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Depends entirely on the conversation obviously, but perhaps important details should eventually be coalesced and moved to a more permanent document or project management system before the deletion deadline. It's a good discipline to have.

I don't think anyone would argue with the value side of the question. The tricky part is calculating the cost side. (The cost of not deleting old messages.)

Surely we can agree that the cost side is > 0.

I'd argue that the benefit side is generally at least a little lower than what we think it's going to be. And if the expiration limit is set to say, 1 year, the cost of deleting old messages goes down considerably.

As with many things in life, it's a tradeoff. Do you want to accept a higher risk of security incidents or make it easier to recall information from a long ago IM conversation?

There are rational reasons for an organization to do either.