More Than Any Workplace Incentive, a Playful Boss Keeps Employees Engaged - Five Ways to be a More Playful Boss

Employees don’t leave companies – they leave bosses, a familiar theory confirmed time and again in management science everywhere. I read this again today, and it sent me on a journey back through my research on play. I looked at the bosses I interviewed and found some wonderful testimonials from managers who had found playful ways to build stronger connections among their team, so I know it works.

I also did an image search on “playful boss,” and got a page of pictures of predacious men peering down the blouses of their female subordinates, which, it turns out, is an excellent indicator of the real problem. Thank you, Google Images for your unvarnished perspective on cultural misconceptions. When it comes to being playful, bosses walk a thin tight rope over possible disaster.

“Play” is a word our culture wrongly associates with behavior inappropriate for the office. When an adult has fun, he or she might be engaging in something naughty, yes. If that naughtiness involves another adult and everyone is safe and participating willingly, it’s healthy. When this kind of play enters the workplace, it victimizes people and violates legal employment standards – AKA disaster. The trouble is: bosses don’t always know how to distinguish healthy, G-rated adult play from the kind that doesn’t belong in the office, so they avoid playfulness altogether. They throw the baby out with the bath water.

Other things associated with the word play that actually aren’t playful at all: glibness, laziness, recklessness, chaos, ineptitude, pandering, and childishness. Playfulness, in fact, is one of the most mature approaches any boss can take towards leadership. It can aid efficiency, inspire creativity, and help establish accountability in non-threatening ways. It can add structure and process when needed and give employees a much-needed sense of belonging and acceptance. It can be a method of demonstrating compassion and understanding, and it can be an effective way to serve the emotional needs of a hard-working team.

A boss holds many powerful cards in the life of any employee, which is why they can make the difference between a truly rewarding career and daily madness that steals your joy. Your boss can put you out of a job or into a promotion. He or she can make you feel valued or worthless. A boss can enable your productivity, or severely hinder it, depending on the approach they take to leading you.

If you’ve ever been a boss, you know how frightening it can be. You have a daunting job with a lot riding on success. You will be judged, hated, criticized and picked apart by everyone. A small percentage of you will get it right, and based on my research, the ones who will, are almost always playful. I’ve identified five playful habits that appeared within the successful leaders we studied.

1 Cultivate a team identity

2 Use rituals

3 Accept people the way they are while maintaining expectation

4 Use candor with levity

5 Have fun, be flexible, and improvise

A team identity

A team identity within an employer organization functions much like a street gang – but without the crime. Kids join street gangs because, in a world of abject poverty, racism, and the threat of violence, they have a strong need to belong. From their association they derive protection and also a sense of pride, which is why they gravitate to it. Employees who work in stressful conditions and crave support inevitably feel isolated. They will experience vulnerability similar to the kids in rough neighborhoods. They will gravitate to a team that makes them feel wanted and safe. When they find the leader that cultivates a team identity, they will stay.

Playful bosses cultivate a team identity. Any given company will have a culture and brand, but an internal team can have a unique identity within it, and this can create a fertile environment for loyalty, collaboration, and working effectively towards common goals. Many companies are too large to fully exploit this phenomenon across the organization, so they create identities for departments and working teams.

Playful ways to create a team identity:

Do fun things together like lunches, escape room evenings, or competing with other teams in the office for the best de-motivational poster or best Lego diorama explaining safety violations

Write fictional stories about how the team was formed

Have a mascot

Assign a funny superpower to each member based on quirks and odd talents

Create a logo, slogan, and silly mission statement

Organize entertaining events for the whole office hosted by the team

Have an Intranet home page and share valuable information with other teams, always with a funny twist

Create funny code words and signals that only the team knows

Turn processes and systems you use into a game, like in/out boards or work orders

Volunteer in the community as a team or gather donations for the team’s chosen charity



Playful bosses have rituals. Don’t worry - they don’t involve anything weird like chanting or lighting candles. These rituals are unique to the team and are done as a matter of routine. Playful bosses attach to the rituals a playful significance that strengthens relationships and encourages supportive behaviors.

