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!<a href="https://www.learntoimproveit.com/leadership-playground" target="_blank"...

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 <a href="https://www.linkedin.com/in/catharine-savage-09590245/" target="_blank"...

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 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 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.

In this episode of Workday Playdate, Erin sits down with Laurie Jadick to explore what it really takes to lead people through change in today's rapidly evolving workplace. With decades of experience in human resources, leadership development, and executive onboarding, Laurie shares why successful transformation is about people first.If you've ever struggled to help your team embrace new ways of working, this conversation offers practical wisdom and a refreshing reminder that human connection remains at the center of great leadership.Inside This Episode:Why Change Starts with Trust: Laurie shares why trust is the foundation of any successful transformation effort and how leaders can build credibility during times of uncertainty.The Human Side of Change Management: Organizational change often focuses on systems and strategy, but Laurie explains why understanding emotions, resistance, and individual experiences is equally important.Creating Meaningful Onboarding Experiences: Drawing from her extensive work in executive onboarding, Laurie discusses how intentional onboarding experiences can accelerate impact, strengthen culture, and set leaders up for long-term success.Leading Through Uncertainty: Erin and Laurie explore what leaders can do when they don't have all the answers and why transparency, curiosity, and adaptability matter more than ever.Why Learning Never Stops: The conversation highlights the importance of continuous learning, reinvention, and staying open to new ideas throughout every stage of your career.What to Do Now:Assess Your Change Communication: Think about a current change happening on your team. Are you communicating only the "what," or are you also addressing the "why" and the emotional impact?Schedule a Connection Conversation: Set aside time this week to check in with a colleague or team member not to discuss tasks, but simply to understand how they're doing and what support they need.Reflect on Your Learning Edge: Identify one new skill, mindset, or area of growth you'd like to develop over the next month and take one small step toward it this week.About the GuestLaurie Jadick is a seasoned human resources and talent leader with more than two decades of experience helping organizations navigate transformation, leadership development, and employee experience. Throughout her career, Laurie has led global learning, leadership, and onboarding initiatives for large organizations, with a particular passion for creating people-centered experiences that drive both business results and human connection. She currently serves as a leader at Publicis Sapient, where she focuses on executive onboarding and leadership integration, helping leaders thrive from day one. Laurie is known for her thoughtful approach to change, commitment to continuous learning, and belief that people are at the heart of every successful organization.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 Laurie JadickLaurie’s LinkedInConnect with Erin Diehl x improve it!<a...

In this episode of Workday Playdate, Erin sits down with workplace researcher, organizational psychologist, and meeting culture expert Rebecca Hinds to tackle one of the biggest drains on modern work: bad meetings. If you've ever stared at a packed calendar or wished collaboration felt more energizing, this conversation is packed with practical ideas to help you reclaim your time and redesign how your team connects.Inside This Episode: Meeting Doomsday Is Coming: Rebecca introduces the concept of "meeting doomsday" and explains how a simple 48-hour calendar cleanse can help organizations break free from unnecessary meetings and reset workplace norms.Why We're Meeting More Than Ever: Learn how meeting hours have exploded over the past several decades, why calendars became the default communication tool, and the hidden costs of constant collaboration.The 4D CEO Test: Before scheduling your next meeting, Rebecca shares her simple framework to determine whether the goal is to Decide, Debate, Discuss, or Develop—and whether a meeting is actually necessary.The Visibility Trap: Discover how visibility bias keeps unnecessary meetings alive and why being busy isn't always the same as being productive.Design Meetings People Actually Want to Attend: From intentional titles to clear outcomes, Rebecca shares practical ways to create meetings that foster connection, collaboration, and momentum. What to Do Now:Audit Your Calendar: Review your recurring meetings and ask: "Does this truly need to happen, or could it be handled another way?"Use the 4D Test: Before scheduling a meeting, identify whether the goal is to Decide, Debate, Discuss, or Develop.Title Meetings with Intention: Replace vague meeting names with clear, outcome-driven titles that tell attendees exactly why they're there. 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.About the GuestRebecca Hinds is an organizational psychologist, workplace researcher, and leadership strategist who helps organizations create healthier, more effective ways of working. She serves as the Head of Asana's Work Innovation Lab, where she studies collaboration, productivity, workplace culture, and the future of work. Rebecca's research has been featured in major publications and helps leaders rethink how teams communicate, meet, and thrive. Her work focuses on helping organizations reduce friction, improve collaboration, and build work environments where both performance and wellbeing can flourish.Connect with Rebecca Hinds Rebecca’s LinkedInRebecca’s websiteRebecca’s book: Your Best Meeting EverConnect with Erin Diehl x improve it!Leadership Playground online membership communityErin’s <a href="https://www.itserindiehl.com/" target="_blank" rel="noreferrer...

