Product & Technology Leadership in the Era of AI and Human Connection with Hilary Aylesworth

In this episode of Emotional Business, Olga Skipper speaks with Hilary Aylesworth—a former educator turned product strategist and AI leader. Hilary brings a unique perspective on leadership, weaving together her background in teaching, her work in AI at CoachHub, and her lived experience as both a professional and a parent. This conversation explores how intuition, transparency, and emotional intelligence can shape leadership in the fast-moving world of technology. From the ethics of AI in coaching to the realities of systemic loneliness at the top, Hilary offers both practical and deeply human insights. This conversation explores: How a background in education shapes product and leadership decisions Why emotional intelligence is the bedrock of effective tech leadership The ethics of AI in coaching and development Balancing professional ambition with motherhood Caregiving as a leadership strength—not a weakness Why executives underestimate loneliness—and the power of asking for help For leaders navigating technology, AI, and human connection, Hilary’s perspective is both refreshing and essential.   https://www.coachhub.com/  https://www.linkedin.com/in/hilaryaylesworth