🏴‍☠️ 30 Prompts for Decision Making

From Blank Page to Plan

Author

Captain YAR
September 27, 2025 • Estimated Reading Time: 7 minutes

The single biggest skill successful leaders have isn’t money or luck, it’s the ability to make better, faster decisions.

It’s a skill that can feel overwhelming when you’re staring down a huge choice. That’s why I was so impressed when I stumbled upon a post that turns this challenge into a structured process! The original poster shared a brilliant collection of ChatGPT prompts designed to act as your personal decision-making framework.

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The big idea is to stop staring at a blank page and instead use AI to build a logical analysis. This contributor shows how you can prompt ChatGPT to create decision matrices, weigh pros and cons, and analyze risks for you. It’s like having a team of analysts on standby.

This savvy professional breaks it down into key areas:

  • Strategic Business Moves Get help evaluating multiple options for your business by creating a structured decision matrix that looks at ROI, risks, and feasibility.

  • Major Career Paths Analyze different career trajectories by comparing salary potential, required skills, long-term growth, and how they align with your core values.

  • Complex Personal Choices Apply the same logical rigor to your personal life, getting an AI-assisted breakdown of choices based on your budget, lifestyle, location, and financial stability.

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Prompt of the Day

To give you an idea of how powerful this is, check out the prompt this talented creator shared for career decisions:

I’m torn between pursuing [Career Path A] and [Career Path B]. Analyze both paths in terms of salary potential, required skills, long-term growth opportunities, and career stability. For each option note risks and rewards, highlight career paths made by others with similar roles, and decide which one is the best fit for my values [insert personal values].

Credit to Adam Biddlecombe

The mind behind it wisely adds that AI is there to help with analysis, but you should always add your human intuition to make the final call.

This is just one of 30 awesome prompts covering business, investing, time management, and more.


I highly recommend checking out the original post to see the full list for yourself!

Used by Execs at Google and OpenAI

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