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