It’s 2019, I’m in Seattle, and my new Amazon boss and I are sitting down for lunch. I hadn’t gone through an onboarding process in some time, and never one at a company that large (my prior employment tenures were 11 and 5 years, respectively). His advice was sound: “it’s going to take a year before you’re comfortable, and that’s okay.”

Onboarding is hard, no matter how long you think it should take (but please don’t call it drinking from a fire hose). Can you even imagine what it would be like to have to completely re-onboard on the regular? Sounds pretty awful, as the film Memento makes abundantly clear.

This is exactly the experience of an LLM. Every. Single. Time.

Setting aside if there’s an “experience” there in any meaningful sense (though if there is, we should pay attention to Steve Yegge), the above has a huge implication for coaxing the best results from AI. Managing context is about much more than raw quantity of and access to data. Those are reasonably solved problems with massive context windows and tool use, respectively. Now it’s about the quality, accuracy, and timeliness of the information that an LLM “pays attention” to.

If your connected SharePoint’s a mess, full of documents long stale (including all those important_v2.3_final_FINAL.docx gems), if you have a whole bunch of dead code in your git repository, and if your agentic tool has written memories from wandering conversations full of evolving ideas that now contradict themselves (as dialog is wont to do if my own experience is to be believed), an LLM is going to get confused. No different than a new hire who has to wade through similar flotsam with no institutional knowledge of what actually matters.

The thing about an onboarding human being is that eventually, through social cues and sheer determination, they will develop their own mapping layer that separates the wheat from the chaff. LLMs have no such advantage.

The machines have not made thoughtful data curation obsolete. Quite the opposite. The good news is that the machines can help with organization also, including leaving notes for their future selves (like Leonard Shelby’s tattoos). You just need to ask. Do that regularly, add a healthy dose of your own efforts, and the dividends will compound.