You should Let your Boss be the Funny One.
There's always one guy at every comedy club that sits there, stone-faced in the third row while everyone else is laughing.
It's one thing to have been dragged there by the girlfriend or not finding the comedian funny, but if it is a chronic condition - then it likely means that the guy isn’t being honest with himself - is practicing self deception*.
If that guy is your boss you might not want to be telling jokes around the office. As a matter of fact you might want to switch your career to another office altogether.
If you decide to stay, remember that with humour, it’s best if you don’t jump the org chart. Being funny can be seen as a lack of seriousness by individuals who hold power over your future, so if you are not in the same snack bracket, I’d recommend you let the boss be the funny one.
HAVING SAID THAT,
Business is serious for the most part, but when you are reaching out to make a connection through your advertising, your newsletters and such, sometimes it is reasonable to do so with humour. Speaking to the person behind the job title can be an indication that you are speaking from an informed (INFORMAL) position, that you have insight into their world. A well placed wink and a nod are effective ways to show that you know your audience.
Starting a presentation with a joke is pretty standard stuff and it is for good reason that a little self deprecation will break the ice. When you are in front of a group, even before you start speaking you are by default in a position of power and knocking yourself down a peg for the assembly puts people at ease and speaks to your humanity. It is inclusive.
Working with humour takes practice and to strike the right balance between the absurdities of life and the seriousness of business means walking a fine line. There are places where you can practice in a safe environment. Personal emails, introductory posts on your various profiles, places in your Blogs are all relatively risk free ways of seeing if you are actually funny or are the fool at the party with the lampshade over your head.
When producing serialized messages, such as tweets or social posts, even in a business context, try having every fifth one being off topic and just for fun. It will make you be seen as a real person, not just a narrow job title or shill. When considering your tag lines and elevator speeches consider the irreverent and poetic and fun before you settle for parsimony. Nothing wrong with dialing it back, but if you don’t try and be funny at least once in a while your absolute grip on reality may come into question.
Among those whom I like or admire, I can find no common denominator, but among those whom I love, I can: all of them make me laugh.
*According to newly published research, self-deception inhibits laughter. “Humor deals with the absurdities of life,” Rutger s University anthropologists Robert Lynch and Robert Trivers write in the journal, Personality and Individual Differences. “The less you are in tune with reality, the less likely you are to see the absurdities.”