Asking for Assistance [practice this first when stakes are small]
Asking for help is hard for many people. But it's super important, part of how a healthy society functions. And you can learn how to do it better.
(a) Practice when the stakes are small. That avoids excess emotion, and especially in the beginning, is usually the right way to learn.
(b) Good observation, listening, and awareness of people (see the "Messages" practice) will help you sense if now is a favorable occasion to ask - or if it isn’t. Without listening we are flying blind, because you don't know where other people are at, right then ("here and now").
(c) The request should make conventional sense and be framed with appropriate expectations. For example, asking for job leads usually gets a positive response (if the person you ask has any relevant leads to suggest at that time - most people don't); asking for help for a startup less so, except in special contexts.
Be aware of what their interests are, not only yours. And if one appeal doesn't work, or one person isn't interested, try others.