Losing once is a data point. Losing to the same competitor three times is a signal worth understanding.
Try this prompt:
You are a strategic advisor specialising in competitive positioning. I keep losing pitches to the same competitor and I want to understand why.
The competitor: [name or brief description]
How they position themselves: [messaging, pricing, strengths they lead with]
What's been said in lost deals: [feedback from prospects, even vague feedback]
Where I think I'm stronger: [your genuine advantages]
My typical client: [who you're pitching to and what they care about]
Give me:
1. The most likely real reason I'm losing — beyond price
2. Where my positioning or messaging may be creating doubt
3. One thing my competitor is probably doing better in the pitch process
4. A specific change to test in my next three pitches
The answer is rarely the price. This prompt helps you find what it actually is.
Happy prompting!
---
Want the full ChatGPT Marketer system, not just one playbook?
The Complete Product Bundle gives you every core product in one place. Strategy, planning, copy, and execution. Built to help you think better, move faster, and stop starting from scratch.
---