Pre-call planning doesn’t have to be complicated. Before a significant call or meeting: What do we know about this person? What are we trying to find out? What’s the most likely resistance we’ll face and how do we handle it? What does a good outcome look like?
Post-call debrief: What happened? Where did it go sideways? What would we do differently?
Do that consistently and your team gets better. Skip it and they accumulate years of experience making the same mistakes.
There’s a common belief I run into that someone with 15 or 20 years of experience has somehow compounded their skills the way money compounds in an account. It doesn’t work like that. A lot of people are making the same errors today they were making a decade ago. Experience without feedback is just repetition. It’s not growth.
On the Awkwardness
Yes, roleplay feels artificial. That’s partly the point.
If you can execute in a slightly uncomfortable, artificial environment, you’ll execute fine when it’s real. The awkwardness is part of the training, not a flaw in it.
Actors don’t skip rehearsal because it’s not a real performance. A lawyer preparing to argue in front of a serious court isn’t going to skip prep because the practice run didn’t feel authentic. They know the discomfort of rehearsal is exactly what makes the performance possible.
Your team doesn’t have to love it. They just have to do it. And if you make it a normal part of how you operate, the resistance fades. It becomes how things work.
The teams that get better are the ones where practice is expected. The teams that stay stuck are the ones where it’s optional.
If you need to fill sales roles and want to talk about how we do it differently, email me at adam@thenorthwoodgrp.com
