Henna Pryor: How to Stop Being Awkward

Henna Pryor: How to Stop Being Awkward

From Start With A Win by Adam Contos

March 18, 2026 · 23 min · Episode 370

About this episode

Adam Contos and Henna Pryor discuss the role of awkwardness in leadership and how embracing discomfort can enhance performance.

In this lively and eye-opening episode of Start With a Win, Adam Contos sits down with Workplace Performance Expert and bestselling author Henna Pryor to unravel one of the most misunderstood emotions in modern leadership: awkwardness. With humor, science, and refreshingly real stories, Henna exposes the hidden ways awkward moments shape our confidence, communication, and ability to lead under pressure. Together, they explore why today’s increasingly “smoothed-out” world desperately needs leaders who can navigate discomfort with authenticity and courage. This conversation invites listeners to rethink what being confident truly means - and why embracing the messy, human moments might just be the ultimate performance advantage. Henna Pryor, CSP is a Workplace Performance Expert who helps leaders and teams elevate their performance mindset, communication, and interpersonal effectiveness. A regular Inc. Magazine columnist and 18x award-winning author of Good Awkward, she blends two decades of experience with a science-backed approach to taking strategic risks and boosting social and mental fitness. A global keynote speaker and clients’ self-described “secret weapon for impossible…

People in this episode

Host: Adam Contos

Guest: Henna Pryor

Topics covered

  • leadership
  • awkwardness
  • communication
  • confidence
  • performance
  • authenticity

Keywords

  • leadership
  • awkwardness
  • confidence
  • communication
  • performance
  • authenticity
  • Henna Pryor

Mentioned in this episode

Organizations: Inc. Magazine, SUCCESS Magazine, LinkedIn Learning, FastCompany, INSIDER, HuffPost, NBC, FOX

Books & works: Good Awkward

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