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by Erin Diehl - Workday Playdate
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.
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- 3 days ago41 min
376: Craig Conover & Hillary Keller on the Lessons We Teach Our Kids—but Forget Ourselves
What if the lessons we work so hard to teach our kids are the very ones we need to practice ourselves? In this episode of Workday Playdate, Erin sits down with Craig Conover, Southern Charm star and entrepreneur, and Hillary Keller, publisher of World of Kids Books, to talk about their new children's book that was an instant New York Times best-seller, Patchwork: Be Brave, Be Kind, Be You. Together, they explore why empathy, kindness, and bravery matter at every age, and why the lessons we teach our kids can be easy to forget in our own lives. They dig into the importance of anti-bullying, raising empathetic kids, and creating space for children to understand their emotions. Plus, Craig and Hillary join Erin for a few playful challenges in a new format of Workday Playdate, designed to put empathy into practice and remind us that learning doesn't have to feel like work! Inside the Episode: Lead by example. The lessons we teach our kids about kindness, bravery, and being yourself are just as important for us to practice as adults. Empathy is a skill worth building. Explore why empathy matters, how it helps prevent bullying, and why it's an essential part of raising emotionally aware kids. Stories can shape how kids see the world. Craig and Hillary share the inspiration behind Patchwork: Be Brave, Be Kind, Be You and why children's books can be powerful tools for social-emotional learning. Put yourself in someone else's shoes. Play along with an empathy game that challenges us to see situations from different perspectives and put kindness into action. Make room for a little play. From icebreakers to unexpected challenges, discover how play can create connection, spark conversation, and make learning more memorable. About the Guests Hillary Keller is the publisher behind World of Kids Books, where she combines her experience in marketing, business development, brand building, and content strategy with a passion for empowering children through storytelling. A mom of four, Hillary brings a personal perspective to creating books that entertain while supporting social-emotional learning, helping children navigate their emotions and develop a lifelong love of learning. Craig Conover is a fan favorite on Bravo's hit series Southern Charm and the co-founder of Sewing Down South, a growing Southern-based sewing lifestyle brand. A board-certified attorney, entrepreneur, and author of the memoir Pillow Talk: What's Wrong with My Sewing?, Craig has expanded his business ventures into restaurants and event spaces in Charleston. He also serves on the board of Hope For The Warriors. His debut children's book, Patchwork: Be Brave, Be Kind, Be You, was released October 13, 2026. Links Mentioned in the Episode Purchase the New York Times Best-Seller, Patch Work: Bee Brave. Bee Kind. Bee You. World of Kids Books website Connect with Erin Diehl x improve it! For workshops and keynotes: improve it!’s website Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn 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: <a href="ht
- 1 weeks ago30 min
375: How to Write and Publish Your First Book
You've had a book idea in your notes app for years. In this episode of Workday Playdate, Erin explains how she wrote her Amazon bestseller I See You: A Leader’s Guide to Energizing Your Team through Radical Empathy, shares what she learned going hybrid publishing, and what she's learning now as she pursues a traditional deal for book number two. She breaks down how to write and publish your first book & how self-publishing, hybrid publishing, and traditional publishing compare on cost, timeline and control. Inside the Episode: Learn the game first. Understand the publishing landscape and how to write a book proposal before you write a word. Every route costs money. Self-publishing is cheapest upfront (about 6–8 months). Hybrid is roughly $15–20K and 11–14 months. Traditional offers an advance but takes a year or more, and you still fund most of the marketing. Build your platform now. Agents and publishers look at your audience, newsletter and podcast. Choose your team like a scene partner. Hire a real editor and designer, and pick an agent who believes in your work. A book is a portal, not a product. Its value is the stages, credibility and legacy it opens. The DRAFT framework: Develop your knowledge, Route your path, Assemble your team, Fund the mission, Take it to the world. Links Mentioned in the Episode Gabby Bernstein’s Bestseller Masterclass Greenleaf Publishing Connect with Erin Diehl x improve it! For workshops and keynotes: improve it!’s website Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn 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.
