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Workday Playdate

Workday Playdate

Written by: Erin Diehl - Workday Playdate
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TOP 1% GLOBAL PODCAST for People-First Leaders Formerly the "improve it! Podcast." #9 in BEST 100 SELF LEADERSHIP PODCASTS. I’m Erin Diehl, keynote speaker, business improv edutainer, and founder of improve it! (AKA your work bestie). Every Wednesday, Workday Playdate with improve it! helps HR professionals, people leaders, and culture-driven humans bring more laughter, levity, and purpose to their workdays. Because work is better when you play. This is not your average leadership podcast. You’ll get research-backed strategies, improv-inspired tools, and candid conversations with top leaders, speakers, improvisers and authors who are rethinking how we work and lead. Our promise is to give you tangible takeaways you can use immediately, plus a few laughs along the way. Interested in partnering with us? Workday Playdate reaches thousands of people-first leaders who care about workplace culture, leadership, and team development. Contact info@learntoimproveit.com to learn more about sponsorship opportunities. We promise laughs, impact, and zero awkward small talk. Think ROI with a side of LOL’s. Let’s make it happen!Copyright Erin Diehl Careers Economics Management Management & Leadership Personal Success
Episodes
  • 354: The Improv Advantage in Leadership with Anne Libera

    354: The Improv Advantage in Leadership with Anne Libera
    Jul 1 2026
    In this episode of Workday Playdate, Erin sits down with Anne Libera to explore how improvisation can unlock stronger leadership. From flow states and vulnerability to humor and human behavior, Anne shares why improv is about discovering what's possible. If you've ever wanted to lead with more creativity, communicate with more confidence, or simply become more yourself at work, this episode is for you.Inside This Episode:Discovery Is the Real Superpower: Anne unpacks why the heart of improv—and great leadership—is discovery. Learn how staying curious, present, and open can lead to stronger teams and better decisions.Flow Isn't Just for Artists: Discover what flow feels like for improvisers and leaders alike, and why creating the conditions for flow can boost creativity, innovation, and performance.Improv Is More Than Comedy: Anne busts common myths about improv and explains how these practices help us build new behaviors, embrace vulnerability, and connect more authentically.Try "Thank You Because": Learn one of Anne's favorite improv exercises for strengthening communication, navigating conflict, and creating warmer conversations at work and home.Yes, You Can Be Funnier: Drawing from insights in her new book, Funnier: A New Theory for the Practice of Comedy, Anne explains why humor is a skill, and how anyone can develop it.What to Do Now:Practice Discovery: In your next meeting or conversation, focus less on performing and more on noticing what emerges when you're fully present.Use "Thank You Because": The next time you're in conflict or giving feedback, begin with gratitude to create a more constructive conversation.Experiment With Humor: Try sharing a story, observation, or moment of recognition rather than aiming for the perfect joke.About the GuestAnne Libera is the Director of Comedy Studies at Columbia College Chicago and one of the country's leading voices at the intersection of improvisation, comedy, and education. She has spent decades training performers, leaders, and professionals to use improvisation as a tool for creativity, communication, and human connection. Anne has worked extensively with renowned improv institutions and organizations, helping people discover new ways of thinking, collaborating, and leading. She is also the author of Funnier: A New Theory for the Practice of Comedy, a groundbreaking exploration of how humor works and how anyone can develop it.Your FreebieHow do you lead through failure and uncertainty?Today’s workplace demands adaptability, creative problem-solving, and leaders who can navigate uncertainty without freezing in perfectionism.This quick quiz will reveal your unique approach to failure and uncertainty, plus give you simple ways to strengthen your adaptability muscles and help your team thrive when things don’t go according to plan.Connect with Anne LiberaAnne’s LinkedInAnne’s Columbia College Chicago website pageAnne’s book: Funnier: A New Theory for the Practice of ComedyConnect with Erin Diehl x improve it!Leadership Playground online membership communityErin’s websiteErin’s InstagramErin’s TikTokErin’s LinkedInimprove it!’s websiteimprove it!’s InstagramFor more information on improve it! visit www.learntoimproveit.com.
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    53 mins
  • 353: Turns Out Failing Is Kind of Fun? with Catharine Savage

