Success Leaves Clues with Robin Bailey and Al McDonald

A Starting with One Podcast
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"If your actions inspire others to dream more, learn more, do more and become more ... you are a leader." ~ John Quincy Adams. We love sending our listeners on a journey of discovery as they learn about the inspiring lives of industry thought leaders, business owners, & entrepreneurs from all walks of life, who share one thing in common – SUCCESS! And it all starts with one—one idea; one conversation; one dream. Brought to you by Aria Benefits and Life & Legacy Advisory Group

  1. Success Leaves Clues: Ep281 with guest Stephanie Hollingshead, CEO of TAP Network

    3D AGO

    Success Leaves Clues: Ep281 with guest Stephanie Hollingshead, CEO of TAP Network

    In this episode of Success Leaves Clues, host Robin Bailey and Al McDonald sit down with Stephanie Hollingshead, CEO of TAP Network, for a candid conversation about leadership, burnout, and the power of collaboration in Canada’s tech sector.  Stephanie shares how TAP Network has evolved from a small group of competing tech companies into a national community and infrastructure for people and culture leaders. What began as a conversation about competing for scarce talent has become a model for how collaboration, trust, and shared learning can strengthen an entire industry.  The conversation dives into the often-unspoken reality of leadership roles, particularly for people and culture professionals who sit in the uncomfortable middle of organizations. Stephanie speaks openly about burnout, isolation, and the emotional weight of roles that require balancing advocacy, execution, and trust from all sides.  Robin, Al, and Stephanie explore why collaboration works even among direct competitors, how trust is built over time, and why peer communities provide critical support when leaders are navigating layoffs, uncertainty, and rapid change. Stephanie also reflects on stepping into the CEO role, what surprised her about the broader leadership ecosystem, and why support and mentorship are far more available than many leaders realize.  The episode closes with a reflection on long-term impact, leadership responsibility, and the importance of building systems and communities that future leaders can rely on when navigating pressure, change, and complexity.  You’ll hear about:  Why TAP Network is more than a professional network, it’s industry infrastructure Collaboration versus competition in the tech sector How trust is built among peers and direct competitors Burnout and isolation in people and culture leadership roles Sitting in the uncomfortable middle of organizations Why peer community matters during layoffs and organizational change What surprised Stephanie most after becoming a CEO Leadership support systems many people overlook Where Canadian tech does people and culture well Where equity, diversity, and inclusion still need bold change Why small efforts aren’t moving the needle Building leadership systems that outlast individuals  We talk about:  00:00 Introduction and welcome 01:00 Stephanie’s background and leadership journey 03:00 What TAP Network is and why it exists 05:00 Collaboration as the foundation of the community 07:00 Choosing leaders and facilitators who energize the sector 09:00 Collaboration versus competition in tech 11:00 Building trust among peers and competitors 13:00 Burnout and the emotional weight of people and culture roles 15:00 Sitting in the uncomfortable middle of leadership 18:00 Community as protection against isolation and disengagement 20:00 Stepping into the CEO role and seeing the ecosystem differently 23:00 Mentorship, generosity, and leadership support 25:00 What tech companies get right about people and culture 27:00 Where equity, diversity, and inclusion still fall short 30:00 Why bold change is required to move the needle 33:00 Staying anchored through listening and connection 35:00 The signature question, planting trees for the future 37:00 How to connect with Stephanie and TAP Network  Connect with Stephanie  LinkedIn: https://www.linkedin.com/in/stephaniehollingshead  Website: https://tapnetwork.ca/   Connect with Us  LinkedIn: Robin Bailey and Al McDonald   Website: Aria Benefits and Life & Legacy Advisory Group

    33 min
  2. Success Leaves Clues: Ep 280 - Power, Trust, and Leadership with Dean Benard, Founder and CEO of Benard & Associates

    JAN 29

    Success Leaves Clues: Ep 280 - Power, Trust, and Leadership with Dean Benard, Founder and CEO of Benard & Associates