In this episode of Workday Playdate, Erin sits down with Meredith Stepien to explore how small moments of joy can become anchors during life's most chaotic seasons. Known for her work as a performer, writer, musician, improviser, and creative leader, Meredith shares why chasing massive life-changing moments isn't always the answer, and how cultivating sparks of delight can help us stay grounded.If you've ever felt overwhelmed by the pace of work or simply being human, this conversation is a reminder that joy doesn't have to be earned. Sometimes it's found in the smallest moments hiding in plain sight.Inside This Episode:Why Small Joys Matter More Than We Think: Meredith shares how tiny moments of delight can help regulate our nervous systems, shift our perspective, and create steadiness during difficult times.The Myth of Waiting for Happiness: Many of us postpone joy until we hit a milestone, solve a problem, or achieve a goal. Meredith discusses why joy is something we can practice now—not something we have to wait for.Creativity as a Survival Tool: Drawing from her background in performance, music, and improv, Meredith explains how creativity helps us navigate uncertainty and stay connected to what makes us feel alive.Finding Presence in the Everyday: The conversation explores how paying attention to ordinary moments can create extraordinary meaning, even when life feels overwhelming.The Connection Between Play and Resilience: Erin and Meredith discuss why play is a critical tool for maintaining energy, perspective, and emotional well-being.What to Do Now:Create a Tiny Joy List: Write down five small things that consistently bring you joy. Keep the list somewhere visible and intentionally seek out one of them each day this week.Practice Noticing: Throughout your day, pause and identify one moment that makes you smile, laugh, feel curious, or experience gratitude. The goal is to increase awareness of the good that is already here.Schedule Play on Purpose: Block out 15 minutes this week for something that feels playful, creative, or energizing with no productivity goal attached.About the GuestMeredith Stepien is a Chicago-based comedian, musician, writer, producer, and improviser best known for her work with the musical theater company Team StarKid. A graduate of the University of Michigan with a BFA in Acting, Meredith has performed in numerous StarKid productions and co-wrote the music and lyrics for the cult-favorite musical Firebringer. She is also a creative producer, podcast host, and longtime improviser who brings humor to everything she does. In addition to her performance and creative work, Meredith serves as a facilitator for improve it! workshops, helping individuals and teams build stronger confidence through the power of improv.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 Meredith StepienMeredith’s InstagramMeredith’s YouTubeMeredith’s <a href="https://www.linkedin.com/in/meredith-stepien-39ab2517"...

