EPISODE · Mar 18, 2026 · 23 MIN
Henna Pryor: How to Stop Being Awkward
from Start With A Win · host Adam Contos
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 change,” Henna has spoken at TEDx and SXSW and is featured in outlets like FastCompany, INSIDER, HuffPost, NBC, and FOX. She’s also a SUCCESS Magazine Woman of Influence, LinkedIn Learning Instructor, Glassdoor WorkLife Pro, and her book was named a Kirkus Reviews Best Book of the Year.00:00 Intro01:27 Did you just want to fit it? The three word tag line…04:26 Is this parallel to this? No, it’s this!07:05 Name the awkwardness that exists in the situation.11:30 The best tip!16:01 Do you use AI and how?18:55 This first then this second…21:28 I snuggle my puppy however this is the best way that will help most.www.pryoritygroup.comhttps://www.linkedin.com/in/hennapryor/ https://www.instagram.com/hennapryor/===========================Subscribe and Listen to the Start With a Win Podcast HERE:📱 ===========================YT ➡︎ https://www.youtube.com/@AdamContosCEOApple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT===========================Connect with Adam:===========================Website ➡︎ https://adamcontos.com/Facebook ➡︎ https://facebook.com/AdamContosCEOTwitter ➡︎ https://twitter.com/AdamContosCEOInstagram ➡︎ https://instagram.com/adamcontosceo/#adamcontos #startwithawin #leadershipfactory
What this episode covers
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 change,” Henna has spoken at TEDx and SXSW and is featured in outlets like FastCompany, INSIDER, HuffPost, NBC, and FOX. She’s also a SUCCESS Magazine Woman of Influence, LinkedIn Learning Instructor, Glassdoor WorkLife Pro, and her book was named a Kirkus Reviews Best Book of the Year.00:00 Intro01:27 Did you just want to fit it? The three word tag line…04:26 Is this parallel to this? No, it’s this!07:05 Name the awkwardness that exists in the situation.11:30 The best tip!16:01 Do you use AI and how?18:55 This first then this second…21:28 I snuggle my puppy however this is the best way that will help most.www.pryoritygroup.comhttps://www.linkedin.com/in/hennapryor/ https://www.instagram.com/hennapryor/===========================Subscribe and Listen to the Start With a Win Podcast HERE:📱 ===========================YT ➡︎ https://www.youtube.com/@AdamContosCEOApple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT===========================Connect with Adam:===========================Website ➡︎ https://adamcontos.com/Facebook ➡︎ https://facebook.com/AdamContosCEOTwitter ➡︎ https://twitter.com/AdamContosCEOInstagram ➡︎ https://instagram.com/adamcontosceo/#adamcontos #startwithawin #leadershipfactory
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Henna Pryor: How to Stop Being Awkward
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