The Power of Awkwardness: Transforming Cringe into Courage with Henna Pryor

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Table Of Contents

Henna Pryor, PCC is a highly sought-after Workplace Performance Expert and an award-winning 2x TEDx and global keynote speaker, virtual presenter, author, and professional executive coach. She’s known for her science-backed approach to improving the performance, habits, and actions of hungry high achievers – in her fun, no-nonsense, no-jargon way – to move them from their first level of success to their next one.

She has been invited to speak twice for TEDx in New York City and Wilmington, DE and brings her expertise to a variety of global organizations including Google, Workday, FIS Global, and Johnson & Johnson. She has also been featured in top TV, podcast, and print media including Forbes, NBC, Washington Post, Fast Company, and more.

Henna founded Pryority Group – a fast-growing performance growth firm – to expand on her belief that the key to most people’s success is leaning into awkwardness a little bit longer to skyrocket strategic risk-taking and be braver in the work that we do.

Her best-selling book, Good Awkward, published in September has been endorsed by NFL Quarterback Russell Wilson, former HBR Editor Karen Dillon, and received the rare Kirkus Star for excellence in writing.

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  • (1:57) Henna's TED talk
  • (2:22) Mike's awkward story from last night
  • (3:20) One of Henna's awkward stories and how she got the name Helen
  • (5:30) Avoidance of awkwardness
  • (6:07) Root of self-consciousness and defining awkward
  • (9:58) Our brains are hard-wired for social acceptance
  • (11:24) How Mike sees uncertainty/awkwardness in career changers
  • (12:24) FOPO - fear of other people's opinions
  • (15:40) Personal creative destruction
  • (16:30) Awkwardness vs being uncomfortable
  • (18:45) Tactics for developing social prowess
  • (20:38) Vicarious embarrassment
  • (23:22) What your feelings about cringe comedy say about your empathy
  • (24:30) Self-assessment of emotions and expectations
  • (24:43) Contamination vs redemption stories
  • (28:20) The spotlight effect and the pratfall effect
  • (30:34) How to lean into awkwardness
  • (31:33) Naming awkwardness
  • (34:23) Conditioning for awkwardness/make it intentional
  • (38:15) How leaders/teams can create an environment to admit their own blunders and allow space for others to bring them up
  • (41:55) Why Henna describes herself as a recovering overachiever
  • (46:05) How Henna started to author her own version of success
  • (50:48) Creating space to explore other career paths
  • (54:02) Creating opportunities to rehearse awkward moments
  • (55:10) Approval or improvement
  • (57:57) Mindset of choosing yourself
  • (59:46) What Henna does and who she works with
  • (1:04:03) Taking micro bets


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