Workday Playdate

In this episode of Workday Playdate, Erin sits down with Kelly Burlage, Chief Human Resources Officer at Lineage, to explore how our relationship with failure changes as we grow in our careers. From early-career mistakes that feel world-ending to high-stakes leadership decisions that impact entire organizations, Kelly shares why failure is something to learn from.If you've ever found yourself replaying a professional setback or questioning whether you're ready for the next level, this conversation offers a refreshing perspective on resilience and leading through uncertainty.Inside This Episode:Why Failure Evolves as Your Career Grows: Kelly shares how her definition of failure has shifted throughout her career and why the challenges that once felt devastating often become the foundation for future success.The Leadership Lessons Hidden Inside Setbacks: Not every failure feels productive in the moment. Kelly reflects on how some of her most difficult professional experiences ultimately accelerated her growth and strengthened her leadership.How to Lead Through High-Stakes Misses: As leaders advance, mistakes become more visible and carry greater consequences. Kelly discusses how to navigate setbacks without losing trust, momentum, or confidence.Balancing Innovation with Smart Risk-Taking: Growth requires experimentation, and experimentation comes with the possibility of failure. Kelly explains how data, curiosity, and calculated risks help organizations move forward without becoming paralyzed by fear.Creating a Culture Where People Can Learn from Failure: In industries where precision matters, psychological safety still matters. Kelly shares how leaders can create environments where people feel empowered to take ownership, learn, and improve.What to Do Now:Revisit an Old Failure: Think about a professional setback from earlier in your career that still makes you cringe. What lessons did it teach you that success couldn't have?Audit Your Current Response to Failure: Ask yourself whether you're approaching today's challenges with outdated fears or limiting beliefs that no longer serve you.Look for the Lesson, Not the Label: The next time something doesn't go as planned, resist the urge to immediately call it a failure. Instead, ask: "What is this experience teaching me?"About the GuestKelly Burlage is the Chief Human Resources Officer at Lineage, the world's largest and most innovative temperature-controlled logistics provider. She leads enterprise-wide people strategies that align business growth with operational excellence while fostering a culture of inclusion, collaboration, and high performance. With more than two decades of global HR and talent leadership experience, Kelly has built and scaled high-performing teams across complex, high-growth organizations. She is known for delivering innovative, data-driven people strategies that drive meaningful business results. Kelly is a Korn Ferry Certified Coach, a Leading Women Executives alumna, and has been recognized among TAtech's Top 100 Most Influential Talent Acquisition Thought Leaders.Your FreebieHow do you lead through failure and uncertainty?Today’s workplace demands adaptability, creative problem-solving, and leaders who can navigate uncertainty without freezing in perfectionism.This quick quiz will reveal your unique approach to failure and uncertainty, plus give you simple ways to strengthen your adaptability muscles and help your team thrive when things don’t go according to plan.Connect with Kelly BurlageKelly’s LinkedInLineage’s websiteConnect with Erin Diehl x improve it!Leadership Playground online membership communityErin’s websiteErin’s InstagramErin’s TikTokErin’s LinkedInimprove it!’s websiteimprove it!’s InstagramFor more information on improve it! visit www.learntoimproveit.com.

In this episode of Workday Playdate, Erin sits down with Rosie Moan to talk about one of the most challenging combinations many women face: becoming a new mom while navigating uncertainty in work, identity, and life. If you've ever felt like you're simultaneously capable and completely overwhelmed, this conversation offers a refreshing reminder that confidence is about trusting yourself through the unknown.Inside This Episode: Why Confidence and Uncertainty Often Arrive Together: Rosie shares how some of life's biggest growth moments happen when we feel both competent and terrified at the same time, and why that tension is often a sign we're expanding into something new.The Identity Shift of New Motherhood: Becoming a parent can reshape how we see ourselves. Erin and Rosie discuss the emotional and professional adjustments that come with this transition and how to navigate them with more self-compassion.Improvisation as a Tool for Real Life: Drawing from her background in improv, Rosie explains how embracing a "yes, and" mindset can help us respond to unexpected challenges, uncertainty, and change with greater flexibility.Learning to Trust Yourself Again: The conversation explores why confidence isn't about having every answer. It's about building trust in your ability to figure things out as you go.The Power of Letting Go of Perfection: Rosie shares insights on releasing unrealistic expectations and creating space for growth, learning, and grace during demanding seasons of life.What to Do Now:Ask Yourself a Better Question: Instead of asking, "What if I fail?" try asking, "What if I can handle whatever comes next?"Practice "Yes, And" This Week: When something unexpected happens, look for one way to accept reality and build forward rather than resist it.Celebrate Evidence of Your Resilience: Take a few minutes to write down three challenges you've already navigated successfully. Use them as reminders that you've handled uncertainty before and can do it again.About the GuestRosie Moan is a Chicago-based actor, improv performer, coach, and acting coach who has spent more than 15 years helping people build confidence, take creative risks, and trust themselves on and off camera. A graduate of Emerson College, she performs, teaches, and coaches within Chicago's renowned improv community and facilitates workshops designed to strengthen communication, collaboration, and personal growth. Her work centers on helping people move past self-doubt and step more fully into their potential. She is also a lead facilitator for improve it! Your FreebieHow do you lead through failure and uncertainty? Today’s workplace demands adaptability, creative problem-solving, and leaders who can navigate uncertainty without freezing in perfectionism.This quick quiz will reveal your unique approach to failure and uncertainty, plus give you simple ways to strengthen your adaptability muscles and help your team thrive when things don’t go according to plan.Connect with Rosie Moan Rosie’s websiteRosie’s InstagramRosie’s LinkedInConnect with Erin Diehl x improve it!Leadership Playground online membership communityErin’s websiteErin’s InstagramErin’s TikTokErin’s LinkedInimprove it!’s websiteimprove it!’s InstagramFor more information on improve it! visit www.learntoimproveit.com.

