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.

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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 infertility

Who 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.

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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.

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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 relationships

Who 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.

Connect with Jay Fields

• Jay’s website

Connect with Erin Diehl x improve it!

• Erin’s website

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

Connect with Erin Diehl x improve it!

• Erin’s website

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

Connect with Erin Diehl x improve it!

• Erin’s website

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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:

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.

Connect with Erin Diehl x improve it!

• Erin’s website

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

Connect with Erin Diehl x improve it!

• Erin’s website

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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. 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.

Connect with Erin Diehl x improve it!

• Erin’s website

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

Connect with Jenny Wood

• Jenny’s LinkedIn

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• Erin’s website

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.