Beyond the Checkbox

Why a 100-year-old origin story still drives worker engagement | #76 ft. Stephen Fletcher


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Practical strategies for employee engagement across a distributed workforce in decentralized teams.

Host Dr. Ryan Todd sits down with Stephen Fletcher, CHRO of Canada Cartage, to explore what it really takes to keep people engaged, supported, and psychologically safe in one of the most decentralized and traditional industries: transportation.

Watch this episode to find out:

  • Why meaningful work and shared purpose still drive engagement across every sector.
  • How economic pressures and workforce turnover are reshaping the transportation industry.
  • The role frontline supervisors play in employee engagement—and why they make or break culture.
  • How origin stories and organizational history build pride and discretionary effort.
  • What psychological safety looks like in a male-dominated, “toughness-first” environment.
  • Why isolation, access barriers, and time pressures keep employees from seeking mental health support.
  • How HR leaders can “meet people where they are” with practical, realistic strategies.

Stephen offers a grounded look at the realities of engaging a highly distributed workforce while navigating industry change. This conversation equips leaders with a clearer view of psychological safety, modern engagement practices, and what it means to support people through unprecedented pressures.

Guest Speaker

Stephen Fletcher, M.B.A., CHRL, is the Chief Human Resources Officer at Canada Cartage and an award-winning HR executive known for guiding complex, decentralized organizations through growth and transformation. With deep expertise across private equity, public companies, and regulated sectors, he specializes in strategic planning, change leadership, and building scalable people systems. Stephen is also a former Board Director and Chair of the Human Resources Compensation Committee for the Human Resources Professionals Association, where he advanced governance, succession planning, and professional standards.

Podcast Host

Dr. Ryan Todd is a psychiatrist, mental health advocate, and co-founder of Headversity, a workplace mental health training solution. Dr. Todd combines his clinical expertise with innovative approaches to empower individuals and organizations to thrive.

👉 Connect for the latest insights directly in your feed: Headversity on LinkedIn

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Beyond the CheckboxBy Dr. Ryan Todd


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