Workday Playdate - podcast cover

Workday Playdate

Erin Diehl | Business Improv Edutainer, Failfluencer, Keynote Speakerfaileditpodcast.libsyn.com
*TOP 1% GLOBAL PODCAST* Pssst…it’s your work bestie again tapping you on the shoulder telling you to take a breather from sending another email because I’ve got some tea–piping hot, actually. I’m Erin Diehl, founder of improve it!(AKA, your work bestie), and I’m going to take you on a much needed excursion from your workday from the comfort of your very own headphones. Every Wednesday, your Workday Playdate will give you research-based, tangible strategies to transform yourself through improv comedy techniques and play. It’s all designed to bring the fun back to your job and remind you that taking a break from your workday is ironically what improves it the most. And with a little play date snack every Monday, you’ll start your week off on the right foot with a fresh idea to incorporate, pronto. Oversharing and knee-slappers guaranteed. Welcome, my friend. Let’s play!
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Episodes

Snack 20: Your Career, Your Move: Stop Waiting and Start Choosing What’s Next

In today’s Workday Playdate Snack, Erin's busting one of the biggest myths in the career playbook: that the “perfect job” will just... show up and fix everything. Spoiler: It won’t. And waiting for it? That can keep you stuck. The Problem: 52% of workers are eyeing a career change. 70% feel disengaged. Why? Because they’re waiting. For the dream job. For clarity. For permission. But it's important to remember one crucial truth: you are the plan. The Improv Hack to Try: Tag Yourself In When impro...

Jun 30, 20259 min

296: Hybrid Headaches? Here’s How to Make the Office Return Less Awkward & More Awesome

In this episode of Workday Playdate, Erin tackles the awkward elevator small talk, the lukewarm return-to-office bagels, and the actual leadership challenges of hybrid work. From re-establishing team rituals to defining the “why” behind your office days, this episode is a field guide for anyone trying to rebuild connection in a flexible work world without burning out. Whether you're managing Zoom fatigue, leading a team that’s half-in, half-out, or just trying to make Tuesdays feel less like a g...

Jun 25, 202523 min

Snack 19: Hybrid Work is Hard, But This Trick Will Make Office Returns Smooth

In today’s Workday Playdate Snack, we’re tackling the hybrid work headache—and no, we’re not talking about the flickering office lights or the ancient coffee machine no one remembers how to clean. We’re talking about the emotional fog that creeps in when your team is half-on-Zoom, half-in-person, and 100% disconnected. The Problem: You’ve asked your team to return to the office a few days a week. Some show up with smiles. Others show up with...resentment. And some just show up for the snacks. Hy...

Jun 23, 202510 min

295: Play More, Fight Less: The Secret to Happier Relationships with Greg Tavares and Amber Nash

In this episode of Workday Playdate, Erin explores what every team—at work and at home—needs more of: play. Joined by real-life partners and improv powerhouses Greg Tavares and Amber Nash, this episode dives into how playful communication can defuse tension, deepen connection, and make conflict feel a whole lot less... combative. Greg, an improv teacher and facilitator with decades of experience helping teams collaborate more creatively, joins forces with Amber, a voiceover actor best known as P...

Jun 18, 202552 min

Snack 18: How Playfulness Can Save Your Relationships

In today’s Workday Playdate Snack, we’re talking about the kind of conflict resolution that doesn’t involve a six-part text thread or passive-aggressive dishwasher loading. We’re diving into how playfulness —yes, even mid-fight—can be your secret weapon for stronger, happier relationships. Whether it’s your partner, roommate, or that one family member who treats the group chat like a TED Talk… this snack is for you. The Problem: You’re crushing deadlines at work—but stuck in a weird silence at h...

Jun 16, 20259 min

294: Layoffs Ahead? Here’s How to Stay Human (and Keep Your Team’s Trust)

In this episode of Workday Playdate, Erin tackles one of the toughest parts of leadership: layoffs. When budgets shrink and change feels unavoidable, how do you show up with empathy, clarity, and integrity? Spoiler: it’s not just about delivering the news—it's about leading through uncertainty with heart. From the emotional toll of workforce reductions to the ripple effects on culture and trust, Erin shares what leaders often get wrong—and how to get it right. With seven actionable tips, this ep...

