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The Session You Should Never Delete

By Nigel Guy · 2 min read

Most people treat each conversation as disposable by default — ask the question, get the answer, close the tab, start fresh next time. For one-off tasks that's fine and arguably tidier. For an ongoing piece of work — a project, a role, a long-running piece of research — it means re-explaining the same background, the same constraints, and the same decisions already made, every single time you come back to it.

The mechanism: the Standing Session

1. Start it deliberately, not by accident. Pick the moment a task turns from "one question" into "a thing I'll come back to," and open a conversation specifically for it, named clearly enough that you can find it again in a list of dozens.
2. Put the durable facts in early, not scattered across later messages: what the project is, who it's for, the constraints that won't change, the decisions already made and why. This is the material a new conversation would otherwise force you to retype each time.
3. Add to it as the project moves, rather than starting a new thread for each sub-question. Each addition inherits everything already established, which is the entire advantage over starting fresh.
4. Periodically ask it to summarise where things stand. This does two jobs at once: it gives you a checkpoint to sanity-check against your own memory of the project, and it keeps the thread's own sense of context sharp as it grows long.
5. Use memory or a saved project note alongside it, where that feature is available, so the standing facts survive even if you eventually do need to start a new session for some reason.

What to skip

Skip making every conversation a standing session — most questions really are one-off, and forcing them into a long-running thread just accumulates irrelevant clutter that makes the genuinely important thread harder to use. And skip letting a standing session become a dumping ground for unrelated tasks just because it's open; a project log stays useful because it stays about the project.

Guardrails

• A very long-running conversation can eventually run into context limits; if you notice answers referencing older material getting vaguer, that's the moment to ask for a fresh summary and consider starting a new session seeded with it, rather than assuming something's simply gone wrong.
• This is a workflow habit, not a backup — if the log matters, keep the key facts somewhere durable outside the conversation too (a document, a saved note), since a conversation isn't a guaranteed permanent record.
• Don't put anything in a standing session you wouldn't want persisting indefinitely — see the checklist on handling sensitive documents before logging anything personal, financial or confidential into an ongoing thread.

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