Anthony (Tony) Middlebrooks, Ph.D., is a leadership expert, focusing his research, writing and teaching on the integration of creativity and leadership development. He is currently an associate professor and director of graduate programs in the Horn Program in Entrepreneurship at the University of Delaware, but before his academic work Tony spent a decade in leadership positions in the non-profit sector. This experience provided him a hands-on laboratory for leadership development. Tony has multiple scholarly interests that ultimately tie back to developing creative leaders who do good. This interview focuses on the work Tony has done regarding the concept of fun, specifically ideas from his book chapter The Paradox of Serious Fun, found in Beghetto, R. A., & In Sriraman, B. (2017). Creative Contradictions in Education: Cross Disciplinary Paradoxes and Perspectives.


1) You have noted that one of the best ways to have more fun in an environmental setting, especially with others, is to just start playing.  Can you please explain this a bit more?

My background with the concept of fun started with my work with kids, specifically at a summer camp. What I tried to do as an undergraduate and graduate student working in youth programs was to infuse a bit of learning into the fun we were having. When I transitioned to formal teaching as a professor, then suddenly the tables turned and I found myself trying to infuse fun into learning. I have found through experience the best way to start doing that is to set the tone, whether that be the classroom or your organization. Setting the tone can be anything from an authentic smile, a quirky pun or a joke, or just doing something different. This also gives you an opportunity to get a sense of how willing people are to engage in fun. It opens the door for other people to start having fun and contribute in their own way.

My friend Nat Measley from a company called The Fun Dept would come into my classes and do this really interesting activity. He’d put two circles up on the board, and he would ask two individuals from the class to come to the front and fill in their respective circle with all the things that they thought of as fun. The participants would work on their lists and then Nat would draw a little Venn diagram with the circles overlapping and say, “OK, now together look at each other’s lists and try to figure out what you think would be fun together.” The two participants would work that out and then Nat would ask the class, “Imagine what this would look like if there were 20 people up here. 20 overlapping circles, they’re trying to find that one overlapping bit of fun.”

Of course the students are like, “Wow, that’s really hard to do.” Nat goes on to explain that it is not as hard as one would think. If the task or activity is defined, then the participants can decide how they can have fun given what is already happening. It is important to note there are different kinds of fun. Researchers have described three types of fun in the work setting: Organic fun, which just sort of emerges from people’s interactions; managed fun, which is more orchestrated; and task-based fun, which results from people’s interaction with the specific task.  I would add a fourth category and call it designed fun, where it is not necessarily that you are dictating what people do, or how they have to do it, but rather thinking through how they are going to interact with the environment (as well as with each other).

I would also add that more fun is probable with a mastery mindset versus a performance mindset. A mastery approach is more about the process. It’s a process of learning, trying things out, failing and learning from them. And, it can be a process of fun and enjoying it along the way. A performance mindset is less forgiving:  “We must perform. We must achieve. It must be done right.” And this makes a performance mindset more stressful, and less likely to be fun, and you will lose some people that might have been great contributors before you even get started.

2) You have written about research that suggests that fun is generally not supported within chaotic environments but rather is better obtained through some structure and a set of norms? Why is fun better supported when boundaries exist?

You need to create a culture that is welcoming and safe. This requires boundaries. A psychological safety net where people feel they are not going to be judged and feel safe taking calculated risks with the things that they say and do. They don’t have to worry about jeopardizing their job, or a specific performance outcome, right at that moment. Fun, in this context, develops from trust and relationship building.

If you were to say, “Look, you have to start at zero, and we’re going to end at fun.” That process is going to start with getting to know each other and getting to trust each other, and this takes time. To some degree, fun requires everyone to be on the same page. Once you are on the same page (as a group), collaborative norms, boundaries and rules can be established.

The other important aspect regarding boundaries is the importance of the leader and leadership. Many leaders, whether they are leading a classroom or an organization, they are a little afraid of fun getting carried away. You get these flashbacks of middle school, and kids taking things too far, getting carried away with the fun. Adults are better at setting and adhering to boundaries. When I teach creativity, people in leadership positions will often give me the same pushback. “Oh, you know, I’m in a leadership position. We cannot just sit here and generate wild and crazy ideas.” Well, yeah you can. You can if you say, “For the next hour, we are going to generate wild and crazy ideas. That is what we are going to do, but it is time-bound. When the hour is up, we’re done. And then we’re going to take that big list, and you can go back to the comfort of critical thinking. Then we will pick an idea that looks like it might work, tweak it and talk about implementation and strategy. But for now, in this hour, we’re going to have fun, and we’re going to be crazy creative.”

When you set boundaries, it makes everyone feel much more comfortable and creates the space where fun can flourish — for those in leadership positions as well as other participants.

3) Now more than ever, many people at work avoid opportunities for fun because of the perceived risk and/or various types of stigma that surround the social construct of fun. You indicate in your findings that when done right, fun actually effectively mitigates office politics and drama. What are some of the right ways to have fun in the workplace?

