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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 their head, but they haven’t chimed in.Or maybe... that person is you.
Too many workplaces reward the loudest voice in the room. But when we only value volume, we silence vision. And let’s be real—your quiet teammates? They’re not zoned out. They’re tuned in.
The Improv Hack to Try: The Character Swap Hack
What can you do to make space for that quiet brilliance? Here’s a leadership tweak I’ve never shared before—and it’s straight from the improv stage.Before your next meeting, mentally pick a quieter teammate. (No need to tell them—it’s your secret leadership lab.) Then ask:
How would they run this meeting? What would they focus on? How would they pace it?Now the fun part: Kick off the meeting as if you were them. Use their tone, their cadence, their intentionality.
In improv, we step into other characters to explore new perspectives. And when you do this in leadership? You build empathy, highlight hidden genius, and create meetings that feel less like a race—and more like a rhythm.
Bonus: You might just change your whole team vibe for the better.
Coming Up Wednesday: Loved this Snack? Don’t miss Wednesday’s full episode: Episode 292: 5 Improv Leadership Tips to Bring Out the Best in Your Quiet Teammates. It’s jam-packed with research, real stories, and tools you can use immediately to turn down the noise—and turn up the impact.
Ready to take one small step toward showing up with more clarity and confidence?
Download our newest freebie—The Confident Leader’s Toolkit—a 4-step guide to crafting a professional persona that actually feels like you. This plug-and-play resource helps you define how you want to be seen, align your presence with your purpose, and lead with authenticity (not performance).No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 her introverted identity—and how that shift changed the way she leads, connects, and recharges. This episode is a powerful reminder that leadership doesn’t require being the loudest in the room. Sometimes, it starts with simply knowing your limits and honoring them.
Whether you're leading workshops, giving keynotes, or just trying to survive your next Zoom call, this one’s for anyone who's ever wondered if quiet can still be commanding. (Spoiler alert: it absolutely can.)
Inside This Episode:
Why Cristy used to think she was an extrovert—and what changed How improv became a launchpad for her confidence The importance of creating safe, inclusive workshop spaces What keynote speaking taught Cristy about energy management The link between vulnerability and powerful facilitation Why collaboration between introverts and extroverts matters more than ever The mindset shift that helped Cristy find joy (and her voice) at workWho This Episode Is For:
This episode is for the introverts in leadership roles, the workshop facilitators who crave real connection, and the quiet professionals looking to own their power without pretending to be someone they’re not. If you’re a recovering over-functioner who wants to lead with authenticity, boundaries, and a sense of play—pull up a chair.
Take a break from your emails, slam your laptop shut for 30ish minutes, and come have a Workday Playdate with us.
Ready to take one small step toward showing up with more clarity and confidence? Download our newest freebie—The Confident Leader’s Toolkit—a 4-step guide to crafting a professional persona that actually feels like you. This plug-and-play resource helps you define how you want to be seen, align your presence with your purpose, and lead with authenticity (not performance).
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy.
Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode.
Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.”
Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back.
Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.
Connect with Cristy von
Cristy’s LinkedIn Cristy’s Instagram Contact improve it! about Cristy’s keynote: The Introverted LeaderConnect with Erin Diehl x improve it!
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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 them. That’s not a flaw. That’s a missed opportunity…for everyone else.The Improv Hack to Try: “The Power Pause”
Next time you're in a meeting and have something to say—don’t jump in fast to prove you’re ready. Wait. Take a beat. Let the room settle. Then drop your insight with intention. That pause? It signals thoughtfulness, confidence, and leadership—without you ever raising your voice.In improv, silence isn’t awkward—it’s powerful. Use it to own your space and lead, your way.
Want More Like This? Don’t miss Wednesday’s episode—Episode 291: “Introvert to Bold Leader: How Small Risks Turn Into Big Wins (Without Burning Out).” You’ll hear from Cristy Von, our Director of Talent at improve it!, as she shares her journey from quietly capable to boldly confident—and how improv helped her lead without changing who she is.
Ready to take one small step toward showing up with more clarity and confidence?
Download our newest freebie—The Confident Leader’s Toolkit—a 4-step guide to crafting a professional persona that actually feels like you. This plug-and-play resource helps you define how you want to be seen, align your presence with your purpose, and lead with authenticity (not performance).No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 inbox zero is the holy grail. This episode is a reminder that thriving doesn’t require over-functioning—and that real productivity begins with personal peace.
