I run client proposals through ChatGPT as a "hostile client" before sending them. It's saved me more deals than any template.
I work at a digital marketing agency, so a big part of my week is writing website proposals and pitch decks. For a long time I used ChatGPT to polish the wording, and the proposals came out sounding nice but generic.
Now, before anything goes to a client, I paste it in with this prompt:
>"You're the client receiving this proposal. You're busy, a bit skeptical, and you've seen 5 other agency pitches this week. Give me the 5 reasons you'd reject this or ghost us, ranked by how likely they are. Don't be polite."
Some things it caught that I missed:
- Example 1: Hospitality client's proposal listed features but never tied them to bookings or revenue. Its feedback was "I don't care about a CMS, I care about more reservations." It was right.
- Example 2: Pricing section showed one big number with no breakdown, which reads as "overpriced" at first glance. I split it into phases and the client signed the first phase.
- Example 3: A pitch deck spent 6 slides on us and 2 on the client's actual problem. I flipped the ratio.
What I've learned after doing this for a while:
- Give it a persona with pressure. "Busy, skeptical, seen 5 pitches" gets much sharper feedback than "review this."
- Ranking by likelihood stops it from listing 20 edge cases nobody cares about.
- Follow up with "Now tell me the one thing that would make you say yes today." That answer usually becomes my opening line.
- It's not always right. Sometimes it invents objections a real client would never raise. Use it as a stress test, not the final word.
It's like having a tough client review every proposal before the real one sees it.
Anyone else use ChatGPT for stress-testing their work instead of writing it? I'd love to know what personas or prompts work for you, especially in sales, freelancing or agency work.