Workday Playdate

By Erin Diehl - Workday PlaydateBusiness Education How To Careers Management

Workday Playdate episodes

July 28361: The Unexpected Career Power of Improv with Nnamdi Ngwe
In this episode of Workday Playdate, Erin sits down with Emmy Award-winning writer, actor, comedian, facilitator, and longtime improve it! family member Nnamdi Ngwe to explore why the most valuable career skills often come from the places you least expect. From playing college soccer to performing with The Second City, creating viral content, facilitating workshops for global organizations, and winning an Emmy, Nnamdi's career is proof that following your curiosity can lead to opportunities you never could have planned.
If you've ever wondered whether your creative interests "count," questioned whether it's too late to pursue something different, or struggled to connect your unique experiences into a meaningful career path, this conversation will inspire you to see your strengths in a whole new way.
Inside This Episode:
Why Your Nontraditional Skills Are Your Competitive Advantage: Nnamdi shares how the experiences that don't fit neatly on a resume often become the skills that make you indispensable in your career.

From College Soccer to Comedy Stages: Hear how an unexpected path led Nnamdi from the soccer field to improv theaters, television sets, and corporate boardrooms, proving that careers rarely unfold in a straight line.

What It Really Takes to Create Viral Content: With a massive following across TikTok and Instagram, Nnamdi pulls back the curtain on his creative process and explains why content that looks effortless usually comes from consistent practice and experimentation.

The Workplace Lessons Hidden Inside Improv: After facilitating workshops for companies like LinkedIn, TikTok, Motorola, and T-Mobile, Nnamdi explains the powerful moment when people realize improv isn't just entertainment—it's a practical skill for communication, collaboration, leadership, and innovation.

Trusting Your Scene Partner and Yourself: Nnamdi reflects on collaborating with his twin brother and creative partner, Amechi, sharing lessons about trust, flexibility, and building successful partnerships both on stage and in business.
What to Do Now:
Identify Your Hidden Career Skill: Think about one strength you have that doesn't appear on your resume. Whether it's calming people during stressful moments, reading a room, making others laugh, or adapting when plans change, recognize it as a real professional asset.

Stop Waiting for the Perfect Career Path: Your experiences don't have to make sense to everyone else. Trust that the skills you're building today may become the foundation for opportunities you can't yet imagine.

Follow What Energizes You: Instead of asking whether a creative interest is practical, ask what it's teaching you. The projects that light you up often develop the very human skills that set you apart.
About the Guest
Nnamdi Ngwe is an Emmy Award-winning writer, actor, comedian, facilitator, and educator. After playing collegiate soccer at the University of Alabama-Birmingham, he went on to study and perform comedy at iO Theater and The Second City. Alongside his twin brother and creative partner, Amechi Ngwe, he has written and starred in acclaimed productions including Julius, Rap Skool, and House Sitters. His television credits include The Amber Ruffin Show, A Black Lady Sketch Show, The Bold and the Beautiful, Blippi, Comedy Central's 3Peat, and the Emmy Award-winning Tab Time. Beyond entertainment, Nnamdi facilitates interactive workshops for organizations around the world, helping leaders and teams build communication, adaptability, and collaboration skills through applied improvisation. Whether performing on stage, creating viral content online, or leading a workshop, he's passionate about helping people embrace creativity, trust themselves, and discover that their most unexpected skills are often their greatest strengths.
Your Freebie
You’re calm, capable, and composed… until things take an unexpected turn (as they tend to do)! This is exactly why we created The Clarity Under Pressure Toolkit: What to Do in the First 5 Minutes of Any Uncertain Situation.
It’s your go-to guide for staying grounded when it matters most. Download it here.
Connect with Nnamdi Ngwe
Nnamdi’s Instagram
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
Connect with Erin Diehl
🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.
Loved this episode?
If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.
32 min
July 22360: Confidence Hacks for Speaking Up at Work
In this episode of Workday Playdate, Erin explores why speaking up at work has far less to do with competence and far more to do with confidence. If you've ever left a meeting thinking, "I should have said something," you're not alone—and you're probably more prepared than you think.
If you've ever had the perfect idea thirty seconds too late, watched someone else say what you were thinking, or struggled to find your voice in meetings, this conversation is for you. Using improv principles and practical strategies, Erin shares how to stop disappearing on the back line and start contributing with more confidence, more quickly, and more consistently.
Inside This Episode:
Speaking Up Is Usually a Confidence Issue, Not a Competence Issue: Most people already know what they want to say, they just hesitate when the moment arrives. Erin explores why the gap between thinking and speaking is often driven by fear, not ability.

