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Comment by georgemcbay | Hacker News Reader

> My favorite bit about this is how none of the execs want to take ownership of the change, but instead trying to put someone else in the hot seat and/or start a Committee.

And with the exception of John Martin's reply (which recognizes that there are deeper problems they should think about, but seems resigned to the fact that that won't happen) the focus is pretty much entirely: "let's fix the exact issues Bill Gates ran into trying to download this one product we produce" (out of many hundreds/thousands) rather than "let's fix the root causes that caused us to arrive in this place to begin with".

I haven't worked at any companies as large and siloed as Microsoft, but I'd assume this is pretty common for them, at least if they don't have a Steve Jobs-like tyrant who both has all the power and is singularly product focused.

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There was nothing surprising in that email chain at all, looking at it as someone with lots of experience in large companies.

In a twisted kind of way, the replies were reasonable and logical. They're not dumb, they can see it was crap. No one org can actually own this fix, so in that kind of situation it realistically requires someone like Bill to choose someone to drive it, and demand updates to ensure that everyone gets aligned. Telling his execs, especially in a company so notoriously political and "empire" oriented as it was, isn't going to work.

I actually liked that in Amazon, Jeff Bezos used to send out the infamous "question mark" emails on such a regular basis that they built an exec commitee specifically for the purposes of driving direct action on problems. Didn't matter where you were, or what you were working on, if that question mark email came you dropped everything to work on it.

>In a twisted kind of way, the replies were reasonable and logical. They're not dumb, they can see it was crap. No one org can actually own this fix, so in that kind of situation it realistically requires someone like Bill to choose someone to drive it, and demand updates to ensure that everyone gets aligned. Telling his execs, especially in a company so notoriously political and "empire" oriented as it was, isn't going to work.

This goes right back to the leadership failure on Bill's part. If your company is structurally incapable of producing good products (which Microsoft assuredly is and still was) then it's on you as the CEO to implement the correct structures.

That's literally the purpose of upper management: you create the conditions for success to happen.

Yeah. In context the answers make a lot of sense: it’s a dysfunctional company where ownership is non-existent and getting shit done is hard.

This is how learned helplessness looks like when you’re a high level executive.

I think they also suspect/know that Gates won't revisit the issue. The email is a flame as the subject line admits. Gates wasn't going to go back every week for the next six months to track progress.

> This is how learned helplessness looks like when you’re a high level executive.

Must be nice being so useless, yet getting paid so much.

Though I guess these people must have been good at politicking to rise so high.

I mean, you're 100% right, but what's the alternative? They wanna keep the salary. The machine rewards political people, not people who pick fights to improve the product. It's a perfect pair. :/

It's very common. From a certain level up, execs rarely use the products they are responsible for. It's all about strategy, committees, meetings, plans and reports. For them the product is just an abstract thing. When I rented a Buick car, I thought to myself that there is no way any decision maker ever tried the car and thought that this is ok.

I think one of the strengths of Apple during the Jobs days was that Jobs actually sometimes seemed to use the products himself and gave feedback. When I look at the blatant bugs MacOS and iOS had in the last years, I also think that the current Apple big shots never use their stuff or they would have noticed.

> I also think that the current Apple big shots never use their stuff or they would have noticed.

Or they do and they don't think it's worth their time and energy to get them fixed. I think they just don't care about their products, unlike Jobs.

If you'd take the Gates email and give them to my colleagues, saying "this was some random guy complaining about Windows", they'd all react along the lines of "Well, that's just an idiot who makes things up because he's bored and hates Windows. There are good reasons for everything he complained about. He just reports it in a quite dramatized way."

> When I look at the blatant bugs MacOS and iOS had in the last years, I also think that the current Apple big shots never use their stuff or they would have noticed.

The crazy thing is that it's more likely that most people in Apple are using their own products, versus any of the Android phone manufacturers or within Google, where it's likely a few of them would be using the Apple ecosystem instead.

Many of them are definitely dogfooding it, but it's possible that there are communication or empowerment issues.

One thing that drives me nuts for example is the indicator for remaining disk space. I have this icon on my desktop that says "Macintosh HD | 995 GB, 273 GB free". This used to work great until a few years ago. Copy 1 GB onto the disk and it displays 1 GB less free disk space.

But since a few years it goes up and down daily by 100 GB or more. Sometimes I have 350 GB, sometimes I have 100 GB. I think it has to do with Time Machine snapshots and purgeable space (whatever that means) but it's totally useless now. I can't tell for sure if I can copy 250 GB to my disk or not. It may fail now but work 2 hours later. How come nobody notices such a fundamental thing not working? Somehow the dogfooding doesn't seem to work. Or maybe the Apple people all have 8 TB disks so they don't care.

Looks like this was covered by Eclectic Light:

https://eclecticlight.co/2025/02/28/friday-magic-how-to-make...

Yeah, I wonder what's going on within the macOS division, but then again Liquid glAss is a thing.

> I haven't worked at any companies as large and siloed as Microsoft, but I'd assume this is pretty common for them.

Doesn't need to be that large, I worked for a company that ~4500 employees with about 1000 at HQ, that entire email chain looks exactly like what would ensue every time someone at the C-level flagged an issue.

I suspect the reason is much the same, no one wants to be in the hot seat to fix a problem they have no faith they can fix so everyone plays hot potato with the flaming sack of shit until it bursts and lands on someone.

> Fish begins to stink at the head, not the tail. (13th Century Persian Proverb)

I have worked at MS-sized orgs that are like this, but have also worked at 100 employee startups that are exactly the same.

Once bad culture gets to your company, it doesn’t matter the size.

Also I suspect that there's no real teeth in that angry email.

If the big boss is frustrated by the UX, they might send an angry email or even yell at you in person. If your division doesn't meet its sales projection for the quarter, you might get fired.

If BillG had wanted a company that made good user experiences, he'd have hired (and fired) for that. Sending a pissy email is what you do when you're annoyed but don't actually care enough to do anything about it.

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