    In this episode of Success Leaves Clues, host Robin Bailey and co-host Al McDonald welcome back returning guest Dean Benard, Founder and CEO of Benard & Associates, for an in-depth conversation on workplace investigations, leadership accountability, and organizational culture.  With more than 30 years of experience in regulatory and workplace investigations, mediation, and conflict resolution, Dean offers a rare inside look at how investigations really work, and why independence, fairness, and process matter more than speed or optics. He explains how power dynamics show up in investigations, from titles and tenure to fear of retaliation, and why investigations can act as a great equalizer when handled correctly.  The conversation explores what trauma-informed investigations actually mean, why they should apply to every participant, and how dignity and psychological safety improve accuracy rather than dilute outcomes. Dean also shares where leaders unintentionally undermine investigations, how rushing the process creates long-term risk, and why one complaint is often a signal of deeper cultural issues beneath the surface.  The episode closes with a powerful reflection on legacy, building systems that outlast us, and Dean’s vision for creating safer, fairer workplaces through education, innovation, and leadership responsibility.  You’ll hear about:  What workplace investigations really involve, beyond the stereotypes How power dynamics influence truth-seeking and trust Why investigator independence is non-negotiable Trauma-informed investigations and why they apply to everyone Common leadership mistakes that undermine investigations Speed versus quality and the hidden cost of rushing What makes a strong investigator, skill sets over credentials When one complaint reveals broader cultural problems Using investigations as an opportunity for organizational learning Building systems that create long-term workplace fairness  We talk about:  00:00 Introduction and returning to the conversation 01:00 Dean’s background and the work of Benard & Associates 03:00 Power dynamics and the role of independence in investigations 06:00 Treating everyone with dignity and respect in the process 08:00 Trauma-informed investigations and psychological safety 11:00 How leaders unintentionally interfere or undermine trust 14:00 Speed versus quality and why rushing creates risk 17:00 The skill sets that make a great investigator 20:00 When investigations reveal deeper cultural issues 22:00 Management insights and learning beyond the complaint 25:00 What’s next for Benard & Associates and the Bernard Group 28:00 Working with a spouse and building a business together 30:00 The signature question, planting trees for the future 33:00 How to connect with Dean  Connect with Dean  Personal LinkedIn: https://www.linkedin.com/in/deanbenard/  Company LinkedIn: https://www.linkedin.com/company/benard-associates/  Facebook: https://www.facebook.com/BenardInc  Instagram: https://www.instagram.com/benardinc/  YouTube: https://www.youtube.com/BenardAssociates  Website: https://www.benardinc.com/   Connect with Us  LinkedIn: Robin Bailey and Al McDonald   Website: Aria Benefits and Life & Legacy Advisory Group

    30 min
  3. Success Leaves Clues: Ep279 - Closing the Care Gap in Women's Health with guest Christine Lacey, VP of Revenue at Lume Women’s Health

    JAN 22

    Success Leaves Clues: Ep279 - Closing the Care Gap in Women's Health with guest Christine Lacey, VP of Revenue at Lume Women’s Health

    In this episode of Success Leaves Clues, host Robin Bailey is joined by special co-host Billi Moyer for a timely conversation with Christine Lacey, VP of Revenue at Lume Women’s Health, a Toronto-based women’s health clinic built for women by women, focused on proactive, personalized care that helps close longstanding gaps in women’s healthcare.  Christine shares how Lume was founded by four women (three physicians), and why women’s healthcare cannot be compared “apples to apples” with traditional models historically built around the male body. She explains why women are not “small men,” and how reproductive and hormonal health influences whole-body outcomes, from brain health to cardiovascular health, making sex-specific care essential across a woman’s life.  The conversation highlights the midlife care gap, how the system supports puberty and family planning, but often drops women when disease prevention, longevity, and true healthspan should be the focus. Christine also shares a striking stat, women live longer, but spend about 25% more time in poor health than men, strengthening the case for proactive care models.  They explore accessibility, equity, and why corporate Canada may be one of the fastest levers for progress, including advocacy like the push for a menopause billing code in Ontario. The episode closes with the future Christine wants for the next generation of women.  You’ll hear about:  What Lume Women’s Health is, and why it was founded “for women by women” Christine’s role as VP of Revenue and how she found her way into women’s healthcare Why traditional healthcare models weren’t built with women in mind Why women’s care can’t be compared “apples to apples” to existing models Hormones and reproductive health as the missing whole-body foundation The midlife care gap, prevention, longevity, and why women get “dropped” The stat that reframes everything, women spend ~25% more time in poor health Equity and access challenges, and who is most at risk of being left behind Why corporate benefits matter, and the ROI case for investing in women’s health The legacy Lume is building for the next generation  We talk about:  00:00 Introduction  01:00 Meet Christine Lacey, VP of Revenue at Lume Women’s Health 02:00 What Lume is, the mission, and who they serve 04:00 Christine’s path into women’s health and joining Lume early 05:00 The biggest misconception, why “apples to apples” comparisons fail 07:00 Hormonal and reproductive health as whole-body health 08:00 The midlife gap, prevention, longevity, and what’s missing 13:00 Lifespan vs healthspan, Peter Attia, and longevity-aligned care 15:00 The 25% stat, why women live longer but spend more time in poor health 17:00 Accessibility and equity, and why the current system isn’t fair 20:00 Who’s most at risk of being left behind (minority and remote communities) 21:00 Corporate Canada, women’s health ROI, and workplace leverage 25:00 Benefits utilization, friction, and what women need to feel supported 28:00 The signature question, planting trees for the next generation 31:00 How to connect with Christine and Lume  Connect with Christine  Personal LinkedIn: https://www.linkedin.com/in/christine-lacey-6073b94  Company LinkedIn: https://www.linkedin.com/company/lumewomenshealth/  Instagram: https://www.instagram.com/lumewomenshealth Website: https://www.lumewomenshealth.com/   Connect with Us  LinkedIn: Robin Bailey and Al McDonald   Website: Aria Benefits and Life & Legacy Advisory Group