I have come up with 10 rules, the first four are courtesy of my friends at The Fun Dept:

  • Rule 1: Fun requires leadership buy-in and participation
  • Rule 2: Fun is a shared experience
  • Rule 3: The 3C’s: Consistency, company time, culture compliance
  • Rule 4: Fun for all the senses
  • Rule 5: Fun comes in many flavors
  • Rule 6: The sources of fun are broad and endless
  • Rule 7: Forced fun, isn’t
  • Rule 8: Know what is NOT fun (and what is not funny)
  • Rule 9: Facilitating serious fun is a balancing act
  • Rule 10: Surprise the group by ending early, because everyone enjoys recess!

Fun at Work | Dr. Anthony Middlebrooks
In the workplace, fun starts at the top. If leaders in an organization are critical of fun, cynical about it, unwilling to engage, fun is likely not going to happen. I’m not saying that the leader has to be the person who gets the pie thrown at them or the person in the dunk tank. That would be the cliché of fun at the boss’s expense. Leaders do have to believe and feel that fun is an important part of the work culture for it to thrive. If a leader is not willing to engage in fun, then it’s not going to happen. Because like it or not, leaders are employees’ role models. They’re modeling the norms of the organization.

You also need to play to your strengths as an individual. For example, my wife is a professor as well, and her approach to engaging with students and having fun is much more empathetic, much more relationship-based. It’s much quieter and kinder and nurturing. In contrast, my approach to fun with the students is still relationship-based, but it’s much more through joking around, and throwing puns around, and being a bit louder. Fun should fit the personality of the facilitator and the nature of the group.

4) You have indicated that delivering educational material in a fun way can be more impactful than merely making the activity and/or experience fun. What can one do to improve their ability to be “fun” when it comes to delivery?

Having fun needs to become a habit. It needs to become a series of mental habits. In my case, there are two or three mental habits that I will typically try to keep in mind and work to develop. For instance, I will create little notes and I will put them in front of my computer to remind me – things like: Remember to explore the world, generate ideas beyond the first one you like, or even something simple like don’t forget to smile.

“Toys” are also an important part of my practice. I have all kinds of little artifacts around my office. In fact, I was talking with a grad student today who was looking around my office and I said, “Every one of these things is used in my teaching, nothing in here is for decoration.” I have a plastic brain; a singing bowl; I’ve got a plastic elephant; a prism; a genie lamp; I have a roll of toilet paper from Sweden. Each of these “toys” can be used to communicate lessons because it captures people’s interest. Suddenly it’s not a PowerPoint, it’s not me up there babbling, it’s not a handout, but instead, it’s an interesting object. And it starts to pull people in. They are engaged and thinking differently. It opens them up to having a little fun, doing things a little differently.

Lastly, I ask folks to ask themselves on a regular basis: How can I do what I do differently? How can I do it so it’s more interesting, more engaging, more memorable or more impactful?” We all get stuck in this habitual way of thinking and functioning –  no matter what we do, no matter how fun we think we are. So, an effective way to improve is to check in with ourselves on a regular basis and critically ask ourselves these types of questions.

5) If someone is trying to optimize the amount of fun they have in their life, what are some strategies they can use to improve in this area? What precautions and/or landmines should they be mindful of as the fun increases in their life?

To “optimize” fun mindfully, reflect on what works for you in context, as well as what doesn’t. You have to be really observant and mindful about how you go about infusing fun in various aspects of life. Your credibility as a leader is all you have, and if you lose it — one offensive joke, one stupidly inconsiderate activity— it is going to really hurt your ability to connect with others, communicate, and lead – much less facilitate fun.  As such, three things come in to play. One is your intention, and communicating that intention to whomever you’re working with. For example: “My intention is for us to be the best we can be, to accomplish what we want to accomplish, to enjoy our time here together, and work with one another effectively.” Those positive intentions, and reinforcing those on a regular basis, is one important piece.

A second aspect is authenticity. People are smart, and they see through bullshit so quickly. For instance, some contrived effort, “Oh, we’re going to have fun because it’s going to help us all bond.” Yeah. No. Not being authentic will kill fun quickly. Third and possibly the most important is empathy. Empathy and understanding how others are seeing things are so key to doing anything. If you are going to design a fun experience, you have to understand what people find fun, and what they think is interesting, what they will spend their time doing, and what might intrigue them. Whatever you can do to build your empathy will help you to develop your fun as well.

Regarding precautions, the current political climate in this country has gone from we’re all in this together…sort of, to, some of us are in it, and some of us aren’t, to, wow, I’m not sure what’s going on. We have such a diverse country, and that diversity is mirrored in our organizations, and our classrooms. That diversity is a super positive thing for creativity, and for leadership, and for understanding, and for progress. Unfortunately, because our current climate is so divisive, you really need to take the time to communicate your intent, display your authenticity, and really engage with empathy – all are key to make sure any effort to have fun does not get derailed (or something even worse).

I think your use of the word ‘optimize’ is a really good way to think about fun. You have to find the right balance, application, and type of fun depending on the context, ‘audience’, and situation. Generally, people learn to find that balance in informal settings but struggle with how to infuse fun into the ‘serious’ contexts of work or classroom. That is why I find this work so interesting and important.

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