Silence Feels Safe, But It Can Make You Invisible: Staying quiet may protect you from saying the wrong thing, but it can also prevent others from seeing your ideas, expertise, and leadership potential. Early and frequent participation changes how people experience you.

Confidence Is Built Through Reps, Not Perfection: The goal isn't to feel ready before you contribute. The goal is to contribute and let confidence catch up. Erin shares why speaking up is a skill built through practice, not personality.

The SPEAK Framework Makes Participation Easier: Erin introduces the improv-inspired SPEAK framework to help you contribute more naturally in meetings: Set up the scene, Preload your line, Enter early, Anchor the room, and Keep building.

Consistency Changes Your Identity: Speaking up once feels brave. Speaking up repeatedly changes how you see yourself and how others see you. Confidence isn't built in a single moment; it's built in patterns.
What to Do Now:
Set Up the Scene: Before your next meeting, identify one idea, question, or perspective you want to contribute before the conversation begins.

Preload Your Line: Prepare a simple opener such as, "One thing that stands out to me is..." or "I'd like to build on that idea..." so you're not starting from zero when the moment arrives.

Enter Early: Challenge yourself to speak within the first ten minutes of your next meeting. Momentum is easier to maintain than it is to create.

Anchor the Room: Remember that your contribution doesn't just help you—it creates permission for others to participate, ask questions, and share ideas too.

Keep Building: Confidence is earned through repetition. Every time you speak up, you're collecting evidence that your voice belongs in the room.
Your Freebie
You’re calm, capable, and composed… until things take an unexpected turn (as they tend to do)! This is exactly why we created The Clarity Under Pressure Toolkit: What to Do in the First 5 Minutes of Any Uncertain Situation.
It’s your go-to guide for staying grounded when it matters most. Download it here.
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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
Connect with Erin Diehl
🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.
Loved this episode?
If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.
23 min
July 21359: The 5 Lessons: What a Month in Asia Taught Me About Thinking on Your Feet
“Sometimes you have to leave home to see home.”
In this episode of Workday Playdate, Erin takes listeners on a journey through Shanghai, Singapore, and Bali to unpack what a month abroad taught her about thinking on her feet and appreciating the life waiting back home.
What starts as an international travel adventure quickly becomes a masterclass in working parenthood, and the improv mindset required when every plan goes sideways.
If you've ever had to pivot quickly, parent imperfectly, navigate uncertainty, or figure it out as you go, this episode is a reminder that flexibility is a skill you can practice.
Inside This Episode:
The Plan Is Just a Suggestion: Delayed flights, closed restaurants, language barriers, and disappearing Wi-Fi become an unexpected lesson in adaptability. Erin shares why asking, "New scene, what's the move?" is often more useful than clinging to the original plan.

How Discomfort Expands Your Capability: Whether it's navigating unfamiliar cities, managing food restrictions abroad, or solving problems without your usual routines, Erin explores why confidence often shows up after comfort leaves the room.

The Truth About Good Enough Parenting: Forget perfect parenting. Erin reflects on what it means to be present, resourceful, and human while parenting on the road—and why that's more than enough.

Why Your Village Matters More Than Ever: From family support to travel companions to the people who step in when life gets complicated, this episode is a celebration of the teams, communities, and ensembles that make hard things possible.

Sometimes You Have to Leave Home to See Home: Distance has a funny way of creating clarity. Erin shares how stepping away from everyday life gave her a deeper appreciation for her routines, her community, and the life she built.
What to Do Now:
Treat the Plan Like a Draft: The next time something changes unexpectedly, ask yourself: "What's possible now?" instead of "How do I get back to the original plan?"

Collect Evidence of Your Capability: Keep track of moments when you handled something difficult, unfamiliar, or inconvenient. Your resilience deserves receipts.