Jun 11, 202523 min

Snack 17: Trust Falls, But Not Like That — Keeping It Real During Reorgs

In today’s Workday Playdate Snack, we’re talking about the kind of trust fall that doesn’t involve closing your eyes and hoping Linda from Accounting catches you. Nope—we’re talking about the invisible, emotional kind. The one that happens during reorgs, layoffs, and those delightfully vague “strategic shifts” when your team is quietly wondering, “Are we safe? Can we trust you? Or should I start updating my LinkedIn headline to ‘Open to Work’?” If you're leading through change (or just trying to...

Jun 09, 20259 min

293: PAY UP! Why Women Deserve More & How to Get It – with Reshma Saujani

In this powerful episode of Workday Playdate, Erin sits down with Reshma Saujani—founder of Girls Who Code, CEO of Moms First, and author of Pay Up—for a no-holds-barred conversation about what it really takes to thrive as a woman in today’s workplace. Spoiler: it's not just about negotiating harder or leaning in. It's about rewriting the entire playbook. From the impossible pressures of pandemic parenting to the unspoken challenges of midlife, Reshma and Erin talk truth about uncertainty, burno...

Jun 04, 202550 min

Snack 16: Tired of Settling? Here’s How Women Can Start Earning What They Deserve at Work

In today’s Workday Playdate Snack, we’re serving up some truth for anyone who’s ever screamed into their steering wheel after a one-on-one like, “How does Brad STILL make more than me?” If you’ve ever been underpaid, undervalued, or under-celebrated—this snack is for you. The Problem: Here’s the tea: Women are doing the absolute most. More emotional labor. More coordinating. More everything. And yet—less recognition, less pay, and fewer opportunities. We’ve been fed a narrative that if we just n...

Jun 02, 202511 min

292: 5 Improv Leadership Tips to Bring Out the Best in Your Quiet Teammates

In this episode of Workday Playdate, Erin flips the script on traditional leadership by spotlighting the power of the quiet ones. Through a playful and practical lens, she explores how introverted teammates can be supported, celebrated, and set up to thrive—not just survive—in today’s fast-paced work environments. Erin shares five improv-inspired leadership strategies that help draw out the brilliance of quieter team members without forcing them to be louder. From private validation to the power...

May 28, 202521 min

Snack 15: Yes, And...for Introverts: Leadership Tweaks That Actually Work

In today’s Workday Playdate Snack, we’re sending a leadership love letter to the quiet ones—the deep thinkers, the spreadsheet whisperers, the back-row observers who see everything. Because if you’ve ever left a meeting thinking, “Why didn’t they speak up?” or “I wish I’d said that…”—this snack’s for you. The Problem: Okay, picture this: You’re in a team meeting. The extroverts are riffing, the whiteboard is filling up, and you notice someone hasn’t said a word. You know they’ve got gold in thei...

May 26, 20259 min

291: Introvert to Bold Leader: How Small Risks Turn Into Big Wins (Without Burning Out) with Cristy von

In this episode of Workday Playdate, Erin welcomes keynote speaker, facilitator, and introverted powerhouse Cristy von to the mic for a conversation that redefines what it means to lead from a place of quiet strength. Together, they dig into the surprising overlap between improv and introversion, showing how safe spaces, self-awareness, and a little bit of “yes, and” can transform leadership from the inside out. Cristy shares her journey from mistaking herself for an extrovert to fully embracing...

May 21, 202547 min

Snack 14: Lead Loudly (Even If You’re Quiet): Introvert Lessons

In today’s Workday Playdate Snack, we’re giving the quiet leaders in the room a standing ovation—and a strategy. Because if you’ve ever felt invisible in loud leadership spaces, this one’s for you. The Problem: Corporate culture often rewards the boldest brainstormer, the fastest talker, the loudest voice. But what if you’re the deep thinker, the one who shines in 1:1s, and recharges solo? Too often, introverted leaders are overlooked—not because they lack ideas, but because they don’t shout the...

May 19, 20259 min

290: Leaders Who Want to Thrive (Not Just Survive) NEED These 10 Self-Care Moves

In this episode of Workday Playdate, Erin takes the mic solo to spotlight a crucial topic often overlooked in hustle culture: self-care as a leadership strategy. Drawing from her own experience, she unpacks the often-misunderstood concept of introverted leadership and why rest, boundaries, and joy aren't just nice-to-haves, but non-negotiables for modern leaders. Erin shares a Top 10 list of creative, practical self-care strategies tailored for professionals who are tired of pretending that inbo...

