moriez-
I struggle with the same things. So this is what I'm doing to fix #1:
I believe that you and I have a need to impress or a need for approval. "Needs" are desires that require fulfillment by someone or something else. These "needs" are hard to fulfill because there's no telling whether someone will be impressed or not. When the need isn't fulfilled, we experience a negative emotion. So we subconsciously take the safe route: don't say anything and that will guarantee that the need to impress won't result in a negative emotion.
So it's not good enough to try to focus on getting rid of the need. You have to replace it with other desires that are easier to fulfill. In social situations, I try to focus on: being nice, asking questions, using "in my opinion", utilizing small talk.
Take a look at this article:
How I Stopped Being Needy
As for #2:
I think it's annoying because in my mind it implies that they think I'm not capable of figuring out that that task needs to be done. Or it implies that I don't take the initiative and that I'm lazy. This means that they don't approve of me or my actions. Again, there's the need to impress or the need for approval. So just like #1, switch your focus. Focus on keeping the workplace clean and efficient, keeping the customers happy, etc. Act as if you own the place, what needs to be done?