Episode 320: 5 Years Strong: The 10 Episodes You Loved Most

Written By Erin Diehl
 
 
 

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In this episode of Workday Playdate, Erin celebrates a milestone: five years of podcasting and some truly unforgettable guests. What began as “Failed It!” has evolved into Workday Playdate: a space where leaders learn to communicate with more candor, connection, joy, and humanity. 

As she reflects on the evolution of the show, Erin revisits the 10 most-loved episodes of all time—the ones you shared with your teams, quoted, and returned to again and again. These conversations helped thousands of leaders rethink how they communicate, negotiate, lead, work, and live. 

Whether you’ve been here since episode one or you’re showing up for the first time today, this episode is a reminder of what we’ve built together, and why the best is still ahead. 

Episode 80: Lead Like You Mean It 

Kim Scott teaches us that real leadership means radical candor. When you care personally and challenge directly, people grow, teams strengthen, and honesty becomes the norm. 

Episode 307: The Components to Becoming a Recovering People-Pleaser

Amy Green Smith shares how overcoming people-pleasing requires setting boundaries and clear communication.

Episode 101: Empathy Is a Strategic Advantage 

Ryan McCrea showed us that smart leadership includes empathy as its driving force. When people feel seen, supported, and safe, they perform better, connect more deeply, and solve problems with greater collaboration and creativity. 

Episode 234: You Don’t Have to Choose 

Tiffany Sauder opened the door to a new narrative: you can pursue a meaningful career and a meaningful life. With strategy, support systems, and surrender, ambition and family can coexist. 

Episode 258: Rewrite Your Money Story 

Dr. Darnyelle Jervey Harmon helped us release scarcity thinking and embrace financial confidence. When you detach worth from wealth and align decisions with values, abundance follows clarity. 

Episode 266: The Power of Perception 

Alison Fragale reminded us that influence mainly involves perception. When you communicate with intention, humility, and respect, you build positive authority. 

Episode 268: Everyone Is Negotiating—Even If They Don't Know It 

Kwame Christian showed us negotiation isn't just contracts, it's conversations about needs, boundaries, and outcomes. When you negotiate with curiosity and courage, relationships get stronger. 

Episode 299: Engagement Is an Inside Job 

Dr. Angela Jackson revealed the truth about employee engagement: people stay when they feel aligned with a mission. Ownership fuels loyalty, and loyalty fuels results. 

Episode 301: Up Isn’t Off-Limits 

Melody Wilding helped us navigate the skill of managing up. When we communicate expectations clearly and honor boundaries, we strengthen psychological safety. 

Episode 303: Design the Life You Want 

Steffani LeFevour reminded us that fulfillment is something that’s consciously created. With intention, practice, and alignment, your work and life can finally feel like they belong to you, not the other way around. 

Your Play Challenge 

This week, hit play on the episode from this list that sparked your curiosity or revisit the one that changed something for you. 

Ask yourself: “What lesson from that conversation is still here waiting for me?” 

Let it inform how you lead, communicate, and connect. 

Your Freebie

You’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) 

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Top 10 Episodes of All Time 

  • Episode 301: Real Talk: How to Stop Guessing What Your Boss Wants and Start Managing Up with Confidence with Melody Wilding 

  • Episode 299: Want to Nail Employee Engagement? Here’s What Actually Works (No Gimmicks Needed) with Dr. Angela Jackson 

  • Episode 307: Stop People-Pleasing: Lead with Clarity and Confidence with Amy Green Smith 

  • Episode 303: Are We Settling Without Even Knowing It? Steffani Lefevour Spills the Truth and How to Break Free 

  • Episode 80: You CAN give feedback as a Leader, and it CANNOT be triggering with Kim Scott 

  • Episode 95: Building a Kick A$$ Culture of Inclusivity with Kim Scott + Trier Bryant 

  • Episode 101: The Rise of the Empathetic Leader with Career Development Visionary, Ryan McCrea 

  • Episode 268: How Can Top Corporate Leaders Use Negotiation to Drive Unstoppable Success? Unlocking Secrets with Kwame Christian 

  • Episode 266: What Does It Take for Women to Gain Respect, Power, and Influence in the Workplace? Alison Fragale Spills the Tea 

  • Episode 258: Is the Way You Think About Money Holding You Back? Dr. Darnyelle Reveals THE Million Dollar Mindset Secrets 

  • Episode 234: Tiffany Sauder on Dual Career Families: Can You Really Have it All Without Sacrificing What Matters Most? 

Connect with Erin Diehl x improve it! 

 
Erin Diehl
Next

Episode 319: Authenticity at Work: Building Resilient Teams with the REAL Model with Nathan Andres