In this episode of Success Leaves Clues, hosts Robin and Al are joined by Naomi Titleman, Co-Founder of future foHRward and former CHRO of American Express Canada, for a deeply thoughtful conversation about leadership, HR, and what it truly means to make work better in today’s complex world.

Naomi shares her journey from consulting at Deloitte to senior HR leadership at American Express, and eventually to building future foHRward, a consultancy and community dedicated to empowering HR leaders to lead with empathy, curiosity, and courage. She offers a refreshingly human perspective on HR’s evolving role, explaining why the function is no longer about policy and gatekeeping, but about supercharging human performance.

Together, they explore the realities of modern leadership, including the loneliness of senior HR roles, the tension between flexibility and productivity, and why culture lives or dies through day-to-day leadership behavior. Naomi also dives into how AI can free HR leaders from administrative overload, allowing them to focus more deeply on people, relationships, and critical thinking.

The conversation wraps with a powerful reflection on legacy, mentorship, and the responsibility today’s leaders have to plant trees for future generations, even when they may never sit in the shade themselves.

This episode is an insightful, grounded exploration of leadership, culture, and the future of work through a human-centered lens.

You’ll hear about:

• Naomi’s journey from consulting to CHRO to co-founding future foHRward
• Why HR leadership can be deeply lonely at the senior level
• What it truly means to “make work better”
• The shift from efficiency to effectiveness in leadership
• Why culture is shaped by everyday leadership behavior, not slogans
• The real meaning of flexibility and hybrid work
• How asking and listening builds trust inside organizations
• Why leaders must own people outcomes, not outsource them to HR
• How AI can enhance, not replace, the human side of HR
• Planting long-term impact through mentorship and leadership

We talk about:

• 00:00 Introduction
• 03:30 From consulting to American Express Canada
• 05:30 Founding future foHRward and building an HR community
• 08:00 Why HR leadership can feel isolating
• 10:00 Supercharging human performance
• 12:30 Flexibility, hybrid work, and the power of “and”
• 15:00 Leadership effectiveness versus efficiency
• 17:30 Culture, wellbeing, and day-to-day employee experience
• 19:30 Asking employees for feedback and actually listening
• 22:00 Handling feedback you cannot act on immediately
• 24:30 Common blind spots organizations still face
• 26:30 AI, automation, and the future of HR
• 29:00 Preserving the human in human resources
• 31:00 Planting trees through mentorship and legacy leadership
• 33:00 Final reflections on purpose and making work better

Connect with Naomi

• LinkedIn: https://www.linkedin.com/in/naomititlemancolla/
• Website: https://www.futurefohrward.com/

Connect with Us

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

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

In this episode of Success Leaves Clues, hosts Robin and Al sit down with Jocelyne Moyer, Senior Vice President of Strategy and Operations at Zeitview, to explore the intersection of operations, artificial intelligence, leadership, and sustainable growth in high-risk, high-impact industries.

Jocelyne shares her journey from engineering and large-scale food manufacturing at Maple Leaf Foods and PepsiCo, through consulting at Bain & Company, to leading AI-powered infrastructure inspections at Zeitview. Along the way, she reveals the surprising through line that connects manufacturing, data, and modern asset intelligence, and how operational discipline becomes the foundation for innovation.

Together, they dive into how AI is transforming industries like solar, wind, and utilities through aerial imaging and anomaly detection, how leaders balance long-term strategy with short-term execution, and why people, not just processes or technology, remain the true drivers of performance.

This conversation blends sharp operational insight with grounded leadership philosophy, offering listeners a masterclass in building systems that scale, teams that thrive, and businesses that plant trees for the future.

You’ll hear about:

• From factory floors to AI platforms: Jocelyne’s unique career arc
• Why sustainable systems outperform heroic effort
• How AI is used to inspect solar, wind, and utility infrastructure at scale
• The real role of human analysts in AI-powered environments
• Balancing short-term revenue with long-term strategic alignment
• Making difficult customer and resource allocation decisions with integrity
• Why operations is where strategy becomes real
• Building high-performance teams that still have fun
• The importance of repeatable, scalable process design
• Planting trees for the future through operational leadership

We talk about:

• 00:00 Introduction
• 03:30 Jocelyne’s early fascination with engineering and manufacturing
• 06:30 From food manufacturing to Bain and back to operations leadership
• 09:00 The hidden connection between stale inventory and data backlog
• 12:00 Why people drive performance in operational environments
• 15:00 How Jocelyne evaluates systems, metrics, and bottlenecks
• 17:30 Cost structures, pilot networks, and operational decision-making
• 19:30 Balancing short-term pressures with long-term strategic vision
• 22:30 Customer fit, service levels, and sustainable growth
• 24:30 How Zeitview uses AI for aerial infrastructure inspections
• 27:00 Training AI models on proprietary industrial datasets
• 29:30 Scaling anomaly detection with human-AI collaboration
• 31:30 Leadership philosophy: serious work, lighthearted teams
• 34:00 Planting trees through sustainable systems and process design
• 36:30 Final reflections on change, systems, and people-first leadership

Connect with Jocelyne

• LinkedIn: https://www.linkedin.com/in/jocelyne-moyer/
• Website: https://www.zeitview.com/

Connect with Us

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