Is it the values written on the wall… or the behaviors happening behind closed doors?

In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Jessica Lewis from PointsBet to explore what it really takes to build high-performing teams, strong workplace cultures, and leadership environments where people genuinely thrive.

Jessica shares her journey from executive assistant to senior people leader, unpacking the lessons she’s learned while scaling teams in fast-paced, high-growth organizations. From mentorship and strategic hiring to difficult feedback conversations and leadership accountability, this conversation reveals why culture is never owned by one person. It’s built collectively, reinforced daily, and tested most during difficult moments.

This episode dives into the realities of modern leadership, including the growing role of AI in HR, the importance of trust and transparency, and why the best leaders understand that people strategy is business strategy. Jessica also shares her passion for creating more opportunities for women in leadership and building workplaces where more voices are welcomed to the table.

If you’ve ever wondered why some organizations create loyalty, growth, and energy while others quietly lose their best people, this conversation offers a powerful look at what separates healthy cultures from performative ones.

You’ll hear about:

• Why company culture is built through everyday behavior, not mission statements
• What leaders reveal about culture behind closed doors
• The hiring mistake that quietly damages organizations over time
• Why technical skill alone is never enough for leadership success
• How mentorship changes careers and builds long-term confidence
• The importance of giving feedback early and with kindness
• Why trust and transparency are critical for strong workplace cultures
• How AI is reshaping HR and the employee experience
• The role frontline managers play in reinforcing company values
• Why creating more women leaders matters for the future of business

We talk about:

• 00:00 Introduction to Jessica Lewis and PointsBet
• 02:00 From executive assistant to people leadership
• 04:30 Why HR became Jessica’s purpose and passion
• 06:30 Staying ahead in leadership through mentorship and community
• 08:30 The connection between leadership and company culture
• 10:00 What actually causes workplace culture to break down
• 11:30 Why culture is revealed behind closed doors
• 13:00 Hiring for values, not just technical competence
• 15:30 How fast-growing companies redefine leadership needs
• 17:00 Giving feedback early and building accountability
• 19:00 Technical skill vs cultural alignment, which matters more?
• 21:30 The leadership lessons mentorship creates
• 23:30 Building confidence as a woman in leadership
• 25:00 Why representation and equity in leadership matter
• 26:30 The future of workplace culture and leadership

Connect with Jessica

• LinkedIn: https://www.linkedin.com/in/jessica-lewis-86744352/ 
• Website: https://on.pointsbet.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, Robin Bailey and Al McDonald sit down with Dan Turner, CEO at Xperigo, to unpack a career built not on perfect timing or traditional paths, but on courage, persistence, and the willingness to step through doors before they fully open.

Dan’s journey starts far from the boardroom, as an 18-year-old tow truck driver with no clear direction. But one moment, one story, one decision to believe something bigger was possible, set him on a path that would eventually lead him to the CEO seat.

This conversation dives deep into what it really takes to grow into leadership, how calculated risks can redefine your career, and why the leaders who win today are the ones who lead with trust, vulnerability, and genuine care.

From spotting opportunity before it’s obvious, to building a culture that fuels performance, to redefining what great leadership actually looks like, this episode is a powerful reminder that success is not a straight line, it’s a series of brave choices made consistently over time.

If you’ve ever questioned whether you’re capable of more, or felt the pull toward something bigger but hesitated to act, this conversation will challenge you to rethink what’s possible.

You’ll hear about:

• Why one moment of belief can completely change the trajectory of your life
• How Dan Turner turned a bold hunch into a multi-million dollar opportunity
• The real reason most people stay stuck in their comfort zone
• Why risk is required if you want to reach your full potential
• How confidence is built through action, not certainty
• The mindset shift that turns “failure” into growth
• Why opportunity rarely announces itself, and how to spot it early
• How proactive thinking separates top performers from everyone else
• The role persistence plays in long-term success
• Why stepping outside your comfort zone is non-negotiable for growth

We talk about:

