In this guide
Context leaks, it rarely vanishes
When a piece of work goes wrong, the cause is often not a bad decision. It is a decision made without the full picture. Someone did not know about the earlier complaint, the promise in an email or the reason a request was flagged last time.
That missing picture is context. And it is rarely lost in one dramatic moment. It leaks away a little at a time, at predictable places.
In short
Context gets lost at handovers between people, in side channels like spreadsheets and inboxes, and in the gaps between systems. Finding those points is the first step to fixing them.
Where it leaks
- Handovers. When work moves from one person or team to another, the summary travels and the detail stays behind.
- Side channels. Spreadsheets, inboxes and chat threads hold the real story, while the main system holds a status.
- Disconnected systems. Each program knows its part. None of them knows the whole case.
- Memory. Some context lives only in an experienced person's head, and leaves when they are away.
Many bad decisions are good decisions made with half the picture.
Why it matters for agentic software
AI agents are only as good as the context they work with. An agent drafting a reply without the complaint history is likely to draft the wrong reply, and quickly. That is why understanding where context gets lost comes before deciding what to build.
When software keeps the work, its history and its decisions together, the people and agents acting on it work from the same picture. Start with the business, not the software covers the wider approach.
A simple exercise
Pick one piece of work and follow it from start to finish. Every time someone has to ask a colleague, search an inbox or copy something between programs, mark it. Those marks are your context leaks, and often your best opportunities.
Questions
Frequently asked.
Everything someone needs to act well on a piece of work: its history, what was promised, who decided what, and why. The facts in the system are only part of it.
Software can reduce how much of it leaks, by keeping the work, its history and its decisions together. But first you have to know where it leaks, which is a question about how the organisation works.
Follow one piece of work from start to finish and note every point where someone has to ask, search or re-key something. Those points are where context is being lost.
Written by
Mare Pomana
Plumb Digital