Workday Playdate

What if the key to stronger leadership, deeper team connections, and a more engaged workplace wasn’t another corporate training—but a well-timed joke? In this episode of Workday Playdate, Erin sits down with comedian, speaker, and leadership coach JaMarr John Johnson to explore how humor, storytelling, and community can transform the way we work and lead. From his journey in the military to the comedy stage—and even learning from legends like Dave Chappelle—JaMarr shares powerful insights on how to balance playfulness with professionalism, inject laughter into leadership, and build teams that thrive on connection. Inside This Episode: Why humor isn’t just about being funny—it’s about connection, engagement, and trust. The lessons JaMarr learned from Dave Chappelle about values, ethics, and leadership. How storytelling can turn workplace challenges into opportunities for growth. Light roasting: When playful humor enhances team culture (and when it doesn’t). The key to creating a workplace where laughter fuels productivity instead of being a distraction. Who This Episode Is For: Leaders who want to build teams that thrive in uncertainty, handle challenges with ease, and stay engaged—even when things don’t go as planned. If you’re tired of stiff, disengaged meetings and want to inject some energy, connection, and creativity into your workplace, this one’s for you. And if you’re interested in taking one small action right now, you can check out our newest freebie, The Empathy Cheat Sheet, here. It’s a 3-part list of helpful phrases you can use before heading into any conversation or meeting, responding to an email, or hosting a one-on-one call. 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 JaMarr John Johnson JaMarr’s website JaMarr’s LinkedIn JaMarr’s LinkedIn course Connect with Erin Diehl x improve it! Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn improve it!’s website improve it!’s Instagram See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hey, hey, Workday Playdate peeps! It’s time for your quick bite of leadership wisdom—a little boost of inspiration, energy, and of course, playfulness to brighten your workday.  Today, we’re talking about one of the most underrated leadership tools: humor. That’s right—if you want to build connection, trust, and motivation within your team, you don’t need a corporate retreat or a 100-slide deck. Sometimes, all it takes is a well-placed joke, a moment of levity, or the courage to not take yourself too seriously.   Want to add more fun to your leadership style? Try this improv-inspired game: The Mis-Translation Game Pick a ‘translator’ and a ‘speaker.’ The ‘speaker’ delivers a serious workplace announcement—but in complete gibberish. Example: “Gloobity blop floo fandango periwinkle!” The ‘translator’ must confidently ‘interpret’ what was just said. Example: “Ah yes, that means today’s meeting will be catered by an army of penguins!” Rotate roles and let the laughter flow. Why does this work? Because it helps teams embrace the unknown, think on their feet, and find joy in the unexpected. And a team that laughs together? That’s a team that trusts each other. Take it further: Reflect on a leader who used humor to inspire you. What did they do? What’s one way you can bring more humor into your leadership style this week? How can you create an environment where your team feels safe to have fun? And don’t forget—next up, we’re going even deeper with JaMarr Johnson, the "Entrepremedian" who helps leaders use humor to build stronger workplace cultures. You don’t want to miss it! Journal Prompt: Who on your team might be feeling unheard? What’s one small way you can make space for their voice this week? Write it down—and take action.   If you’re interested in taking one small action right now, you can check out our newest freebie, The Empathy Cheat Sheet here. Break out this 3-part list of helpful phrases before heading into any conversation or meeting, responding to an email, or hosting a one-on-one call.    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! Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn improve it!’s website improve it!’s Instagram See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Your team just hit a wall. A project derailed. A curveball out of nowhere. What happens next? If the answer is stress, scrambling, or radio silence, it’s time for a new approach. Enter improv—the secret weapon for building resilient teams that can roll with the punches and come back stronger. Inside This Episode: Why most teams struggle with resilience (and how to fix it) The four-step improv framework that turns setbacks into stepping stones Simple, high-energy activities you can steal for your next team meeting A personal story of resilience from Erin’s own business journey How to create a team culture where change isn’t scary—it’s fuel Who This Episode Is For: Leaders who want their teams to handle challenges with confidence instead of chaos. If you’re tired of watching your team freeze up when things go sideways, this one’s for you. And if you’re interested in taking one small action right now, you can check out our newest freebie, The Empathy Cheat Sheet, here. It’s a 3-part list of helpful phrases you can use before heading into any conversation or meeting, responding to an email, or hosting a one-on-one call. 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! Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn improve it!’s website improve it!’s Instagram See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

