How do you decide who to reach out to first when you have a warm intro path?

I am building a product around relationship-driven outreach, and one workflow keeps coming up:

When someone has a goal like hiring, sales, fundraising, partnerships, or career exploration, the hard part is often not writing the message. It is deciding who is actually worth reaching first, why now, and what the smallest good ask should be.

I am curious how other makers and operators handle this today.

When you are trying to reach someone through your network:

1. Do you start with the most senior person, the closest connection, or the person closest to the context?
2. What makes a first ask feel easy to answer?
3. Where does the workflow usually break: choosing the person, explaining the reason now, finding the warm path, or writing the first message?

I am building Netlio in this space, so I am asking partly from product research, but I am more interested in the workflow than in pitching the product here.