I pray and wait to hear what He says. Sometimes I peruse through my folders of songs and see if one jumps out at me. Some days I just want to pick five songs and be done with it.
I'm leading worship again. We're attending a great local church here that has seen some rough times and it taking a turn for the better. Now I have two small babies (two years and 4 months) running around as I prepare for rehearsal and Sunday service. Sometimes I just wish God would spell out what would please Him most and just give me the set list. It might be easier and less time consuming.
But the truth of the matter is, there is a lot to consider, and I don't take it lightly. Yes, I believe God would still be pleased with our worship and I believe that the people would still worship if I just pulled five song titles out of a hat. But, I personally think that doing it that way is scraping by with the barest of effort and with minimum respect for the position.
There's a lot to consider. What kinds of things are the congregation going through? What (style, type, lyrics) would speak to them? What would transition well into another chosen song? What song would take them to a place of humility and transparency that would please God most? What would they identify with? Just because I pick five songs doesn't mean that they flow well together, or speak a consistent thought from the heart.
I'm a fan of themes. I pray and ask God what He wants this Sunday to be about. (Desperation for God, reckless abandonment, humility, appreciation for His love, etc.) Then I ask for direction in choosing specific songs that will speak to that theme. But sometimes, He picks out five songs for me that seem to have no connection--until I'm in the middle of worship on Sunday and it all starts to make sense.
There's really no exact science to it. It's different every time. But there is always one common denominator. I ask for the leading of the Holy Spirit every time. I don't carry the role of leader lightly. I spend time in prayer, I wait, I listen, I'm thoughtful, intentional, and purposeful about it. I keep the people in mind, I keep the musicians in mind. And I do it expecting God to show up every time. And I'm always glad that I did it that way.