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I would say it's time to get confrontational.

One thing that separates a start-up from a regular company is that you shouldn't have normal office politics. You both (probably) have equalish equity so the only things preventing you from confrontation are the social norms and stigma against that.

At Paypal, people used to wrestle to settle arguments. I'm not saying that physical dominance is the right way to get things done, but I do think there should be a "no fear", open environment where people can be completely up front without worrying about hurting/offending their peers.

It's ok to say, "look, we need to have a no-excuses deadline, and we need to pull consecutive all-nighters to get it done."

It's also ok to spec out exactly what minimum requirements your product needs.

I can also say that I've been on teams where people weren't up front about problems that they had with me. It led to an unhealthy dynamic, and things didn't pan out.



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