    26 min
  4. Success Leaves Clues: Ep278 - Energy First, Growth Follows with guest Mark MacLeod, founder of Limitless CEO

    JAN 8

    Success Leaves Clues: Ep278 - Energy First, Growth Follows with guest Mark MacLeod, founder of Limitless CEO

    In this episode of Success Leaves Clues, hosts Robin Bailey and Al McDonald are joined by Mark MacLeod, founder of Limitless CEO and longtime advisor to high-growth founders, for an expansive and deeply honest conversation about leadership, burnout, energy, and what it truly takes to scale sustainably.  Mark shares his journey from serving as CFO to iconic Canadian tech companies like Shopify and FreshBooks, to venture capital, investment banking, and ultimately coaching CEOs through the most demanding chapters of their leadership lives. He explains why most startups fail not because of strategy or talent, but because founders run out of energy, physically, mentally, and emotionally.  Together, they explore why hustle culture quietly drives burnout, how founders normalize chronic stress, and why putting the CEO first is not selfish, but essential. Mark introduces his two core pillars of leadership, personal energy optimization and revenue growth, and explains how physical health, mental clarity, and even spiritual practices directly influence business outcomes.  The conversation also dives into identity loss after divorce, the role of journaling and gratitude in building self-awareness, and how leadership becomes a personal transformation journey disguised as a company. Mark offers practical tools leaders can use immediately, from sleep and breathwork to reframing success and reconnecting with purpose.  This episode is a powerful exploration of leadership from the inside out, challenging conventional startup narratives and inviting founders to scale with intention, clarity, and longevity.  You’ll hear about:  Mark’s evolution from CFO and venture capitalist to CEO coach Why founders burn out long before companies fail The normalization of stress in startup and executive culture Putting the CEO first as a strategy for sustainable growth Energy as the true driver of performance and valuation The hidden cost of hustle culture and constant comparison Leadership as a personal development journey The role of gratitude, journaling, and self-awareness Rebuilding identity after divorce and major life disruption Why inspiration, not force, fuels lasting success  We talk about:  00:00 Introduction and Mark’s background 03:00 Founding Limitless CEO and redefining scale 05:00 Energy as the foundation of leadership performance 07:00 Burnout, stress normalization, and founder identity 10:00 Physical, mental, and spiritual health in leadership 14:00 Hustle culture, fear, and comparison traps 17:00 Divorce, personal reckoning, and redesigning life 21:00 Journaling, self-awareness, and learning through reflection 25:00 Gratitude as fuel, not complacency 28:00 Why founders sell companies due to burnout 31:00 Leadership, legacy, and planting trees for the future 35:00 Practical tools, sleep, journaling, and next steps  Connect with Mark  LinkedIn: https://www.linkedin.com/in/themarkmacleod  Website: https://limitless.ceo/  Connect with Us  LinkedIn: Robin Bailey and Al McDonald   Website: Aria Benefits and Life & Legacy Advisory Group

