331: Stop Dodging Hard Talks with Henna Pryor

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 fluff
• People managers craving stronger team connection and communication
• High achievers unlearning perfectionism
• Remote and hybrid teams rebuilding social confidence
• Humans ready to trade polished for present

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 LinkedIn
• Henna’s website
• Henna’s Instagram
• 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’s website
• Erin’s Instagram
• Erin’s TikTok
• Erin’s LinkedIn
• improve it!’s website
• improve it!’s Instagram

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