The Roleplay Dojo – How to Stop Practising on Your Best Leads

A Deal You Only Get One Shot At

A UK logistics firm lost a £50,000 ARR deal after a polite but unsuccessful meeting. The rep had rehearsed for an hour with his manager, covering objections, the deck, and pricing.

The problem wasn’t the prep; it was the quality of the rehearsal. The manager realised she was too close to the product to play a true sceptic. The rehearsal was polite, but the buyer wasn’t.

The Roleplay Dojo: A Three-Phase Method

The Roleplay Dojo fixes this by separating the character from the critique. First, it builds a realistic Persona of the buyer you’re actually facing. Second, it defines a ruthless Grading Rubric based on what that specific buyer cares about. 

The result is a sparring partner that doesn’t just act like the buyer; it judges like them, too.

Phase 1: Building the Dojo

Constraint: Each Dojo is built for one live prospect. If the deal changes materially, the Dojo changes with it.

1. Create the Persona

Start with what you already know. Past CRM notes often capture the objections, tone, and internal constraints that matter most. Some gaps are fine. The persona just needs to be coherent enough that reps can’t bluff their way through it.

Here is an example of a persona built for the UK Logistics buyer:

Attribute	Value
Role	Operations Manager, Large UK Retailer
Key Pain Point	Under board pressure to cut operational costs by 10% without disrupting service
Budget Authority	Can approve up to £25k; needs Director sign-off for more
Buying Process	Three-month evaluation, needs proof of non-disruptive integration
Primary Objection	‘We already have an in-house team that’s cheaper. Your ROI isn’t clear enough.’
Secondary Objection	‘How will you integrate with our custom WMS without downtime?’
Communication Style	Blunt, impatient, interrupts frequently and demands hard numbers

2. Design the Scorecard & Grading Rubric

The scorecard defines how this specific buyer judges success. Each skill area maps directly to where the deal is likely to stall. Scores are relative to this deal only—a ‘3’ here means something different than a ‘3’ on another prospect.

Skill Area	Grading Logic (How the Agent Judges the Rep)	Example Feedback
Opening Statement	High Score (4–5): Rep immediately links the solution to the 10% cost reduction target.Low Score (1–3): Rep uses a generic company introduction.	‘Clear and direct, but you missed the cost reduction angle this buyer cares about.’
Price Objection	High Score (4–5): Rep proves Total Cost of Ownership is lower than the in-house team, using hard numbers.Low Score (1–3): Rep offers a discount without a clear ROI case.	‘You didn’t counter the in-house cost comparison with recognised numbers.’
Integration Objection	High Score (4–5): Rep explains the specific sequence and safeguards of the integration process.Low Score (1–3): Rep only names a team or says the process is ‘seamless’.	‘You named a team, not the integration path or sequence.’
Value Proposition	High Score (4–5): Rep focuses on concrete financial impact, for example inventory waste reduction.Low Score (1–3): Rep talks about features instead of financial outcomes.	‘You focussed on features instead of inventory waste and financial impact.’
Closing	High Score (4–5): Rep proposes a low-risk, paid pilot to de-risk the decision.Low Score (1–3): Rep pushes for a full contract despite the budget freeze.	‘You asked for a follow-up instead of a paid pilot to de-risk cost.’

3. Build the Dojo Agent

Below is an example system prompt based on the persona and scorecard above.

Role: Adopt the Persona of the buyer defined below.

Task: Engage in a ten-minute roleplay conversation with the sales rep. You are a harsh but fair critic. Your goal is to stress-test the rep’s ability to handle your specific objections.

Output: After the conversation, use the Grading Rubric to score the rep from 1 to 5 on each skill area. For any low score, you must quote the exact sentence from the rep that caused the failure.

[PASTE PERSONA TABLE HERE]

[PASTE GRADING RUBRIC TABLE HERE]

Phase 2: Run the Dojo

When a deal enters the final stages, the sales manager runs the Dojo built for that prospect. Before the rep enters the room, the manager chooses which objection to stress-test: price, integration risk, or an internal competitor.

The rep runs a ten-minute simulation. The score and feedback are logged in the CRM.

High Score: The rep proceeds.

Borderline Score: The manager initiates a quick check-in.

Low Score: The manager schedules a formal coaching session.

Phase 3: Refine the Dojo

After every lost deal, ask:

• Did the buyer raise objections the persona missed?
• Did their tone match what was modelled?
• Did the rep fail in ways the scorecard didn’t measure?
• Was the Dojo reused without updating the persona?

If yes, the process is drifting toward generic roleplay. Stop and rebuild.

Executive Takeaway

Top prospects aren’t rehearsal space. Most teams practise for the objections they hope to hear, then rely on confidence to carry them through the room. The Roleplay Dojo replaces polite rehearsal with a focussed stress test, tuned to the buyer who actually decides the deal.