- 2 weeks ago37 min
Episode 374: The Power of Pausing (Yes, Really) with Shawn Vanderhoven
What if slowing down is actually the fastest way to get better work done? In a work culture obsessed with speed, pausing can sound a little counterintuitive. But for leaders, a deliberate pause is about creating enough space to think clearly, focus on what matters, and make better decisions. In this episode of Workday Playdate, Erin talks with Shawn Vanderhoven, author of Pause: How to Lead Brilliant Work in a Busy World, about why the best leaders shift from a bias toward action to a bias toward impact. They dig into focus, productivity, workflow, delegation, AI, discernment, and the small pauses that can help teams move faster in the right direction. Inside This Episode: Pause to Create Focus: Why deliberate pauses can help leaders reduce distraction, clear emotional noise, and create the conditions for better work. Trade Busyness for Brilliant Work: Why the best leaders prioritize impact over activity, and why clarity about what matters is more valuable than simply doing more. Fix the Workflow, Not Just the Motivation: How chaotic workflows can undermine even the most motivated teams, and why the way work gets structured can have a bigger impact than asking people to “try harder.” Build Human Discernment Alongside AI: Why faster answers don’t necessarily mean better answers, and how leaders can use human judgment to evaluate quality, relevance, and what great work actually looks like. Tune In Before You Jump In: Shawn’s simple approach to delegation: understand someone’s workload and priorities before adding another task to their plate. Because “quick ask” has entered the chat. What to Do Now: Run a Distraction Inventory: Ask your team: What’s stealing your attention right now? Identify the meetings, messages, priorities, or processes getting in the way of focused work. Choose Impact Over Action: Before adding another task to the list, ask: What does success actually look like? Clarity first. Busyness second. Tune In Before You Delegate: Before dropping a new priority on someone’s plate, ask what they’re currently working on, what might need to move, and what support they need to make the new priority successful. Your Freebie Not sure which learning experience your team needs most right now? Answer 5 quick questions about your team, their current challenges, and what you want to strengthen. We’ll recommend the learning track that best fits your team’s needs. Take the Learning Track Quiz here. About the Guest Shawn Vanderhoven works with companies and leaders around the world to scale impact through talent, focus, and speed. He is the author of Pause: How to Lead Brilliant Work in a Busy World, based on original research with leaders at more than 150 companies, including Amazon, Google, and LinkedIn. Shawn is also a collaborator on the second edition of the New York Times bestseller, Multipliers: How the Best Leaders Make Everyone Smarter and has co-designed leadership development strategies with executives at Capital One, Deloitte, Google, Intel, LinkedIn, and Salesforce. Connect with Shawn Vanderhoven Shawn’s LinkedIn Shawn’s book, Pause: How to Lead Brilliant Work in a Busy World Connect with Erin Diehl x improve it! For workshops and keynotes: improve it!’s website Leadership Playground online membership community Erin’s website Erin’s Instagram Erin’s TikTok Erin’s
- 3 weeks ago35 min
Episode 373: Take the Risk Before You Feel Ready with Erika Johnson
What if waiting to feel ready is actually holding your career back? For high achievers, it’s easy to think you need one more sign that you’re ready before making the big career move. But sometimes, the next step only becomes clear after you take it. In this episode of Workday Playdate, Erin talks with Erika Johnson, Senior Vice President of Member Experience and Community at Chief, about taking career risks before you feel fully prepared. With 20+ years of experience across American Express, Capital One, Ernst & Young, Kantar, and Chief, Erika shares how transparency builds trust, how customer experience and leadership intersect, and why the smallest everyday behaviors can have a big impact on how people experience you as a leader. This conversation is a reminder that readiness is about being willing to bet on yourself. Inside This Episode: Stop Waiting to Feel Ready: Why high achievers can get stuck overthinking, overediting, and looking for external proof, and how taking action can create the confidence you’re waiting for. Bet on Yourself: What readiness really looks like, how to navigate imposter syndrome, and why bringing your unique perspective can be more valuable than having every answer. Build Trust Through Transparency: How being candid, steady, and clear can help you build credibility, even when you’re navigating unfamiliar work, difficult conversations, or unexpected career detours. Lead Through Everyday Experience: Why leadership and customer experience are deeply connected, and how the way you enter a room, hold silence, and push back can shape how people experience your leadership. Turn Big Moves Into Micro Steps: How to stop waiting for the perfect plan and start moving forward by breaking a career goal, idea, or conversation into one small action. What to Do Now: Ask “What Are You Waiting For?” Identify one career