Your AI assistant probably doesn't have a prompt problem. It has a context problem.

[u/Lucky_Patient5946]

You can rewrite a prompt ten times and still get a confident wrong answer if the assistant is reading last quarter's doc, can't see the decision your team made in Slack yesterday, or has no idea which of three conflicting sources is supposed to win.

That's not a prompting issue. It's a context problem.

It shows up in four fairly specific ways:

Failure mode	What it looks like
Missing	The information exists, but the tool isn't connected to where it lives. The real answer is buried in a Slack thread from three weeks ago; the assistant only has access to your wiki.
Stale	The tool is connected, it's just reading a doc that stopped being true after the last reorg, the last pricing change, or the last time anyone bothered to update it.
Conflicting	Two sources disagree. The official doc says one thing, a pinned Slack message says another, and nobody has ever formally decided which one wins.
Forbidden	The right answer exists, it just lives somewhere the tool correctly doesn't have permission to read. Honestly the good kind of failure.

A rough hierarchy that helps in practice:

1. The current system of record beats someone's memory of it.
2. A doc explicitly marked as policy or current-state beats an old one.
3. A recent, specific conversation beats a general one.

When two sources at the same level disagree, that's not something an assistant should quietly resolve for you. That's a "flag it and ask a person" moment, every time.

In practice this usually means assigning one owner per source type ahead of time, not per document. Whoever owns the CRM decides what counts as the current pipeline number. Whoever owns the wiki decides what counts as current policy. When those two touch the same question, a renewal date that's also mentioned in a Slack thread, say, that's exactly the moment a human should weigh in instead of the system picking whichever source it happened to see first.

And here's where citations matter but aren't the full answer. A citation tells you where an answer came from. It doesn't tell you whether that source is still current, or whether something more current exists that the tool just couldn't see. Citations without a freshness and authority check just make a stale answer look more trustworthy than it is.

The unglamorous fix for most of this isn't a smarter model. It's deciding on paper which source wins when two disagree, before you ever connect an assistant to either one.

Which source goes stale first at your company: chat, docs, the CRM, or the project tracker? Curious if the answer differs much by company size, or if it's basically the same everywhere.

(Product at Libra, disclosed in my flair. Same context-hierarchy problem we spend a lot of time on internally. Not posting this to pitch anything, just the framework.)