PROBLEM In my previous organization, teams would often make important decisions repeatedly but didn’t learn which ones were good or bad, and importantly, the reason behind them (why?). Q1 – WHAT PROBLEM The decisions live across different scattered documents, emails, meetings, and Slack threads. Outcomes happen weeks or months later, disconnected from the original context. As a result: - The same bad decisions are repeated - Good Judgment isn’t recognized - Retrospectives focus on outcomes, not decision quality under uncertainty Teams usually optimize for speed and alignment without focusing on the learning aspect. Q2 – SHOULD WE USE AI AI is essential in this case because decision quality is contextual and retrospective. Simple documentation or checklists can capture what was decided but rarely capture the WHY, constraints, or how decision-making took place over the course of meetings. AI is needed to connect decision context to outcomes over time and across teams. Q3 – DO WE HAVE THE DATA Yes, but it’s fragmented and exists across: - Documentation (Decision docs, PRDs, RFCs) - Emails, meeting notes, and async threads - Metrics and business outcomes - Reversals, rollbacks, or follow-on decisions The data exists; it’s just never linked. Q4 – TRANSLATE TO A MODEL The model reconstructs decision narratives: - What assumptions were made - What signals were considered or ignored - How outcomes compare to expectations Outputs will be the decision quality patterns (e.g., “decisions made with X signal tend to succeed”)—not judgments of individuals. Q5 – USER EXPERIENCE The management and PMs see a decision timeline: context → options → choice → outcome → learning. This tool answers, “What should we repeat? What should we avoid next time?” The focus is entirely on learning instead of individual decision-making Q6 – LAUNCH & QUALITY Good enough when teams reference it during planning and retros. Early success = fewer repeated mistakes and clearer rationale in future decisions.