In this episode of Success Leaves Clues, hosts Robin Bailey and Al McDonald welcome Neena Gupta, Partner at Gowling WLG and one of Canada’s most respected voices in employment, labour, and human rights law. Neena brings a refreshingly human lens to the legal world, blending precision with empathy, mentorship, and real-world practicality.

Neena shares her journey as a South Asian woman in law, her passion for mentoring the next generation, and how trust in leadership is built at the intersection of competence and kindness. Together, they explore today’s workplace challenges including generational shifts, inflation pressures, hybrid work, recruitment struggles, and the evolving definition of work life balance.

The conversation also dives into what foreign companies must understand when expanding into Canada, the importance of strong employment agreements, and why proactive legal relationships save time, money, and stress. Neena closes with a powerful reflection on community, service, and planting trees for future generations through her leadership with United Way.

This episode is a grounded, insightful masterclass on leadership, people-first systems, and building businesses with integrity in complex economic times.

You’ll hear about:

• Neena’s path into law and mentoring young professionals
• Why trust is built through competence and kindness
• Generational shifts in work life balance and employee expectations
• The real challenges employers face with recruitment and retention
• How inflation is impacting employees and businesses across Canada
• Why hybrid work is here to stay
• Key pitfalls for foreign companies expanding into Canada
• The importance of employment agreements as risk management tools
• How to build a proactive relationship with your lawyer
• Planting trees for the future through community leadership and service

We talk about:

• 00:00 Introduction
• 03:00 Neena’s journey into law and mentoring young professionals
• 05:30 Balancing legal precision with personal approachability
• 07:30 Trust at the intersection of competence and kindness
• 09:30 Recruitment, retention, and generational workplace shifts
• 12:00 Inflation pressures on employees and employers
• 14:30 Hybrid work, flexibility, and modern leadership
• 17:00 Expanding into Canada, legal pitfalls and must know foundations
• 20:00 Employment agreements and foreign employer risk management
• 22:30 Benefits, compliance, and cross border considerations
• 25:00 How to work effectively with your lawyer
• 28:00 Building proactive legal relationships
• 30:00 Planting trees through mentoring and community leadership
• 32:30 Neena’s work with United Way and giving back
• 35:00 Final reflections on leadership, service, and purpose

Connect with Neena

• LinkedIn: https://www.linkedin.com/in/neena-gupta-0107aa4
• Website: https://gowlingwlg.com/en-ca

Connect with Us

• LinkedIn: Robin Bailey and Al McDonald
• Website: Aria Benefits and Life & Legacy Advisory Group