9 ChatGPT Prompts That Solve Stuck Problems

You know that feeling when you’re stuck on a problem and your first move is to open a search tab? Type in the issue, scroll ten blue links, skim a forum thread, and still end up guessing. I’ve been there more times than I want to admit. So when I came across this post from an AI professional who sold his last company, I stopped scrolling.

The original poster made a point that stuck with me: most people Google their problems, but smart operators prompt their way out. And the difference between the two groups isn’t intelligence. It’s tooling. One side searches and guesses. The other has a structured system for working through anything.

The teams who win aren’t the ones with the most resources. They’re the ones with the tightest feedback loops between thinking and deciding.

That line from the creator reframed how I look at problem-solving. When he sold his last company, he says the thing that separated them from competitors wasn’t the product. It was how fast they could diagnose what wasn’t working, decide what to do next, and move. And here’s the part I love: that skill is now available to anyone with ChatGPT and the right prompts.

The expert covered 20 of them in total. Below are the nine he reaches for most when he’s stuck, each one a different angle on the same goal, think clearly, then decide fast.

The 9 Prompts Worth Stealing

  1. Root Cause Analyzer. Stop treating symptoms. This one forces you to find what’s actually broken before you take a single action. Most bad decisions come from fixing the wrong thing, and this prompt kills that habit fast.
  2. Decision Matrix Builder. It scores every option across time, cost, risk, and upside. No more gut-feel calls that quietly waste months. You see the tradeoffs laid out in one clean grid.
  3. First Principles Breakdown. Strip the problem down to its raw components, then rebuild from scratch with fresh eyes. It’s the antidote to “we’ve always done it this way” thinking.
  4. Constraint Removal. It maps every limit holding you back, then sorts them into two piles: the real ones and the ones you invented in your head. You’ll be surprised how many are imaginary.
  5. Tradeoff Analysis. Shows you exactly what you gain and lose with each path. The author calls it a cure for “false clarity,” that feeling of certainty that isn’t backed by anything real.
  6. Failure Prevention. Run a pre-mortem before you launch. You assume the project already failed, then work backwards to figure out why. It surfaces risks you’d never spot looking forward.
  7. Reverse Engineering. Start from the outcome you want and map every dependency backwards to today. Instead of guessing your first step, you build the whole chain in reverse.
  8. Strategic Risk Mapping. This covers the scenarios most founders skip: legal, financial, execution, and market. The uncomfortable stuff that sinks companies quietly.
  9. Complete Problem Solving Framework. One master prompt that runs the full sequence, from diagnosis all the way to an action plan. Think of it as all eight above stitched into a single flow.

What I appreciate about the creator’s list is that none of these are clever tricks. They’re structured thinking tools dressed up as prompts. You could run any of them on a whiteboard. ChatGPT just makes the process faster and keeps you honest when you’d rather skip a step.

How to Actually Use These

Reading a list like this is easy. Building the habit is the hard part. Here’s how I’d put the original poster’s ideas to work without overthinking it:

  • Pick one problem you’re stuck on right now. Not a hypothetical. A real one sitting on your desk today.
  • Start with Root Cause Analyzer. Before you brainstorm solutions, make sure you’re solving the right problem. This alone saves hours.
  • Move to Decision Matrix Builder once you have options. Let the scoring expose your bias instead of defending it.
  • Run Failure Prevention before you commit. A five-minute pre-mortem beats a five-week cleanup.

Notice the loop there. Diagnose, decide, stress-test, move. That’s the feedback loop the expert says separates winning teams from busy ones. The prompts are just the rails that keep you on it.

The second group is not smarter. They just have better tools for thinking.

I think that’s the real takeaway here, and why I wanted to share it. There’s a quiet gap forming inside every company right now. On one side, people who search, scroll, and guess their way through hard problems. On the other, people who have a repeatable system for working through anything. The good news is the system isn’t gated behind a fancy degree or a big budget. It’s a handful of prompts and the discipline to use them.

The person who shared this suggested passing it along to any founder or operator who spends too long stuck on problems that should be solved faster. I’d second that. If you’ve got someone in your circle who’s always drowning in decisions, these nine prompts might be the nudge they need.

Want the exact wording and the full set of 20? Check out the original LinkedIn post for the complete breakdown.

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