move, conversation, or idea you’ve been putting off because you don’t feel ready yet. Just Do It, But Smaller: Break that big scary thing into the smallest possible next step. Send the email. Write the draft. Schedule the meeting. Make the introduction. Practice Transparency: In your next high-stakes conversation, be a little more candid than usual. Say what you know, what you don’t know, or where you see an opportunity to push back, and notice what happens to the trust in the room. Your Freebie This is your plug-and-play guide to building an environment where your team feels safe to share bold ideas, take creative risks, and fully engage in the work that matters most. Download your Psychological Safety Playbook for Leaders here. About the Guest Erika Johnson is a dynamic executive leader with 20+ years of experience shaping customer and member experience at some of the world’s most recognized brands, including American Express, Capital One, Ernst & Young, Kantar, and Chief. As Senior Vice President of Member Experience and Community at Chief, Erika leads the strategy, operations, and experiences that shape how executive women grow and thrive. Her work sits at the intersection of strategy, leadership, and experience, helping leaders turn complexity into clarity, build stronger relationships, and move forward with confidence. She is passionate about redefining experience as a critical leadership skill, and using it to drive engagement, belonging, and results. Connect with Erika Johnson Erika’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 <a href="https://www.learntoimproveit.com/" tar
- Oct 7, 202638 min
Episode 372: How Great Leaders Build Their Inner Circle with Shona Kamath
What actually makes a people strategy work? It’s not just having the right talent in the right seats. It’s building a workplace where people feel trusted, included, challenged, and connected to something bigger than their job description. For HR and people leaders, that can feel HUGE. You’re balancing employee engagement, leadership development, retention, performance, culture, and business results...all while trying to make work feel a little more human. In this episode of Workday Playdate, Erin talks with Shona Kamath, Head of Human Capital and Human Resources at MegaMex Foods, about what it really takes to build a strong people strategy and a culture where talent can thrive. They dig into trust, belonging, empathy, high-potential talent, leadership development, and why employees are more likely to stay when they can see how their work connects to the bigger picture. Inside This Episode: Invest in People, Not Just Output: What a successful people strategy really requires—from the right talent and capabilities to strong leadership, a supportive environment, and a clear connection between individual work and business impact. Build a Culture of Trust, Accountability & Inclusion: How belonging influences employee engagement, retention, and culture, and why real-time feedback and meaningful workplace relationships matter just as much as survey scores. Develop the Leaders of Tomorrow: The leadership qualities that matter most in high-potential talent, including emotional intelligence, empathy, communication, business acumen, strategic thinking, and integrity. Build a Talent Pipeline Before You Need One: How to identify potential early, create stretch opportunities, build supportive networks, and help employees reflect on what they’re learning so they’re less likely to disengage and leave. Take Creative Risks With Your Career & Your Team: Why raising your hand, creating “heat,” and embracing experiences like improv can help people learn faster, take ownership, and make work more playful and memorable. What to Do Now: Connect the Dots: Help someone on your team see how their day-to-day work connects to the bigger picture. Clear line of sight can turn a task into a purpose. Create Some Career Heat: Raise your hand for an opportunity that stretches you, or someone on your team. Growth usually starts right outside the comfort zone. Invest in the Human: Ask what someone actually needs to feel supported, challenged, and included at work. Then make space for trust, feedback, relationships, and a little more play. Your Freebie This is your plug-and-play guide to building an environment where your team feels safe to share bold ideas, take creative risks, and fully engage in the work that matters most. Download your Psychological Safety Playbook for Leaders here. About the Guest Shona Kamath is a highly experienced human capital and HR leader with expertise across organizational development, talent management, leadership development, performance management, culture, employee engagement, HR systems, and organizational effectiveness. As Head of Human Capital and Human Resources at MegaMex Foods, Shona advises senior leaders on strategic talent and organizational priorities and has presented to C-level executives and boards across financial services and consumer packaged goods organizations. A recognized high-potential leader herself, Shona is passionate about developing talent, building high-trust cultures, and helping people take ownership of their careers. Connect with Shona Kamath Shona’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 <a href="https://www.linkedin
- Sep 30, 202623 min
Episode 371: Should I Quit My 9-to-5?