Inside This Episode:
Why introverted leadership is powerful, not passive The link between play and productivity How sleep is an underrated leadership tool Why saying “no” is a radical act of self-preservation A refreshing top 10 list of self-care strategies you actually want to tryWho This Episode Is For:
This episode is for the quietly powerful, the recovering overachievers, the leaders who feel stretched thin but want to thrive without burning out. If you’re craving a leadership style rooted in wellness, boundaries, and joy—this one’s for you.Take a break from your emails, slam your laptop shut for 30ish minutes, and come have a Workday Playdate with us.
If you’re interested in taking one small action right now, you can check out our newest freebie, The Psychological Safety Playbook for Leaders here. Use this 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.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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: “Play the Wrong Character on Purpose” Today, in just one meeting, switch it up: Usually the fixer? Be the one who asks all the questions. Constantly over-prepared? Wing it (just a little). The quiet one? Try on bold, bubbly energy—just for fun.
This isn’t about being fake. It’s about giving your overused identity a break and waking up parts of yourself that miss the spotlight.
Want More Like This? Don’t miss Wednesday’s episode—Ep 290: Leaders Who Want to Thrive (Not Just Survive) NEED These 10 Self-Care Moves. We’re talkin’ naps, wiggling, calendar boundaries, and something called an LSD Day (no, not that LSD—but yes, it’s still life-changing).
If you’re interested in taking one small action right now, you can check out our newest freebie, The Psychological Safety Playbook for Leaders here. Use this 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.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 emotional toll of overwork, the quiet power of introversion, and how small, joyful rituals can help us heal from grief, anxiety, and the hustle-at-all-costs culture. This episode is a call to redefine ambition on your own terms—and to choose joy, even on a Tuesday.
Inside This Episode:
Why managing your energy matters more than managing your time The hidden trauma behind overwork, caregiving, and grief What it really means to rest with intention How small moments of joy can spark big change The power of creativity and play in daily work lifeWho This Episode Is For:
This episode is for anyone who’s tired of chasing someone else’s definition of success, who’s healing from burnout or loss, or who just needs permission to rest, reset, and realign.Take a break from your emails, slam your laptop shut for 30ish minutes, and come have a Workday Playdate with us.
Here is the previous episode with Rha that’s mentioned: Episode 219: Crave Purpose in Your Life and Career? Rha Goddess Tells All.
If you’re interested in taking one small action right now, you can check out our newest freebie, The Psychological Safety Playbook for Leaders here. Use this 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.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Rha Goddess
Rha’s LinkedIn Rha’s websiteConnect with Erin Diehl x improve it!
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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-the-top voice.Then reflect: What felt real? That’s your purpose, hidden in plain sight.
Journal Prompts:
1. What parts of my work feel most meaningful?
2. What’s draining me—and why am I holding onto it?
3. What would my ideal workday look like?If you’re interested in taking one small action right now, you can check out our newest freebie, The Psychological Safety Playbook for Leaders here. Use this 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.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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), and what improv can teach us about personal growth and taking creative risks.
Inside This Episode:
The difference between connection and proximity How we somaticize emotional struggles Why feeling awe might be the key to breaking through lonelinessWho This Episode Is For:
This episode is for anyone feeling a bit disconnected—from others, from themselves, or from the creative spark they used to have.Take a break from your emails, slam your laptop shut for 30ish minutes, and come have a Workday Playdate with us.
If you’re interested in taking one small action right now, you can check out our newest freebie, The Psychological Safety Playbook for Leaders here. Use this 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.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Dr. Adam Dorsay
Dr. Adam’s LinkedIn Dr. Adam’s LinkTreeConnect with Erin Diehl x improve it!
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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 your next meeting: “Role Call Remix.”
Before your next meeting, toss out one unexpected, totally non-work prompt—but assign everyone a role to answer in.
Like:
“Answer as if you’re a pirate who just got promoted.”
“Respond like your teenage self.”
“Pretend you’re your favorite snack food come to life.”
It’s weird. It’s wonderful. And it gets people out of robot mode and into real connection—fast.
That’s the snack. Show up human. Get a little weird. And remember—work gets way better when we stop pretending and start playing.
Journal Prompts:
Where could I bring a little more humanity into my next meeting? Who on my team might be craving real connection? What part of my personality doesn’t usually show up at work—but could?If you’re interested in taking one small action right now, you can check out our newest freebie, The Psychological Safety Playbook for Leaders here. Use this 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.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 work performance How leaders can create safe spaces for conversations about infertilityWho This Episode Is For:
Anyone who has experienced challenges from infertility/IVF and knows someone who has—this one’s for you.Take a break from your emails, slam your laptop shut for 30ish minutes, and come have a Workday Playdate with us.
And if you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset, here. It’s a plug-and-play exercise that will get your team mentally present, engaged, and committed before any meeting.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 the room.” You start. Keep it honest. That one moment of realness makes it safer for others to show up, too.That’s the snack. Lead with your whole self. Keep it honest, keep it human. More soon.
