Stop tossing and turning—let AI interrogate your indecision

Welcome to Prompt, tinker, innovate—my AI playground. Each edition gives you a hands-on experiment that shows how AI can sharpen your thinking, streamline your process, and power up your creative work.

This week’s playground: AI as your socratic decision coach

We all face moments where logic gridlocks. Should you pivot the business strategy? Is it time to quit that "safe" job for a risky venture? Should you hire the candidate with the perfect resume or the one with the incredible potential?

This week, we aren't asking AI to make the decision for you. We are using AI to force you to uncover the answer you likely already have but are too afraid to acknowledge.

Why this matters

Decision paralysis is rarely about a lack of information; it’s usually about an excess of noise. Our brains are wired to fear loss more than we value gain, and we often get stuck in "what if" loops that cloud our judgment.

Traditional "pro/con" lists are flat. They don't account for emotional weight, long-term alignment with your values, or hidden biases.

By using AI as a socratic guide—a teacher that asks questions rather than giving answers—you gain an objective, tireless sparring partner. It helps you separate fear from intuition and logic from rationalization.

Escaping the echo chamber

When we are stuck on a tough decision, we usually consult friends or colleagues. The problem? They are biased. They want you to be safe, or they want you to agree with them.

Top strategists and executive coaches don't tell clients what to do; they ask the right questions to unlock the client's own wisdom. AI can mimic this coaching dynamic instantly.

Imagine you are torn between two marketing strategies. One is data-backed but boring; the other is creative but risky.

• The old way: You agonize for weeks, lose sleep, and eventually flip a coin or delay the choice.

• The AI way: You feed the scenario to an AI persona configured to be a "ruthless essentialist." It asks you: "Which of these choices makes the other irrelevant?" or "If you knew you couldn't fail, which path would you choose instantly?"

Your AI experiment: try this prompt

Ready to clear the fog? We are going to prompt the AI to act as a seasoned decision consultant. It will interview you to help you reach a conclusion.

👉 Time to tinker: Copy and paste the prompt below into ChatGPT, Gemini, Claude, or your preferred LLM.

📝 Prompt: "Act as a world-class decision consultant and psychologist using the socratic method. I am facing a difficult decision and I need you to help me gain clarity.

The rules:

1. Do NOT tell me what to do. Your goal is to guide me to my own conclusion.

2. Start by asking me to briefly describe the decision I need to make.

3. Once I reply, ask me one single, probing question at a time. Wait for my answer before asking the next one.

4. Your questions should challenge my assumptions, force me to rank my values, and explore worst-case scenarios (pre-mortems) and best-case outcomes.

5. Continue this process until I state that I have reached a decision.

My goal: To move from paralysis to action with confidence.

Please start by asking me to describe my dilemma."

💡 Pro tip: Once you have gone through the interview process and reached a conclusion, you can stress-test your decision with a follow-up prompt: "Okay, I have decided to [Insert your decision]. Now, I want you to play 'devil's advocate.' Give me the 3 strongest arguments against this decision and tell me what the most likely point of failure will be."

This ensures you aren't just feeling good about the choice, but that you are prepared for the reality of it.

What did you discover?

Did the AI ask a question that stopped you in your tracks? Sometimes, the most powerful thing AI can do isn't writing code or generating images—it's holding up a mirror to our own thinking.

I’d love to hear from you: Did this process confirm your gut feeling, or did it make you completely change direction? Let me know in the comments below.

Until next time—keep tinkering, keep prompting, keep innovating.

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