Senior leadership seems to be more far sequestered now, a bit like Trump, surrounded by lackeys giving them an entirely false impression of the world. That’s how they could legitimately believe they were going to bury the IPhone.
there is still the issue that this might have been classified as "a crazy letter"
a lot of the article reminds me of people which might (or might not) have competency but insists they know better and are very stubborn and very bad and compromising on solutions. The subtext of the articles is not that far afar from "everyone does everything wrong, I know better, but no one listens to me". If you frame it like that it very much sounds like a "crazy" letter.
Strictly speaking it reminds me a lot about how Pirate Software spoke about various EA related topics. (Context: Pirate Software was a streamer and confidence man who got complemented up due to family connections and "confidently knew" everything better while having little skill or contributions and didn't know when to stop having a "confidently bad" opinion. Kinda sad ending given that he did motivate people to peruse their dream in game design and engage themself for animal protection.).
Or how I did do so in the past. Appearing very confident in your know-how ironically isn't always good.
And in case it's not clear: The writing reminding me of it and having patters of someone trying to create a maximally believable writing to make MS look bad doesn't mean that he behaves like that or that the writing is intended to be seen that way.
It's more about how we have a lot of "information" which all look very believable, but in the end miss means to both: Verify many of the named "facts". And, more importantly, judge the sentiment/implicit conveyed information.
Especially if we just take the mentioned "facts" without the implicit messages and ignore the him<->management communication issues I would guess a lot of that is true.
In my experience - a loooong time ago ago now - executive leadership would participate in high-level escalations/critsits for large/key customers on calls. I was just a lowly field-engineer - but over the course of nearly 4-years, was on calls about 5 times with some of the big-names from that era that everyone knows about... And they seemed to emit enough empathy with the specific customer situation to move things forward.
However - being on the "other-side-of-the-fence" (i.e. external, consulting with Microsoft customers - some of them who even spend $1.5billion/year in M365/Azure licensing) and assisting clients with issues and remediations for the last 10-years, things are no longer the same. No amount of escalation gets further than occasionally reaching some level of the product team - and it can take 8-12 months before that even occurs. Troubleshooting and deep-engineering support skills for cloud customers are typically non-existent, and the assigned resources seem to just wait until the issue resolves itself...
I work for myself now, for less money, but I do get to build things to the quality level that I want.
I’m sure everything he said is completely true, Azure is one of the few tech stacks I refuse to work with and the predominant reason I left.
If you’ve joined an org and nothing works the reason is usually that the org is dysfunctional and there is often very little you can do about it, and you’re probably not the first person who’s tried and failed at it.