How can we mention Jesus without it being awkward?
How can you tell someone "I'm praying for you" without it sounding weird?
I love those two questions because they pretty much sum up the entirety of evangelism. If you're someone who mentions Jesus a lot, who prays for your friends and tells them you're praying for them, you are basically the Billy Graham of personal evangelism. Honestly, it doesn't get any better than that.
You mightn't have a clue what to think about current affairs, let alone how to bring Jesus into it. You may have no answer to "the problem of evil" (of course the person we should really worry about is the guy who 'solves' the problem of evil). It may never have occurred to you that the latest Box Office Hit echoes the gospel in its redemptive plotline. But if you awkwardly but repeatedly mention Jesus, and if you pray for your friends and - weirdo alert! - tell people you're praying for them - you are my evangelism hero and I want to be just like you.
The only thing I'd add to this odd-ball strategy would be - cringe factor!! - invite folks to church. Not necessarily the polished evangelistic event. I just mean church with all its embarrassments which you, as a family member, are very aware of. At that point, it's pretty much job done: mention Jesus, pray for your friends, invite them to church. There's my evangelism training in a nut-shell.
Now, if you want to do those things and not feel awkward... me too. But I'm not sure there's training in the world that can disarm the jarring power of the name of Jesus. And if there is, you should avoid it like the plague.
Evangelism means identifying with Christ in the world of Adam. No training can prevent a mortifying clash. But... if you embrace the mortification you'll be a better evangelist than all the training in the world can make you!