Episode 331: Stop Dodging Hard Talks with Henna Pryor

Written By Erin Diehl
 
 
 

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In this Workday Playdate, Erin explores a leadership truth that’s impossible to ignore right now: teams disengage when leaders avoid discomfort especially in a world that’s socially rusty. Joined by Henna Pryor, this episode unpacks why social muscles have atrophied and how vulnerability, humor, and micro-bravery rebuild social connection. 

Henna reframes awkwardness as a leadership advantage and offers practical tools to strengthen communication, normalize imperfection, and increase your recovery rate when things get uncomfortable. 

Stop Avoiding Awkward 

Discomfort is data. Avoiding micro-conflict and hard conversations weakens team trust. Leaning in builds resilience, connection, and authentic leadership presence. 

Your Social Muscles Need Reps 

Technology, remote work, and pandemic isolation have quietly eroded our social fitness. Small talk feels harder. Asking for help feels risky. This episode explores how social repetition and micro-disagreements rebuild confidence and communication skills. 

Reframe Asking for Help 

One in three employees would rather clean a toilet than ask for help. That stat alone explains burnout. Erin and Henna share practical language to make collaboration feel safe for boosting teamwork and psychological safety. 

Build Language for Discomfort 

Most workplace tension escalates because we lack the words. Learn simple scripts to validate emotions, express discomfort clearly, and deepen trust without over-explaining. 

Good Enough > Perfect 

Perfectionism kills connection. High-performing teams focus less on flawless delivery and more on recovery and comeback rate. The goal is bouncing back faster rather than freezing yourself into inaction. 

Your Freebie 

You 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 Pryor 

  • Henna’s book, Good Awkward: How to Embrace the Embarrassing and Celebrate the Cringe to Become The Bravest You 

Connect with Erin Diehl x improve it! 

 
Erin Diehl
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Episode 330: How to Not Suck at Being a Boss