• 00:00 Introduction to Dan Turner and Xperigo
• 02:30 From tow truck driver to CEO, the origin story
• 05:00 The moment that sparked a bold, long-term vision
• 08:00 Why big goals feel overwhelming, and how to start anyway
• 11:00 Comfort zones vs. growth, why staying safe keeps you stuck
• 14:00 The Apple iPhone story, spotting opportunity before the world sees it
• 17:30 Turning a bold idea into a multi-million dollar deal
• 20:00 Risk, doubt, and why the upside is always worth it
• 23:00 The mindset that separates leaders from followers
• 25:30 Culture vs performance, why they fuel each other
• 28:00 Building trust, transparency, and high-performing teams
• 31:00 Leadership today, why vulnerability is a strength, not a weakness
• 34:00 The future of leadership and building a legacy that lasts

Connect with Dan

• LinkedIn: https://www.linkedin.com/in/turnerdan/ 
• Website: https://www.xperigo.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, Robin Bailey and Al McDonald sit down with Alison Kaizer, Partner of Talent at Golden Ventures, to break down the real mechanics behind building high-performing teams inside early-stage startups.

Alison has helped scale companies from dozens to hundreds of employees, and now supports founders across an entire portfolio, shaping the people decisions that determine whether a company grows or stalls.

This conversation pulls back the curtain on what actually makes a great hire, why most founders get it wrong, and how to build a hiring system that works before your company even knows what it needs.

From ditching resume bias to hiring for aptitude, from building structured interview systems to creating transparency in compensation, this episode is a masterclass in hiring as a strategic advantage.

If you’re building a team, scaling a company, or making critical early hires, this episode will completely shift how you think about talent.

You’ll hear about:

• Why resume-driven hiring is one of the biggest mistakes founders make 
• The difference between hiring for experience vs. hiring for aptitude 
• How to identify high-impact talent before it’s obvious on paper 
• Why past success doesn’t guarantee future performance 
• The role of structured interviews in eliminating hiring bias 
• How to build a repeatable hiring system that scales with your company 
• The hidden cost of hiring “safe” candidates instead of adaptable ones 
• Why early-stage companies should prioritize learning ability over playbooks 
• How transparency in compensation builds trust and closes top candidates 
• The real reason culture fit is often misunderstood and misused 
• How to assess values in a short interview process without guesswork 
• What founders need to understand about motivation, ambition, and timing

We talk about:

• 00:00 Introduction to Alison Kaizer and Golden Ventures
• 02:00 From consulting to recruiting, the unexpected career path
• 05:30 Scaling talent functions inside high-growth startups
• 08:30 The moment pattern recognition becomes a superpower
• 11:00 The biggest hiring mistake founders make (resume bias)
• 14:00 Why aptitude beats experience in early-stage companies
• 17:30 How to build structured interviews that actually predict success
• 20:30 The truth about “culture fit” and how to assess values properly
• 23:30 Scaling hiring without lowering the bar
• 26:00 Compensation transparency and building trust with candidates
• 29:00 Hiring in startups vs. enterprise environments
• 31:30 How AI is reshaping hiring and talent evaluation
• 33:30 The future of work and why adaptability wins

Connect with Alison

• LinkedIn: https://www.linkedin.com/in/alisonkaizer/ 
• Website: https://www.golden.ventures/ 

Connect with Us

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

In this episode of Success Leaves Clues, Robin and Al sit down with Sarah O’Brien, Chief Operating Officer at SMS Security, to explore the real leadership transformation required to grow a family business into a scalable, modern organization.

Sarah shares what it actually feels like stepping into a second-generation leadership role, navigating expectations, earning trust, and redefining what leadership looks like in a company built on legacy relationships.

From letting go of being the problem-solver, to building systems that don’t rely on one person, to leading in a 24/7 high-stakes industry, this conversation unpacks the mindset and operational shifts required to build a company that lasts.

If you’re leading a team, scaling a business, or transitioning leadership in any capacity, this episode will challenge how you think about control, trust, and long-term success.

