How do I talk to my family about what I want when I die?

The best time to start this conversation with family is actually before you've formally made these decisions. That way, their first engagement with the conversation isn't you telling them what you want them to do for you, but asking them what they would think you would/should do. This can also be a good way to gauge who is "on the same page as you" as you decide who to appoint as your executor or proxy.