    39 min
  5. Success Leaves Clues: Ep277 - Supercharging Human Performance & HR Leadership with guest Naomi Titleman, Co-Founder of future foHRward

    12/18/2025

    Success Leaves Clues: Ep277 - Supercharging Human Performance & HR Leadership with guest Naomi Titleman, Co-Founder of future foHRward

    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

    30 min
  6. Success Leaves Clues: Ep276 - The Human Side of Employment Law with guest Neena Gupta, Partner at Gowling WLG

    12/11/2025

    Success Leaves Clues: Ep276 - The Human Side of Employment Law with guest Neena Gupta, Partner at Gowling WLG

    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

    34 min
  7. Success Leaves Clues: Ep275 with guest Jocelyne Moyer, Senior Vice President of Strategy and Operations at Zeitview

    12/04/2025

    Success Leaves Clues: Ep275 with guest Jocelyne Moyer, Senior Vice President of Strategy and Operations at Zeitview

    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

    30 min
  8. Success Leaves Clues: From the Vault - Redefining Leadership and the Future of Work with guest Jodi Kovitz, CEO of the Human Resources Professionals Association (HRPA)

    11/27/2025

    Success Leaves Clues: From the Vault - Redefining Leadership and the Future of Work with guest Jodi Kovitz, CEO of the Human Resources Professionals Association (HRPA)

    In this From the Vault episode of Success Leaves Clues, hosts Robin and Al sat down with Jodi Kovitz, CEO of the Human Resources Professionals Association (HRPA), to explore how empathy, innovation, and inclusion are redefining leadership in today’s workplace.  Jodi shares her insight on why HR leaders must have a strategic seat at the table to influence the future of work. Drawing on her experience leading HRPA through transformation, she discusses how people-first leadership fuels performance, why empathy and accountability can coexist, and how hybrid work, AI, and generational diversity are changing what it means to lead.  This conversation is a masterclass in modern leadership, showing how purpose-driven strategy and human connection can drive both organizational success and national prosperity.  You’ll hear about:  The strategic seat at the table: Why HR leaders are essential to shaping business strategy and driving productivity. Empathy as strength: How leading with compassion builds trust, engagement, and loyalty. The brave workplace: Why leaders should focus on creating brave spaces instead of safe ones. Balancing five generations: How to meet diverse needs and build connection across changing workforce expectations. Preventing burnout: How proactive empathy, transparency, and mental health support protect teams in times of change. Redefining hybrid work: How to design flexibility that balances autonomy, collaboration, and inclusion. Humans and AI: Why the future of work depends on people guiding technology, not the other way around. Keeping talent in Canada: How people-first leadership can strengthen national prosperity and competitiveness. Authentic leadership: How showing vulnerability as a leader can inspire courage and connection across an organization.  We talk about:  00:00 Introduction   02:00 Why HR leaders deserve a strategic seat at the table 05:00 How people strategy drives business success 08:00 Empathy and vulnerability in leadership 10:00 Creating a brave workplace culture 13:00 Leading through generational change 16:00 Building flexibility and inclusion across teams 18:00 Preventing burnout and supporting mental health 20:00 Rethinking hybrid work and flexibility 25:00 The importance of communication in strong cultures 27:00 Investing in people to drive national prosperity 29:00 The role of AI and the human connection in future growth 31:00 HRPA’s upcoming summit and AI Skill Up course 33:00 How empathy and innovation shape the future of leadership   Connect with Jodi  LinkedIn: https://www.linkedin.com/in/jodikovitz  HRPA LinkedIn: https://www.linkedin.com/company/hrpa  YouTube: https://www.youtube.com/user/HRPATV  Instagram: https://www.instagram.com/hrpa_organization/  Facebook: https://www.facebook.com/TheHRPA/  Website: https://www.hrpa.ca/   Connect with Us  LinkedIn: Robin Bailey and Al McDonald   Website: Aria Benefits and Life & Legacy Advisory Group

    32 min
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"If your actions inspire others to dream more, learn more, do more and become more ... you are a leader." ~ John Quincy Adams. We love sending our listeners on a journey of discovery as they learn about the inspiring lives of industry thought leaders, business owners, & entrepreneurs from all walks of life, who share one thing in common – SUCCESS! And it all starts with one—one idea; one conversation; one dream. Brought to you by Aria Benefits and Life & Legacy Advisory Group

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