When reaching out to ask for a coffee meeting, be immensely specific about why you want to meet, and what you hope to get out if it. If the reason is only as good as “let’s connect!” don’t be sour if they pass / forget about it. That kind of “just saying hi” serendipity is best for parties/networking events you both happen to be at, not worthy of asking someone to carve out a new slot in their schedule.
The more specific you are, the more value you’ll get from your potential coffee-partner. If you communicate a clear possible path for the conversation, coffee partners who can’t provide value will self-select out, but even then if your ask is clear, it will make it so much easier for them to forward you to the right person. And if they do take the meeting, they are far more likely to show up prepared & ready to help.
(1) Cf. How to request a meeting — Steve Blank.
(2) Cf. How to request a meeting — Scott Britton.
(3) As someone on the receiving end of meeting requests, I’ve found that this advice from Aaron White is the most effective.