May 14, 202523 min

Snack 13: The Real Reason You’re Tired (And It’s Not Just Your Calendar)

In today’s Workday Playdate Snack, we’re tackling the kind of tired a nap can’t fix. Because if your soul is sighing—not just your body—this one’s for you. The Problem: You’re not just exhausted from meetings, deadlines, and life logistics. You’re tired because you’re performing all day and rarely just being. You’re juggling ten roles at once—boss, parent, mentor, inbox warrior—but none of them feel like the full, real you. That’s not burnout. That’s identity fatigue. The Improv Hack to Try: “Pl...

May 12, 20258 min

289: Success, But Make It Joyful: How to Align Your Work with What Lights You Up with Rha Goddess

Rha Goddess ( Intentional Ambition: Redefining Success in a Post-Pandemic World ) is a soul coach, author, cultural innovator, and founder of Move The Crowd. Rha Goddess returns to Workday Playdate to unpack what it means to lead with clarity, rest, and purpose in a world still recovering from burnout. She and Erin explore how our definitions of success have evolved, why rest is a leadership skill, and how intentional ambition is changing the way we work and live. Rha and Erin discuss the emotio...

May 07, 202551 min

Snack 12: How to Align Your Work with What Truly Lights You Up

In today’s Workday Playdate snack, we’re talking about moving beyond the checklist version of success—and finding work that actually energizes you. The Problem: You’ve hit the career milestones, but something still feels off. You’re busy, sure—but not fulfilled. That’s not laziness or burnout. It’s misalignment. The Improv Hack to Try: “The Commercial Break” Take 30 seconds and pitch your dream job like you’re in a commercial. Say what you do, who you help, and why it matters—in your most over-t...

May 05, 202510 min

288: You Spend 90,000 Hours of Your Life at Work - Here's How to Create Real Connection with Adam Dorsay

Dr. Adam Dorsay ( Super Psyched: The Power of the 4 Types of Connection ) is an author, psychologist, TEDx speaker, and podcast host. Dr. Adam Dorsay joins Workday Playdate to talk about the four kinds of connection that can radically transform your life, why enthusiasm is a secret superpower, and how adult friendships are often more vital—and more fragile—than we realize. Adam and Erin discuss the emotional lift of reviving past passions, the surprising benefits of JOMO (joy of missing out), an...

Apr 30, 202554 min

Snack 11: How to Stop Hating Your Job & Actually Like the People You Work With

In today’s Workday Playdate snack, we’re talking about how to stop hating your job—and maybe even enjoy the humans you work with. The Problem: If you’re dreading Slack pings, counting down to Friday, or secretly fantasizing about moving to a remote island with zero meetings… it might not just be burnout. It might be a connection problem. We spend 90,000 hours of our lives at work—if we’re not feeling seen or having any fun, that’s a soul issue, not a schedule issue. The Improv Hack to try at you...

Apr 28, 202511 min

287: Breaking the Silence: A Male Perspective on Infertility & Leadership

John Diehl is the head of talent development, a results-oriented HR professional, and Erin’s life partner. John joins the Workday Playdate to share his perspective on infertility, what it means to let go of a “fix it” mentality, and why having a core support group is instrumental to processing life events. Inside This Episode: Why men may feel pressure to take on a supportive role without knowing how when it comes to infertility/IVF The emotional toll infertility can take on mental health and wo...

Apr 23, 202544 min

Snack 10: How to Lead with Vulnerability & Break the Silence

In today’s Workday Playdate snack, we’re talking about vulnerability at work and why speaking up might be the boldest move you make all week. The Problem: We’re taught to keep it polished and professional. But when life—grief, burnout, infertility—shows up, we go quiet. That silence creates distance. Between teammates. Between leaders. Even within ourselves. The Improv Hack to try at your next meeting: “Before we dive in—quick vibe check. I’m feeling ___ today, and that’s what I’m bringing into ...

Apr 21, 202510 min

286: The "Hey Wait" Technique: How to Set Boundaries Like a Leader with Jay Fields

Jay Fields is an author, somatic coach, and experiential educator. Jay joins the Workday Playdate to discuss the importance of setting boundaries, the emotional complexities of relationships, and how to navigate communication overload while maintaining empathy. Jay introduces the “Hey Wait” technique, a simple yet powerful tool for asserting yourself in conversations when you may be used to leaving yourself out. Jay also shares why we develop people pleasing patterns (hint: it has something to d...