In this Workday Playdate, Erin sits down with Lily Zheng to unpack why traditional DEI efforts keep falling flat. Lily and Erin discuss what leaders can do instead to create workplaces that are actually fair, inclusive, and built to last.If you’ve ever wondered why diversity trainings, performative culture initiatives, and “quick fix” belonging strategies rarely create real change, this episode is your invitation to rethink workplace equity through a practical, people-first lens.Inside This Episode:Why DEI Efforts Keep Missing the Mark: Despite decades of workplace initiatives, discrimination rates remain shockingly high, and many solutions are still surface-level.The FAIR Framework Changes the Conversation: Lily shares a practical, problem-solving approach to building inclusion that focuses on fixing real workplace barriers.Belonging Is Measurable: Learn how employee experience connects directly to retention, engagement, performance, and long-term business success.Middle Managers Have More Power Than They Think: Practical ways to influence leadership, advocate for change, and create safer workplaces from any level.Human-Centered Leadership Creates Lasting Change: Why authentic leadership, psychological safety, and consistent action outperform performative workplace culture efforts every time.What to Do Now:Audit Your Workplace Culture: Ask whether your organization is solving real employee problems or simply signaling values externally.Translate Human Issues Into Business Metrics: Use turnover, burnout, retention, and engagement data to advocate for meaningful workplace change.Create One Honest Conversation This Week: Invite feedback without defensiveness and focus on listening before fixing.Your FreebieWhat’s your leadership style and next business move? Find out by taking a fun little quiz here.And thank you to our sponsors Intuit Quickbooks Payroll.To learn more visit: https://quickbooks.intuit.com/workforce/About the Guest:Lily Zheng is a DEI strategist, consultant, speaker, and the author of Fixing Fairness: A Framework for Equity and Organizational Change. Lily works with organizations to move beyond performative diversity efforts and build measurable, sustainable systems for fairness, inclusion, and accountability. Their work focuses on practical, problem-solving approaches that help leaders create healthier workplace cultures rooted in trust, transparency, and real human impact.Connect with Lily ZhengLily’s LinkedInLily’s websiteLily’s book Fixing Fairness: 4 Tenets to Transform Diversity Backlash into Progress for AllConnect with Erin Diehl x improve it!Leadership Playground online membership communityErin’s websiteErin’s InstagramErin’s TikTokErin’s LinkedInimprove it!’s websiteimprove it!’s InstagramFor more information on improve it! visit www.learntoimproveit.com.

