In the story of Passover, there are four sons: the wise one, the wicked one, the simple one, and the one who does not even know how to ask a question. 

My boss has this philosophy: whenever someone tells you something, you need to question it and challenge it until you feel comfortable with the answer or until you (or the other person) have action items to get the answers you desire.

And it is fucking tiresome. 

Recently he asked me to do something. I planned for the something and told him my plan before doing it. He immediately asked me why I wasn’t doing it a different way (read: the way he thought it should be done). Now, I had a good answer, and he accepted my plan, but the fact that I was questioned rubs me the wrong way. He hired me to do a job; he needs to trust that I’m going to do it in the way I think is best for the company, the project, and the people. 

But what’s worse is that he expects all of us to question and challenge everything, and I don’t even know what questions to ask or challenges to make. Every time I think I do, I’m either wrong or missing something. Whenever he’s in a status meeting with me and one of my guys he takes it over, I guess trying to show me what to do, but it doesn’t work that way. 

We had a meeting where he explained to us what he wants us to do in project meetings. Someone said it would be great if we have a checklist to make sure we don’t miss anything, and he had the gall to say “I don’t want you doing things just because I said to do them.” 

That is the whole fucking point! You told us what to do, but you don’t want us to do it now? Then what is the expectation? 

I know what he wants: he wants us to be exactly like him and know everything he knows. But there’s no possible way for me to do that; I was never a junior engineer in the company, and I didn’t work my way up. I will never, ever be able to gain the knowledge gained by more than eight years of actually doing the job, unless I actually start doing the job, and I’m too far ahead in my career to start over that low. 

I’m so sick of being the son who does not even know how to ask a question. If there’s a bright side, it’s that I’m not the only one, but that’s more like the light at the end of the tunnel being the headlamp of an oncoming train.