I have been told that I'm witty/funny. I was pretty small as a kid and was not good at sports which meant it was that bit harder for me to make and keep friends. I remember noticing one day that one of my fellow students was funny and he was pretty popular. I made a conscious decision to try and be funny. I focused on it, I kept trying different approaches. I studied being funny far more than any other subject. I'm sure I drove everyone nuts at first by trying to make stupid jokes at every opportunity but gradually it improved until I could crack people up pretty easily.

That was 20 years ago when I was a kid but it became an important part of my identity. Even now when I meet someone for the first time I try to work out what will make them laugh, sometimes I get it right away, sometimes it takes longer but if you have a sense of humor i'll find it. The biggest part of it for me is speed and timing, a great joke with bad timing is just a bad joke, an OK joke with good timing can bring the house down. Once I get into the rhythm of someones thought/speech process I can land a joke into their mid-sentence pause. This works really well when its a formal-ish setting and the joke is unexpected but welcome. Team meetings are great for that.

I don't act the clown or constantly make jokes but every now and then I can nail you with a comment that will crack you up. The (slight) downside is that I unfortunately have a dark sense of humor and a sharp tongue that I need to keep in check. The problem with delivering a killer line at the right moment is that you run the risk of shortcutting some of those common sense filters your brain uses to keep you from sounding like a total asshole. In the past I have made jokes that perhaps were slightly beyond what people are used to. Those types of jokes are normally the ones that crack people up the most when they get to know me. I regret nothing :)

The most important thing is to turn it off and leave it off until you need it or else you run the risk of being thought of as clownish or insecure. It has helped me get hired, it has helped me get promoted, it has helped me when speaking with people from different backgrounds, it has helped me when I have to speak publicly, it really helps me when I socialize with people I barely know. If it was an optional extra I'd buy 'funny' with every resurrection.

I could give examples of things I have said in the past that have killed but that wouldn't work. Those things were crafted for different people, in different contexts. I can't see you, I can't get a read on you from the other side of this screen; but if I was there I'd make you laugh.