Should you quit your 9-to-5 and start a business or build your idea while you’re still employed? For aspiring entrepreneurs, that question can feel HUGE. You’re craving more freedom, creativity, or control, but leaving a stable paycheck can feel like jumping off a financial cliff. But what if you don’t have to choose between playing it safe and burning it all down? In this episode of Workday Playdate, Erin shares a five-step approach for quitting your 9-to-5, starting a business, and making the leap into entrepreneurship with more clarity. Drawing from her own experience building improve it! while working a full-time recruiting job, Erin breaks down how to test your idea, understand your finances, involve your support system, and create a gradual path toward self-employment. Instead of asking, “Should I quit my job?” Erin invites you to ask a better question: What can I build before I leave? Inside This Episode: The “Stay or Go” Gut Check: Use a simple gut check to understand whether you’re ready to leave your job or just ready for something to change. Build Before You Bail: Why you don’t need to quit your 9-to-5 before you start building your business. Erin shares how she built improve it! while working full time. Know Your Numbers: Get clear on your monthly expenses, income needs, and financial runway before making a career transition. Bring Your People In: Why talking openly with your boss, partner, friends, or trusted supporters can make a big career decision feel less scary and more strategic. Make the Leap Less Leap-y: Explore part-time work, freelancing, side hustles, and small business pilots as ways to test entrepreneurship before going all in. Start Small, Learn Fast: You don’t need the perfect business plan. Build the smallest viable version, get feedback, and let the real-world data guide your next move. What to Do Now: Ask “What Can I Build Before I Leave?” Identify one small piece of your business or idea you can test while you still have the stability of your current job. Do the Math: Calculate your monthly expenses, income target, and financial runway. A dream gets a lot less scary when you know your numbers. Run a Tiny Experiment: Test your idea with a small offer, pilot, freelance project, or first customer. You don’t need to quit to find out if there’s demand. Talk to Your People: Bring a trusted person into the conversation. You don’t have to make a major career decision alone or in secret! Build Before You Bail: Remember: quitting your 9-to-5 isn’t the first step. Sometimes, it’s the next step after you’ve built enough evidence to make the leap. Your Freebie Take the quiz: What’s Your Leadership Style and Your Next Business Move? Find out how your leadership style drives motivation, and walk away with 3 specific ideas you can start building into your business right away. Workshop mentioned in the episode: Taking Initiative & Creative Risks 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.
- Sep 23, 202647 min
370: When High-Achieving Women Carry Too Much Alone with Meghan French Dunbar
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 LinkedIn Meghan’s website Meghan’s book, This Isn’t Working ZingTrain academy ZingTrain books Connect with Erin Diehl x improve it! <a href="ht
- Sep 16, 202640 min
369: The Leadership Skill Nobody Teaches: Stopping Before Burnout Hits with Brent Freeman
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 LinkedIn Brent’s website Brent’s book, The Alchemy of Joy Brent’s meditations Connect with Erin Diehl x improve it! Leadership Playground online membership community Erin’s website Erin’s Instagram Erin’s <a
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About Workday Playdate
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.
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