Workday Playdate Podcast By Erin Diehl - Workday Playdate cover art

Workday Playdate

Workday Playdate

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 Career Success Economics Management Management & Leadership
Episodes
  • 370: When High-Achieving Women Carry Too Much Alone with Meghan French Dunbar

    370: When High-Achieving Women Carry Too Much Alone with Meghan French Dunbar
    Sep 23 2026
    For high-achieving women, that belief can run deep. We’re taught to be capable, composed, productive, and independent, and to keep going no matter what. But what happens when “I can handle it” becomes burnout? In this episode of Workday Playdate, Meghan French Dunbar joins Erin for a candid conversation about burnout, leadership, vulnerability, women at work, and what it really takes to build humane workplaces. Drawing from her experience as a founder, CEO, and mother, Meghan shares the personal wake-up calls that forced her to rethink what success and leadership actually mean. Together, Erin and Meghan unpack chronic busyness, workplace vulnerability, trust, overwork, and the pressure to be an unbreakable leader. They explore how small shifts in the way we lead can create more sustainable work rhythms and teams. Inside This Episode: When Work Becomes Your Identity: Meghan shares the airplane story, miscarriage, and burnout experiences that forced her to confront the personal cost of being an “unbreakable” leader.The Myth of the Busy Season: What happens when “I’m just in a busy season” becomes your permanent state? Meghan explains how chronic busyness can become a system—not just a season.Vulnerability Builds Trust: Discover why being honest about struggles can actually make leaders more trustworthy and help teams feel safer opening up.Women Don’t Have to Do It All: Erin and Meghan unpack the pressure high-achieving women face to be endlessly capable—and why asking for help doesn’t make you a burden.Rethinking Leadership: Move beyond the superhero leader. Meghan explores a healthier blend of decisiveness, empathy, compassion, listening, and vulnerability. What to Do Now: Question Your “Busy Season”: Is this actually a season—or has chronic busyness become your normal? Identify one expectation or habit that’s keeping you stuck in overload.Let Someone In: Share one honest thing with your team that you might normally keep hidden. Vulnerability doesn’t mean oversharing—it means letting people see the human behind the role.Ask for Help: Identify one thing you’re carrying alone and invite someone in. Strong leadership isn’t about proving you can do everything yourself. It’s about creating a culture where no one has to. About the Guest Meghan French Dunbar is a purpose-driven business leader, author, speaker, and former co-founder and CEO of Conscious Company Media, the first nationally distributed print magazine focused on purpose-driven business in the U.S. Over the course of her career, she has interviewed more than 1,000 leaders about what it takes to build businesses that create meaningful impact. Her book, This Isn’t Working, explores why traditional approaches to work are failing people—and what it looks like to build careers, companies, and lives that actually lift people up. Today, Meghan helps exceptional organizations develop narrative strategies that stand out, and she hosts Unbehaved, a podcast featuring leaders who are challenging the old rules of work and business. Your Freebie Confidence at work doesn’t mean pretending to have it all figured out. Download our Confident Leader’s Toolkit for a practical, four-step guide to crafting an intentional professional persona so you can lead with more clarity and confidence. Whether you’re stepping into a new leadership role, navigating a high-stakes conversation, or simply looking to show up more intentionally, this toolkit will help you build a leadership presence that feels sustainable. Connect with Meghan French Dunbar Meghan’s LinkedInMeghan’s websiteMeghan’s book, This Isn’t WorkingZingTrain academyZingTrain books 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 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.
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    48 mins
  • 369: The Leadership Skill Nobody Teaches: Stopping Before Burnout Hits with Brent Freeman

