How To Deal With Awkward Moments At Work with Henna Pryor

What if the skill most missing from the modern workplace isn’t technical at all—but social? And what if our discomfort is actually the secret to our success?In this episode of The Future of Less Work, host Nirit Cohen sits down with Henna Pryor—workplace performance expert, Inc. columnist, and author of Good Awkward—to unpack why relational discomfort has quietly become one of the biggest blockers to trust, collaboration, and innovation at work.Drawing on new national research, Henna shares that 30% of employees would rather clean a toilet than ask for help—a stat that reveals just how far our social muscle has atrophied. Together, they explore why hybrid work environments have made it harder to be vulnerable, how AI is making human connection even more optional, and why leaders must rethink influence as a relational—not positional—skill.This episode is a call to rebuild what Henna calls “discomfort tolerance”—the willingness to engage with imperfection, disagreement, and awkwardness as core competencies for the future of work. From conflict avoidance to surface-level relationships, from solo productivity to relational blind spots, Henna and Nirit unpack the hidden costs of too much comfort—and how to start training your social fitness like a real skill. If you’ve ever hesitated to speak up, avoided asking for help, or wondered what soft skills really look like in an AI-powered world, this is a conversation you won’t want to miss.Want to dive deeper into this topic? Read Nirit’s Forbes article, ⁠⁠⁠"⁠One In Three Employees Would Rather Clean A Toilet Than Ask For Help", to explore these ideas further.   https://youtu.be/HS6PWctsAbs Guest Information:Henna Pryor is a workplace performance expert, executive coach, Inc. Magazine columnist, and the author of Good Awkward: How to Embrace the Embarrassing and Celebrate the Cringe to Become the Bravest You. A two-time TEDx speaker, Henna specializes in helping high-achievers and teams improve their influence through social confidence and intentional discomfort. Her work draws on neuroscience, communication research, and real-world coaching insights to reframe awkwardness as a workplace asset.Learn more at: https://www.hennapryor.comThe Study: socialmusclereport.comGood Awkward: https://www.amazon.com/dp/1646871456 Chapters:00:00 — What is the future of social skills at work?03:04 — Why do we avoid asking for help at work?06:39 — What is social muscle and why does it matter?10:42 — How do you train for discomfort at work?15:48 — Why awkward moments are good for your career19:23 — How to build disagreement intelligence24:51 — Can you grow influence without power?29:10 — What is relational fluency and how do you build it?33:58 — How can leaders foster human connection in hybrid work?39:44 — What’s one question we should all ask about the future of work?