Then the eleven disciples went to Galilee, to the mountain where Jesus had told them to go. When they saw him, they worshiped him; but some doubted. -Matthew 28:16-17
How do you begin to talk to someone about spiritual matters? Does it come out organically? Is it forced? Is it rehearsed? Maybe you just avoid it altogether. The thought of discipling someone can be intimidating. I often find myself hesitant to speak, especially regarding topics that may end up being awkward. I don't like to look dumb by exposing myself to questions I can't answer. I don't want to be seen as judgmental, or "holier than thou". I don't want to be "that guy" - the one everyone avoids. Can you see what's happening here? I have allowed fear of imagined uncomfortable scenarios to ruin my possible influence.
Then Jesus came to them and said, “All authority in heaven and on earth has been given to me." -Matthew 28:18
There are two categories of things I am comfortable with. The first is stuff I have always liked, things I never had to learn, adjust to, or even try at. An example, and this will sound strange, is I like things neat and clean. I feel better in an orderly environment, so picking up, straightening a picture, wiping off a table comes naturally to me. I don't think I'm compulsive about it, though some in my family may disagree - I can tolerate a mess, I'm just more comfortable when things are tidy.
The second category is things that did not come naturally, but now feel completely normal. A good example of this is driving a manual transmission vehicle. This was a learned skill, and one that I had to work hard to master. But once I had it down, I loved it. I have owned standard-shift vehicles for years now, and taught all my kids to drive a stick. Each vehicle is just a bit different, but I have not come across one yet that I couldn't master within a few minutes.
"Therefore go and make disciples of all nations, baptizing them in the name of the Father and of the Son and of the Holy Spirit, and teaching them to obey everything I have commanded you." -Matthew 28:19-20
So maybe the "trick" to making myself comfortable with discipling conversations is to adapt them to my communication style and practice until they become natural to me. This reminds me of a carpenter I once knew (No, not THAT carpenter!). His name was Lon, and I worked with him a couple of summers when I was in high school. Lon was a quiet guy, pretty humble, and a Christian. I was a Christian too, but a very immature one. I thought I was there to help Lon, but Lon was discipling me, though I barely realized it at the time.
Lon was extremely conscientious about doing a good job and never cutting a corner, even on stuff that no one else would ever see. He was almost always smiling and never cursed, even when the project was not going according to plan or I had messed something up. If he was working on something routine, say mudding drywall, he'd keep his rhythm by singing or whistling an old hymn. During breaks, he'd ask me questions about my future and we'd talk about life and the Bible. A few years later, as his wife was dying of cancer, I was impressed by the grace they showed. They both knew her race was nearly over, but neither had any fear of the future. He stayed at her side almost constantly, and if you went to visit them you always left with a smile, feeling you had seen the face of God.
And surely I am with you always, to the very end of the age. -Matthew 28:20