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Me, it immediately makes me think I'm talking to someone fake who's opinion I can't trust at all. If you're always agreeing with me why am I paying you in the first place. We can't be 100% in alignment all the time, just not how brains work, and discussion and disagreement is how you get in alignment. I've worked with contractors who always tell you when they disagree and those who will happily do what you say even if you're obviously wrong in their experience, the disagreable ones always come to a better result. The others are initially more pleasent to deal with till you find out they were just happily going alog with an impossible task.

Absolutely this. Its weird creepy enthusiasm makes me trust nothing it says.

I want friends who poke holes in my ideas and give me better ones so I don't waste what limited time I have on planet earth.

No. People generally don’t like sycophantic “friends”. Insincere and manipulative.

Only if they perceive the sycophancy. And many people don’t have a very evolved filter for it!