In this Workday Playdate, Erin dives into the discomfort of “good awkward” with Henna Pryor. Henna is a workplace performance expert, keynote speaker, and author who helps teams build social fitness in a world that’s forgotten how to human. Together, they unpack why our social muscles have atrophied (thanks, tech + pandemic isolation) and how leaning into micro-discomfort can radically improve leadership, communication, and team cohesion.This episode is your permission slip to stop polishing and start connecting.Inside This Episode:Social Muscles Are Flabby: Why hyper-connectivity is sabotaging real connection—and what it’s doing to workplace communication and confidence.Micro-Disagreements, Major Growth: How low-stakes conflict and social repetition build trust, resilience, and stronger teams.Asking for Help Without Spiraling: The surprising stat: 1 in 3 employees would rather clean a toilet than ask for help. Let’s fix that.The Neuroscience of Shared Moments: Why laughter, eye contact, and shared awkwardness boost psychological safety and belonging.Normalize the Awkward: How naming “good awkward” in real time reduces fear and strengthens authentic leadership.Language Builds Safety: Practical scripts to express discomfort, validate emotions, and create space for real dialogue.Humor as a Leadership Strategy: Why playfulness lowers defensiveness, reduces conflict anxiety, and makes feedback easier to hear.Good Enough > Perfect: Ditching perfectionism to build faster recovery and stronger comeback rates in tough moments.Recovery Rate > Failure Rate: Why resilient leaders focus less on avoiding discomfort and more on how quickly they bounce back.Make Work a Playground Again: Micro-exercises and small social reps teams can use immediately to rebuild connection and confidence.Who This Episode Is For:Leaders who want to build psychological safety without the corporate fluffPeople managers craving stronger team connection and communicationHigh achievers unlearning perfectionismRemote and hybrid teams rebuilding social confidenceHumans ready to trade polished for presentYour FreebieYou want to support your people the same way you want to be supported—but in fast, emotionally charged moments, the right words can be hard to find.Enter, your free resource - Human Leadership in the Age of AI: An Empathy Playbook. It gives you a simple, 3-part list of human-first phrases you can use in meetings, emails, and one-on-ones.Empathy isn’t extra anymore. It’s essential. Download your Empathy Playbook here.Connect with Henna PryorHenna’s LinkedInHenna’s websiteHenna’s InstagramHenna’s book, Good Awkward: How to Embrace the Embarrassing and Celebrate the Cringe to Become The Bravest YouConnect with Erin Diehl x improve it!Erin’s websiteErin’s InstagramErin’s TikTokErin’s LinkedInimprove it!’s websiteimprove it!’s InstagramFor more information on improve it! visit www.learntoimproveit.com.

In this Workday Playdate, Erin welcomes leadership trailblazer Claude Silver, Chief Heart Officer at VaynerX, for a conversation about authenticity, empathy, and emotional fluency at work. This episode is a heart-forward guide to showing up as your full self so you can build trust, spark creativity, and lead with courage in today’s complex workplace.Erin and Claude explore how emotional safety, vulnerability, and presence directly impact performance, innovation, and connection. At the heart of the episode is a call to expand at work. Through improv principles like “yes, and,” culture addition (not culture fit), Erin and Claude offer leaders real ways to create psychologically safe, high-trust environments where people actually thrive.Inside This Episode:Authentic Leadership: Why being yourself at work is strategicEmotional Safety at Work: How trust and psychological safety unlock creativity, loyalty, and performanceClaude’s Journey: From surf instructor to Chief Heart OfficerWater as Wisdom: Flow, movement, and calm as leadership metaphorsImprov at Work: Using “yes, and” to build collaboration, presence, and connectionCulture Addition: Moving beyond exclusionary culture fit to build stronger, more inclusive teamsEmotional Fluency: Learning to “speak human” and release outdated professionalism normsTrusting the Long Game: Patience, vulnerability, and leadership lessons from Gary VaynerchukPurpose & Joyful Service: Choosing love over fear to create real impactPractical Takeaways:Discover your authentic self through values, triggers, and feedbackPractice grounded presence and emotional regulationExpand instead of shrink in moments of discomfortLead with love, clarity, and courageWho This Episode Is For:Leaders ready to show up more authenticallyPeople managers building emotionally safe, high-performing culturesAnyone navigating burnout, disengagement, or uncertaintyRemote and hybrid leaders creating connection without proximityHumans who want to lead with more empathy, purpose, and playYour FreebieYou want to support your people the same way you want to be supported—but in fast, emotionally charged moments, the right words can be hard to find.Enter, your free resource - Human Leadership in the Age of AI: An Empathy Playbook. It gives you a simple, 3-part list of human-first phrases you can use in meetings, emails, and one-on-ones.Empathy isn’t extra anymore. It’s essential. Download your Empathy Playbook here.Connect with Claude SilverClaude’s LinkedInClaude’s InstagramClaude’s websiteClaude’s bookConnect with Erin Diehl x improve it!Erin’s websiteErin’s InstagramErin’s TikTokErin’s LinkedInimprove it!’s websiteimprove it!’s InstagramFor more information on improve it! visit www.learntoimproveit.com.

