I've found it's remarkably easy to have that conversation with people. Ultimately, telling someone you'd support them if they ran for elected office is a pretty major compliment. And you don't really need any context or permission to bring it up; like saying "that's a nice jacket", you can say it any time. More importantly: when someone they know gives them permission, people actually will consider running.

I would much rather get 10 of my friends into local office around the country than run myself, so that's the goal I've set for myself. I'm making decent progress!

You or your friends should consider (and probably prefer) local administrative offices, like park districts or water reclamation. You don't need to be a subject matter expert to run for these --- that's not expected of you (source: friends who have these jobs). If you're wondering "why bother?", the answer is that having any kind of elected office magnifies your influence with other representatives and stakeholders. It's also great practice.

Running for the kinds of offices everyone has heard of --- Congress and Senate --- is extremely expensive (in the multiple hundreds of thousands of dollars) and, depending on the state you're in, might have a large component of building relationships with your state party. I say this not to discourage people from trying --- especially if you're thinking of running D in an unopposed R district or vice versa --- but to set expectations. Running your first time is easier than you probably think it is, as long as you pick the right office to run for.

If you're on a (recreational) Slack right now, consider opening up a channel and inviting people into it and spontaneously getting a couple people interested in running. I was on IRC channels in the 1990s that started companies that later sold for 9 figures (and the #!w00w00 people can tell you better stories). Getting a couple friends elected to their local library board seems like an extremely reasonable expectation to set for yourself.

If you're organizing something to get people to run for local office, I'm interested in talking/helping. I think there are a bunch of useful applications to be built here, and also a lot of opportunities for people to get together to share encouragement and notes.