Ask HN: “Managing Up” – Working with the C-level

This is from the perspective of someone on the IT side, non-dev, in the corporate trenches (2k-3k person org).

1) I like the people I work with, I moderately like the work I'm doing, but one of the constant blockers for having work done is that it runs through the CTO to complete stuff, like ordering equipment/software. They have explicitly stated before that the company doesn't have any issues spending yet they want to be involved in every approval, which can 1-2 weeks.

2) I'm trying to convince myself of the Amazon "disagree and commit" mantra but maybe I am not emotionally mature enough to do so? For some of the proposals and teams that I think have a high chance of failure and really don't move the needle on the change this person wants to see, I want to be able to shrug and tell myself that it is what it is but the thing is I'll be forced to but time and energy into mitigated it if it does fail.

Plenty of people would say 'Look for something else' but I was already passed up for role by this person because of my 'lack of experience'. The person that then took the role, when I passed over my docs and proposals, said they were amazing and they look forward to working on it. I've found myself at crossroads, don't really know where to go in the working world because I keep running into barriers like the above where I question if I'm even fit to work in a company at all.

Thanks for any advice. Feel free to PM.