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

"Eventually" often means 30 years later. Computer Associates was a pure customer abuse house for 20 years; many Oracle products have been that way for 35 years.

Enterprise software—software bought by people who don't have to use it—is as a rule abysmal. My model of how this happens is that there are large barriers to entry, and actually working well is not one of them, because the guy signing the PO doesn't have visibility into whether they work well or not. I don't know what the barriers are, but I suspect they include hiring people who already know CTOs, bribing ignorant shills like the Gartner Group, and having a convincing appear you'll still be in business in 10 years.

This is pretty sad. It sounds like emotion-driven FOMO than reason-driven decision-making. Or maybe CYA-driven decision-making ("migrated infrastructure to AWS", nobody ever was fired for buying AWS!).

I would very much understand it if the reasons given were like "We miss the following capabilities that our competitors have: ...", or "We have trouble interoperating with key partners", etc. These would be actually good reasons to pay more, and risk more.

Yeah that’s what I thought I said - that sometimes it’s legitimate need, sometimes it’s not, and sometimes it’s...complicated.

I don’t think this phenomenon is unique to software - there are people who redo their kitchens every year because they can and people who are doing it for the first time in 30 years - it’s just what it is

"we want something that is standard".

Yeah? cool. Just get microsoft's cloud suite, its standard across non-cool companies.

Life is not worth living bikeshedding about chat apps.

We use Microsoft at our startup because it’s so cheap - 12$ for storage, chat, Video Call, Office, email.

Except the software is often pretty annoying. And even in 2025, MS will still randomly eat random files and the auto recovery still doesn’t work reliably.

Google Suite is $14 at the Standard level: 2 TB per user, email, custom domain, video calls, docs / sheets, etc. Approximately 15% more expensive, but, really, it's two dollars more expensive, and I'd say the quality is better.

The problem with Google is that it is impossible to ever talk to anyone when you need support.

No support, poor integration with local file systems, their office is pretty basic. Plus it's Google, I personally trust it less than Microsoft. I still need Teams for calls with external partners, and I need proper Excel.

yeah its kind of annoying.

its not the amazing stack when i worked at $startup, but also we dont really spend any time futzing with it.

Microsoft releases a new feature, we get it. cool.

I was adding a calendar event on Teams (or was it "JS"-Outlook). I wanted to copy from another area in the app, but since it was a modal dialog, I couldn't. There's a button to pop up the "add event" dialog to be its own window. I clicked it, the add event window is now detached. But if course all the stuff I previously entered disappeared, what did I expect, that someone would bother to add code to prevent them from disappearing!?!