At this point, you’ve probably taken one (or several) brainstorming sessions to ChatGPT and said, “Give me 10 ideas for X.”
That’s fine for volume, but volume doesn’t equal insight. Without friction, ideas remain unexamined. That’s how you end up greenlighting the first thing that sounds good.
Instead of operating in an echo chamber, you can use an AI chatbot to act as an on-demand red team, helping you uncover weaknesses and prepare for objections before they ever get raised.
Here’s how to turn it into a creative sparring partner that makes your thinking stronger.
Start with your core idea.
Before you ask AI to critique anything, you need something to push against. Summarize your idea clearly in just a paragraph or two. Then copy-paste that into ChatGPT, and prep the model for what’s coming:
You’re not here to agree with me. I’m going to give you an idea, and your job is to push back hard. I want counterarguments, risks, and overlooked edge cases.This context matters. You’re priming the model to simulate resistance, not provide support. You’re creating useful tension.
Now give it your idea, and let it break it apart.
Use role-based critiques to explore blind spots.
Here are 3 highly effective personas you can assign to ChatGPT to get different types of pushback:
🧢 The Skeptic:
Act like a skeptical advisor. What about this idea is most likely to fail or get ignored? What assumptions are untested?The Skeptic helps identify where your reasoning may be built on sand. Use it to spot false confidence early.
👨 The Customer:
You’re a skeptical end user. What would confuse or frustrate you about this? Where would you hesitate to try it?The Customer forces clarity. If your idea depends on someone adopting it, they need to understand it—and trust it.
🏁 The Competitor:
You’re my biggest rival. You see this idea and want to beat me to market. How do you out-execute it in 90 days?The Competitor flips the table. Now you’re defending your idea from real-world pressure, not just theoretical failure.
Probe the top objections.
The initial critique gives you a high-level view of your plan’s vulnerabilities. The next step is to probe those weaknesses for more detail. Use follow-up prompts to understand the root of the objection and explore potential solutions.
For a specific weakness it raised, ask:
Regarding weakness <#>, what specific data or evidence would you need to see to believe this is not a major risk?
Or to force a trade-off:
Imagine you were forced to approve this plan. What is the one change you would demand we make first, and why?
These questions push the AI to give you actionable feedback you can use to strengthen your pitch.
Make it a second brain, not a second guess.
There’s no substitute for real human thought. But with some clever prompting, you can use ChatGPT to pressure your thinking in ways you can’t always simulate alone.
This isn’t just useful for product ideas. You can use this method to:
- Challenge a marketing strategy
- Refine a pitch before a meeting
- Break through team groupthink
- Build a case before you present it
It works because ChatGPT doesn’t have ego or status bias. You’re free to explore dead ends, bad takes, and worst-case scenarios without social cost.
📌 Key takeaway: Creative output without resistance is just a list. If you want stronger ideas, add friction on purpose. Use ChatGPT to push back, poke holes, and flip perspectives, then let your best ideas survive the fight.
For more info on this topic checkout – 6 Tips for Using ChatGPT to Brainstorm Better
