Conflict Resolution

Five Failed Attempts Is a Signal, Not a Streak

Inspired by Episode 12: All-Seeing Rubber Ducky

You’re reading a subscriber article on a free read. You have 1 free read left. Subscribe free for the whole archive.

Paul’s screen in Episode 12 shows five attempted fixes, five red crosses. Each one looked reasonable. None of them were based on anything new, because the assistant had the same information every time and simply tried a different guess.

The two-strike rule

  1. Attempt 1 fails: fine. Ask what it learned from the failure before it tries again.
  2. Attempt 2 fails: stop. Don’t ask for attempt 3. The assistant has run out of information, not ideas.
  3. Change the input, not the luck. Add the exact error, a failing test, the real data, or a log. Then ask again.

Signs it’s circling

  • Each fix touches a different file, with no explanation of why the last one was wrong.
  • The explanation of the bug changes every attempt.
  • It proposes changing something that isn’t in the stack trace.
  • “Let me try a different approach” with no mention of what the first approach got wrong.

Prompt to steal

Stop. Before another fix: in one paragraph, say exactly why the last two
attempts failed, citing the error output. Then tell me what information
you are missing to be sure of the cause. Don't propose a fix yet.

The duck never suggests attempt three. That’s its whole appeal.

More lessons from Episode 12

Paul’s Desk · Affiliate picks

Paul’s Desk

Gear for the fix.

As an Amazon Associate, Commits and Conflicts earns from qualifying purchases.

All of Paul’s Desk ›