It’s time for your Workday Playdate snack—just a quick bite of leadership wisdom before we go deeper on Wednesday. Today, we’re talking about empathy—the leadership skill that turns good teams into great ones.   Want a quick and easy way to help your team feel heard? Try this improv-inspired exercise:   “Last Word, First Word” One person starts with a simple sentence. Example: “Our team is growing fast.” The next person must start their sentence with the last word of the previous sentence. Example: “Fast changes require clear communication.” Keep going around, building off each other’s words. Notice how this forces people to really listen and build on what’s being said—just like in a strong, empathetic workplace. Why does this work? Because it shifts conversations from waiting to speak to actively responding. And that’s where trust starts.   Journal Prompt: Who on your team might be feeling unheard? What’s one small way you can make space for their voice this week? Write it down—and take action.   If you’re interested in taking one small action right now, you can check out our newest freebie, The Empathy Cheat Sheet here. Break out this 3-part list of helpful phrases before heading into any conversation or meeting, responding to an email, or hosting a one-on-one call.   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! Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn improve it!’s website improve it!’s Instagram See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Diversity, Equity, and Inclusion (DEI) programs have been a driving force behind innovation, employee retention, and workplace culture—but now, many companies are slashing these initiatives, leaving employees feeling unseen, unheard, and disconnected. In this solo episode of Workday Playdate, Erin dives into the corporate DEI backslide and the very real consequences of these cutbacks. But she’s not here to dwell on the problem—she’s here to talk solutions. And here’s the twist: one of the most effective (and unexpected) ways to rebuild belonging, inclusion, and collaboration might just come from the world of improv. From psychological safety to leadership development, Erin unpacks how improv training fosters trust, empathy, and innovation in the workplace—and why now, more than ever, companies need to rethink how they create cultures where people thrive. Here’s what’s inside: Why Cutting DEI is a Costly Mistake—Real data on how eliminating DEI initiatives is impacting businesses and employees. The Power of Psychological Safety—How companies with inclusive cultures see stronger performance, engagement, and retention. How Improv Training Fills in the Gaps—The science behind “Yes, And,” active listening, and collaboration as tools for belonging. Case Study: Improv in Action—A real-world success story of how improv training transformed workplace culture. Your Playful Challenge—A simple improv-inspired exercise to help foster more inclusion at work today. No, you hang up first… If this episode resonated with you, Erin wants to hear from you! Share your biggest takeaway, your own DEI experiences, or how you’re bringing more empathy and inclusion into your workplace. And if you’re ready to take the next step, grab a copy of I See You! or bring improv-based training to your team. Let’s create workplaces where people feel valued, seen, and empowered. And if you’re interested in taking one small action right now, you can check out our newest freebie, The Empathy Cheat Sheet, here. It’s a 3-part list of helpful phrases you can use before heading into any conversation or meeting, responding to an email, or hosting a one-on-one call. Also, here's a link to the Kelly Scullin episode that Erin mentioned in today’s episode: Episode 96: How American Marketing Association Created a Company Culture Centered Around Yes, And with Kelly Scullin.   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! Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn improve it!’s website improve it!’s Instagram See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

You care about your people, but leadership can feel like an uphill battle—burnout, disengagement, awkward silences. Sound familiar? Enter: Radical Empathy. In today’s Workday Playdate “Snack,” Erin gives you a quick-win improv activity that you can try in your next meeting: 1.     Pair up your team members (or do this in a group!). 2.     One person starts making simple movements—raising an arm, nodding, shifting posture. 3.     The other person mirrors those movements exactly, as if they were a reflection. 4.     Switch roles after a minute. 5.     Debrief with the question: “How did it feel to be fully seen and in sync with someone else?” Boom. Instant connection. Try it and watch what shifts. For more, grab Erin’s book I See You! or book our Empathetic Leader Keynote. Journal Prompt Who on your team might be feeling unseen? How can you acknowledge them today? If you’re interested in taking one small action right now, you can check out our newest freebie, The Empathy Cheat Sheet here. Break out this 3-part list of helpful phrases before heading into any conversation or meeting, responding to an email, or hosting a one-on-one call.   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! Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn improve it!’s website improve it!’s Instagram See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Think empathy is just a “soft skill”? Think again. It’s your leadership superpower—one that builds trust, fuels innovation, and keeps teams engaged. But here’s the kicker: real empathy isn’t just about feeling—it’s about leading with it. In this episode of Workday Playdate, Erin takes you beyond the pages of her book I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy to unpack the ripple effect it’s had on leaders, teams, and workplaces over the past year. From boardrooms to book clubs, keynote stages to personal breakthroughs, this book has sparked real change—and today, Erin’s sharing the stories that prove it. Here’s what’s inside: Why Empathy is a Leadership Game-Changer—According to Harvard Business Review, empathetic leaders drive higher trust, innovation, and employee satisfaction. The iDiehl Day Framework—One simple shift that increased a team’s productivity by 20%. From South Carolina to Tokyo—How I See You! made its way into the hands of thought leaders like Gabby Bernstein and global teams navigating burnout. How Writing This Book Changed Everything—From trusting her voice to realizing this message belongs to you—the leaders making an impact. A Practical Empathy Exercise—One small step to bring more radical empathy into your workday right now. A Quick Favor… If you’ve read I See You! or been inspired by this episode, Erin wants to hear from you! Send a note, share your story, and let’s keep the empathy ripple effect going. And if you haven’t grabbed your copy yet—what are you waiting for? It’s time to put empathy into action. So, grab your coffee, tea, or whatever fuels your inner rockstar, and let’s dive in. Because every workday is a playdate waiting to happen! Listen now to start leading with radical empathy. And if you’re interested in taking one small action right now, you can check out our newest freebie, The Empathy Cheat Sheet, here. It’s a 3-part list of helpful phrases you can use before heading into any conversation or meeting, responding to an email, or hosting a one-on-one call.   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! Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn improve it!’s website improve it!’s Instagram See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Welcome to Workday Playdate—new name, same mission, more fun! If you're a leader looking to energize your team, you're in the right place.   You care about your people, but leadership can feel like an uphill battle—burnout, disengagement, awkward silences. Sound familiar? Enter: Radical Empathy.   In today’s Workday Playdate “Snack,” Erin gives you a quick win improv activity that you can try in your next meeting:   1. Ask: “What’s been your biggest challenge this week?” 2. Listen. Repeat back what they said in your own words. 3. Say: “If I were in your shoes, I might feel… Does that resonate?”   Boom. Instant connection. Try it and watch what shifts.   For more, grab Erin’s book I See You! or book our Empathetic Leader Keynote at learntoimproveit.com.   Journal Prompt Who on your team works hard but may not feel seen? How can you acknowledge them today?   If you’re interested in taking one small action right now, you can check out our newest freebie, The Empathy Cheat Sheet here. Break out this 3-part list of helpful phrases before heading into any conversation or meeting, responding to an email, or hosting a one-on-one call.  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! Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn improve it!’s website improve it!’s Instagram  See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Radical empathy in leadership isn’t just a buzzword—it’s a game-changer. But practicing it? That takes intention, self-awareness, and a willingness to evolve. In this episode of the improve it! Podcast, Erin sits down with Wendy Gonzalez to dive deep into what it truly means to lead with radical empathy. Wendy is the CEO at Sama and is passionate about building high-performing, high-functioning teams that develop and scale innovative, impactful technology. Wendy shares her bold philosophy of "firing yourself" annually—a practice that keeps leaders accountable to the ever-changing needs of their organizations. They break down the power of vulnerability, the necessity of introspection, and why stepping back doesn’t mean stepping away. Wendy also reveals why natural curiosity is a superpower and how surrounding yourself with passionate people leads to greater impact. And in a moment of pure inspiration, she shares her personal purpose—raising good humans. If you're ready to rethink leadership, embrace change, and lead with more heart—this episode is for you. And if you’re interested in taking one small action right now, you can check out our newest freebie, The Tomorrow Ready Checklist, here. Use this checklist to remember who you are, what you stand for, and what you actually want to spend your time doing.   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 Wendy Gonzalez Wendy’s LinkedIn Connect with Erin Diehl x improve it! Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn improve it!’s website improve it!’s Instagram See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Empathy at work (and outside of work) is simpler than you think, but that doesn’t mean it’s easy. In Episode 276 of the improve it! Podcast, Erin discusses why mastering empathy will unlock deeper connections, increase employee engagement, and give you more meaningful results. Erin gives you her 2-step shortcut for leading with empathy that you can bring to work tomorrow. She also gives you the deets on the improv game that you can play 100% of the time in your head to help you be more empathetic. If you’re working on training your empathy muscles this year—this is the episode for you. And if you’re interested in taking one small action right now, you can check out our newest freebie, The Tomorrow Ready Checklist, here. Use this checklist to remember who you are, what you stand for, and what you actually want to spend your time doing.   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! Erin’s website Erin’s Instagram Erin’s TikTok Erin’s LinkedIn improve it!’s website improve it!’s Instagram See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.