Strengthen Your Village: Reach out to someone who has supported you recently and let them know the difference they made. Gratitude is one of the fastest ways to strengthen community.
Your Freebie
You’re calm, capable, and composed… until things take an unexpected turn (as they tend to do)! This is exactly why we created The Clarity Under Pressure Toolkit: What to Do in the First 5 Minutes of Any Uncertain Situation.
It’s your go-to guide for staying grounded when it matters most. Download it here.
Connect with Erin Diehl x improve it!
Join Leadership Playground

Erin’s website

Erin’s LinkedIn

Erin’s Instagram

Erin’s TikTok

improve it!’s website

improve it!’s Instagram
Connect with Erin Diehl
🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.
Loved this episode?
If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.
25 min
July 15358: How Quick Coffee Chats Can Transform Work Culture with Rosalind Cohen
“Connection is the foundation of effective leadership.” -Dr. Rosalind Cohen
In this episode of Workday Playdate, Erin sits down with Dr. Rosalind Cohen to explore why authentic human connection is the foundation of effective leadership. In a world filled with engagement surveys, Dr. Roz makes the case that what people truly want at work is something much simpler: to feel seen, valued, and like they belong.
If you've ever wondered why some workplace cultures thrive while others struggle, this conversation is for you. Using research and practical examples, Dr. Roz shares how leaders can create radically connected cultures where people feel safe, included, and inspired to do their best work.
Inside This Episode:
Engagement and Belonging Are Not the Same Thing: Dr. Roz unpacks the critical difference between employee engagement and belonging, explaining why participation alone isn't enough. True belonging happens when people genuinely feel seen, valued, and included.

Why Perks Can't Replace Connection: Free snacks, flexible work policies, and office perks have their place—but they cannot substitute for authentic relationships. Dr. Roz explores why meaningful conversations remain the heart of strong workplace culture.

Small Moments Create Big Culture Shifts: Culture isn't built during annual retreats alone. Dr. Roz shares how simple practices like coffee chats, intentional check-ins, and curiosity-driven conversations can strengthen trust and connection every day.

Inclusive Leadership Is Built Through Behavior: Creating a connected culture requires more than mission statements and slogans. Dr. Roz discusses the leadership behaviors that foster psychological safety, including curiosity, thoughtful responses, and a "yes, and" mindset.

Belonging Is a Leadership Strategy: Dr. Roz explains how intentional rituals, leadership habits, and human-centered communication create stronger teams and higher-performing organizations.
What to Do Now:
Schedule One Connection Conversation: Reach out to a colleague for a coffee chat or informal check-in with no agenda other than getting to know them better.

Create a Ritual of Belonging: Introduce a simple team ritual, such as personal check-ins or moments of appreciation, to strengthen connection and trust.

Remember That Culture Happens in Small Moments: Every interaction is an opportunity to build belonging. Notice how the everyday conversations you have shape the culture around you.
About the Guest
Dr. Rosalind Cohen is an organizational psychologist, speaker, researcher, and workplace culture strategist dedicated to helping organizations build more inclusive, connected, and human-centered workplaces. Dr. Roz specializes in employee belonging, engagement, and leadership development, partnering with leaders and organizations to create cultures where people feel seen, valued, and empowered to thrive. Through her research, consulting, and thought leadership, she challenges organizations to move beyond surface-level engagement efforts and intentionally cultivate cultures rooted in trust, inclusion, and authentic connection.
Your Freebie
You’re calm, capable, and composed… until things take an unexpected turn (as they tend to do)! This is exactly why we created The Clarity Under Pressure Toolkit: What to Do in the First 5 Minutes of Any Uncertain Situation.
It’s your go-to guide for staying grounded when it matters most. Download it here.
Connect with Dr. Rosalind Cohen
Dr. Rosalind’s LinkedIn

Dr. Rosalind’s website
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
Connect with Erin Diehl
🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.
Loved this episode?
If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.
39 min
July 14357: Tarot Cards and Hard Work Decisions with Phylicia McLeod
In this episode of Workday Playdate, Erin sits down with Phylicia McLeod to explore why thinking on your feet has less to do with having the right answer and more to do with trusting yourself. As an improviser, facilitator, teacher, and performer with the The Second City National Touring Company, Phylicia has built a career around navigating uncertainty in real time.
If you've ever found yourself overthinking a decision, freezing under pressure, or wishing you trusted your instincts more, this conversation is packed with practical wisdom and an unexpected case for tarot cards.
Inside This Episode:
Why Intuition Deserves a Seat at the Table: Phylicia and Erin discuss how intuition, reflective practices, and self-trust can help us make faster, more confident decisions when uncertainty strikes.

How Improv Trains You to Think on Your Feet: Performing improv for a living means making thousands of decisions in real time. Phylicia shares the biggest lessons improv has taught her about trust, adaptability, and moving forward without a script.

Tarot Cards, Creativity, and Decision-Making: Before you roll your eyes, hear us out. Phylicia explains how tarot serves as a powerful reflective tool that helps people access intuition, uncover blind spots, and make meaning during uncertain moments.

