Slack has raised our charges by $195k per year

I can sympathize, but this was always the end deal for cloud SaaS apps. Give em a taste, get em hooked, get years of institutional knowledge and process embedded in the app, refuse to let them export it, and crank the price up.

It's not only guys named Larry who are lawnmowers. Don't stick your hand in. *Own* your shit. Be suspicious of anyone who tries to convince you not to. If it's "easy" it might come back to bite you.

Even if some self-hostable software stack does a rug pull and changes the license, you just don't have to update. You can go log into the database and export to whatever format you want.

I had a job where everything was self hosted and some things custom made and the company abandoned it and moved everything to cloud providers. We had internal IRC and XMPP servers, internal accounting apps, wikis, etc. and moved it all. We paid substantially more money and our previous internal apps were actually better. The reasons given for this were kind of strange.

It was things like "internally hosted wikis were too hard to use for non-technical staff", "even though they work, the internal apps are old", "we want something that is standard", "we can't fall behind the other firms". The point about cloud provider apps all being familiar is valid but none of this stuff was that hard. It felt like the reason we switched (apart from persistent rumors about deals between sales teams) was because executives decided our internal apps lacked a cool factor. So good luck convincing non-technical executives that the cloud apps they are accustomed to seeing shouldn't be used.

As someone who leads and has led large organizations in the past, I can tell you that believe it or not, users across different companies talk to each other and tell each other about the shitty software they are forced to use

Eventually this leads to pressure to give them newer/better tools

Sometimes, these nontechnical users are dealing with problems as real power users that technical users may not see - there really might be a better way to do something and they may have already seen it at another company or something like that

It also happens that something might be working great but looks really dated and right or not, it can give new employees a bad impression

Still another thing is of course that sometimes someone is just throwing a hissy fit and wants something for no good reason but they somehow get the powers that be to listen to them

I’m dealing with this now - everyone is going out and buying AI tools because there is so much pressure to have AI tools and everyone feels like they are falling behind if they don’t go out and buy 10 task-specific AI tools

All that is to say that it could be that those users you referred to were facing problems that you may have been too far removed from the business to understand, it’s not a knock on you, it happens. It’s also possible they just wanted something new and shiny. The pressure to do that kind of stuff is real - I can’t imagine forcing people off of slack, for example