Apr 16, 202543 min

Snack 9: Dare to Speak Up: The Leadership Skill You’re Overlooking

Today, we’re talking about why teams hesitate to speak up and how to change that. If you’ve ever felt like your voice doesn’t matter in meetings, that stops now. The Problem – Why Teams Aren’t Engaged: When a leader asks, “Any questions?” and no one speaks, it’s not because there’s nothing to say. It’s because people don’t feel safe to share. When voices stay silent, innovation stalls, ideas get repetitive, and a few people dominate conversations. The Solution – The Wrong Answers Only Challenge:...

Apr 14, 20256 min

285: Redefining Family: A Candid Talk on Secondary Infertility

What happens when the path to family doesn’t go as planned? In this episode of Workday Playdate, Erin gets deeply personal, sharing her journey through secondary infertility—a topic that too often goes unspoken. From the rollercoaster of IVF to the emotional weight of grief and resilience, she opens up about the heartbreak, the healing, and the powerful lessons learned along the way. We dive into the complex emotions that come with infertility, the stigma surrounding secondary infertility, and t...

Apr 09, 202528 min

Snack 8: How to Turn Challenges into Courageous Choices

Today, we’re talking about something you can use anytime, anywhere: flipping fear into fuel. If you want to turn challenges into courageous choices, you’re in the right place. The Problem: Why We Freeze at the Edge of Big Decisions Ever find yourself standing at a crossroads, knowing the bold choice is the right one, but feeling stuck? That’s your brain clinging to predictability like a security blanket. It’s not that you don’t have what it takes—it’s that uncertainty freaks your brain out. But ...

Apr 07, 20257 min

284: From Quiet Dreamer to Bold Leader: Her Make-A-Wish Story

What if one wish could change everything? In this episode of Workday Playdate, Erin sits down with Dana and her family to talk about the incredible journey of how a single wish turned a shy, quiet dreamer into a bold, confident leader. Through the power of Make-A-Wish, Dana found her voice—and a love for beluga whales along the way. We dive into the emotional and unexpected ways a wish can transform not just a moment, but a lifetime. From overcoming fears to finding confidence in the little thin...

Apr 02, 202526 min

Snack 7: How to Turn Dreams into Team Wins: The Leadership Glow-Up You Need

Today, we’re talking about something anyone could use at any given time: a leadership sprucey spruce. If you want to turn team dreams into company wins, you’re in the right place. The Problem: Why Teams Are Not Engaged Ever feel like your team is running on autopilot? Like they’re doing just enough but not really bringing their A-game? It’s not because they don’t care—it’s because they don’t feel like their ideas matter. They’re waiting for permission to be bold. And guess what? You can give it ...

Mar 31, 202510 min

283: From Mistakes to Mastery: Career Tips for Bold, Courageous Leaders

What does it take to leave a prestigious job at Google to chase your true passion? In this episode of Workday Playdate, Erin sits down with Jenny Wood, the visionary behind Google's Own Your Career program. Jenny candidly shares her transformative journey from a high-powered corporate role to embracing the uncertainties of entrepreneurship. She delves into the challenges of imposter syndrome, the courage required to be unapologetically selfish in pursuing personal goals, and the art of setting b...

Mar 26, 202540 min

Snack 6: How to Turn Career Mistakes into Growth

Hey, hey, Workday Playdate peeps! It’s time for your quick bite of leadership wisdom—a little boost of inspiration, energy, and playfulness to brighten your workday. Today, we’re talking about something we ALL have in common: mistakes. Yep, those cringe-worthy, face-palm moments that keep us up at night. But guess what? Your mistakes aren’t just embarrassing bloopers; they’re your greatest career growth hacks. So, what do we do? We improvise, using the The "Next Line, Please" Hack. What it is: I...

Mar 24, 20258 min

282: Why Leaders Are Obsessed with Improv for Team Growth

What if the secret to high-performing teams wasn’t another strategy session—but an improv game? In this episode of Workday Playdate, Erin dives into how improvisation is transforming team dynamics, leadership, and workplace culture. From LinkedIn to Amazon, top companies are embracing improv as a tool for boosting psychological safety, engagement, and creativity. If you’ve ever struggled with silent meetings, hesitant team members, or a lack of collaboration, this episode is for you. Inside This...

Mar 19, 202513 min
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