Many Christians feel significant guilt around the topic of evangelism because they know this is a high value of God according to his word, but they feel handicapped. You don't have to operate at a phenomenal level of skill to be effective. Going out is downright healthy and invigorating to the life of a group. Our job isn't to see everyone we encounter come to Christ on the spot. My business friends had the right idea in going to the homeless, it's just that they were biting off more than they could handle.
Big goals are fine, but there's such a thing as goal overload.
Going to the homeless was a good idea, but it was just too much for their group. Going from no outreach to visiting a crack neighborhood with Christmas gifts was too large a venture. We need to be incremental. Start doing outreach in small ways that will provide successful experiences. Once we've had several small positive experiences with outreach, then we can add elements of depth, risk, and complication as we grow in faithfulness and confidence.