There are as many reasons to switch to the pipe (or use for the first time) as there are pipe smokers. It's a completely personal thing. For some people, encouragement and giving them a pipe might work, for others that might just be too easy. Some would probably come to it if there were hoops to jump through, like actually making an investment in a pipe and tobaccos. Some would be more encouraged by being told that it's probably too hard for them. Some just needs someone to hold their hand through it.
My friend who owns several restaurants in town here is a cigar guys, and when asked, he'll tell you that you probably couldn't afford cigars, it's for the wealthy, and throws his nose up in the air. And, yet guys will approach him with handfuls of $15 cigars to show him that he was wrong. Telling people that the houses in their neighborhood are just too rich for them, or their cars or clothes are just too expensive for them, works wonders for getting people to "keep up with the Jones."
Some people just need a free pipe.
Personally, I just smoke my pipe and do my thing. I am not a walking salesman in a direct sort of way. I don't care to walk around trying to convert people. I don't want to either deter or try to sell the idea. I just do my thing. I don't "need" others around me socially justify my pipe smoking. But, by always having my pipe in my mouth as I go about my day in public, I get folks all the time that come in my shop to show me their new pipes, some have even come in to show me pipes they made.
I'll answer questions and help if asked, but I'm not about to put myself in a situation where they'll blame me for a new addiction (whether nicotine, TAD or PAD) or habit. Pipe smoking in general is fairly popular here. I just do my part as a walking role model, rather than by being the "free candy" dude, handing out pipes and tobacco.
But, whatever works for you. If you want to be the salesman, then go for it. Sure, I like to see interest in this pastime grow, but it takes a variety of approaches to reach the variety of future pipe smokers.