# The night before a big call, Claude plays the skeptical buyer

Give Claude everything you know about the buyer and tell it to push back like they would.

Category: Enablement and roleplay
Difficulty: easy
Updated: Oct 18, 2026
URL: https://revstackai.co/use-cases/night-before-skeptical-buyer-roleplay

## Problem

Reps hear the hardest objection for the first time on the live call.

## How AI solves it

Prompt: 'You're a [VP of Sales] at [company]. Here's everything I know about you and your business. I'm about to pitch you [product]. Roleplay the call. Push back like you actually would. Be sceptical. Be busy. Be a bit annoyed.'

Run the pitch end to end.

Note every objection you fumbled and prepare an answer.

## Verdict

Part of a three-prompt routine the rep credits for two closed deals in a month.

## Tools

- [Claude (Projects)](https://claude.com/): LLM with Projects that keep account context across meetings.

## RevStack prompt

Written by RevStack. This is not the sourced result below.

Inputs:
- Buyer title and company
- Everything you know about them
- What you are pitching

You're a {{title}} at {{company}}. Here's everything I know about you and your business: {{context}}. I'm about to pitch you {{product}}. Roleplay the call. Push back like you actually would. Be skeptical, busy and a bit annoyed. When I say 'stop', list every objection you raised and which ones I handled weakly.

Example output, written by RevStack, not a reported result:

Buyer: I've got ten minutes and we already have a tool for this. Why would I switch mid-year?
...
Weak: switching cost, and you never asked who else signs off.

## Result

'Three prompts. Two closed deals.' (self-reported; roleplay was one of the three)

Independent. Reported by [Holly Allen, Founding Account Executive UK&I, FullEnrich](https://www.linkedin.com/posts/hollyallen1_3-claude-prompts-that-helped-me-close-2-deals-activity-7468582202281181185-HXZe).

## Setup

1. Paste the buyer's LinkedIn, company site and your call notes
2. Run it the night before, not five minutes before