Journal Prompts:
Where am I playing it safe instead of being real? Who on my team might need more space to be seen? What story am I holding back that could connect us?And if you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset here. Use this plug-and-play exercise at the start of any meeting to get your team mentally present, engaged, and committed.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 do with how we think about connection).
Inside This Episode:
Why empathy does not mean sacrificing your own needs in relationships Why acknowledging your own reality is crucial for healthy communication Why people pleasing doesn’t equal being a “good” person in relationshipsWho This Episode Is For:
Anyone who identifies as a “recovering people pleaser,” anyone looking to set stronger personal and professional boundaries, or anyone who’s looking for techniques to advocate for themselves in conversations of all kinds—this one’s for you.Take a break from your emails, slam your laptop shut for 30ish minutes, and come have a Workday Playdate with us.
And if you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset, here. It’s a plug-and-play exercise that will get your team mentally present, engaged, and committed before any meeting.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Jay Fields
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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:
At your next meeting, challenge yourself (or your team) to go first—but start with a deliberately wrong answer.
Example: If someone asks, “How should we improve client engagement?”
You say: “Let’s start responding to emails in Morse code.”
Or if your boss asks, “How do we cut costs?”
You respond: “Sell our office chairs and replace them with bean bags.”
Why? Removing the pressure to be right makes it easier to contribute. It also lightens the mood and gets people thinking more creatively. When you practice this exercise regularly, it will overflow into the moments when you’re not practicing it—creating a culture that’s not afraid to share, speak up, and contribute creative solutions.
Journal Prompts to chew on:
When have I held back from sharing an idea? Why? How can I bring more playfulness to work conversations? Has a wrong answer ever led me to a breakthrough?And if you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset here. Use this plug-and-play exercise at the start of any meeting to get your team mentally present, engaged, and committed.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 the unexpected ways leadership and loss intertwine. Erin also shares the spiritual moments that helped guide her through, offering a message of hope to anyone facing a challenge that reshapes their definition of family.
Inside This Episode:
The raw reality of secondary infertility and why it’s often overlooked. The trauma and complexity of IVF—and how it impacts mental health. How grief and leadership can coexist in both personal and professional spaces. The power of spiritual insights in navigating difficult decisions. Redefining family on your own terms and finding peace in the process.Who This Episode Is For:
Anyone who has struggled with infertility, faced unexpected detours in life, or felt the weight of grief while still showing up as a leader. If you need a reminder that healing isn’t linear, that your story matters, and that joy is still possible—this one’s for you.Get ready for an honest, heartfelt conversation that just might change the way you think about resilience, family, and the strength it takes to rewrite your own story.
Here is the link to listen to the episode that Erin mentioned—Episode 49: Failures in Fertility: Why Sharing Our Stories Matter.
And if you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset, here. It’s a plug-and-play exercise that will get your team mentally present, engaged, and committed before any meeting.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 here’s the kicker: YOU are the flashlight in the unknown. You get to light the way.
The Solution: The Inner DJ Remix Hack
Time to shake things up with a little mental DJ-ing. Your brain loves to spin the same old fear-based tracks on repeat.
Here’s how you remix it:
Next time your brain says, “This is too scary. I can’t do this,” STOP. Out loud (or in your head if you’re in public), say: “REMIX!” and swap the thought. Turn “I can’t” into “I’m learning how.” Turn “This is too much” into “I can handle hard things.” Make it FUN. Be dramatic. Pretend you’re a DJ scratching a record. Your brain thrives on novelty, and this playful shift rewires your fear response.Journal Prompts to chew on:
What’s the current fear-based ‘track’ my brain keeps playing? What’s my new ‘REMIX’ thought? How can I physically embody this shift to make it stick?And if you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset here. Use this plug-and-play exercise at the start of any meeting to get your team mentally present, engaged, and committed.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 things—like paying for groceries or speaking in front of a crowd—Dana’s story is proof that sometimes, the biggest waves come from the smallest voices.
Inside This Episode:
How an eight-year-old’s wish to visit the Georgia Aquarium became a turning point in her life. The surprising confidence boost that came after petting a beluga whale’s tongue (yes, really). Why small steps—like asking for help in a grocery store—can lead to big personal growth. The ripple effect of a wish: how one moment of courage can change an entire mindset. What Dana’s parents learned about pushing past comfort zones and embracing new challenges.Who This Episode Is For:
Anyone who has ever felt too small, too quiet, or too afraid to step outside their comfort zone. Parents looking for ways to empower their kids. And anyone who needs a reminder that courage isn’t always about being fearless—it’s about taking that first step, even when it’s scary.Get ready for a story that will warm your heart, make you laugh, and just might inspire you to take a bold step of your own.
