I actually have a fair amount of experience with this. I've talked a few people off the pipeline in the past. I've made a lot of mistakes and lost some friends along the way, but I like to think I'm pretty good at it now. A few of biggest tips I can give are:
Don't push too hard. This isn't a debate, and debate is for dweebs. This is a dialogue between friends. Keep it light, but persistent. You are teaching him to think critically, not what to think.
Be prepared for burnout and pushback. If you push too hard they will shut down. It will turn into a debate, at which point they are no longer receptive to your attempts. If it happens, drop the subject and move on to something light. Give them time to think. This is more about planting seeds than it is about harvesting results.
Learn the Socratic method. It's a powerful tool for this kind of stuff.
Be prepared to land on and argue from softer opinions than what you actually believe. Be prepared to fight dirty. You don't have to be 100% in good faith all the time. The metaphor I use for this is that critical thought is like a building you're constructing with them. you've already climbed the stairs and know what the roof looks like. Even if you really want them to climb them with you, you're going to have to stop on lower floors. And you need to be ok with that. Small steps win the race here.
And above all else, your safety is top priority. If things go south, bail. You don't need to put yourself into danger.
I actually have a fair amount of experience with this. I've talked a few people off the pipeline in the past. I've made a lot of mistakes and lost some friends along the way, but I like to think I'm pretty good at it now. A few of biggest tips I can give are:
Don't push too hard. This isn't a debate, and debate is for dweebs. This is a dialogue between friends. Keep it light, but persistent. You are teaching him to think critically, not what to think.
Be prepared for burnout and pushback. If you push too hard they will shut down. It will turn into a debate, at which point they are no longer receptive to your attempts. If it happens, drop the subject and move on to something light. Give them time to think. This is more about planting seeds than it is about harvesting results.
Learn the Socratic method. It's a powerful tool for this kind of stuff.
Be prepared to land on and argue from softer opinions than what you actually believe. Be prepared to fight dirty. You don't have to be 100% in good faith all the time. The metaphor I use for this is that critical thought is like a building you're constructing with them. you've already climbed the stairs and know what the roof looks like. Even if you really want them to climb them with you, you're going to have to stop on lower floors. And you need to be ok with that. Small steps win the race here.
And above all else, your safety is top priority. If things go south, bail. You don't need to put yourself into danger.