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Prompt Details

Model
Chat - (gpt-5.5)
Token size
647
Example input
[DESCRIBE THE PLAN, DECISION, OR APPROACH YOU'RE ABOUT TO COMMIT TO — the more specific, the better the premortem]: I'm launching a weekly automated email report every Monday at 7am. A Python script on a shared internal Linux server queries our Salesforce CRM via a read-only API key (belongs to my personal Salesforce login), formats the sales totals into an HTML table, and sends it via our SendGrid account to eight leadership team email addresses hardcoded in the script. It runs off a cron job with no retry logic and no alerting if it fails silently. I'm the only person who's touched this script, and there's no documentation. We plan to turn it on in two weeks and I'm leaving for a two-week vacation the week after that.
Example output
## Step 1: Plan specificity check Your plan is already specific enough. Moving directly to Step 2. ## Step 2: The failure is already true It's three months from now, and this plan failed. The automated weekly report stopped being delivered at some point. Nobody noticed for several weeks. Why? ## Step 3: Three causes from different angles 1. Technical: The API key is tied to your personal Salesforce login. Your password expires or the key rotates. The script fails silently with no alerting. 2. People: You're the only person who's touched this script, and you're on vacation the week after launch. No documentation means no one else can debug it. 3. Drift: The email list is hardcoded. Three months in, someone leaves the leadership team and the report still goes to their old address, bouncing silently. ## Step 4: Test each cause All three: yes, I'd change the plan right now. Dedicated service-account API key, not a personal login. Retry logic and failure alerting. A README and a 15-minute handoff to a second person. Email list moved to a config file instead of hardcoded. ## Step 5: Revised plan Dedicated Salesforce service account. Retry logic with alerting on failure. Recipient list in a config file. A short README covering schedule, credentials location, and how to test manually. A quick handoff before vacation. ## Step 6: What I decided not to fix - Automated schema-change detection — schema changes rarely, manual quarterly review is enough for now. Ready to build once the service-account key and alerting are in place — not before.
🤖 GPT
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GPT-5.5
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Runs the premortem technique: ask why your plan already failed, not whether it might. This reframe surfaces real risks a normal review misses, then helps you fix what's fixable before you build.
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Added 6 days ago
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