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I feel you can also sell from the bottom.

Slack, for example, a lot of the requests came from engineers to work with it.

The product has to be REALLY good though, for most, this is a very hard sell

Ehh, most of the engineers at our org would have been happy to stick with Hangouts and just commenting on PRs and JIRA tickets. Slack adoption ended up being driven from non-engineering groups like marketing and sales, and then eventually mandated from the executive level.

Too many conversations are held in Slack and not in the tickets, now.

It's a weird thing, because JIRA can end up having so many fields and so much enforced process that it feels like there's a lot of overhead associated with creating and closing tickets, and you always know that those actions are potentially feeding into and messing up someone's reporting somewhere.

So you end up talking on Slack about an issue someone's noticed, and then trying to decide whether it's "worth" the bother of creating a ticket for, or if someone's aware of a ticket already for it, or or or.

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