Of course it must be coupled with genuine flexibility to change your mind when someone points out actual, real difficulties.
But he is an engineer, more so than most managers. He would know what goes into making an application like this, and so know that things are moving slower than they should.
I see nothing obnoxious about asking this very valid question under those circumstances.
If you're missing deadlines, you can't both complain a) when there's no accountability and the business is going poorly, and b) when your managers are trying to hold you accountable.
Ultimately your employer has to make money to pay you for your work. Keeping this in mind is one way to help you avoid yak-shaving, bike-shedding, and other weed-entering activities.
Team dysfunction is inseparable from tech dysfunction. Imagine one team owns three quarters of this service as another owns half of it. Or more likely, one owns a tenth of a problem space and another owns a fifth. Suddenly you need a fully realized solution. Who will step up? Well, you’re the one who actually needs it…but surely you don’t have to start from scratch? Surely…?
Then there’s just the fear of showing your ass. The day after it launches, who will be in hot water? Will it be you, because you agreed with the PM that your substandard code could ship? Why didn’t you flag the problem earlier? Get more help? Tell someone you weren’t already a superstar at this infra or that architecture?…
And then recall they did ship, it sucked, they bought Instagram. Then WhatsApp. And dozens of others
I guess the lesson is: yelling “go faster!” at a blocked-up engine is only gonna go so far. Mark’s (and many others’) move is to apply money to replace or get additional engines. Or roll up your sleeves and fix the org and culture…doesn’t have exactly “founder mode” romance to it tho, and there’s scarcely a harder task out there.
consider where that management debt may have come from, and whether accepting the current crunch will somehow alleviate it, or signal that crunch will solve all problems and should be used, likely more aggressively, in the future