How long you keep the conversations, and who decided that
An assistant answering questions produces a transcript of every exchange, and transcripts are useful: they show what people actually ask and what the answers looked like. They are also a holding of other people's words, sometimes including things said in confidence to what the person assumed was a machine with no memory. The useful question is not whether to keep them but for how long, and that question has never been asked in most organisations because no default forced it.
Decide the period before launch, not after the first request
Thirty days, ninety days, a year: the number matters less than having one, because the alternative is indefinite and indefinite is what you have to defend. Pick the period from what the transcripts are actually used for. If they are read to find documentation gaps, a quarter is generous; if nobody reads them at all, the honest retention period is short.
Separate the transcript from the thing you learned from it
The useful part of a conversation is usually a pattern, not the words: eleven people asked about the same policy, four of them could not find the document. That finding can be kept forever and costs nothing to hold. The transcript it came from does not need to be. Extracting the lesson and deleting the source is the arrangement that keeps the value without keeping the risk.
Know what deletion actually deletes
A conversation lives in more places than the obvious one: the primary store, the search index built from it, a backup, possibly an export someone made into a spreadsheet. A deletion that clears the first and leaves the second is not a deletion, and the only way to know which happened is to ask the question specifically rather than to accept a yes. On this platform identifiers are replaced with tokens before the text is stored for search, so the searchable copy carries tokens rather than the original values.
Someone has to be able to answer a request
A person asking what you hold about them, or asking you to delete it, is exercising a right rather than making a complaint, and the answer has a deadline. Decide who receives that request, where they look, and what they can do, before one arrives. The organisations that handle this badly are not the ones with the wrong policy; they are the ones where nobody knew it was their job.
Frequently asked questions
How long should conversation transcripts be kept?
Can the lesson be kept without keeping the conversation?
Does deleting a conversation delete it everywhere?
What is stored for search?
Who should own retention?
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