Massin SystemsProductivity & thinkingClaude
🧠 Use AI as a thinking partner
Everyone uses AI to write. Almost nobody uses it to think — and that's the more valuable half. These are thinking prompts: pressure-testing decisions, finding blind spots, and arguing both sides before you commit money or time.
1. The pressure test
Before any significant decision — a hire, a big purchase, a new service line:
I'm considering: [decision, with context and numbers]. Play the role of a skeptical business partner who has seen this go wrong before. Ask me the 5 hardest questions about this plan, one at a time, and push back on weak answers. Don't be agreeable — your job is to find the hole before reality does.
2. Argue both sides
Make the strongest honest case FOR this decision in 200 words. Then the strongest honest case AGAINST it in 200 words. Then tell me: what would have to be true for each side to be right? What's the cheapest way to test which one is true?
3. The pre-mortem
Borrowed from project management, brutal and useful:
Assume it's one year from now and this decision failed badly. Write the honest story of what went wrong — the 3 most likely failure paths, in order of probability. For each: the early warning sign I'd see first, and what I could do this month to lower the risk.
4. Find what you're not seeing
Here's my thinking on [situation]: [paste]. What am I not considering? Specifically: whose perspective is missing, what assumption am I treating as fact, and what would someone from a completely different industry notice here?
Make it a habit, not an event
The compound version: keep one running "decisions" document. Log each big decision, the reasoning, and what you expected. Every few months, paste it in and ask what your patterns are — where your judgment runs hot, where it runs scared. That's a level of self-awareness most people never get.
AI is a sparring partner, not an oracle. It doesn't know your town, your customers, or your gut. Use it to sharpen your thinking; make the call yourself.
Want this done for you?
We set up these exact systems for businesses like yours. One call, honest scope, no pressure.