Exploring Character-Driven Leadership and Learning from Mistakes with Kimberley Milani

My Favorite Mistake: Business Lessons from Failures and Success

My guest for Episode #272 of the My Favorite Mistake podcast is Kimberley Milani, the Director of the Ian O. Ihnatowycz Institute for Leadership and Co-Founder of its Women’s Leadership and Mentoring Program at Ivey Business School in London, Ontario.

Episode page with video, transcript, and more

She is the co-author of the book Character: What Contemporary Leaders Can Teach Us about Building a More Just, Prosperous, and Sustainable Future.

She is passionate about elevating people’s strength of character to not only enhance their leadership skills, but to generate systemic social and organizational change. She is the co-host of Sip & Speak, a webinar series that explores social justice issues from a gendered and intersectional perspective.

Prior to joining Ivey, Kimberley spent 10 years as the Director of The Circle Women’s Centre, a community-facing feminist centre at Western’s Brescia University College.

The Circle operated in collaboration with London’s women’s, Indigenous, and social justice organizations to facilitate respectful, inclusive, multicultural, and inter-faith relationships, dialogue, events, and initiatives.

She was also a founding member of the Institute for Women in Leadership (IWIL) at Brescia and was its Director for seven years. Kimberley is a graduate of the University of Toronto.

In today's episode, Kimberley shares her journey from studying science with plans to pursue medicine to finding her true passion in Celtic Studies—a "mistake" that led her to a fulfilling career in leadership and academia. We discuss the importance of character in leadership, how it’s developed over time, and the impact of legacy. Kimberley also offers insights on how we can all cultivate strong character and the role it plays in achieving meaningful success.

Questions and Topics:

• What would you say is your favorite mistake in your career?
• How did studying Celtic mythology shape your views on leadership?
• Did you ever imagine your career path leading to academia or university-related centers?
• How do you define character, and what is character-based leadership?
• Can people with strong character still make mistakes, and how do they respond?
• How do you evaluate someone’s character when considering a job or a new leader?
• How much of character is innate versus developed over time?
• What can contemporary leaders teach us about character-based leadership?
• How important is it for leaders to consider the legacy they want to leave behind?