Now that I’m back in a quota-carrying role, I’ve made roleplay a regular part of my prep. Not as a box to check. Not as a team exercise that goes nowhere. But as a deliberate way to sharpen conversations before they matter.
The difference between average and excellent performance in sales is rarely knowledge. It’s execution under pressure. Roleplay is where I pressure-test that execution.
Here’s how I approach it.
1. I Never “Wing” a Roleplay — I Set a Clear Scenario
Bad roleplay sounds like this:
“Okay, pretend I’m the customer.”
Good roleplay starts with context:
- What stage is the deal in?
- Who is on the call?
- What objection is likely coming?
- What outcome are we trying to drive?
If I’m preparing for a CFO call, I’ll define:
- They’re skeptical about budget.
- They’ve been burned by a vendor before.
- They have 20 minutes.
- The goal is agreement on evaluation criteria.
Clarity makes the roleplay real. Without structure, it turns into generic back-and-forth that doesn’t translate to real conversations.
2. I Roleplay the Hardest Part — Not the Easiest Part
It’s tempting to practice the polished demo section.
That’s not where deals break.
I focus on:
- The first 3 minutes of the call
- The pricing conversation
- The objection I’m hoping doesn’t come up
- The close
If something makes me slightly uncomfortable to rehearse, that’s probably what I need to practice.
Comfort doesn’t need rehearsal. Pressure does.
3. I Ask for Brutally Specific Feedback
After roleplay, I don’t ask:
I ask:
- Where did I lose confidence?
- What sounded unclear?
- Did I actually answer the objection?
- Where did I talk too long?
And I want specifics. Not “that was good.” Not “maybe tighten that up.” Specific language feedback.
This is especially important when roleplaying with sales partners. If we’re going to sharpen together, we have to be honest with each other.
4. I Use AI to Stress-Test Objections
AI has become one of my favorite roleplay partners.
I’ll prompt it with:
- The persona (CFO, VP Sales, IT Director)
- The context of the deal
- The likely concerns
- The tone (skeptical, rushed, aggressive)
Then I ask it to:
- Push back hard
- Interrupt
- Challenge assumptions
- Ask follow-up questions
What I like about AI is that it doesn’t get tired of being difficult. I can run the same objection five different ways until my answer becomes natural instead of memorized.
But here’s the key: I don’t memorize AI-generated responses. I use it to refine my own thinking. If I can’t explain something in my own words, I’m not ready.
5. I Record Myself and Watch It Back
This is the uncomfortable one.
Occasionally, I record my side of the roleplay. Not for perfection — for awareness.
I look for:
- Rambling
- Filler language
- Defensive tone
- Over-explaining
- Missed pauses
The camera doesn’t lie. Neither does playback.
Most of us think we’re clearer than we are. Watching yourself once will change how you communicate permanently.
Roleplay isn’t about pretending. It’s about preparing.
Customers don’t care how knowledgeable you are. They care how you respond in the moment. They care how you handle tension. They care whether you can think clearly when challenged.
That clarity doesn’t magically appear in a live call.
It’s built in practice.
If you’re carrying a quota and not roleplaying — especially the uncomfortable parts — you’re choosing to rehearse in front of the customer.
I’d rather do the hard work beforehand.
