In this episode of Motivation Local, host Corey sits down with Dianne Wilkins, a born-and-raised Hatter whose journey has taken her from Medicine Hat to Mobile, Stockholm, Manhattan, Palm Springs, Calgary, and beyond. A former CEO of global digital agency Critical Mass and a Harvard Advanced Leadership Fellow, Di shares her reflections on place, leadership, identity, and resilience. From her early ambitions to “get out” of Medicine Hat, to her eventual pride in her roots while thriving on global stages, she offers a rich and thoughtful conversation. She also explores how community confidence, grit, and personal connection — formed at places like Connaught Golf Club and Swirls — fuelled her leadership path. Throughout, she speaks candidly about transition, the challenges of post-career life, and the power of mentorship, particularly for women in leadership.Timestamps:00:00 – 01:26 Corey introduces the season’s theme01:26 – 02:09 Land acknowledgment and context-setting 02:09 – 02:54 Introduction of guest Dianne Wilkins: global CEO, Harvard Fellow, and Medicine Hat native.02:54 – 04:14 Starting with Dianne’s recent transitions: stepping down as CEO, moving into consulting, investing, and chair work.04:14 – 05:06 Explaining the Nama Fund: investing in female-led companies and proving the value of female leadership.05:06 – 06:13 Harvard Advanced Leadership Fellowship experience — a life-changing return to education.06:13 – 07:01 Staying connected to Harvard through board work and ongoing leadership contributions.07:01 – 08:10 Dianne’s thoughts on redefining retirement as “post-achievement” — choosing passion over proving value.08:10 – 09:13 The shift from a team environment to solo projects and the impact on motivation.09:13 – 10:37 Reflections on identity: moving from constant collaboration to self-driven work and solitude.10:37 – 12:00 Exploring how living in diverse places like Alabama, Stockholm, Manhattan, and Palm Springs shaped Dianne’s identity.12:00 – 13:25 Medicine Hat’s impact: ambition, drive, and a desire for more, forged from small-town roots.13:25 – 16:14 Contrast between Medicine Hat upbringing and thriving in New York City’s corporate world.16:14 – 17:53 Dianne’s knack for building lifelong friend groups at every stage — from high school to Harvard.17:53 – 19:00 Early examples of leadership tendencies — from neighbourhood lemonade stands to professional leadership.19:00 – 22:10 The importance of decision-making as a core leadership skill, developed over time through career experiences.22:10 – 24:01 First memories of Medicine Hat — the Stampede Parade and cowboy culture.24:01 – 25:25 Nostalgia for local landmarks: Riverside Waterslide, Swirls, and golf culture at Connaught.25:25 – 27:02 Recreating the joy of teenage summers — evening golf games and community connections.27:02 – 28:06 Exchange trip memories — a pivotal experience spending time in Quebec during high school.28:06 – 30:00 Confidence built through a tight-knit community and early leadership experiences in Medicine Hat.30:00 – 31:03 How hometown experiences shaped Dianne’s leadership and commitment to mentoring women.31:03 – 33:08 The importance of building networks, mentorship, and supporting female leadership through Norma Fund and other initiatives.33:08 – 36:20 Personal board of directors concept — the power of having diverse, trusted voices in life and leadership.36:20 – 39:04 Female leaders Dianne admires — spotlight on Lisa Su, CEO of AMD, and her remarkable leadership story.39:04 – 41:13 Stories about Dianne’s childhood home — including a freezing bedroom that might have forged resilience!41:13 – 44:07 Advice for communities like Medicine Hat: building identity through core values and clear vision, not structures.44:07 – 47:02 Potential future guests for the podcast: Trevor Linden and Jim Horsman.47:02 – 48:01 Closing remarks, gratitude, and a reflection on new things learned during the conversation.