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.

Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode.

Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.”

Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back.

Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.

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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.