257: Tony Dina: "The Empty Feeling After The Title And The Money"

Tony Dina shares how his shift from CTO work into Jungian depth coaching led him to a central belief: when you rush toward answers, metrics, and momentum, you lose human judgment, creativity, and meaning. Using dreams, shadow work, and “sitting with the mystery,” he explores what it takes to reclaim purpose in careers shaped by AI. 👤 About the Guest Tony Dina is a Jungian depth coach and founder of Crucial Canvas. After nearly 30 years in technology leadership, including roles at Dell in AI and

Henna Pryor traces her path from Big Four auditing to executive search to keynote and best-selling books, sparked by a desire to move the needle for leaders, not just check boxes. We explore “social muscle atrophy,” the new “verification era,” and why leaders must build trust through “costly signals” and proactive honesty. 👤 About the Guest Henna Pryor, CSP is an award-winning author and keynote speaker with a background at a $2B executive search firm. She helps leaders navigate influence, beli

🧠 Erik’s Take This short review mattered because it challenged a habit Erik has seen in leadership and in himself: focusing on what’s being said while ignoring whether the other person is willing and able to participate. He feels Molly’s lens cut through the “better communication will fix everything” storyline. What stuck is the shift from persuasive accuracy to relational conditions, where honest exchange depends on both a speaker’s skill and a listener’s openness. 🎯 Top Insights from the Inte

🧠 Erik’s Take Erik reflects on how the conversation with Jason Lauritsen landed because it challenges a very familiar leadership pattern: treating “connection” like something that happens after work starts, rather than something leaders design before performance expectations are set. What stuck is the inversion. If connection drives motivation, then building relationships and meaning is not a soft add-on. It is upstream management. Erik also feels the discomfort of how often leaders measure what

Erik and Molly dive into the real skill behind “speaking up” and why organizations fail: they don’t have an accurate shared reality—essential to actually make the best decisions, execute, and deliver great outcomes. Molly shares a simple, flexible framework that all professionals can apply: “Me–You–We” and explains how leaders and teams can create mutual understanding, hear tough truths, and turn communication into trust and faster execution. 👤 About the Guest Molly Tschang is a founder of Abe

Erik and Jason Lauritsen dig into what “connection” really means at work, what drives it, and how it translates into motivation, performance, and retention. Jason shares findings from the Human Connection Study, including why “resonance” with purpose can matter more than human-to-human rapport. 👤 About the Guest Jason Lauritsen is CEO of Connected Performance Group and an advisor to leaders who refuse to choose between results and people. He developed Connected Performance Systems and helped pu