If you love your boss, then Boss's Day can be an opportunity to show your appreciation and have a little fun at the same time. Plan a Boss's Day party that recognizes your boss's contributions to the company while poking a little fun as well. Keep your mocking to a reasonable level -- after all, this person controls your future with the company. A good-natured boss will appreciate a little ribbing, though.
If your boss appreciates a good joke and has thick skin, incorporate a roast as part of your Boss's Day party. Before the party, ask some of her favorite employees -- or those with a particularly good sense of humor -- to say a few words about your boss during the party. The comments during the roast might pick on one of your boss's bad habits or mock her a bit, but they should end on a positive note to keep the roast in good fun.
Everyone has their favorite sayings and mannerisms, and if you've worked for your boss for a while, you've probably picked up on his habits. Place posterboard on the wall, and have employees anonymously write their boss's favorite quirks on the board. Maybe he always uses the phrase "get 'er done" or has a habit of slurping his coffee. Keep things light -- don't dwell on obvious bad habits like spending the day outside smoking. Your boss will be amused by all of his quirks that his employees have picked up on.
If you have a lot of company events, you probably have an employee or two who goes around snapping pictures of those moments. Go through past photo archives to uncover some of the best and funniest pictures of your boss. If she's been at the company for a while, you can even discover some pictures from her younger years. Decorate your Boss's Day party with photos of your boss -- the sillier, the better.
Make your boss feel extra special by giving him some gifts at the Boss' Day party. Set aside time for your boss to open your humorous gifts during the party, and everyone will be laughing. If you have a graphic designer on staff, use his talents to create a "Best Boss" magazine cover. Include some of your boss' biggest accomplishments and funniest quotes on the cover. Or take a photo of all of the employees with the caption, "Thanks for putting up with us!" Mat and frame the picture, and have each employee sign the mat with well wishes.
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