You’ll hear about:

• What it really means to step into leadership in a family business 
• Why second-generation leaders are natural disruptors 
• The hidden challenge of earning trust inside your own company 
• How to shift from reactive problem-solving to scalable systems 
• Why leadership can feel lonely and how to build external support 
• The difference between technical competence and true trust-building 
• How listening, not solving, creates stronger teams and clients 
• Why consistency and communication define leadership credibility 
• How to lead in a 24/7, high-pressure industry without burning out your team 
• The mindset shift from being needed… to building something that doesn’t need you

We talk about: 

• 00:00 Introduction to Sarah O’Brien and SMS Security
• 02:00 Transitioning from corporate to a family business
• 04:30 The reality of stepping into leadership and earning trust
• 07:00 Navigating legacy, expectations, and comparison to previous leadership
• 10:00 Resistance, accountability, and evolving company culture
• 13:00 Building support systems as a leader and overcoming isolation
• 16:00 Leading in a high-stakes, reactive industry
• 19:00 Customer trust, vulnerability, and service under pressure
• 22:00 The power of listening and creating space in leadership
• 25:00 Developing people and leading in a 24/7 environment
• 28:00 Preventing burnout while maintaining high performance
• 30:00 The shift from problem-solver to system builder
• 33:00 Building a company that scales beyond any one person

Connect with Sarah

• LinkedIn: https://www.linkedin.com/in/sarah-o-brien/ 
• Website: https://www.smssecurity.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, Robin Bailey and Al McDonald sit down with Alisha Patel, VP People & Culture at CanadaHelps, to unpack what it really means to design a workplace where people, performance, and business outcomes actually align. 

Alisha brings a rare combination of people leadership and financial expertise, offering a perspective most organizations are missing. She breaks down why employee experience is not an HR function, but a business strategy, and how leaders can finally connect culture, retention, and performance in a way that drives real results. 

From listening tours and multi-generational workforce design to global cultural nuance and flexible benefits, this conversation challenges the “one-size-fits-all” approach most companies are still relying on. 

If you’re leading a team, building culture, or trying to retain great people in a rapidly changing workforce, this episode will shift how you think about leadership, investment, and what actually creates sustainable growth. 

You’ll hear about: 

• Why employee experience strategy is a business function, not an HR initiative  
• How combining finance and people strategy changes leadership decisions  
• The real reason “people are our greatest asset” often falls flat  
• What listening tours are and how they shape high-impact people programs  
• Why one-size-fits-all benefits and policies are failing modern teams  
• How to design for five generations in today’s workforce  
• The connection between flexibility, retention, and productivity  
• Why culture must evolve across global teams and local contexts  
• How to build trust through clarity, not just perks or programs  
• The leadership shift from process-driven HR to experience design  
• Why humility, curiosity, and listening are the most underrated leadership skills  
• How mentorship and inclusive leadership shape future organizations 

We talk about: 

• 00:00 Introduction to Alisha Patel and her leadership background 
• 02:00 How finance + people strategy creates better business decisions 
• 04:00 Why employee experience is tied to business outcomes 
• 06:30 What “people are our greatest asset” actually means in practice 
• 09:00 Why most HR functions are too transactional 
• 11:00 What a “listening tour” is and how to run one effectively 
• 14:00 Designing benefits and programs based on real employee needs 
• 17:00 Global workforce insights across Canada, US, Europe, and beyond 
• 20:00 Why culture cannot be one-size-fits-all 
• 22:30 The biggest missed opportunity in how companies invest in people 
• 24:00 Flexibility as a low-cost, high-impact benefit strategy 
• 26:00 Measuring success beyond usage, focusing on engagement and retention 
• 28:00 Leadership legacy, mentorship, and building inclusive systems 
• 30:00 Why listening is the most important leadership skill moving forward 

Connect with Alisha 

• LinkedIn: https://www.linkedin.com/in/alishapatel/  
• Website: https://www.canadahelps.org/  

Connect with Us 

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

In this episode of Success Leaves Clues, Robin and Al sit down with Ashlea Desroches, People & Culture Leader at Elastic Path, to unpack a powerful shift in how organizations think about culture, performance, and leadership. 

Ashlea challenges the idea that employee experience is a “nice to have,” and reframes it as the true competitive advantage driving engagement, retention, customer experience, and ultimately, business results. 