Helping People Move Through the Freeze Response: As a longtime improve it! facilitator, Phylicia has helped countless participants navigate those deer-in-headlights moments. Learn how creating psychological safety and lowering the stakes can help anyone think more clearly under pressure.

Unlearning the Need for Certainty: Through her work as co-host of the podcast Unlearning, Phylicia explores what it means to let go of old stories, trust yourself more deeply, and embrace uncertainty as part of growth.
What to Do Now:
Listen to Your Gut First: The next time you're facing a difficult decision, give yourself five uninterrupted minutes to write down what your intuition is telling you before seeking outside opinions.

Practice Imperfect Action: Thinking on your feet isn't about certainty. It's about making the next move with the information you have and trusting yourself to adjust along the way.

Get Curious About Your Patterns: Notice where you tend to overthink, freeze, or seek external validation. Awareness is the first step toward building greater self-trust.
About the Guest
Phylicia McLeod is a Chicago-based improviser, writer, voice actor, and educator. She currently tours with The Second City National Touring Company and has been a beloved improve it! facilitator since 2018. In addition to performing and teaching, Phylicia co-hosts the podcast Unlearning, where she explores growth, identity, and the stories we tell ourselves. Whether she's on stage, in the classroom, or reading tarot cards, Phylicia is passionate about helping people trust themselves, embrace uncertainty, and lead with curiosity.
Your Freebie
You’re calm, capable, and composed… until things take an unexpected turn (as they tend to do)! This is exactly why we created The Clarity Under Pressure Toolkit: What to Do in the First 5 Minutes of Any Uncertain Situation.
It’s your go-to guide for staying grounded when it matters most. Download it here.
Connect with Phylicia McLeod
Phylicia’s LinkedIn
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
Connect with Erin Diehl
🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.
Loved this episode?
If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.
32 min
July 08356: Your Intuition Is Your Career Superpower
In this solo episode of Workday Playdate, Erin explores why your intuition might be the most underutilized leadership skill you have. In a world obsessed with data and overthinking, Erin makes the case for trusting the wisdom you've already earned through experience. If you've ever ignored a gut feeling only to say, "I knew it," two weeks later, this episode is for you.
Using cognitive science to practical exercises for better decision-making, Erin shares how to stop outsourcing your knowing and start using your intuition as a career superpower.
Inside This Episode:
Your Gut Is Smarter Than You Think: Erin unpacks the science behind intuition and explains why gut feelings aren't "woo-woo"—they're actually your brain processing years of experience, pattern recognition, and emotional intelligence at lightning speed.

Why We Stop Trusting Ourselves: Somewhere between spreadsheets, stakeholder meetings, and requests for "more data," many of us learn to ignore our instincts. Erin explores how workplace culture often trains us out of self-trust—and why it's time to relearn it.

Introducing the G.U.T.S. Framework: When you're stuck, uncertain, or under pressure, Erin shares her four-step framework for making better decisions by combining intuition with action:

Get Quiet: Create enough space to hear what your intuition is trying to tell you.

Uncover the Signal: Learn how to distinguish intuition from fear, anxiety, or overthinking.

Trust the Move: Stop waiting for perfect certainty and commit to the next right step.

Speak It Out: Turn internal knowing into visible leadership by confidently sharing your instincts with others.

Intuition Is Thinking Quickly on Your Feet: Great improvisers don't succeed because they overthink. They succeed because they trust their first instinct, commit, and build from there. Erin explains why the same principle applies to leadership, communication, and decision-making at work.
What to Do Now:
Do a Gut Check: Identify three decisions or situations where you feel stuck. Ask yourself, "What does my gut already know?" and write down the first answer that appears.

Practice the G.U.T.S. Framework: The next time you're facing uncertainty, walk through Get Quiet, Uncover the Signal, Trust the Move, and Speak It Out.

Take One Intuitive Action: Choose one decision this week where your intuition serves as the primary input. Commit to the choice and notice what happens.
Your Freebie
You’re calm, capable, and composed… until things take an unexpected turn (as they tend to do)! This is exactly why we created The Clarity Under Pressure Toolkit: What to Do in the First 5 Minutes of Any Uncertain Situation.
It’s your go-to guide for staying grounded when it matters most. Download it here.
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
Connect with Erin Diehl
🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.
Loved this episode?
If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.
22 min
July 07355: Think Fast Without Panicking at Work
In this episode of Workday Playdate, Erin sits down with John Ulrich and Olga Flores to explore how improvisation can help teams think faster without panicking. As leaders at Antunes, John and Olga have spent the last three years partnering with improve it! to build a culture of adaptability, communication, and creativity across their organization.
If you've ever wondered how to help your team respond instead of react under pressure, this conversation is packed with practical insights and one unforgettable story involving something called Antunes Night Live.
Inside This Episode:
Why Thinking on Your Feet Is a Trainable Skill: John, Olga, and Erin discuss why the ability to stay calm and respond under pressure is a skill that can be practiced and strengthened over time.

