Leadership Playground offers a joy-filled reset from the corporate grind, using improv-based experiences to master the human skills that have become the new professional advantage. By joining this monthly rhythm of practice and play, you will foster deep community, and gain the clarity to lead with renewed confidence and courage.
In the age of AI, your advantage is human. Answer these 10 quick questions to discover your top leadership strength.
What’s your Human
Leadership Edge?
Leadership Playground is a vibrant community designed as a counter-space to the heavy, rigid, and performative nature of traditional corporate training.
It is specifically built for people leaders such as those in HR or Talent Development who are navigating burnout, change fatigue, and the pressure to do more with less in an increasingly automated world.
By trading the corporate grind for a joy-filled reset, members use improv-based experiences to master the human skills (communication, creativity, and confidence) that serve as the new professional advantage.
Through improv-based experiences and practical leadership exercises, members develop the human skills that technology cannot replace:
confident communication
creative thinking
adaptability under pressure
authentic connection
courageous leadership
A Break From the Grind.
A Return to Human Leadership.
This is not a box-checking program.
It’s a space to loosen the corporate armor, experiment without fear of failure,
and lead with renewed confidence and courage.
The Leadership Playground
is for you if…
You lead people and want to feel more confident in how you show up
You’re tired of leadership development that feels theoretical or performative
You want practical tools you can immediately use in conversations, meetings, and presentations
You believe leadership should feel human, not robotic
You’re looking for community with other thoughtful, growth-minded leaders
How Leadership Playground Works:
Leadership Playground follows a sustainable monthly rhythm designed to
support growth without adding to leadership fatigue.
Each month includes:
Week 1:
Set the intention
Short pre-work helps you reflect on the monthly focus and enter the experience with clarity.
A live interactive workshop where you actively practice leadership skills through improv-based experiences and real workplace scenarios. (Workshops always happen on the second Tuesday of every month at 1:00 pm EST.)
Week 2:
Play the Practice
Week 3:
Field Notes
Simple post-session worksheets help
you apply what you’ve learned to real conversations, meetings, and leadership moments at work.
Week 4:
Joyflow
A live 30-minute interactive session that is a combination of yoga, meditation, and visualization to help you integrate your learning and celebrate your progress. (Joyflow occurs the last Thursday of every month at 12:00 pm EST).
Continuous Community Building Community at “The Buddy Bench”
A dedicated peer-support space inside the community where members can ask for encouragement, perspective, or a sounding board from fellow leaders. Because leadership shouldn’t be lonely.
“Tag, You’re It” Experiences
Members have opportunities to step into leadership conversations, share experiences, and even guest spot on the Workday Playdate podcast to explore real-world challenges together.
About improve it!
improve it! is a professional development company that uses improv comedy to help leaders and teams build connection, confidence, and adaptability at work. Through workshops, keynotes, and experiential learning, improve it! has helped thousands of leaders create more human-centered workplaces.
Meet Your Facilitators
Erin Diehl
Erin “Big” Diehl is a Business Improv Edutainer, Failfluencer, and Professional Zoombie. Through a series of unrelated dares, she created improve it!, an improv-infused talent development company for the new generation of work.
Recently featured in The New York Times,
Erin is also the proud host of The Workday Playdate Podcast with improve it!, a Top 1% Global Podcast that helps develop leaders and teams through play, improv, and experiential learning. She is the first-time author of the Amazon Best Seller & Top New Release, I See You! A Leader’s Guide to Energizing Your Team Through Radical Empathy.
Among her many accolades, Erin is most proud of successfully coercing over 56,000 professionals to chicken dance.
Nicole Entzeroth
Nicole Entzeroth is the Learning Experience Manager at improve it!, where she designs and facilitates learning experiences that help folks think more clearly, communicate effectively, and lead authentically. She creates practical, engaging spaces where leaders can experiment with new skills and translate insight into action.
A graduate of Loyola University Chicago, Nicole began her career as a classroom teacher in St. Louis. She later earned her 200-hour yoga teacher certification in Chicago and is currently pursuing her Master’s in Business Psychology at The Chicago School of Professional Psychology.
With a background in storytelling, research, and strategy, Nicole approaches learning design with one guiding question: "What will actually stick and shift how someone shows up on Monday?" She is driven by curiosity and committed to creating environments where people feel safe to explore, challenge assumptions, and grow.
Ready to join
Leadership Playground?
Join now and step into a monthly rhythm of practice, play, and growth.
Frequently Asked Questions
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Leadership Playground is a live, interactive membership community designed for people leaders who want to grow, connect, and actually practice leadership in real time. Think less theory and more doing with workshops, coaching, and a community that gets it.
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This space is for current and aspiring people leaders, HR professionals, and anyone responsible for leading humans (aka… all of us). If you want to build confidence, improve communication, and lead with more impact, you're in the right place.
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Inside Leadership Playground, you’ll get:
Monthly live workshops (interactive + practical)
Coaching, tools, and frameworks you can use immediately
A community of like-minded leaders
Access to replays and resources inside Circle
A space to ask questions, practice, and grow in real tim
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Jump in anytime! You’ll get immediate access to everything inside the platform, including past workshops and resources. You can go at your own pace and catch up whenever it works for you.
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Yes, you can cancel anytime. That said, there are no refunds for past payments. -
Nope! Stay as long as it’s serving you. We hope you’ll stick around, but you’re never locked in.
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Everything happens inside our community platform, Circle. That’s where you’ll access workshops, replays, discussions, and connect with other members. You’ll receive access as soon as you join!
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Our workshops are live (because that’s where the magic happens), and replays are available if you can’t make it.
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Totally up to you.
You can:Show up live each month
Pop in when you need support
Or binge resources when you have time
This is designed to fit into your real life.
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This isn’t passive learning.
You’re not just listening-you’re participating.We use improv-based techniques, real-life scenarios, and interactive coaching so you can actually practice leadership
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Both 😄
We believe people learn best when they feel safe, energized, and engaged. So yes, it’s fun, but it’s also deeply practical and results-driven. -
Yes, and we love that idea. Reach out if you’re interested in bringing multiple team members in, and we can talk through options.
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Totally normal. Most people are at first.
You can participate at your own pace—whether that’s observing, engaging in chat, or jumping fully in. This is a judgment-free, supportive space.