From psychological safety and leadership behavior to pay transparency and growth-driven management, this conversation goes deep into what actually creates high-performing teams… and why most organizations are still getting it wrong. 

If you’re leading a team, scaling a company, or trying to build a culture people don’t want to leave, this episode will change how you think about performance, trust, and what it really takes to win. 

You’ll hear about: 

• Why employee experience is the operating system of your business  
• The link between culture, customer experience, and profitability  
• Why high performance does not always equal high engagement  
• How employee referrals reveal your true internal culture  
• The role of psychological safety in innovation and team performance  
• Why great cultures are built on clarity, safety, and recognition  
• The difference between comfort and true psychological safety  
• How avoiding difficult conversations destroys team trust  
• Why growth conversations outperform performance reviews  
• The one question every leader should be asking their team  
• How leaders create conditions where performance becomes inevitable  
• Why pay transparency is becoming a leadership imperative  
• The hidden trust gap created by compensation secrecy  
• How to implement pay transparency without exposing salaries  
• Why compliance is the floor, not the strategy  
• The long-term impact of developing first-time leaders 

We talk about: 

• 00:00 Introduction to Ashlea Desroches and her approach to people & culture 
• 02:00 Why employee experience is a true competitive advantage 
• 04:30 The connection between employee satisfaction and business performance 
• 06:00 How culture shows up in customer interactions and reputation 
• 08:00 Why retention is built when hiring is easy, not hard 
• 10:00 What actually shapes the employee experience end-to-end 
• 12:00 Common traits of high-performing cultures across industries 
• 14:00 Psychological safety vs comfort, and why it matters 
• 17:00 The danger of avoiding difficult conversations as a leader 
• 19:00 How to create safe, open dialogue within teams 
• 21:00 The leadership shift from performance to growth conversation 
• 23:00 The question that transforms employee development 
• 25:00 Where growth conversations should actually happen 
• 27:00 The biggest people-related challenge leaders face today 
• 29:00 Pay transparency, trust, and the future of compensation 
• 32:00 Why most organizations misunderstand transparency 
• 34:00 Building trust through clarity, not secrecy 
• 36:00 Leadership legacy and developing future leaders 

Connect with Ashlea 

• LinkedIn: https://www.linkedin.com/in/ashleadesroches/  
• Website: https://www.elasticpath.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, Robin and Al welcome back Michelle Brooks, Chief People Officer & Head of Operations at Security Compass, to explore one of the most important shifts happening inside modern organizations. 

The role of HR is evolving fast. What was once seen as a support function is now becoming central to how businesses scale, operate, and perform. 

Michelle shares how the CPO role is expanding into operations and even technology, why organizations are moving from departments to workflows, and how leaders can rethink structure, decision-making, and culture in a rapidly changing environment. 

The conversation also dives into a surprising redefinition of burnout, why it’s no longer about working too much, but about working inefficiently, and how removing friction inside organizations can unlock both performance and engagement. 

If you are a CEO, founder, HR leader, or operator navigating growth, complexity, and change, this episode offers a clear lens on where leadership and organizational design are heading next. 

You’ll hear about: 

• Why the Chief People Officer role is expanding into operations and technology  
• How organizations are shifting from departments to workflow-based thinking  
• The concept of the CPO as an “organizational architect”  
• Why HR and operations are no longer separate functions  
• How COVID accelerated the strategic importance of people leadership  
• The real reason burnout is rising, and why it’s not about hours worked  
• How inefficient processes and bottlenecks create modern burnout  
• Why removing friction is the fastest path to productivity and performance  
• The balance between empowerment and structure inside organizations  
• How clarity of mission drives better decision-making across teams  
• Why decision-making should live closest to the information  
• How strong leadership creates ripple effects across entire organizations  
• Why the future of business is less about hierarchy and more about flow 

We talk about: 