In this episode of Workday Playdate, Erin tackles AI anxiety and how to address it on your own and with your team at work. If you've ever wondered whether AI is coming for your job, felt overwhelmed by new technology, or weren't sure where to begin, this episode offers a practical, human-centered approach to navigating AI with confidence. Erin shares a simple framework to help leaders and teams embrace AI without losing the creativity, connection, and humanity that make work meaningful.Inside This Episode:Why AI Feels So Scary Right Now: Erin breaks down the most common fears surrounding AI, from job displacement to information overload, and explains why uncertainty (rather than technology itself) is often what makes change feel uncomfortable.Leadership's Role in the AI Era: Every major workplace shift requires leaders who can guide people through ambiguity. Learn why curiosity, transparency, and empathy are essential leadership skills in the age of AI.The Four-Step "AI Scene" Framework: Inspired by improv, this practical approach helps leaders and teams navigate AI adoption with less fear and more confidence:Accept the Scene: Acknowledge that AI is here and part of the workplace conversation.Improvise Your Entry Point: Start small by choosing one task where AI can support your work.Build the Scene with Your Team: Create shared learning experiences and normalize experimentation.Take Your Encore: Integrate AI intentionally in ways that enhance human creativity and impact.How to Create an AI Playground at Work: Discover how low-stakes experimentation can reduce fear and build confidence. Erin shares ideas for creating safe spaces where teams can learn, test, and explore together.Small Experiments Create Big Confidence: Forget mastering AI overnight. Learn how simple 15-minute AI labs can help you build skills, uncover opportunities, and reduce overwhelm one step at a time.What to Do Now:Start With One Task: Identify a single repetitive task you do each week and explore how AI could support or streamline it.Create a 15-Minute AI Lab: Set aside fifteen minutes this week to experiment with an AI tool. Just for curiosity and play!Build an AI Playground: Invite your team to share wins, lessons learned, and questions about AI in a judgment-free environment focused on learning rather than perfection.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 Erin Diehl x improve it!Leadership Playground online membership communityErin’s websiteErin’s InstagramErin’s TikTokErin’s LinkedInimprove it!’s <a href="https://www.learntoimproveit.com/"...

In this episode of Workday Playdate, Erin sits down with Kelly Burlage, Chief Human Resources Officer at Lineage, to explore how our relationship with failure changes as we grow in our careers. From early-career mistakes that feel world-ending to high-stakes leadership decisions that impact entire organizations, Kelly shares why failure is something to learn from.If you've ever found yourself replaying a professional setback or questioning whether you're ready for the next level, this conversation offers a refreshing perspective on resilience and leading through uncertainty.Inside This Episode:Why Failure Evolves as Your Career Grows: Kelly shares how her definition of failure has shifted throughout her career and why the challenges that once felt devastating often become the foundation for future success.The Leadership Lessons Hidden Inside Setbacks: Not every failure feels productive in the moment. Kelly reflects on how some of her most difficult professional experiences ultimately accelerated her growth and strengthened her leadership.How to Lead Through High-Stakes Misses: As leaders advance, mistakes become more visible and carry greater consequences. Kelly discusses how to navigate setbacks without losing trust, momentum, or confidence.Balancing Innovation with Smart Risk-Taking: Growth requires experimentation, and experimentation comes with the possibility of failure. Kelly explains how data, curiosity, and calculated risks help organizations move forward without becoming paralyzed by fear.Creating a Culture Where People Can Learn from Failure: In industries where precision matters, psychological safety still matters. Kelly shares how leaders can create environments where people feel empowered to take ownership, learn, and improve.What to Do Now:Revisit an Old Failure: Think about a professional setback from earlier in your career that still makes you cringe. What lessons did it teach you that success couldn't have?Audit Your Current Response to Failure: Ask yourself whether you're approaching today's challenges with outdated fears or limiting beliefs that no longer serve you.Look for the Lesson, Not the Label: The next time something doesn't go as planned, resist the urge to immediately call it a failure. Instead, ask: "What is this experience teaching me?"About the GuestKelly Burlage is the Chief Human Resources Officer at Lineage, the world's largest and most innovative temperature-controlled logistics provider. She leads enterprise-wide people strategies that align business growth with operational excellence while fostering a culture of inclusion, collaboration, and high performance. With more than two decades of global HR and talent leadership experience, Kelly has built and scaled high-performing teams across complex, high-growth organizations. She is known for delivering innovative, data-driven people strategies that drive meaningful business results. Kelly is a Korn Ferry Certified Coach, a Leading Women Executives alumna, and has been recognized among TAtech's Top 100 Most Influential Talent Acquisition Thought Leaders.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 Kelly BurlageKelly’s <a...