One boss in our research group came to his position inheriting a culture of negativity from his predecessor. Among other measures, rather than scolding his team for fatalistic attitudes, he brought a miniature, black pirate ship to the office. Anyone who said something negative had to have the pirate ship at their cube for the day. The ship made the rounds from cube to cube every week for the first while, gradually creating awareness of negativity in a playful way, without blaming or shaming.

Celebrating success is also an excellent opportunity to create rituals. One boss had a special line dance routine the team did together whenever they won a new contract. For each contract they won, another step would be added to the choreography. At the end of the year they would do the complete routine together for an audience. Dance won’t work for every team, but the example can be modified for a host of other preferred types of play.

Another boss had a ritual for supporting team members having a rough day. Whenever someone had a tough conversation with a client, or a failed proposal, the rest of the team would walk with them to the coffee shop for a round of cookies and a coffee at break time. This ritual encouraged team members to develop empathy and tune into the experiences of others, develop awareness of moments when people needed the team to rally around them.

Rituals once helped tribes to express their tribal identities. They created a sense of continuity and a reason for keeping the tribe together over time. In the modern world they can be used to the same advantage; to acknowledge growth and performance, support people, and nurture community. If rituals include everyone, are affirming and free of blaming and shaming, they will be effective.

Playful ways to establish rituals:

Invite the team to submit ideas for fun rituals

Instead of monthly meetings, arrange a monthly play session during which you discuss necessary topics while playing – play should be targeted at the types preferred among the group i.e. play dough or blocks for builders, writing a song for the music lovers, Chase the Ace for the risk-rewarders, etc.(An Hour of Play created the game, Manic Meetings for this very purpose)

Take team retreats and do something fun together – not just planning strategy for the coming year in a stuffy boardroom

Celebrate success and people; create funny things you repeat whenever something is worth celebrating; honor each other on a day other than a person’s birthday – that way it will be a surprise to everyone


Acceptance with expectation

A lighthearted reaction to failure sets a team at ease. Most employees want to avoid failure and do whatever they can towards that end, but inevitably something will go amiss. Playful bosses will create processes for affirming employees while compelling them to accept responsibility and commit to future problem solving. The key is to swiftly move people through that process and advance to a constructive plan without destroying anyone’s self-esteem.

Nothing brings failure into perspective quite like thinking aloud about how much worse it could have been, even better if the thinking aloud is shared and hilarious. Playful bosses can help employees cope with failure by helping everyone to laugh about it. Entertaining silly, unlikely scenarios that would have made the failure infinitely worse, for instance, eases the sting. One boss encouraged his team to play a round of “Could Have Been Worse” speculations. For one of these sessions, this boss encouraged team members to research epic failures online and share the stories. Laughter is truly the best medicine.

Employees know when they’ve screwed up and they usually know the consequences for the organization. Reminding them might not be necessary every time. Playful bosses build a stronger team by helping people manage the pain of failure rather than trying to eliminate it through lectures, punishments, or taking away advancement opportunities.

Playful ways to accept your team members and affirm them, while maintaining expectation:

Group hugs or affirmation sessions; hugs might not be suitable for every team, but most teams can affirm each other with words of encouragement

One boss had a Naughty Spot in the corner of the office – the employee was required to sit there over coffee, but the rest of the office was encouraged to join them, bring that person goodies, and compliment their looks and personality, so the Naughty Spot was actually a nice place to be

Order a funny cake for the team that reads: “You’re dead to me,” or “Smooth move, Ex-Lax.”

Write down failures, put them into a box, and have a party at the end of the year during which you play “Raise a Little Hell,” on a speaker, cheer, and run the paper through the shredder and start anew – no one is allowed to mention those failures again


Candor with levity

Candor is an essential skill for any boss, but playful bosses find ways to be candid without destroying an employee’s confidence. Or their will to live.