• 00:00 Introduction to Michelle Brooks and her evolving leadership role 
• 02:00 Why the CPO role is expanding into operations and technology 
• 04:00 The shift toward organizational design and workflow thinking 
• 05:30 How COVID accelerated the evolution of HR leadership 
• 07:00 Breaking down silos and creating more efficient workflows 
• 08:30 Benefits and challenges of blending people and operations roles 
• 10:00 Reframing HR and operations as business enablers, not cost centers 
• 12:30 When companies should bring in HR and operational leadership 
• 14:00 How burnout has changed, from overwork to inefficiency 
• 16:00 The impact of processes, bottlenecks, and friction on teams 
• 19:30 Why clarity of mission is foundational to performance 
• 23:00 Connecting individual work to company-wide impact 
• 24:30 Why siloed organizations are becoming outdated 
• 25:30 The shift toward workflow-based operating systems 
• 27:00 Adapting organizational design to a rapidly changing environment 
• 30:00 The ripple effect of strong leadership across teams and organizations 

Connect with Michelle 

• LinkedIn: https://www.linkedin.com/in/michelle-brooks-1747b924  
• Website: https://www.securitycompass.com/  

Connect with Us 

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

With nearly 30 years of experience in leadership, talent strategy, and inclusion, Stewart brings a thoughtful and practical perspective to the conversation, grounded in both strategy and lived experience. 

The discussion reveals a critical truth: many organizations are committed to inclusion, yet struggle to translate that commitment into consistent, everyday experiences for their people. 

Stewart explains how gaps in awareness, psychological safety, and leadership behavior can quietly undermine culture, even in organizations with strong values and clear intentions. He also highlights how belonging drives engagement, performance, and better decision-making across teams. 

If you are a CEO, HR leader, executive, or business owner responsible for culture and performance, this episode offers a clear and practical lens on what it takes to build environments where people and organizations can truly thrive. 

You’ll hear about: 

• Why inclusive leadership directly impacts business performance, not just people strategy 
• The real cost of exclusion, including missed ideas, turnover, and stalled innovation 
• How belonging drives engagement, retention, productivity, and results 
• The hidden gap between the culture leaders think they create and what employees actually experience 
• Why silence in organizations often signals fear, not agreement 
• How cognitive overload and complexity prevent leaders from making intentional decisions 
• The role of bias awareness and how it shapes everyday leadership decisions 
• Why psychological safety is the foundation of high-performing teams 
• The difference between inclusive intentions and inclusive conditions 
• How leaders can identify whose voices are missing and why it matters 

We talk about: 

• 00:00 Introduction to Stewart Whittingham and his leadership background 
• 02:00 How lived experiences shape leadership and inclusion 
• 04:00 Why inclusion improves decision-making and innovation 
• 06:00 The cost of exclusion in organizations 
• 08:00 Belonging as a driver of performance and retention 
• 10:00 Bias awareness and the “who comes to mind” exercise 
• 12:30 Identifying who is missing from the table 
• 14:00 Why inclusion is an awareness game, not a blame game 
• 16:00 The gap between leadership intention and employee experience 
• 18:00 Psychological safety and speaking up at work 
• 20:00 The danger of silence and misinterpreted feedback 
• 22:00 Inclusive intentions vs inclusive conditions 
• 24:00 Leadership barriers, clarity, mindset, and competing commitments 
• 26:00 Cognitive overload and why leaders struggle to pause 
• 27:30 The power of “Stop, Pause, Reflect” in leadership 
• 28:30 The legacy leaders create through culture and people 

Connect with Stewart 

• LinkedIn: https://www.linkedin.com/in/stewart-whittingham-43bb5612/  
• Website: https://www.stewartwhittingham.com/  

Connect with Us 

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

With more than 25 years of experience across healthcare, pharmacy, and insurance, Vincent brings a rare perspective to the conversation. As a licensed pharmacist and health benefits leader, he sits at the intersection of clinical care, digital transformation, and employer-sponsored health strategy. 

The discussion reveals a surprising truth: many benefit plans look rich on paper, yet employees struggle to access them in practice. 

Vincent explains why awareness gaps, fragmented platforms, and overly complex plan designs often prevent employees from engaging with their benefits until a crisis occurs. The conversation explores how employers and advisors can rethink plan communication, simplify access, and organize benefits around real human problems instead of administrative categories. 

