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This is part two of a two-part series. To read part one, click here.

Would you say that if someone is not naturally humorous they should attempt it anyway?

That can be dangerous. Yes, I think everybody needs to be able to incorporate it in a way that fits their personality and style. But worse than having no humor at all is forcing humor that isn't funny.

There are certain things we always need to watch for. Obviously anything that's offensive. It never ceases to amaze me, even at large churches some speakers will make humor about folks who have weight issues. There's no place for that. That's going to hurt people's feelings. Inappropriate ethnic humor. Inappropriate jokes at sacred moments. There are certain moments that are holy, and if you try to make it a light moment, there's going to be a jarring factor.

Another caution is about telling jokes. The best kind of humor is observational humor, humor that flows out of life, the incongruities of life, the way life works. The hardest humor to pull off effectively is a canned joke with a punch line. That's risky. If there's not a big laugh, there's that awkward moment where we say, That story died. Many of us have experienced that kind of death, and it ain't fun. Everybody in the room senses it, and it breaks the momentum of the talk.

On the other hand, I might tell a story about some interaction with my wife or one of my kids, and there is humor in it, but it's not dependent on a punch line at the end. That kind of humor generally works a lot better and is much safer.

How do you cultivate that kind of humor?

A part of my brain is always looking for slices of life, conversations, observations that can help me teach something, and do it in a fun way. I watch people who do this kind of humor well. Tony Campolo is a remarkable communicator with tons of energy who tells stories in engaging ways. Ken Davis is another. I read certain people. Garrison Keillor is a writer who has an enormous gift for observational humor. I read his stuff and think, How does he unpack a story or develop a character in a way that finds this kind of humor? I look for people who do it well and try to learn from them.

I have a friend who made an observation from his visits to churches as a consultant. He said the sense of people connecting with the speaker came at the first moment of laughter in a message. It's a diagnostic indicator—not the only one, not the most important one—but a diagnostic indicator of how strong the connection is between speaker and listener. Humor can be a barometer.

Another important issue is the relationship between humor and tension. Humor is a great tension reliever. I remember a remarkable story Ken Davis told. He talked about how for many years his daughter never said "I love you" to him. That story produced a lot of tension because this speaker is talking about his daughter, and everybody felt a poignant connection with him, but also a tension: Is this going to get resolved?

Then he told about speaking in the chapel service of the college she attended. The students all filled out response cards, and afterward the chaplain handed him a card that read, "I love my dad," and it was signed by his daughter. Davis took quite a while before he got to that line. There was a lot of tension. Then he told how he got up from his seat in the restaurant, went into the bathroom, and said, "She loves me. She loves me. I can't believe she loves me." The he said, "I didn't know there was somebody in the stall right next to me." The laugh that followed broke an enormous moment of tension.

One question you have to ask is, Do I want to relieve the tension with laughter yet? Or is the tension producing change in people, so I need to allow the tension to go on? Great communicators are masters of the art of tension management. Speakers gifted at motivating or at convicting folks are able to discern how much tension they can tolerate. They're careful about using humor to relieve tension prematurely.

Do you think that happens often?

I do. Many go into pastoring with unresolved issues of needing to please people, needing people to like them and tell them they're doing a good job. Because of that we often underestimate how much tension people are able to tolerate, and we underestimate the use of tension in producing change. We get anxious: People might not be liking me, or, They might not be liking this part of the message, so we move to try to relieve tension prematurely.

Another observation: There is a relationship between how effective humor is and how full the room is. The more full a room, the more humor will elicit laughs. If the room holds 100 people and has 120 people jammed in it, the anticipation level, the focus, the energy is high. So when the speaker says something funny, people tend to laugh a lot. If the room holds 300 folks, and there's that same 120 people, there's going to be much less laughter. I have to speak differently when I'm talking to a room that's packed than when I'm talking to a room that's half full. When a room is full, I can tell stories with a timing that expects a big laugh to come at certain points. When the room is less full, the talk has to have more of a continual flow. If there are moments when people laugh, we can enjoy that, but it's going to have a different rhythm to it than a room that's packed.

Earlier you talked about turning from what is humorous to a serious point. How do you make that transition?

Sometimes the transition has to be gradual. Often you can turn on a dime from something light to something dark. For instance, I've told a story of mine I call "Who put the stain on the sofa?" It's a fun story, and it ends up that the joke is on me. Then I say, "Here's the truth about us. We've all stained the sofa." And I pause because everybody is engaged by the humor. After the pause, I say, "I lie. I deceive. I use people. I ignore people. I promote my own agenda." All of a sudden it's gone from light, fun stuff, to a much deeper level where I can talk about sin, darkness, guilt, a holy and just God, and people's hearts are opened. In that case, turning from light to dark is helpful. You can feel it in the room. It's almost like a surfer riding on a wave; they're up high and all of a sudden there's that drop. You can do that.

Much less often can you go from something very serious, dark, somber to a light moment. That usually takes a much longer process. You have to walk one step at a time to a place where things feel lighter. When I'm making a point about sin, guilt, hell, if I try to turn quickly to something light, I'm going to trivialize everything I've been saying. The moves are very different in going from light to dark than they are from dark to light.

Just because something is funny, even hilariously funny, don't use it if it doesn't fit. The three laws of humor are the same as the three laws of real estate—location, location, location. When something fits, it's going to accomplish much more good, if I can discipline myself to wait and save it.

You hear messages that come nowhere near the potential they could have reached because the speaker thought, I heard this story recently. It got a laugh. I'm going to wedge it into this message even though it doesn't fit. That's why you can hear one person tell a story and then somebody else tell it—and may even tell it pretty well—but because it doesn't fit, it doesn't elicit anywhere near the same response. It wasn't the right move at that moment. It has to fit, and it has to serve the ultimate goal of preaching—which is to have Christ formed in people.

John Ortberg is pastor of Menlo Park Presbyterian Church in Menlo Park, California.