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Coowoolf

historian-decision-model

by Coowoolf

105 Product Management Skills extracted from Lenny's Podcast - For use with Claude Code / Cursor / Windsurf

1🍴 0📅 Jan 24, 2026

SKILL.md


name: historian-decision-model description: Use when joining a new company, taking over legacy products, or proposing strategies that were previously attempted to avoid repeating past mistakes

The Historian Decision-Making Model

Overview

A process for improving decision quality by excavating and analyzing organization history to understand the context of past failures before charting a new path.

Core principle: Learn from mistakes you didn't personally live through.

The Process

┌─────────────────────────────────────────────────────────────────┐
│  1. EXCAVATE                                                    │
│     Research past decisions and outcomes                        │
│     Talk to long-tenured employees                              │
├─────────────────────────────────────────────────────────────────┤
│  2. CONTEXTUALIZE                                               │
│     Analyze "Why" decisions were made at that time              │
│     What was the environment/constraints?                       │
├─────────────────────────────────────────────────────────────────┤
│  3. IDENTIFY BAGGAGE                                            │
│     Map internal resistance and emotional blockers              │
│     "We tried that before" = baggage signal                     │
├─────────────────────────────────────────────────────────────────┤
│  4. FORMULATE HYPOTHESIS                                        │
│     Create strategy informed by historical context              │
│     Address what was different then vs. now                     │
├─────────────────────────────────────────────────────────────────┤
│  5. DECIDE & ITERATE                                            │
│     Commit to direction without needing 100% certainty          │
│     Learn from results                                          │
└─────────────────────────────────────────────────────────────────┘

Key Principles

PrincipleDescription
Excavate activelyDon't assume you know the past
Context mattersSame idea can fail or succeed based on timing
Baggage is realEmotional weight blocks rational evaluation
Commit anywayHistory informs but doesn't dictate

Common Mistakes

  • Ignoring "baggage" associated with old ideas
  • Making decisions without understanding historical context
  • Assuming "we tried that" means it can never work

Source: Anneka Gupta (Rubrik CPO) via Lenny's Podcast

Score

Total Score

55/100

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