    369: The Leadership Skill Nobody Teaches: Stopping Before Burnout Hits with Brent Freeman
    Sep 16 2026
    In this episode of Workday Playdate, Erin sits down with entrepreneur, speaker, and author Brent Freeman to unpack what happens when external success stops feeling like success. After building billion-dollar growth machines, Brent found himself burned out, disconnected, and asking a much bigger question: What if the life I’m building isn’t actually the life I want? Brent shares how a “one-degree drift” away from yourself can quietly turn into burnout and how he began rebuilding his life around joy, presence, and intentionality. From canceling every meeting to watch a sunset to creating a daily “list of joy,” Brent explains the neuroscience, nervous system practices, and emotional alchemy tools behind his new book, The Alchemy of Joy. Whether you’re navigating burnout, chasing your next achievement, or simply want to feel more present in your own life, this conversation is a reminder that joy is something you can invest in right now. Inside This Episode: When Success Stops Feeling Successful: Brent opens up about the hollow feeling that came after building massive businesses and achieving the external markers of success he once thought would create fulfillment.The One-Degree Drift: Learn how tiny, seemingly harmless choices can gradually move you away from your values, your joy, and yourself—and why noticing the drift early matters.Burnout Beyond Hustle Culture: Brent explores how burnout can hide behind ambition, impact, productivity, and achievement, and why it’s not simply a matter of “working too hard.”The Return on Joy (ROJ): Discover Brent’s framework for treating joy as an intentional investment with a compounding payoff in energy, fulfillment, presence, and quality of life.The One-Minute Window: Learn a simple 60-second practice for interrupting autopilot, regulating your nervous system, and coming back to the present moment. What to Do Now: Make Your List of Joy: Write down 5–10 things that genuinely make you feel alive, energized, connected, or playful. Then ask yourself: When was the last time I made time for these?Try the One-Minute Window: The next time you feel overwhelmed or triggered, stop for 60 seconds. Breathe. Notice what’s happening in your body. Let yourself come back to the present before deciding what to do next.Invest in Your ROJ: Choose one small thing that brings you joy and intentionally put it on your calendar this week. Don’t wait until everything else is done. Consider it a daily investment in your return on joy. About the Guest Brent Freeman is a visionary entrepreneur, speaker, and author of The Alchemy of Joy. He founded Roozt.com, Stealth Venture Labs, NonnaLive, and Stealth Impact Lab, building businesses and social-impact initiatives that have generated billions in revenue and reached hundreds of thousands of people worldwide. After years of pursuing growth, impact, and achievement, Brent walked away from the hustle and grind to dedicate his work to helping people rediscover joy through neuroscience, inspiration, meditation, and subconscious training. Today, he speaks, teaches, and coaches around his philosophy of the “Return on Joy,” the idea that intentionally investing in joy can create a compounding return across every area of life. Leadership Playground Info Session on September 29th Learn more about Leadership Playground, our interactive cohort for high-potential managers, during our free info session on September 29, 2026. Register here! Connect with Brent Freeman Brent’s LinkedInBrent’s websiteBrent’s book, The Alchemy of JoyBrent’s meditations 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 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.
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    40 mins
  • 368: Are We All Having an AI Identity Crisis? With Cassandra Worthy

    368: Are We All Having an AI Identity Crisis? With Cassandra Worthy
    Sep 9 2026
    In this episode of Workday Playdate, Erin talks with Cassandra Worthy—founder and CEO of Change Enthusiasm Global — about the emotional side of AI-driven change, and why “just adapt” isn’t exactly a strategy. As AI reshapes jobs, workflows, teams, and professional identities, Cassandra explains why people are experiencing a very real sense of loss, or what she calls “AI grief.” Cassandra breaks down her Change Enthusiasm® framework (Signal, Opportunity, Choice) and explains how emotional awareness can help us navigate uncertainty with more agency. Whether you’re navigating AI at work, leading a team through transformation, or trying to make your next move with more clarity, this episode will help you start treating emotions as data. Inside This Episode: AI Grief Is Real: Discover why AI can trigger feelings of loss, mourning, fear, and identity disruption + why leaders shouldn’t rush people past those emotions.Emotion Is Data, Not Weakness: Cassandra explains why difficult emotions are signals that can help us understand what’s happening beneath the surface during organizational change.Build Your Signal Literacy: Learn how to recognize the physical and emotional cues that show up during change, and why getting better at reading those signals can help you move through uncertainty faster.Turn Signals Into Opportunities: Cassandra walks through the second step of Change Enthusiasm® and shows how curiosity can help you move from “What is happening to me?” to “What are my options?”Choose Your Response: Explore the final step (Choice) and how making an intentional decision can turn anxiety into anticipation and help you navigate change with greater agency. What to Do Now: Name the Signal: The next time you feel anxious, frustrated, angry, or discouraged at work, pause before trying to fix it. Ask: What is this emotion trying to tell me?Get Curious About the Opportunity: Once you’ve identified the signal, brainstorm your options. What could you do, learn, ask, change, or try?Make a Choice: Pick the response that feels most aligned with your values—not necessarily the one that eliminates all uncertainty. And if you’re stuck, talk it through with a trusted mentor, colleague, or friend. About the Guest Cassandra Worthy is the founder and CEO of Change Enthusiasm Global, a consulting and leadership development firm helping organizations build the emotional resilience to thrive through change. A former Fortune 100 innovation leader and chemical engineer, Cassandra spent years leading global teams through major corporate transformations before turning her own experiences with change into the Change Enthusiasm® framework. She is a best-selling author, keynote speaker, and trusted advisor to CEOs, HR leaders, and culture-shapers at organizations including Google, Microsoft, Bank of America, Johnson & Johnson, and Kellogg. Through her work, she helps people move from simply going through change to growing through it. Leadership Playground Free Info Session on 9/29 Looking for a scalable, engaging way to support your HiPo talent with leadership development? Join improve it! for a 25-minute information session to explore Leadership Playground, our experiential leadership development membership designed to extend learning beyond one-time workshops. Discover how organizations are using live, improv-based learning to help HiPo managers strengthen communication, adaptability, confidence, and other essential skills. We'll walk through how the program works, what's included, and how it can complement your existing leadership development strategy. Register here! Connect with Cassandra Worthy Cassandra’s LinkedInCassandra’s personal websiteCassandra’s company website, Change Enthusiasm Global 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 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.
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    34 mins
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