November Resource of the Month
Resource of the Month: Mastering the Art of Humor in Leadership
Making workplace humor work, for everyone
This month, we’re highlighting a resource designed to help leaders go beyond casual jokes and use humor in a way that’s purposeful, inclusive, and aligned with organizational values. Our featured resource of the month is Mastering the Art of Humor in Leadership, published in the Organizational Dynamics Journal.
This paper is a great read, backed by supporting research and providing in-depth examples. In this blog we’ve pulled out the highlights but recommend finding the time to read the toolkit. Stay tuned as we’ll be compiling all of the takeaways from this quarter into a new WTT guide!
Why Humor Belongs in Leadership
When used well, humor helps to:
Build trust and psychological safety
Ease tension and encourage openness
Strengthen connection across roles and teams
Model authenticity and flexibility
Research shows that employees see humorous leaders as more effective and approachable. But humor is not just about telling jokes. It’s a skillset. one that can be taught and improved with intention and practice.
What Makes Humor Work
The toolkit introduces five key competencies leaders can practice:
Reading the room – Pay attention to who’s in the space and how they might receive your message.
Knowing your intention – Ask yourself: Are you building connection, or trying to mask discomfort?
Timing and delivery – Sometimes a pause, a facial expression, or a well-placed aside can land better than a full joke.
Audience sensitivity – Avoid anything that punches down or excludes. Humor should lift, not undermine.
Self-awareness – Know your default humor style and when to flex or pull back.
When Humor Goes Wrong
The paper defines humor as “any communication that creates surprise or unexpected meaning that leads to amusement.” But not all humor lands the same way. Effective leadership humor is:
Positive (never sarcastic or aggressive)
Context-aware (sensitive to timing, culture, and team dynamics)
Relationship-based (best used when there’s existing trust)
Humor can backfire when it’s forced, ill-timed, or perceived as punching down. Leaders need to build trust before using humor and pay close attention to how employees respond.
Putting It into Practice
This resource offers not just theory, but also actionable guidance for integrating humor into your leadership practice. The authors recommend:
Starting with humor training for leaders (Join our next event to learn about The Art of Humor for Enhanced Communication)
Practicing with low-risk, relationship-centered humor
Tracking what resonates, and adapting to your team's preferences
Encouraging open communication and psychological safety
Why This Matters
Workplace wellbeing isn’t just about benefits or burnout, it’s about culture. Humor, when used thoughtfully, creates moments of connection, ease, and humanity in the middle of complex work. This resource gives leaders a roadmap for doing just that. Stay tuned as we continue to explore how to thrive with humor in our programs this quarter.
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Let’s keep building cultures of wellbeing, together. Check out what’s next and join us at an upcoming event.