In this Workday Playdate, Erin sits down with Lori Woodley-Langendorff to unpack a leadership truth we don’t practice enough: emotional intelligence isn’t a “nice to have” — it’s essential. Lori is an acclaimed author, educator, and expert in social-emotional literacy (SEL) who co-founded the non-profit "All It Takes" with her daughter, actress Shailene Woodley. Drawing from Lori’s 30-year career as a school counselor (and her lived experience as a parent), this conversation bridges the gap between personal growth and professional leadership, reminding us that the workplace has officially changed… and our emotional skills need to catch up.Together, Erin and Lori explore emotional intelligence (EI) and social emotional literacy (SEL) as learnable, trainable skills, not personality traits you either have or don’t. Lori introduces her SEL Muscle framework, a practical, no-fluff approach to building emotional resilience, strengthening communication, and leading with both connection and accountability. The result? Healthier teams, better relationships, and leaders who can handle overwhelm without passing it down the chain.Inside This Episode:Emotional Intelligence at Work: Why EI is foundational to modern leadership and personal growthSEL Is a Muscle: How social emotional literacy strengthens with intentional practiceConnection + Accountability: Why you need both to build trust and credibilityEmotional Awareness: How noticing feelings early prevents stress, burnout, and breakdownsThe SEL Muscle Framework: Practical tools for emotional resilience and clearer communicationModeling the Way: Why leaders must “walk the talk” emotionally, not just strategicallyCuriosity Without Judgment: How this one shift transforms relationships at work and homeWho This Episode Is For:Leaders who feel the emotional weight of their roleManagers navigating overwhelm, conflict, or disengagementParents and professionals juggling accountability with compassionPeople leaders ready to strengthen emotional resilience and communicationAnyone who wants to lead with more awareness and connectionYour FreebieYou’ve tried the color-coded calendars, the habit apps, and the “this is the week I finally get it together” pep talk… and it still doesn’t stick. That’s because consistency comes from understanding why your routines keep falling apart in the first place.The 4-Step Consistency Planner helps you uncover the four real reasons consistency breaks down and walks you through four practical fixes so you can take back control of your week.Download it here.Connect with Lori Woodley-LangendorffLori’s LinkedInLori’s company websiteLori’s InstagramConnect with Erin Diehl x improve it!Erin’s websiteErin’s InstagramErin’s TikTokErin’s LinkedInimprove it!’s websiteimprove it!’s InstagramFor more information on improve it! visit www.learntoimproveit.com.

In this Workday Playdate, Erin sits down with Carrie Drinkwine to explore a radical (and deeply human) truth: real healing starts with feeling.Carrie shares her powerful journey through chronic illness, emotional reckoning, and life-threatening health challenges. She explains how regenerative practices helped her reconnect to her body, her intuition, and her vitality. Together, Erin and Carrie unpack the emotional–physical connection, why “pushing through” keeps us stuck, and how flow, self-love, and emotional release create lasting wellness at work and in life.Inside This Episode:Flow Over Force: Why flow is essential for overcoming obstacles and supporting long-term health.Issues in the Tissues: How repressed emotions live in the body—and show up as physical symptoms.Healing from Within: Carrie’s journey through chronic illness and emotional healing.The Emotional–Physical Link: Why you can’t separate wellness at work from wellness in your body.Self-Love as Medicine: How acceptance, compassion, and nervous system safety unlock vitality.Listen to the Body: Why intuition—not optimization—is the most powerful health tool you have.Holistic, Not Hustle: How regenerative health practices lead to real, sustainable transformation.Who This Episode Is For:Humans navigating burnout, chronic stress, or chronic illnessLeaders curious about emotional wellness and embodied leadershipHigh-achievers ready to stop overriding their bodiesAnyone exploring self-healing, holistic health, or regenerative practicesFans of flow, intuition, self-love, and healing that actually sticksYour FreebieYou’ve tried the emails, the all-hands rollout, and the polished decks, but the vision still isn’t landing.That’s because people don’t buy into a vision that’s presented to them; they buy into one they help shape.The 30-Minute Vision-Setting Meeting Template gives you a simple, human-centered way to create alignment, spark ownership, and build real momentum. Download it here.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 a 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 1 email a week from us? Our well-loved Fail Fourward Friday gives you 4 Fails, 3 Awakenings, 2 Ideas, and 1 Laugh from the week that reminded us what being human is all about: to make failure a habit, be a lifelong learner, explore more, and never pass up an opportunity to laugh. Subscribe here.Connect with Carrie DrinkwineCarrie’s LinkedInCarrie’s websiteConnect with Erin Diehl x improve it!Erin’s websiteErin’s InstagramErin’s TikTokErin’s LinkedInimprove it!’s websiteimprove it!’s InstagramFor more information on improve it! visit www.learntoimproveit.com.