John Cutler · 7 min read · Product Discovery
TBM 411: Messy Docs As Helpful Pattern
Read the original on cutlefish.substack.com →
The article highlights a common pattern where high-performing teams rely on messy, freeform documentation and frequent migrations across tools to capture real-world product work and discovery. It argues that externalizing working memory through artifacts enables practical sense-making beyond tidy hierarchies, and discusses how AI trends may shift or amplify this habit.
Key Takeaways
- Discovery work often relies on messy, freeform docs with links across multiple tools, rather than clean, centralized hierarchies.
- Externalizing working memory through artifacts (docs, comments, links, dashboards) helps teams manage complexity and preserve context for emergent work.
- Trying to force everything into tickets can hinder experienced teams; the pattern thrives because form follows function and accommodates variation.
- AI trends (e.g., Claude workflows) echo this pattern and may shift or enhance how teams perform and evolve this documentation habit.
Excerpt
Existing stuff, now more accessible! Check out the POM Starter Pack and OS Discovery playbook , now in non-Gdoc form. In my day-to-day work (at Dotwork), I hear about all the real-world exceptions, “things that work,” “things that never work” (but we keep trying), and everything in between. I’m a big fan of saying, “Can you show me?” on discovery calls. A slide, agenda, doc, dashboard, screen, etc., combined with the person talking about the “thing”, is worth a million abstract summaries. I love seeing real examples of how people work every day, especially when they differ from the “official”…