What if the key to stronger leadership, deeper team connections, and a more engaged workplace wasn’t another corporate training—but a well-timed joke?

In this episode of Workday Playdate, Erin sits down with comedian, speaker, and leadership coach JaMarr John Johnson to explore how humor, storytelling, and community can transform the way we work and lead.

From his journey in the military to the comedy stage—and even learning from legends like Dave Chappelle—JaMarr shares powerful insights on how to balance playfulness with professionalism, inject laughter into leadership, and build teams that thrive on connection.

Inside This Episode:

• Why humor isn’t just about being funny—it’s about connection, engagement, and trust.
• The lessons JaMarr learned from Dave Chappelle about values, ethics, and leadership.
• How storytelling can turn workplace challenges into opportunities for growth.
• Light roasting: When playful humor enhances team culture (and when it doesn’t).
• The key to creating a workplace where laughter fuels productivity instead of being a distraction.

Who This Episode Is For: Leaders who want to build teams that thrive in uncertainty, handle challenges with ease, and stay engaged—even when things don’t go as planned. If you’re tired of stiff, disengaged meetings and want to inject some energy, connection, and creativity into your workplace, this one’s for you.

And if you’re interested in taking one small action right now, you can check out our newest freebie, The Empathy Cheat Sheet, here. It’s a 3-part list of helpful phrases you can use before heading into any conversation or meeting, responding to an email, or hosting a one-on-one call.

No, You Hang Up First (Let’s Keep Connecting)

• Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy.
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Connect with JaMarr John Johnson

• JaMarr’s website
• JaMarr’s LinkedIn
• JaMarr’s LinkedIn course

Connect with Erin Diehl x improve it!

• Erin’s website
• Erin’s Instagram
• Erin’s TikTok
• Erin’s LinkedIn
• improve it!’s website
• improve it!’s Instagram