| Sep 19, 2022

Bosses — You Might Not Be ‘Fun’ But You Have to Try

Michael Scott’s attempts at humor in "The Office" may have made us cringe but today’s pressured bosses deserve some sympathy. There are ways for them to get fun right.
By Kyle Pare |

4 minutes

A few weeks ago, one of my talented colleagues wrote about some of his bosses’ awkward attempts at making the workplace fun. His article was an all-too-painful reminder of the “fun” for which many hapless bosses are too often known. I’m reminded of Michael Scott’s constant attempts at fun in “The Office”; Michael’s best-case scenario usually involved a joke falling flat, and the worst would have landed him with an HR complaint in the real world (and quite possibly a lawsuit). What Michael got right, however, was that he needed to try, and that’s a lesson for all of us bosses. 

The Pressures to Make Work Fun

The internet presents a never-ending stream of fun workplaces — places like Google or Apple with game rooms, spontaneous collaboration parties, and gourmet cafeterias. Leaders aren’t immune to that steady drip of pressure from both the top and bottom. Employees look for a sense of meaning and purpose from their work today. The word “fun” doesn’t wholly capture that feeling but it’s a necessary component of belonging. People don’t want to spend 40+ hours a week at a workplace that crushes their souls. 

The pressure from above comes from higher-level leaders trying to staunch the bleeding of talent by getting their mid-level management to improve workplace morale. The result for the unprepared boss is the kind of watercooler hell Dale Grauman described in his article — an awkward guy trying to make his employee laugh and falling short, or the sort of mandatory fun resembling a company wake more than a company rager. 

We can argue the merits of making fun a priority in the workplace but there’s no doubt it has to be a consideration. Current workplace trends do not favor employers who treat their employees like replaceable parts in a machine. Is creating a family-like atmosphere the answer? Michael Scott would answer yes. Today’s real-life bosses, though, are forced to walk an increasingly narrow tightrope of making the office fun without force, giving employees a sense of purpose, maintaining the bottom line, and of course avoiding the snares of workplace lawsuits. Can we blame them if their joke might fall flat every once in a while?

Triumphs and Trials of a Flesh-and-Blood Boss

My last position as a company commander in the Army had me face these pressures in the real world. Army units require a sense of family and teamwork because often we could be facing life-or-death situations. In a purely support role, my last unit didn’t face those situations directly but the pressures remained from above and below to make the workplace a good place to be. Soldiers sometimes don’t have a choice over where they end up, so we have to make the best of it, and part of my job was to help them do so.

I wasn’t always successful. Potlucks are an easy way to bring the team together but they get a bad rap because they are a visibly half-hearted attempt. Without a charismatic master of ceremonies (something I most assuredly am not), potlucks miss the mark by becoming an event where people grab food and take it back to their office. I used potlucks more than I would care to admit but my mistake was letting it stand by itself. By making a potluck lunch one component of a larger morale-building event, I could have brightened a few more days. Sometimes that’s all a boss can do.

I didn’t always fall on my face. I learned quickly in my position that if I was going to make an event fun, I would have to outsource it. Knowing your strengths and weaknesses is key to being a boss, and facilitating a fun workplace is no exception. The event where I selected team members who were themselves fun and outgoing was a great success.


Some Practical Tips

Congratulations on deciding you want to (or have to) make your office a more enjoyable place to work. You have taken your first step into a larger world. But steel yourself because you will fail. Some employees won’t be into it, and if you’re barking up the mandatory fun tree, you’ll get some eye rolls. Don’t despair. There are steps each boss can take.

  • Play to your strengths: If your friends and family laugh at your jokes, you might be funny. If you notice they run away from you at parties, it’s a good chance that humor is not your strong suit and you should vehemently repress all temptations to make your unforgiving employees laugh. This step takes humility and self-reflection but you have to know your personality. 
  • Outsource your weaknesses: On the flip side, be intimately aware of your weaknesses, and outsource them whenever possible. Your job isn’t to do all this yourself but to get the right people to do it for you. So find the social butterflies on your staff and enroll them in your strategy.
  • Keep it optional: Dale’s final example of a winning strategy provides the key. Instead of a workplace event, his boss invited him to a no-pressure outing with friends and it was fun. Sometimes it’s hard to make social events optional in the workplace but wherever possible, do it. Play the long game and build a reputation for fun that has people chatting about the next event in anticipation, not in existential dread.

It should go without saying that you need to avoid controversial fun with a 50-foot pole. Workplace “fun” has often led to harassment and even lawsuits, so keeping it clean is essential. That includes off-color jokes. Bosses can get into hot water when they tiptoe too close to the line of acceptable workplace conduct or pole-vault right over it. Know your company’s policies and keep your behavior (and that of your employees) above reproach. 

Fun Or Not, Make the Attempt

Part of your job as the boss is to put yourself out there. There will be times when you succeed and just as many times when you will fail. The modern workplace demands some attempt at fun. Don’t be half-hearted; your employees can usually tell when you’re not committed. Know your strengths, cover your weaknesses, and keep it optional — these are the tried-and-true methods to incorporate a little more joy at the office.

Kyle Pare

Opinion Contributor, Strixus

Kyle Pare has been a freelance writer for two years and a communications officer in the military for nine. view profile


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