If you are a CEO, HR leader, benefits advisor, or business owner responsible for employee wellbeing, this episode offers a strategic look at how benefits plans are evolving and what organizations can do today to ensure employees actually use the support available to them. 

You’ll hear about: 

• Why many employees don’t understand the benefits available to them 
• The concept of “cognitive overload” in complex benefit plans 
• Why rich benefit plans often remain underutilized 
• How multiple platforms and logins create friction for employees 
• Why benefits should be organized around problems, not providers 
• How employers can increase awareness and engagement with benefit plans 
• The growing normalization of mental health support in the workplace 
• How digital mental health tools are expanding access to care 
• Why chronic condition management will shape future benefit plans 
• The role of navigation and care pathways in modern healthcare 
• How new medications and treatments are changing health outcomes 
• Why access to care remains the biggest challenge in the Canadian system 

We talk about: 

• 00:00 Introduction and Vincent Ng’s background in healthcare and benefits 
• 02:30 Why rich benefit plans are often underutilized 
• 04:00 Cognitive overload and lack of awareness among employees 
• 05:30 Decision paralysis created by complex benefit ecosystems 
• 07:00 Why employees often engage with benefits only during crises 
• 08:30 The importance of ongoing communication with employees 
• 10:30 Reducing friction through better technology and integrated platforms 
• 12:30 Designing benefits around employee problems and needs 
• 14:00 Using industry data to better understand employee expectations 
• 15:00 Mental health benefits and proactive wellbeing support 
• 17:00 Integrating mental health into broader health management 
• 19:00 The growing normalization of therapy and mental health care 
• 21:00 The evolution of digital mental health tools and support 
• 23:00 Future trends in group benefits and personalized care pathways 
• 24:30 Chronic condition management and integrated care models 
• 26:00 The strategic role of health and wellness spending accounts 
• 28:00 The importance of medications in improving health outcomes 
• 30:00 Balancing innovation and sustainability in drug coverage 
• 31:30 Fixing healthcare access in Canada’s fragmented system 
• 34:00 Vincent’s mission to make healthy choices easier for Canadians 

Connect with Vincent 

• LinkedIn: https://www.linkedin.com/in/vincentng5/  
• Website:  

Connect with Us 

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

Featuring: Amanda Small, Head of People & Culture; Cerys Goodall, Operations Leader; and Elizabeth Lynch, HR Consultant and Culture Advisor, this discussion moves beyond headlines and into real-world leadership tension. 

Is return to office about location? Or is it about trust, accountability, and clarity of outcomes? If you are a CEO, founder, HR leader, executive, or manager navigating return to office mandates, hybrid models, or remote work performance, this episode offers grounded insight from leaders living this reality every day. 

The panel explores: 

• Why “bums in seats” does not equal performance 
• The difference between visibility and accountability 
• How unclear outcomes create disengagement 
• Why intentional workplace design matters more than policy 
• Generational shifts in how trust is built 
• The role of flexibility in retention and employee wellbeing 
• Why leaders must be considerate without catering 
• How culture either lives in daily behavior or dies in policy 

You’ll hear about: 

• Is return to work a trust issue or a management capability issue? 
• Why accountability must be tied to outcomes, not visibility 
• The difference between listening to employees and catering to them 
• “Considerate without catering” as a leadership philosophy 
• Why the office should function as a teammate, not just a location 
• How poor policy design creates disengagement 
• Coffee badging and what it signals about culture 
• The loneliness epidemic and the hidden cost of remote work 
• Why clarity of outcomes drives performance more than presence 
• How intentional design improves culture and business results 

We talk about: 

• 00:00 Introduction to the Return to Work Roundtable 
• 01:00 Panelist introductions and leadership lenses 
• 04:30 Is return to work about trust or accountability? 
• 07:00 Visibility vs measurable outcomes 
• 10:00 Real estate pressure and office utilization 
• 14:00 How much flexibility should employees realistically have? 
• 17:00 Listening vs catering to employees 
• 21:00 “Considerate without catering” leadership 
• 26:00 When employees should choose to leave 
• 30:00 Operational rigor and remote performance success 
• 37:00 Why clarity of outcomes drives engagement 
• 44:00 Does autonomy improve performance? 
• 52:00 What actually drives performance? Visibility or outcomes? 
• 59:00 The office as a teammate 
• 1:07:00 Loneliness, culture, and human connection 
• 1:11:00 Designing work intentionally 

