In this episode of Executive Success (12-04-2025), host Lesley Everett sits down with Mark Rockliffe, CEO of Pembroke Financial Services, to explore the leadership choices, habits, and defining moments that shape extraordinary executives. Drawing on his experience across SEI, Bank of Montreal, Zurich Group, and his own consultancy, Mark reflects on how early regulatory challenges reshaped his view of leadership—from focusing purely on numbers to prioritizing people, behaviors, and trust.
The conversation dives into practical leadership lessons, including empowering teams during uncertainty, building confidence through culture, and surrounding yourself with diverse talent rather than like-minded thinkers. Mark shares why true performance comes from investing in people, creating environments where individuals can grow beyond their comfort zones, and leading with humility rather than ego. The episode also explores how client-centric values, accountability, and long-term thinking drive sustainable success in highly technical industries.
Whether you’re an executive, entrepreneur, or professional stepping into leadership, this episode delivers grounded insights on building resilient teams, shaping culture with intention, and leading through change without burning out. Tune in for real-world perspectives on trust, empowerment, and the mindset required to lead effectively in today’s evolving business landscape.
Chapters
- (00:00:00) - Executive Success: The Choices Made by Superstars
- (00:00:36) - When Did Leadership Become More About People and Behavior?
- (00:03:01) - What originally drew you to Pembroke?
- (00:07:06) - What Do Leaders Need To Know to Lead?
- (00:08:48) - Executive Success
- (00:09:48) - The Heart of Leadership in Financial Services
- (00:10:43) - How to Balance Trust, Performance, Regulation and Innovation
- (00:11:24) - The culture of the financial services industry
- (00:14:06) - How to create a culture of accountability and growth
- (00:17:34) - Have You Ever Question Your Values?
- (00:19:59) - Mark Flannery
- (00:20:57) - Executive Success
- (00:21:56) - Pembroke Brand: Reputation and Authenticity
- (00:28:11) - Have Authenticity Strengthen the Trust with Clients?
- (00:30:26) - What is Authenticity and Credibility in Leadership?
- (00:33:24) - Executive Success
- (00:34:13) - Executive Success
- (00:34:53) - Staying Connected as a CEO
- (00:40:05) - Have You Been Tested in Your Resilience?
- (00:41:59) - Pembroke Advice's legacy
- (00:43:39) - The Future of Technology in Financial Advice
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