In this episode of Workday Playdate, Erin sits down with wellness expert, bestselling author, and intuitive healer Inna Segal to explore the powerful connection between emotional wellbeing and physical health. If you've ever felt stuck, overwhelmed, burned out, or disconnected from yourself, this conversation offers practical tools to help you unlock your body's innate ability to heal.Inside This Episode:Your Body Is Talking: Inna explains how physical symptoms often carry emotional messages and why learning your body's language can lead to greater self-awareness, resilience, and healing.The Hidden Link Between Emotions and Health: Discover how stress, grief, trauma, and unresolved emotions can manifest physically, and what you can do to release what's been weighing you down.Healing Starts with Connection: From visualization and color work to movement and breath, Inna shares simple practices to help you reconnect with yourself and access your body's wisdom.Why Slowing Down Is a Superpower: For leaders, parents, and high achievers, Inna reveals why creating moments of stillness can unlock clarity, energy, and emotional balance.The Stages of Healing Explained: Learn how healing evolves over time, why discomfort is sometimes part of the process, and how to navigate change with more trust and self-compassion.What to Do Now:Pause Before You Push Through: The next time you feel stressed, exhausted, or overwhelmed, ask yourself: "What is my body trying to tell me?"Create Five Minutes of Stillness: Take a few intentional breaths, slow down, and notice what thoughts, emotions, or sensations are asking for your attention.Experiment with Color and Visualization: Try using color, movement, or imagery to shift your emotional state and release tension.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 Inna SegalInna’s websiteInna’s booksInna’s LinkedInConnect 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...

In this episode of Workday Playdate, Erin sits down with Rosie Moan to talk about one of the most challenging combinations many women face: becoming a new mom while navigating uncertainty in work, identity, and life. If you've ever felt like you're simultaneously capable and completely overwhelmed, this conversation offers a refreshing reminder that confidence is about trusting yourself through the unknown.Inside This Episode: Why Confidence and Uncertainty Often Arrive Together: Rosie shares how some of life's biggest growth moments happen when we feel both competent and terrified at the same time, and why that tension is often a sign we're expanding into something new.The Identity Shift of New Motherhood: Becoming a parent can reshape how we see ourselves. Erin and Rosie discuss the emotional and professional adjustments that come with this transition and how to navigate them with more self-compassion.Improvisation as a Tool for Real Life: Drawing from her background in improv, Rosie explains how embracing a "yes, and" mindset can help us respond to unexpected challenges, uncertainty, and change with greater flexibility.Learning to Trust Yourself Again: The conversation explores why confidence isn't about having every answer. It's about building trust in your ability to figure things out as you go.The Power of Letting Go of Perfection: Rosie shares insights on releasing unrealistic expectations and creating space for growth, learning, and grace during demanding seasons of life.What to Do Now:Ask Yourself a Better Question: Instead of asking, "What if I fail?" try asking, "What if I can handle whatever comes next?"Practice "Yes, And" This Week: When something unexpected happens, look for one way to accept reality and build forward rather than resist it.Celebrate Evidence of Your Resilience: Take a few minutes to write down three challenges you've already navigated successfully. Use them as reminders that you've handled uncertainty before and can do it again.About the GuestRosie Moan is a Chicago-based actor, improv performer, coach, and acting coach who has spent more than 15 years helping people build confidence, take creative risks, and trust themselves on and off camera. A graduate of Emerson College, she performs, teaches, and coaches within Chicago's renowned improv community and facilitates workshops designed to strengthen communication, collaboration, and personal growth. Her work centers on helping people move past self-doubt and step more fully into their potential. She is also a lead facilitator for improve 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 Rosie Moan Rosie’s websiteRosie’s InstagramRosie’s LinkedInConnect with Erin Diehl x improve it!Leadership Playground online membership...