Designing for Humor & Playfulness

Can I just ask… what organization out there wouldn’t want the benefits of increased workplace trust, solidarity and connectedness?

As we discussed previously in “Forces Undermining Conversation,” internal fears, complicated personality types and distorted leadership styles can obstruct any positive momentum an organization has when trying to open the lines of communication and design for more effective and engaging conversations. Labeling these possible underminers isn’t about judgement; it is about diagnostics. As we design for conversations, we can consider the paths of behavior that are well worn, like the analogy to the Grand Canyon from “Identity forms Culture”—what are the ‘comfortable’ paths our conversationalists may naturally take? If there is an engrained “superhero” dynamic, for example, we must be able to plan for group dynamics where members are more naturally inclined to agree. We can design for activities that challenge this propensity and be on the lookout for verbal and nonverbal cues that may indicate agreement isn’t actually shared. Perhaps we know a group tasked with envisioning a new product has a dominator amongst its ranks… Designing for this conversation may look a little different than designing a conversation for a group featuring a notorious ‘Yabut’.

Once established patterns of engagement are identified—in both positive and negative categories—designers’ role is one of challenging those patterns of behavior. How can we get a dominator to become a collaborator? How can we give confidence to a meeker member? How can we avoid the pitfalls of an overly agreeable group?

Getting people out of their comfort zone is a delicate and nuanced art that considers many factors, some of which I explored in “Designing for… trust,” and “Designing for… active listening,” but the mindset designers seek most in play is openness. It is through humor and playfulness that designers can encourage conversationalists to shed their established ‘skin’ and feel safe stepping into a new role.

As a reminder, I wanted to refrain from this research becoming a field guide or ‘how to’ – in other words, this section isn’t about suggesting games or playful activities to engage your team in. There are plenty of books and articles on the web for you to find inspiration. Try some out – see where they take your team. If you’re interested in knowing a little more about the research behind playfulness in work environments, check out the 2018 article “Play at Work: An Integrative Review and Agenda for Future Research.” It provides a great synthesis of current research as well as identifies how we can explore the topic further.

“And research suggests that the upsides of play extend beyond the individual. Teams of workers can benefit from play via increased trust, bonding and social interaction, sense of solidarity, and a decreased sense of hierarchy. Furthermore, findings suggest that play at work can benefit whole organizations by creating a friendlier work atmosphere, higher employee commitment to work, more flexible organization-wide decision making, and increased organizational creativity” (Association for Psychological Science).

Two Considerations of Designing Conversations to Create Playful Environments



“We have developed many excellent thinking tools for argument and analysis. Our information technology methods are constantly improving. But we have developed few tools to deal with our ordinary everyday thinking-the sort of thinking we do in conversations and meetings” (de Bono Group).

Our educational experiences encourage the seeking of truth. For truth, we want data, hard facts, evidence; we expect the “law of the land” and count on argument to get us there. We are taught that, living opposite of truth, is untruth. Here lies falsities, distortions, and misrepresentations of facts and we should navigate through these waters with an expectation of deceit.

But the reality of our existence is somewhat different. Our day to day lives are not so clear cut. Oftentimes we are dealing with conversation offenders, where uncovering exact information can be elusive, or wicked problems, where various truths may technically be correct, but are fraught with unintended consequences, and arguing between two narrow possibilities misses an opportunity to discuss better, broader ideas.

“Our egos are often so hell-bent on getting our own ideas out that we can hardly wait for others to finish talking. What others are saying becomes a terrible interruption in what we are trying to say. In the process, we not only fail to understand what others are saying; we do not even hear them out” (The Institute of Cultural Affairs 9).

In an effort to more accurately capture the nuances of our actual world, Maltese physician, psychologist, and author Edward de Bono developed the concept of parallel thinking. This process, considered an alternative approach to more adversarial, fixed thinking problem solving methods, requires a “thinker” to put “forward his or her thoughts in parallel with the thoughts of others – not attacking the thoughts of others” (de Bono Group). In effect, rather than dismissing other viewpoints and experiences outright, we collect truths like tokens in our mind, allowing equal space for any shared experience or knowledge to coexist alongside our own as equal truths, until a later point when this data can be filtered more constructively.

This is not a natural state of thinking for most of us. A conversation designer, acting in the role of facilitator, can nurture this approach in group settings by explaining it, circling back to it when necessary, and through role playing activities, such as “Six Thinking Hats” (download the chat challenge to explore this further!).



“…with the high stakes and impatience typical in today’s marketplace, the fear of failure is widespread, with sometimes unpredictable and sometimes unintended consequences for interpersonal dynamics, company operations, strategy, creativity, and innovation” (Yorton 7).

If you return to my post “Tools of the Trade,” you will find the section on facilitation explored its relationship to creativity. Conversation designers can use the magic of play to coax the creativity out of the most leery teammates, if used authentically. If not an ingrained approach within the organization, research indicates that this can do more harm than good, especially when employees view the requirement of play as “manufactured“ and “insincere” (Petelczyc et al. 181).

Many times, the root of this leeriness to participate is fear – fear of humiliation, fear of public speaking, fear of ‘letting go’ or being seen as anything but serious to subordinates. Anticipating this resistance, and planning ways to entice everyone to participate is an artform. Tom Yorton, of the famous The Second City, suggests improv as a way to stare down fear and tap into the collective openness needed to create really great ideas. Improv, he touts, can help individuals get more comfortable with failure. The reward for such a risk: organizations “improve productivity, become more innovative, and dramatically increase employee job satisfaction” (7).

Actor Alan Alda has been preaching the benefits of improv for years. This video from 2009, led by Alda, discusses some of the ways this playful activity has helped scientists connect to each other, with the goal to become better communicators.

Conversation designers need not be improv aficionados to plan for a small improv session at the start of a strategy meeting that needs its participants to be open minded, unhindered to their positions or titles, and starting with a positive mindset. In this role, designers can aid in both designing the meeting, and then, acting as facilitators – guiding team members through a creative process, by knowing what each member needs depending on their level of creativity (doing, adapting, making, or creating) beforehand, and planning the nuances that can make the effort a success and goal oriented, rather than haphazardly thrown together.