In this dynamic panel, we will present three long-time coworkers, each having diverged into distinct career paths within technology and leadership, and they will reunite to share their unique perspectives. Covering a span of 30 years, they explore the evolution of technology and leadership through their individual journeys in finance and project management, executive leadership in academia, and varied roles in IT and innovation. This presentation promises a blend of insightful reflections, lively anecdotes, and professional wisdom, offering a fun and engaging look at the intersection of technology and leadership through the decades.