In this milestone episode of Workday Playdate, Erin celebrates five years of learning, laughter, pivots, and powerful conversations. From the early days as “Failed It!” to today’s “Workday Playdate,” Erin reflects on how staying open to evolution have shaped the show and the community behind it.

This special anniversary episode spotlights the Top 10 listener-favorite episodes of all time. These conversations sparked breakthroughs in leadership, empathy, financial mindset, well-being, team culture, emotional intelligence, and authentic communication. Whether you’ve been here since episode one or you’re just joining the fun, this roundup reminds us why soft skills aren’t soft at all… they’re essential skills for the modern workplace.

Erin unpacks how improv comedy continues to unlock creativity, why pivoting creates progress, and what the past five years have taught her about resilience and leading with play.

Inside This Episode:

• Pivoting Is Progress: How changing the show’s name, format, and focus led to deeper alignment and higher impact.
• The Power of Improv Comedy: Why improv is one of the most effective development tools for communication, adaptability, listening, and soft skills. 
• Your Favorite Conversations (Ranked!): A countdown of the 10 most streamed, shared, and talked-about episodes + the big lessons from each one. 
• Radical Candor + Empathy: Why caring personally and challenging directly builds trust, psychological safety, and high-performing cultures.
• Your Money Mindset Matters: How shifting your relationship with finances can expand abundance, reduce stress, and reshape decision-making.

Who This Episode Is For:

• People leaders building cultures rooted in empathy, candor, and psychological safety.
• Professionals craving growth, clarity, and workplace skills that actually matter.
• Anyone who loves learning, laughter, leadership, and a good pivot chapter.

You’ve tried the Slack hacks, rewriting the meeting agendas, and promised yourself you’d protect your team’s time. But somehow hybrid work still feels like an endless game of communication ping-pong. More messages, more overwhelm.

Enter The Remote Leader’s Reset: your 5-step guide to lowering the noise, resetting expectations, and helping your team finally exhale. These simple, human-centered resets will help you reduce friction, create clarity, and make your people feel seen—no matter where they’re working from.

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 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.

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’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.