    353: Turns Out Failing Is Kind of Fun? with Catharine Savage
    Jun 30 2026
    In this episode of Workday Playdate, Erin sits down with Catharine Savage to explore why failure might not be something to avoid after all. As an improviser, facilitator, educator, and performer, Catharine has spent years helping people discover that growth often lives on the other side of discomfort.If you've ever avoided taking a chance because you were afraid to fail, this conversation offers a refreshing perspective on why mistakes can actually be fun.Inside This Episode:Why We Fear Failure So Much: Catharine and Erin unpack the stories we tell ourselves about failure and explore why so many high achievers struggle to take risks in the first place.How Improv Changes Our Relationship with Mistakes: Drawing on her experience with The Second City and years of facilitating workplace workshops, Catharine shares how improvisation helps people build resilience, adaptability, and confidence through experimentation.The Surprising Joy of Failing: Failure doesn't have to mean defeat. Catharine explains how reframing mistakes as data, stories, and opportunities can transform both our careers and our lives.Building Psychological Safety Through Play: Erin and Catharine discuss why teams that normalize mistakes are often the most innovative, collaborative, and successful.Taking Yourself Less Seriously: Some of the best learning happens when we let go of perfectionism. Catharine shares practical ways leaders can create space for humor, curiosity, and growth even in high-pressure environments.What to Do Now:Try Something You're Bad At: Pick one small activity this week that feels uncomfortable or unfamiliar. Give yourself permission to be a beginner and notice what you learn.Celebrate a Recent Mistake: Reflect on a recent failure or setback. What did it teach you? Share the lesson with a colleague or friend.Practice "Yes, And" Thinking: The next time something doesn't go according to plan, challenge yourself to ask, "Yes, this happened...and what might be possible now?"About the GuestCatharine Savage is a facilitator, educator, improviser, and performer with extensive experience helping individuals and teams build communication, adaptability, and leadership skills through the principles of improv. She performs with The Second City National Touring Company and facilitates professional development experiences through The Second City Works, bringing humor and humanity into workplaces across industries. In addition to her performance work, Catharine teaches and coaches others to embrace experimentation, navigate uncertainty, and find growth through failure. Before pursuing improv professionally, she worked in consulting and sales enablement, giving her a unique perspective on the challenges leaders face in today's workplace. Catharine is passionate about helping people become more resilient, collaborative, and willing to take risks—both on stage and at work.Your FreebieHow do you lead through failure and uncertainty?Today’s workplace demands adaptability, creative problem-solving, and leaders who can navigate uncertainty without freezing in perfectionism.This quick quiz will reveal your unique approach to failure and uncertainty, plus give you simple ways to strengthen your adaptability muscles and help your team thrive when things don’t go according to plan.Connect with Catharine SavageCatharine’s InstagramCatharine’s LinkedInCatharine’s websiteConnect with Erin Diehl x improve it!Leadership Playground online membership communityErin’s websiteErin’s InstagramErin’s TikTokErin’s LinkedInimprove it!’s websiteimprove it!’s InstagramFor more information on improve it! visit www.learntoimproveit.com.
    Show More Show Less
    31 mins
  • 352: Burned Out and Overthinking? Try These Mindset Shifts

    352: Burned Out and Overthinking? Try These Mindset Shifts
    Jun 24 2026
    In this episode of Workday Playdate, Erin dives into the exhausting tango between burnout and overthinking, and why these two troublemakers love to keep us stuck in our heads. Erin shares tips for how to stop performing a one-person show in your life and work.

    Inside This Episode:
    • The Scene Reset Framework: Learn Erin's five-step improv-inspired reset for moving from mental chaos to present-moment action: Drop the Script, Play the Scene You're In, Yes-And Yourself First, Edit the Scene, and Trust the Ensemble.
    • Stop Competing in the Overthinking Olympics: Through interactive exercises like the Scene Sweep practice, Erin shares simple ways to clear mental clutter, interrupt anxious thought spirals, and create space for what matters most.
    • Self-Compassion Is a Productivity Strategy: Discover why saying "yes, and" to yourself reduces internal friction, builds resilience, and helps you navigate uncertainty with more ease.
    • You Weren't Meant to Perform Solo: Erin discusses the power of delegation, trust, and community—and why asking for help may be the most productive thing you do all week.
    What to Do Now:
    1. Try a Scene Sweep: Spend five minutes writing down every thought competing for your attention, then identify what needs action, delegation, or release.
    2. Practice the Scene Reset: The next time you catch yourself spiraling, walk through the five-step framework to reconnect with the present moment.
    3. Ask for Backup: Identify one task, decision, or worry you don't need to carry alone and invite someone else into the scene.
    Your Freebie

    How do you lead through failure and uncertainty?

    Today’s workplace demands adaptability, creative problem-solving, and leaders who can navigate uncertainty without freezing in perfectionism.

    This quick quiz will reveal your unique approach to failure and uncertainty, plus give you simple ways to strengthen your adaptability muscles and help your team thrive when things don’t go according to plan.

    Connect with Erin Diehl x improve it!
    • Leadership Playground online membership community
    • Erin’s website
    • Erin’s Instagram
    • Erin’s TikTok
    • Erin’s LinkedIn
    • improve it!’s website
    • improve it!’s Instagram




    For more information on improve it! visit www.learntoimproveit.com.
    Show More Show Less
    19 mins
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