The Story Behind Antunes Night Live: Discover how John and Olga partnered with improve it! to create one of the most creative leadership development experiences imaginable, and why stepping outside your comfort zone can have a lasting impact on team culture.

How Improv Builds Better Sales Teams: In sales, curveballs are inevitable. John and Olga share how improv training has helped their team navigate uncertainty, communicate more effectively, and handle unexpected customer situations with greater confidence.

Building a Culture That Embraces Change: From workshops to team events, learn how Antunes has used improv to create stronger relationships, foster psychological safety, and encourage employees to experiment, learn, and grow together.

Getting Team Buy-In for Something New: Bringing improv into the workplace can feel like a leap. John and Olga offer advice for leaders who want to introduce new approaches to learning and development but worry their teams might resist.
What to Do Now:
Pause Before You Panic: The next time you're caught off guard at work, take one breath before responding. Creating even two seconds of space can help you move from reaction to intention.

Lead With Curiosity: When uncertainty shows up, replace the urge to control with a question. Curiosity creates connection, unlocks new possibilities, and helps teams think more clearly.

Practice "Yes, And": Instead of shutting down ideas or immediately looking for problems, challenge yourself to build on what's possible. Small shifts in language can create big shifts in collaboration.
About the Guests
John Ulrich is the Vice President of Sales, North America at Antunes, where he leads high-performing sales teams focused on unified growth, collaboration, and customer success. With more than twenty-five years of foodservice industry experience, John is passionate about developing people and creating cultures where teams can thrive.
Olga Flores is a Regional Sales Manager at Antunes, where she drives both results and relationships across her territory. Together, John and Olga have been instrumental in championing the partnership between Antunes and improve it!, helping bring innovative, improv-based learning experiences to their teams and proving that play and performance can go hand in hand.
Your Freebie
You’re calm, capable, and composed… until things take an unexpected turn (as they tend to do)! This is exactly why we created The Clarity Under Pressure Toolkit: What to Do in the First 5 Minutes of Any Uncertain Situation.
It’s your go-to guide for staying grounded when it matters most. Download it here.
Connect with John Ulrich and Olga Flores
John’s LinkedIn

Olga’s LinkedIn
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
Connect with Erin Diehl
🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.
Loved this episode?
If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.
28 min
July 01354: The Improv Advantage in Leadership with Anne Libera
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 Guest

Anne 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 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 Anne Libera
Anne’s LinkedIn
Anne’s Columbia College Chicago website page
Anne’s book: Funnier: A New Theory for the Practice of Comedy

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.
Connect with Erin Diehl
🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.
Loved this episode?
If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.
54 min
June 30353: Turns Out Failing Is Kind of Fun? with Catharine Savage
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 Guest

Catharine 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 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 Catharine Savage
Catharine’s Instagram
Catharine’s LinkedIn
Catharine’s website

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.
Connect with Erin Diehl
🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.
Loved this episode?
If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.
31 min
June 24352: Burned Out and Overthinking? Try These Mindset Shifts
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:
Try a Scene Sweep: Spend five minutes writing down every thought competing for your attention, then identify what needs action, delegation, or release.
Practice the Scene Reset: The next time you catch yourself spiraling, walk through the five-step framework to reconnect with the present moment.
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.
Connect with Erin Diehl
🌟 Learn more about Workday Playdate: https://www.learntoimproveit.com/podcast-page
🎤 Book Erin to speak: https://www.learntoimproveit.com/keynote-speaker
📚 Workshops & Team Experiences: https://www.learntoimproveit.com/experiential-training
💌 Learn more about Erin: https://www.itserindiehl.com/meet-erin
📱 For more information on improve it! visit www.learntoimproveit.com.
Loved this episode?
If this conversation made you think differently about work, leadership, or building joyful teams, please follow Workday Playdate on Apple Podcasts or Spotify, leave a review, and share this episode with someone who could use more play in their workday.
20 min

About Workday Playdate

From the publisher's feed

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…