Connect with  

• LinkedIn: Amanda Small
• LinkedIn: Cerys Goodall
• LinkedIn: Elizabeth Lynch

Connect with Us 

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

Dunja shares why simply declaring your company “people first” is not enough, and how values must show up in real decisions, especially when budgets tighten and pressure rises. She explains why her team shifted from saying “people first” to “do right by people,” and how that subtle change drives clearer accountability, stronger performance conversations, and healthier cultures. 

The conversation explores vulnerable leadership, why leaders do not need to have all the answers, and how raising your hand first to admit mistakes builds real trust. Dunja challenges traditional leadership models that reward ego and certainty, and instead advocates for hiring people smarter than you, investing in middle management, and normalizing hard conversations early. 

Robin and Al also unpack how leadership expectations have evolved, why assumption is the enemy of communication, and how culture either lives in daily behavior or dies on the office wall. 

This episode is a practical and grounded guide to culture transformation, accountability, and building a workplace where people thrive without lowering performance standards. 

You’ll hear about: 

• What “people first leadership” really means in practice 
• Why cutting benefits first is a cultural red flag 
• The difference between “people first” and “do right by people” 
• Why accountability and hard conversations are part of empowerment 
• Vulnerable leadership and admitting mistakes as a strength 
• Hiring people smarter than you and overcoming leadership ego 
• Why middle management is where strategy lives or dies 
• How values must be operationalized, not just displayed 
• Assumption as the biggest communication breakdown in leadership 
• Creating psychological safety without lowering standards 

We talk about: 

• 00:00 Introduction and welcome 
• 01:00 What “thought leadership” really means in practice 
• 03:00 Vulnerability versus traditional leadership models 
• 05:00 Testing whether a company is truly people first 
• 06:30 What happens when budgets tighten 
• 08:30 Why benefits matter to employee performance and focus 
• 11:00 Accountability inside people first cultures 
• 12:30 Why values often fail in organizations 
• 14:00 The values bootcamp and operationalizing culture 
• 17:00 Assumptions as the enemy of leadership clarity 
• 18:00 Generational shifts and communication challenges 
• 20:00 Redefining leadership expectations 
• 23:00 Admitting mistakes and building trust 
• 26:00 Hiring people smarter than you 
• 28:00 Why middle management is critical to culture 
• 30:00 Planting trees for future generations of leaders 

Connect with Dunja 

• LinkedIn: https://www.linkedin.com/in/dvujovic/  
• Website: https://dunjavujovic.com/  

Connect with Us 

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

Christine shares why so many high performers feel empty despite doing “everything right” on paper, and how chasing inherited definitions of success quietly erodes energy, confidence, and clarity. The conversation explores the powerful concept of “the gap versus the gain,” why comparison steals momentum, and how leaders can reconnect with progress by recognizing daily wins instead of endlessly moving goalposts. 

Robin, Al, and Christine also unpack how leaders make decisions when data is incomplete, stakes feel high, and ambiguity is unavoidable. Christine offers practical insight into trusting intuition, distinguishing reversible versus irreversible decisions, and stepping out of fear-based paralysis. 

The episode weaves together leadership, values, customer-centricity, and personal growth, emphasizing that clarity comes from alignment, not achievement alone. Christine also shares how leaders can identify misalignment between personal values and organizational culture, and why many perceived conflicts are stories worth examining more closely. 

