Henna Pryor on good awkward, improv exercises, redemption stories, and magic words (#51)

Henna Pryor on Good Awkward

In this episode, we’re getting awkward with Henna Pryor!

We talk about her book Good Awkward, what it is and embracing awkwardness in leadership, using improv exercises with your team to build trust and encourage open communication, the power of telling ourselves redemption stories in place of contamination stories, and so much more. 

You’ll really enjoy the awkward moment in the middle of the podcast where we try to figure out where the bubbles on screen are coming from – you really never know when you’ll experience those quirks and unexpected moments. 

Contact Henna

LinkedIn: @hennapryor
Website: www.pryoritygroup.com

About Henna

Henna Pryor, PCC is a highly sought after Workplace Performance Expert and an award-winning 2x TEDx and global keynote speaker, author, and executive coach. Her clients call her their “secret weapon for impossible change,” an honor she wears proudly. 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.

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.

She’s recognized as a SUCCESS Magazine Woman of Influence, and her best-selling book, Good Awkward, was endorsed by NFL Quarterback Russell Wilson and former HBR Editor Karen Dillon, and was named a Kirkus Reviews’ Best Book of 2023.


Good Awkward by Henna Pryor
TEDx Talk – Why awkwardness is your secret weapon for risk-taking at work
TEDx Talk – Is there such a thing as “good bragging”?
Brené Brown resources
Tom Gilovich Cornell Belief Lab
Dan McAdams
One Direction
This is How We Do It – Montell Jordan
Beis Weekender Bag
Magic Words by Jonah Berger


[03:33] Henna Pryor introduces herself to the audience
[05:04] What inspired Henna to write her book “Good Awkward”
[07:25] Unpacking our relationship to awkwardness and understanding where it’s coming from
[09:50] How to think about awkwardness in leadership
[11:46] Understanding awkwardness as an emotion and not a statement effect
[13:06] Good awkward vs. bad awkward
[14:10] The difference between awkwardness and being uncomfortable
[16:38] Stories of how embracing awkwardness led to professional growth
[19:11] Story of how embracing awkwardness led to a feeling of psychological safety
[21:14] The difficulty surrounding the word authenticity
[22:29] How to embrace your awkwardness
[26:54] Exercises to practice working through awkward feelings
[29:20] Practicing deliberate discomfort and cracked egg stories
[32:38] How to get your team comfortable with speaking up
[38:09] Getting comfortable with failure
[39:13] Telling yourself redemption stories rather than contamination stories
[41:55] How to help your team embrace awkwardness
[43:04] Using improv exercises to lean into awkwardness
[44:41] Finding opportunities for improv outside of work
[46:18] Henna shares a recent time where she experienced an awkward moment
[50:33] The most important takeaway for embracing awkwardness
[52:14] Henna shares the mentor who made a difference in her career
[54:24] Henna shares the daily ritual that she attributes her well-being to
[55:45] The music that gives Henna a confidence or energy boost when she needs it
[56:20] A recent purchase that has improved Henna’s life in some way
[58:08] The one book Henna recommends the listeners check out (besides Good Awkward, of course)
[58:57] The parting words of advice or inspiration Henna wants to leave you with
[59:36] The best way to find and reach out to Henna


“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.”

“Awkwardness is the emotion that we feel when the person we believe ourselves to be is momentarily facing a gap between that and the person on display.”

“Bad awkward occurs when that awkward feeling consumes us… Good awkward is when we take those moments in stride, learn to deal with them, actually lean into them.”

“Improv is an accelerator for embracing our awkwardness because improv is built on this principle that you don’t know what the other person is going to say next, but you’re going to lean in anyway.”

“We can experience it [awkwardness] as a state…but many people do refer to themselves as awkward as a trait…if it’s holding you back, then we need to be careful about using that identity language.”

“The emotion of awkwardness is often one of the obstacles we need to overcome or become friends with more accurately in order to access our true authenticity.”

“Awkward confidence is the new cool. Do it awkward, but do it anyway. Don’t wait until you’re ready.”





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