Success Leaves Clues with Robin Bailey and Al McDonald

In this episode of Success Leaves Clues, host Robin Bailey and Al McDonald sit down with Stephanie Hollingshead, CEO of TAP Network, for a candid conversation about leadership, burnout, and the power of collaboration in Canada’s tech sector.  Stephanie shares how TAP Network has evolved from a small group of competing tech companies into a national community and infrastructure for people and culture leaders. What began as a conversation about competing for scarce talent has become a model for how collaboration, trust, and shared learning can strengthen an entire industry.  The conversation dives into the often-unspoken reality of leadership roles, particularly for people and culture professionals who sit in the uncomfortable middle of organizations. Stephanie speaks openly about burnout, isolation, and the emotional weight of roles that require balancing advocacy, execution, and trust from all sides.  Robin, Al, and Stephanie explore why collaboration works even among direct competitors, how trust is built over time, and why peer communities provide critical support when leaders are navigating layoffs, uncertainty, and rapid change. Stephanie also reflects on stepping into the CEO role, what surprised her about the broader leadership ecosystem, and why support and mentorship are far more available than many leaders realize.  The episode closes with a reflection on long-term impact, leadership responsibility, and the importance of building systems and communities that future leaders can rely on when navigating pressure, change, and complexity.  You’ll hear about:  Why TAP Network is more than a professional network, it’s industry infrastructure Collaboration versus competition in the tech sector How trust is built among peers and direct competitors Burnout and isolation in people and culture leadership roles Sitting in the uncomfortable middle of organizations Why peer community matters during layoffs and organizational change What surprised Stephanie most after becoming a CEO Leadership support systems many people overlook Where Canadian tech does people and culture well Where equity, diversity, and inclusion still need bold change Why small efforts aren’t moving the needle Building leadership systems that outlast individuals  We talk about:  00:00 Introduction and welcome 01:00 Stephanie’s background and leadership journey 03:00 What TAP Network is and why it exists 05:00 Collaboration as the foundation of the community 07:00 Choosing leaders and facilitators who energize the sector 09:00 Collaboration versus competition in tech 11:00 Building trust among peers and competitors 13:00 Burnout and the emotional weight of people and culture roles 15:00 Sitting in the uncomfortable middle of leadership 18:00 Community as protection against isolation and disengagement 20:00 Stepping into the CEO role and seeing the ecosystem differently 23:00 Mentorship, generosity, and leadership support 25:00 What tech companies get right about people and culture 27:00 Where equity, diversity, and inclusion still fall short 30:00 Why bold change is required to move the needle 33:00 Staying anchored through listening and connection 35:00 The signature question, planting trees for the future 37:00 How to connect with Stephanie and TAP Network  Connect with Stephanie  LinkedIn: https://www.linkedin.com/in/stephaniehollingshead  Website: https://tapnetwork.ca/   Connect with Us  LinkedIn: Robin Bailey and Al McDonald   Website: Aria Benefits and Life & Legacy Advisory Group