Brian Shickluna on How Legacy Mindset Limits Tech Teams

Brian Shickluna, Director of Software Engineering at Staples Canada, joins Mudassar Malik on Behind the Growth to unpack the leadership principles and organizational design strategies that have shaped his career. Drawing on experience from startups to large enterprises, Brian shares what it really takes to build and scale high-performing engineering teams. 

The conversation begins with Brian’s reflections on his career path and how working across industries taught him the value of seeing beyond technical expertise. He explains why leaders need a breadth of perspective to guide teams effectively, especially as they move from hands-on roles to broader organizational influence. 

Further diving deep into the concept of “legacy mindset,” Brian explores why outdated thinking and overcomplicated processes often hold organizations back more than their tech stacks. He challenges common assumptions about transformation and describes how simplifying workflows and clarifying roles can unlock speed and agility at scale. 

Finally, Brian shares his approach to fostering a culture of experimentation, empowering teams to take ownership of their ideas, and avoiding the traps of micromanagement. He closes with practical insights on servant leadership, psychological safety, and why senior executives should prioritize structure and mindset as the foundation for sustainable growth. 

Brian unpacks topics like: 
- The silent risks of structural debt 
- Designing orgs that outlast people 
- Breaking out of micromanagement 
- Protecting engineers from alert fatigue 
- When structure beats great ideas 

Visit mobilelive.ca/podcast to learn more about each guest and read key insights for every episode.