ClueCon Weekly with Keith Wedinger [Sn. 15 Ep. 15]: Your Documentation Could Be Holding You Back
In this episode of ClueCon Weekly, host Jon Gray sits down with Keith Wedinger, Principal Consultant at Improving, to talk about one of the most overlooked risks in software teams: documentation. With decades of experience across platforms, companies, and industries, Keith has seen how good (and bad) docs can make or break a project.
Keith explains the “bus factor” in plain language and why relying on a few heroic team members is a recipe for outages, slowdowns, and painful onboarding. He shares practical advice on choosing documentation platforms, making docs part of your delivery culture, and keeping them lean, accurate, and easy to find.
They also dig into how AI is changing documentation—both for writing and consuming it. From using AI tools to wordsmith rough drafts to emerging “notebook LLMs” that sit on top of your existing docs, Keith outlines where AI genuinely helps and where you still need to be careful about security, privacy, and company policy.
Along the way, you’ll hear tips on:
🔹Building onboarding docs that actually get new hires productive fast
🔹Keeping docs alive instead of letting them rot in a wiki graveyard
🔹Avoiding duplicate, conflicting how-tos by enforcing a single source of truth
🔹Measuring the real impact of documentation in saved time, reduced risk, and fewer blocked projects
If you’ve ever spent days reverse-engineering a system because “the person who knew it is on vacation,” this episode is for you.
Topic Participants
chelsea.batschke