Hierarchies and most importantly, parameters for acceptable candor vary and more than that, are never explicitly identified. Every culture is unique. Some people can be handled with raw, brutal honesty. Some need you to wear kid-gloves. Being playful with it might require some experimentation, but eventually it will become a tool for delivering criticism gently and constructively, while quickly restoring enthusiasm and faith in the future.

Playful ways to add levity to candor:

Facetiousness is an excellent place to start – for instance, when your team puts in extra time and delivers, tell them they’re a profound disappointment, then have a laugh together; give out funny Employee of the Month awards like the Noisy Typist Award or Office Fashionista Award or Stinkiest Lunch Award

Celebrate Festivus or some kind of anti-holiday during which people air grievances; it gives people license to indulge levity, which, ironically, makes serious performance discussions easier – even if they have to accept some honest criticism now, they know this tension will be relieved soon, because they work in a lighthearted office

Share a weekly meme or joke related to office life

Have a whiteboard or Intranet page where the team can share clean jokes and funny pictures

Keep toys in your office; one of our bosses led a team of engineers. He kept building tools on his desk so that during difficult conversations, his team could engage in some restorative play appropriate for those who enjoy building. He also had a magic 8-ball on the desk, which he would allow people to use when they had to make tough decisions. It lightened the air.


Fun, flexibility and improvisation

Spontaneity is one of the most important ingredients in creativity. Creative processes in the brain are innate, and they are activated by numerous stimuli. Most people have learned over time to shut them down, however. Pressure to conform and non-constructive criticism discourage people and lead them to avoid creative endeavors. By being flexible and improvising once in a while, a playful boss can reawaken creativity and help people infuse their day with a renewed sense of humor that relieves stress and improves morale.

A playful boss says “no” a lot less than other bosses. For some managers, “no” becomes a destructive habit, and they say it to everything, as a rule. Every idea gets shot down, no matter how small. The goal is not to let people run wild – rather it is to self-evaluate the “nos.” Are you saying it out of irrational fear? Are you worried a yes will spin into chaos? Are you under the impression that saying “no” is what bosses are supposed to do?

A little flexibility goes a long way. You can start slow. Indulge a few small creative ideas here and there. Allow them to launch into a funny story now and then and have a laugh together. Empower them to shape their own experience in the workplace a little more often. Let people laugh during meetings and indulge distraction sometimes. (Leonardo Da Vinci was a big believer in indulging distraction, and he was the most creative man who ever lived!)

Shared fun strengthens relationships. That fun does not have to consume a lot of time or money. It’s more about an attitude towards life and work. If you’re a boss, see the positive, celebrate it, and let people see you do it. Laugh and indulge in joy, no matter what’s happening, and help your team do it too. It sounds cheesy, but it will make your team stronger and more productive. If your employees walk into the office every morning and breathe deeply, knowing it’s a place where they are valued and things are never too serious (even if they are), they will not jump ship on you.

Ways to be fun, flexible and improvise:

Improvisation is about “going with it” and is a skill that makes a team better able to adapt to change – have an improv coach come in and facilitate some sessions and practice saying yes instead of no

Invite the team to start entertaining creative ideas again – start small with ideas for fun things you can do together in short bursts, or new rituals for celebrating success

Be spontaneous – take everyone to a different location in the office for a day, or dress up as clowns and make balloon animals for other employees in the lunch room; hire a massage therapist and follow her around the office with fresh smoothies for everyone over the lunch hour

Celebrate made-up holidays like Procrastination Day or Opposite Day, during which everyone does the opposite of what they normally would (while still doing their work)

If you want to become a more playful boss, forget that fun doesn’t belong in the office. This is a falsehood based on an outdated understanding of the human brain. If your people can relieve stress in healthy ways, more often, and with each other, they will work faster and produce higher quality results. They will collaborate and produce creative ideas. They will love what they do, where they do it, and with whom they do it. A playful boss can bring it all together for competitive advantage.

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