Living Objection Library

What this task does

Static objection docs rot. This routine reads your recent transcripts, spots objections you haven't cataloged, notes how you answered and whether the deal advanced, and folds it all into one living file — so the library reflects what works in your deals, not what a playbook guessed.

Set up once

1. Create objections.md in the workspace (headers: objection, response, outcome, last seen).
2. Keep transcripts flowing into calls/.
3. Run weekly, or after any call with a new objection.

The task brief

Paste this into Claude Cowork:

Read transcripts in calls/ since [FILL IN: date]. Extract every objection raised (verbatim), match against objections.md, and: add new ones with the response I gave and what happened next; update existing entries where a different response worked better; flag the three objections trending up this month. Show me the diff before saving.

What you get back

• An objection file that mirrors your actual market, updated weekly
• Response quality tracked by real outcomes, not opinion
• A trending-objections early warning — messaging drift shows up here first

Guardrails

• Anonymize customer names in the library file.
• A response that worked once isn't a law — watch the outcome column.