Deal Replay: Use AI to Analyze Lost Deals and Turn Failures into a Winning Playbook

Too many tech advisors treat lost deals as a sunk cost. In this episode Bob interviews a practitioner who built a lightweight, practical 'deal replay' process that uses simple AI tools to analyze closed-lost opportunities, surface repeatable patterns, and convert those insights into concrete playbooks, scripts, and automated follow-ups. We break down the exact artifacts to collect (recordings, proposals, CRM notes, competitor mentions), a loss-reason taxonomy you can run in a weekend, prompt templates for LLMs to identify root causes, and the smallest viable dashboard to track improvement. Listeners will get a 5-step pilot plan they can execute in seven days — plus sample prompts, labeling tips, and KPIs to prove ROI. This episode teaches something actionable, solves the problem of revenue leakage from lost deals, and moves advisors to one immediate, measurable action.