Sponsored by
Most big decisions (like raising prices, moving upmarket, cutting a product line, etc) get made in a meeting room based on opinion and optimism. No real stress-test, no modelling, no honest look at what breaks if the bet doesn't land. ‘
Then six months later, you're dealing with churn you didn't see coming or a positioning shift that confused your best customers.
ChatGPT can act as a strategic sounding board. Give it your business context and the decision you're weighing, and it'll map out realistic outcomes, surface the risks, and tell you what to watch for early. It's not a crystal ball, but it's a lot better than going in blind.
Try this prompt:
You are an experienced strategy consultant whose job is to pressure-test business decisions, not validate them.
I'm considering a major strategic change. Your role is to identify likely second-order effects, hidden risks, unintended consequences, and assumptions I'm overlooking.
Business context:
- What I sell: [product/service]
- Target customers: [audience]
- Revenue model: [how I make money]
- Positioning: [how I'm perceived]
- Key constraints: [budget, team size, market conditions]
Decision I'm considering:
[describe the change]
Analyse it from multiple perspectives and provide:
## 1. Pressure test
- Which assumptions does this decision rely on?
- Which assumptions are weakest?
- What would need to be true for this to succeed?
## 2. Scenario analysis
Model:
- Best case
- Most likely case
- Worst case
For each, explain the likely impact on:
- Revenue
- Customer acquisition
- Customer retention
- Brand positioning
- Operations
## 3. Second-order effects
Identify consequences that may not be immediately obvious, including:
- Effects on existing customers
- Sales process
- Marketing
- Team workload
- Competitors' responses
## 4. Failure modes
How could this decision backfire?
What early warning signs should I monitor in the first 30, 60, and 90 days?
## 5. Alternatives
Suggest two lower-risk ways to achieve the same objective.
Challenge my thinking. Don't assume the decision is good simply because I'm considering it. If you think it's a bad idea, explain why.
Run your best idea through this prompt before you commit. If it still survives after ChatGPT has tried to tear it apart, you'll make the decision with far more confidence.
Happy prompting!
---
How 2M+ Professionals Stay Ahead on AI
AI is moving fast and most people are falling behind.
The Rundown AI keeps you ahead of the curve.
It's a free AI newsletter that keeps you up-to-date on the latest AI news, and teaches you how to apply it in just 5 minutes a day.
Plus, complete the quiz after signing up and they’ll recommend the best AI tools, guides, and courses — tailored to your needs.
---