Success Leaves Clues: Ep281 with guest Stephanie Hollingshead, CEO of TAP Network

Success Leaves Clues with Robin Bailey and Al McDonald · 2026-02-05 · 33 min

0:00--:--

Topics in this episode

HR leadership Collaboration People and Culture peer support CEO journey

Episode notes

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.