For big decisions. You get the strongest case for each side, the assumptions hiding underneath, and a cheap test to run before you commit.
I need to decide: [THE DECISION, e.g. "Should we rewrite our app in a new framework?"] Context: [FACTS, CONSTRAINTS, TIMELINE, WHAT IS AT STAKE] Where I'm leaning, and why: [YOUR CURRENT VIEW] Take me through it in this order: 1. Make the strongest honest case for each option, the way a smart person who believed in it would. No weak versions. 2. For each side, list what it quietly assumes. 3. Tell me which of my own assumptions looks shakiest, given the context. 4. If each option were the right call, what would I see three to six months from now? Give me signs I could actually watch for. 5. What's the cheapest experiment, or piece of information, that would cut the uncertainty before I commit? 6. Only then tell me what you'd do, how confident you are, and the one thing that would change your mind.
Your current stack is why hiring takes four months. Good candidates see it and decline. Every feature takes about twice the estimate because of workarounds. A rewrite buys back years of speed, and the team is still small enough to pull it off.
Most rewrites overrun, and some never ship. Customers pay for features, not frameworks, and a nine month freeze hands your roadmap to competitors. The pain you describe sits in three modules, not in the whole app.
"It will take four months." Your last two large projects ran 2.1 times over their estimates. Plan for eight or nine.
Rewrite only the billing module, behind a feature flag. Give it two weeks. Measure how long the next billing change takes, and whether old and new code can share authentication without hacks.
Migrate piece by piece instead of all at once. Confidence: about 75%. I would change my mind if the billing experiment shows the two systems cannot share authentication cleanly.
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A rewrite, a hire, a price change, moving city, quitting a job. It helps most when you already lean one way and have a nagging feeling you might be fooling yourself.
Say which way you lean and why. Step three goes after your weakest assumption, and it can only do that if your assumptions are written down. If you have more than two options, list them all but ask for the full treatment on the top two. For a team decision, paste each person's position and ask which disagreements are about facts and which are about values. Those need very different conversations.
It isn't the recommendation at the end. It's the cheap experiment in step five, because that turns an argument into something you can test in a few days. And if both cases come out sounding equally strong, the decision probably matters less than it feels. Pick whichever is easier to undo.
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