In my experience, what makes for bad software is PM and engineering hubris. You definitely need some vision and confidence as just following user feedback is a recipe for terrible software as well. The key is to find the right balance and straddle that line.
If it's been long enough for insiders to tell the story of Windows Phone and the eventual cancellation, I'd be fascinated to hear the story of that (from inception to death) and how that went internally given the culture.
There is pervasive NIH syndrome, re-inventing the wheel, and massive amounts of over engineering and unnecessary abstraction caused by chasing the endless "But what if...?" dragon.
This behavior is justified, and critics are silenced, by the "But we're an enterprise company!" cop-out
I was already in the Android ecosystem and far less cynical at that point about Google.
Microsoft's security reputation prior to the recent (5ish years?) failures was largely built up on top of the work stemming from the Trustworthy Computing memo.
https://www.wired.com/2002/01/bill-gates-trustworthy-computi...
Satya Nadella in 2024: "If you’re faced with the tradeoff between security and another priority, your answer is clear: Do security."
Microsoft in 2024: Run this software on your computer so we can take a screenshot of everything you do, index it and we promise Security is still, and have always been, the priority. And yes, we do store data unencrypted on your disk, why are you asking?
But don't worry, you need to be an administrator to open the file. What? your average person daily drives an administrator account? How should we have known that???
At least that's how it appears from our POV, selling B2B applications. They don't seem to care that much about actualities as long as the security checklist passes.
What you're saying is equally true for Apple, Google, Amazon and most other public companies today. You're never gonna get "Use this Microsoft product" as an answer from Apple support/engineer even if that product would solve your particular problem better.
To be clear, I could not make the same comment about Apple or Amazon businesspeople. While they may exhibit their own stigmatic qualities, they are, IME, different. Nothing like Microsoft.
Microsoft does not suffer from "delusions of grandeur". It achieved grandeur a long time ago, and then became delusional. Currently, it is either #1 or #2 on the list of the world's wealthiest companies. Comments suggesting that the company has "changed", and such comments have been popular on HN in recent years, are quite amusing.