Meet Andy – Don’t Eliminate Awkwardness, Train for It

Meet Andy. He’s a software program manager with years of experience and a team that counts on him. But lately, he feels like he’s barely holding it together. His mornings are chaotic, he isolates himself at work, and he keeps important thoughts to himself—afraid to speak up, afraid to ask for help. Andy is smart, capable, and well-read, but his confidence is waning. He’s stuck in the rhythm of just getting by, and his default mode has become managing everything alone. What he really wants is to lead with confidence, communicate more clearly, and engage meaningfully—but he doesn't know how to break the cycle. In this episode, Jay is joined by Henna Pryor, a workplace performance expert, global keynote speaker, and author of Good Awkward. Together, they explore how leaders like Andy can stop waiting for comfort to arrive and start conditioning for discomfort instead. From asking for help to building meaningful relationships and showing up with authenticity, Henna offers science-backed strategies to navigate awkwardness and strengthen the social muscles needed to thrive in today’s disconnected world. Notable Quotes “People aren’t necessarily lonely. They’re just comfortable in their aloneness.” — Henna Pryor “The world isn’t short on ideas. It’s short on execution.” — Henna Pryor “We have to be intentional about social strength the same way we are about physical strength.” — Jay Abbasi About Our Guest Henna Pryor is a two-time TEDx speaker, global keynote presenter, and workplace performance expert. Her bestselling book Good Awkward highlights how embracing discomfort can unlock growth, resilience, and leadership potential. As founder of The Pryority Group, Henna helps leaders build mental and social fitness so they can communicate effectively, take smart risks, and elevate their performance. Her work has been featured on NBC, Forbes, and Fast Company, and her research-backed programs help clients stretch outside their comfort zones—and succeed because of it. Resources and Links Henna Pryor Website: https://pryoritygroup.com/ Book (Good Awkward): https://a.co/d/fZjyHpo LinkedIn: https://www.linkedin.com/in/hennapryor/ Instagram: https://www.instagram.com/hennapryor/ Facebook: https://www.facebook.com/hennapryorcoach/ Jay Abbasi Website: https://jayabbasi.me/ LinkedIn: https://www.linkedin.com/in/jayabbasi/ Instagram: https://www.instagram.com/jayabbasi_/ Facebook: https://www.facebook.com/thejayabbasi/ YouTube: https://www.youtube.com/@jayabbasipodcast Join Us Next Time On Friday, Jay will walk you through a simple framework for asking for help—without feeling desperate, inferior, or awkward. If you’re someone who hesitates to reach out, this episode will give you the structure and mindset you need to make asking for help a habit that strengthens—not weakens—your leadership. Stay inspired, stay resilient, and stay connected to what truly matters.