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- Issue 06 - Decision-Making with AI: When You’re Drowning in Options
Issue 06 - Decision-Making with AI: When You’re Drowning in Options
From chaos to clarity: structured thinking powered by AI.
The Short Version
When you’ve got too many options and not enough time, AI can help you think. Not just faster, but more clearly. Whether you’re choosing a vendor, prioritising a backlog, or navigating a tricky career decision, structured thinking powered by AI can reduce overwhelm and sharpen judgement.
The Problem
Most of us don’t struggle with a lack of ideas — we struggle with too many.
You’re facing:
Three competing vendors, each with trade-offs
A dozen product features, but only budget for four
A tempting internal job offer vs staying on your current path
And it’s not that you can’t decide. It’s that you don’t have time to structure the decision properly. You’re juggling shifting priorities, constant context-switching, and inbox overload. Deep thinking gets squeezed out.
The AI Assist: Structured Thinking on Tap
Here’s how you can use ChatGPT or another assistant to bring clarity, on demand.
✅ 1. Frame the Decision
Prompt:
Act as a decision coach. I need to make a choice between X and Y. Help me clarify my goal, define the key criteria, and identify what information I’m missing.
🧠 2. Generate a Comparison Table
Prompt:
Create a pros and cons table for choosing between [Option A] and [Option B], using criteria like cost, complexity, speed, and long-term impact.
Optional: Ask for a decision matrix or weighted scorecard to bring more rigour.
📉 3. Play Out the Scenarios
Prompt:
Imagine I go with Option A. What are 3 likely short-term outcomes and 3 long-term consequences?
What could go wrong with Option B that I’m not considering?
This turns the assistant into a sparring partner — not just repeating facts, but helping you think through implications.
🔍 4. Spot Blind Spots
Prompt:
What cognitive biases might affect this decision? Suggest ways to reduce their impact.
Ideal when you’re making high-stakes choices solo or under pressure.
5. 🧠 Bias-Aware Analysis
Research shows that confirmation bias is the most common cognitive distortion in AI-assisted decision-making
Prompt:
Challenge my thinking on this decision. Act as a devil's advocate and:
What cognitive biases might be influencing my preference for [Option X]?
What evidence contradicts my initial inclination?
How would my biggest competitor approach this choice?
What would I advise if this were someone else's decision?
What could go catastrophically wrong with my preferred option?
6. 🔍 Executive-Level Stress Testing
Prompt:
Act as my board of directors. I'm presenting [decision/strategy] for approval.What cognitive biases might be influencing my preference for [Option X]?
Generate the 5 toughest questions you'd ask:
- About assumptions I might be making
- Regarding downside protection
- Concerning resource allocation
- About competitive response
- Related to execution risks
Then provide data-driven responses to each question.
7. 📊 3. Multi-Scenario Strategic Modeling
Prompt:
Create a decision matrix for [specific choice] with the following scenarios:
Best case, worst case, and most likely case for each option over:
- 3 months (immediate impact)
- 12 months (operational effects)
- 3 years (strategic implications)
Include:
- Financial impact estimates
- Resource requirements
- Risk probability and mitigation strategies
- Competitive positioning effects
- Team/organisational implications
Real-Life Example
Alex, a mid-level product manager, needed to choose between two roadmap directions: refining an existing feature for enterprise clients or launching a new one aimed at growth users.
With AI, he:
Defined five key decision criteria
Built a weighted matrix in minutes
Simulated exec objections with GPT (“Act like my CFO and critique this choice”)
Instead of agonising or bouncing it endlessly in meetings, he reached clarity in under 30 minutes and brought that thinking to his stakeholders.
Try This Today
Next time you’re stuck between competing options, don’t just ask AI for an answer, ask it to help you structure the question. Think of it less like a search engine, more like a McKinsey analyst in your pocket.
Until next time,
Luke & Marco
AI for Business Leaders
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