If you’re interested in donating to Erin’s Make-A-Wish fundraiser to help bring hope, joy, and strength to children facing critical illnesses—click here.
And if you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset, here. It’s a plug-and-play exercise that will get your team mentally present, engaged, and committed before any meeting.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 to them.
The Solution: The Out-of-the-Box Improv Hack You Need
In today’s Snack, we’re shaking things up with a little game called The Fortune Teller Brainstorm.
Have each team member write down a big, wild dream they have for the team—think moonshot ideas with no limits. Fold them up, toss them in a bowl, and randomly pull one out. As a group, pretend it’s five years in the future and this dream has already happened. How did you get there? What steps did you take?
Here’s how it works:Just like that, you’ve turned a dream into a game plan. Try this in your next meeting and watch how quickly your team starts thinking big.
Journal Prompts to chew on:
What’s the wildest dream I have for my team’s success? How can I create a fun way to encourage new ideas? Who on my team needs a confidence boost today, and how can I give it to them?And if you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset here. Use this plug-and-play exercise at the start of any meeting to get your team mentally present, engaged, and committed.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 boundaries to maintain a healthy work-life balance. Jenny also introduces her innovative goal-setting framework, 'Rock, Chalk, Talk, Walk,' designed to help individuals clearly define and achieve their aspirations.
Inside This Episode:
The pivotal moments that led Jenny to leave Google and follow her passion. Understanding and overcoming imposter syndrome in professional transitions. The role of 'wild courage' in embracing one's unique traits and ambitions. Strategies for setting and maintaining boundaries to protect personal time. An introduction to the 'Rock, Chalk, Talk, Walk' goal-setting framework.Who This Episode Is For:
Aspiring entrepreneurs, professionals contemplating a career change, and anyone seeking to overcome self-doubt to pursue their true passions. If you're looking for actionable insights on personal growth, boundary setting, and effective goal planning, this episode is a must-listen.And if you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset, here. It’s a plug-and-play exercise that will get your team mentally present, engaged, and committed before any meeting.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Jenny Wood
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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: In improv, when a scene stalls or someone blanks out, we use a simple trick: we ask for the next line. Instead of panicking, we literally turn to our scene partner and say, "Next line, please?" and they feed us something to work with.
How to use it in real life: Ever been in a meeting where you completely blank on what to say? Or maybe you’re giving a presentation and your brain just short-circuits mid-sentence? Instead of freezing or rambling, do this:
Pause. (Silence feels longer to you than it does to them.) Take a breath. (Gives your brain time to reset.) Ask for the ‘next line.’ This can be as simple as: "Can you repeat the question?" (Buys time and refocuses.) "Let me gather my thoughts for a second." (Gives permission to pause.) "That’s a great point—can you expand on that while I process?" (Keeps the conversation flowing.)This breaks the pressure of perfection and allows you to regroup without the awkwardness.
Try it today! When you get stuck, don’t force it—just ask for the next line.
If you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset here. Use this plug-and-play exercise at the start of any meeting to get your team mentally present, engaged, and committed.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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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 Episode:
Why improv isn’t just for comedians—it’s a powerful leadership tool. The surprising stats that show why most teams are set up for stagnation, not growth. How companies like Uber Freight and The Obama Foundation are using improv to build thriving teams. A simple, actionable improv game (“Last Word, First Word”) you can try in your next meeting. How playfulness fuels productivity (without turning work into a joke).Who This Episode Is For:
Leaders, managers, and team members who want to create a culture where people feel safe to speak up, take risks, and collaborate at their best. If your meetings feel stale or your team plays it too safe, this episode will show you how to shake things up—with fun that leads to real results.And if you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset, here. It’s a plug-and-play exercise that will get your team mentally present, engaged, and committed before any meeting.
No, You Hang Up First (Let’s Keep Connecting)
Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy. Have another question that we can answer? Leave us a Speakpipe audio clip and we’ll answer it in an upcoming episode. Don’t want to miss another episode? If you’re a Spotify listener, find our show here and click “Follow.” If you’re an Apple Podcast listener, click here and make sure to hit “+Follow.” Want access to a bunch of free resources for your work life? This is your personal jackpot that gives you access to the frameworks that help us thrive both personally and professionally. Whether you’re trying to improve your daily routine, flesh out an idea that you’ve had for quite some time, or want to add more play into your day - these resources have got your back. Want 2 emails a week from us? One with a quick tip you can implement right away to enhance your personal and/or professional lives & one of our famous F.A.I.L. Fourward Friday newsletters? Subscribe here.Connect with Erin Diehl x improve it!
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