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

In this episode of Success Leaves Clues, host Robin Bailey and co-host Al McDonald sit down with Connor Bays, Head of Sales and Partnerships at Common Wealth Retirement, to explore how technology, inclusion, and purpose are reshaping financial wellness and the future of retirement.

Connor shares his journey as a competitive runner turned mission-driven leader helping Canadians achieve lifelong financial security. Through his work at Common Wealth, he’s redefining how small and mid-sized businesses can offer accessible, high-impact retirement plans that support employee wellbeing and retention.

Together, they dive into the realities of financial stress, the misconceptions about cost and complexity in group retirement programs, and the profound shift from viewing retirement as an ending to embracing it as a new beginning.

This conversation blends insight and empathy, showing how small changes in how we save, educate, and communicate about money can spark long-term transformation, for both employees and employers.

You’ll hear about:

• Mission-driven innovation: How Common Wealth is closing the retirement gap for Canadians.
• Financial accessibility: Why smaller businesses can and should offer group retirement benefits.
• Common misconceptions: Breaking down the myths around cost and complexity.
• Financial stress and wellbeing: How retirement planning contributes to mental and emotional health.
• Engaging younger generations: Why millennials and Gen Z care deeply about their financial future.
• Technology meets trust: Using digital tools to personalize financial planning at scale.
• Redefining retirement: From an end point to a new phase of meaning, purpose, and contribution.
• Employer wins: Why group retirement plans are a competitive advantage for engagement and culture.

We talk about:

• 00:00 Introduction
• 03:00 From competitive running to leading at Common Wealth
• 04:00 How Common Wealth is closing Canada’s retirement gap
• 06:00 The biggest barriers to offering group retirement plans
• 09:00 Financial literacy and breaking the taboo around money
• 10:00 Retirement planning as part of overall wellbeing
• 12:00 How younger generations are engaging with retirement savings
• 15:00 Making financial confidence accessible through technology
• 18:00 Balancing fees, service, and meaningful financial outcomes
• 20:00 Personalization in benefits: what employees truly want
• 22:00 The evolution of retirement: purpose, health, and longevity
• 25:00 The psychology of retirement and identity beyond work
• 27:00 Wins for employers heading into 2026: new and upgraded plans
• 30:00 Planting trees for future generations through better access and education

Connect with Connor

• LinkedIn: https://www.linkedin.com/in/connorbays
• Website: https://www.commonwealthretirement.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, host Robin Bailey and guest co-host Cory Chadwick sit down with Jessica Pezim, Client Partner at Bedford Consulting Group, to explore how leadership, culture, and human connection shape organizational success.

Jessica shares her journey from practicing securities law to leading executive search and leadership advisory at Bedford. With a unique background spanning law, finance, and talent strategy, she brings deep insight into how the right leadership match can transform not just an organization but lives.

Together, they discuss what it takes to hire beyond the résumé, build cultures that thrive on belonging, and navigate transformation with empathy and purpose. From AI-driven fear to family business dynamics, this conversation blends strategy with humanity, showing that careers are, at their core, deeply human stories.

You’ll hear about:

• From law to leadership: How Jessica pivoted from securities law to executive search and why she never looked back.
• Family in business: The rewards and realities of working with family in a multigenerational company.
• Ripple effects in leadership: How one placement can change lives, organizations, and communities.
• Culture fit vs. skill fit: Why the best person on paper isn’t always the right person for the role.
• Hiring with heart: How Bedford’s 93% success rate comes from prioritizing alignment, not just experience.
• The role of AI in talent strategy: How leaders can navigate technological change with transparency and trust.
• Mentorship and legacy: Why paying it forward and planting seeds for others defines lasting leadership.

We talk about:

• 00:00 Introduction
• 03:00 From law to executive search and Jessica’s bold career pivot
• 07:00 Family business dynamics and lessons learned from twin mentors
• 10:00 The ripple effect of leadership and the power of impact
• 16:00 Preventing burnout and balancing high performance with humanity
• 17:00 The competency model and why Bedford’s 93% success rate matters
• 18:00 The best person vs. the right person and the difference that changes everything
• 20:00 Values, culture fit, and why alignment matters more than perfection
• 22:00 Diversity of thought and inclusive hiring in times of transformation
• 26:00 AI, fear, and the future of work
• 30:00 Legal meets leadership and Jessica’s unique approach to talent strategy
• 34:00 Planting trees for future leaders, mentorship, purpose, and legacy

Connect with Jessica

• LinkedIn: https://www.linkedin.com/in/jessica-pezim-a73b2752/
• Website: https://bedfordgroup.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, host Robin Bailey and guest co-host Cory Chadwick sit down with Mike Daser, Senior Vice President of Human Resources at Pure Technology, to explore what it means to lead with heart, empathy, and inclusion in today’s evolving workplace.

With over 15 years of experience building cultures that balance people and performance, Mike shares powerful lessons from his time at Starbucks and Target, and how those experiences shaped his leadership philosophy. Known for his belief that great leadership starts with empathy, Mike opens up about his passion for supporting newcomers to Canada, building trust-first teams, and creating cultures where everyone feels seen, valued, and supported.

From “Don’t move the mocha” to hiring for values over skills, this episode is packed with insight, authenticity, and heart.

You’ll hear about:

• Falling in love with people: How Mike’s early experiences at Target changed how he sees leadership and humanity.
• The “Don’t Move the Mocha” lesson: Why great leaders listen first, learn second, and lead through trust.
• Culture fit vs. skill fit: Why attitude and alignment matter more than résumés.
• Supporting newcomers to Canada: How employers can create truly inclusive, equitable workplaces beyond surface-level initiatives.
• The power of mentorship: Lessons from coaching newcomers through job searches, interviews, and cultural transitions.
• Storytelling as leadership: How humanizing yourself builds connection, trust, and belonging.
• Resilience and perspective: Why life goes on, and how setbacks can lead to new opportunities.
• Planting trees for the future: Mike’s vision for a global workforce where talent and potential transcend borders.

If you’re an HR professional, business leader, or anyone passionate about people-first leadership, this conversation is a masterclass in leading with empathy, purpose, and connection.

We talk about:

• 00:00 Introduction
• 04:00 Falling in love with people and stories
• 07:00 The “Don’t Move the Mocha” principle of leadership
• 10:00 Lessons from Target and values-driven hiring
• 13:00 Creating inclusive workplaces for newcomers
• 16:00 Bias, belonging, and the hiring gap
• 21:00 Supporting immigrants inside organizations
• 25:00 Mentorship, storytelling, and authenticity in leadership
• 30:00 Building trust through shared humanity
• 33:00 The trees Mike is planting for future leaders

Connect with Suzanne

• LinkedIn: https://www.linkedin.com/in/mike-daser-phri-72b2028a
• Website: https://puretechnology.ai/

Connect with Us

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