It sounds like a lot of passive aggression on both sides. Here's your problem - he thinks he's the boss, and you think you are the boss. He asks you to implem

It sounds like a lot of passive aggression on both sides. Here's your problem - he thinks he's the boss, and you think you are the boss. He asks you to implement a feature. You don't think it's a good idea. You both give each other a bunch of reasons why. He ends the conversation with "OK, it's sounds like it's a bad idea then". He retreats for a while, then decides to go another three rounds. My S.O. and I have similar conversations, though it's usually about tech vs. clothing purchases. Who wants to spend 1000 on a sweater? A DSLR lens is a much better purchase. Anyway ... The point is, you have unaligned goals or unaligned strategies for reaching those goals. As you've said, you aren't on the same wavelength. That's not really unhealthy - sometimes other people are right when they disagree with you. Sometimes not. You have two options (IMO): * You both have to agree that you trust each-other, but you are aware that you disagree at times (due to your separate skill sets, expectations, etc). You both have to work to minimize the impact of the quibbling, and you need mechanisms to help you here - most companies have minute books to record decisions for this very reason. * Split.