I finally gave up on coffee chats and started asking people for one specific piece of advice instead
I used to send the classic 'pick your brain over coffee' message to anyone in my field, and out of about 30 asks I got 4 replies and zero real help. Now I just ask one concrete question like 'what skill got you promoted from analyst to senior' and I get answers almost every time, including one from a guy in Denver who wrote me three paragraphs. Has anyone else noticed people respond way better to a narrow ask than a vague one?
Read a thing once from a guy who studied how people ask for help, and he said the same thing. Vague asks make the other person do all the work of figuring out what you even want, so most just skip it. When you ask one clear question, they know the answer in about five seconds and it feels good to be the expert. That Denver guy writing you three paragraphs proves it. You stopped asking for their time and started asking for their knowledge, which is way easier to give.