You’ll hear about: 

• Why high performers often feel unfulfilled despite outward success 
• The difference between chasing success and defining it for yourself 
• The “gap versus the gain” framework and how it changes motivation 
• How comparison quietly drains confidence and joy 
• Daily wins as a leadership discipline, not a productivity trick 
• Making decisions when data is incomplete and pressure is high 
• Reversible versus irreversible leadership decisions 
• Trusting intuition without abandoning logic 
• What customer-centricity really looks like beyond metrics 
• Values alignment, culture, and leadership integrity 
• Navigating perceived misalignment between personal and company values 
• Strategic influence as a leadership superpower 

We talk about: 

• 00:00 Introduction and welcome 
• 01:00 Christine’s leadership background and coaching work 
• 02:30 Why success often feels empty for high performers 
• 04:30 Defining success for yourself at different life stages 
• 06:30 The gap versus the gain and how comparison steals momentum 
• 09:00 Recognizing progress and celebrating daily wins 
• 11:30 Gratitude, habits, and leadership energy 
• 14:00 Decision-making in ambiguity and high-stakes environments 
• 17:00 Reversible versus irreversible leadership decisions 
• 20:00 Trusting intuition when data is incomplete 
• 23:00 Customer-centricity beyond dashboards and metrics 
• 26:00 Values, culture, and perceived misalignment at work 
• 29:00 Strategic influence and getting things done through others 
• 32:00 Leadership growth through self-awareness and inner work 
• 35:00 The signature question, planting trees for the future 

Connect with Christine 

• LinkedIn: https://www.linkedin.com/in/christinefarrugia/  
• Instagram: https://www.instagram.com/coachwithchristine/  
• Website: https://www.christinefarrugia.com/  

Connect with Us 

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

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 

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 

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 

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 

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 

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 

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 

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 

Jenny shares her inspiring journey from executive search to startup builder to venture advisor, offering hard-won lessons from 25 years of helping founders scale with purpose. As someone who’s helped launch companies from napkin sketches to successful exits, she reveals what makes great leaders, why culture must be built early, and how authenticity and communication can transform a business from the inside out. 

Together, they unpack the emotional highs and lows of startup life, how to lead through uncertainty, and the importance of saying “yes” to growth even when you’re not fully ready. 

You’ll hear about: 

• Curiosity as a compass: How following her questions, not a plan, shaped Jenny’s 25-year career in people and culture. 
• The courage to say yes: Why leaning into challenge matters more than waiting until you’re “ready.” 
• The founder’s formula: What separates successful startup teams from the rest and how self-awareness plays a vital role. 
• The human side of scaling: Why alignment, communication, and connection are every company’s secret weapons. 
• Hiring with intention: How early people strategy can accelerate growth and prevent culture debt. 
• Ego vs. conviction: How great founders balance strong beliefs with humility and collaboration. 
• Authentic leadership: Why clarity is kindness and being yourself is the real competitive advantage. 
• The future of workplace wellness: How benefits, belonging, and flexibility will shape the next era of people strategy. 
• Mentorship and legacy: How sharing wisdom and lifting others creates lasting ripple effects in leadership. 

We talk about: 

• 00:00 Introduction   
• 03:00 The accidental path into people and culture 
• 06:00 Learning to say yes and leading with curiosity 
• 09:00 Lessons from building Nest Wealth from scratch 
• 12:00 From venture capital to TouchBistro: redefining success 
• 15:00 The patterns that define great founders and teams 
• 18:00 Why startups should invest in people and culture early 
• 23:00 How HR shapes growth and alignment 
• 28:00 The role of communication in scaling companies 
• 33:00 Ego, conviction, and collaboration in leadership 
• 37:00 Authenticity and the importance of showing up as yourself 
• 44:00 Rethinking benefits and wellness for a modern workforce 
• 49:00 How strong cultures drive belonging and retention 
• 50:00 Legacy and impact: mentoring future founders 

Connect with Jenny 

• LinkedIn: https://www.linkedin.com/in/jennydoforno/  
• TouchBistro LinkedIn: https://www.linkedin.com/company/touchbistro/ 
• YouTube: https://www.youtube.com/user/touchbistro  
• Instagram: https://www.instagram.com/touch_bistro/ 
• Facebook: https://www.facebook.com/TouchBistroiPadPOS/  
• Website: https://www.touchbistro.com/  

Connect with Us 

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

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 

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 

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 

Drawing from her executive experience at Walmart, Deloitte, and Philip Morris International, Suzanne reveals the real playbook for future-proofing leaders and organizations – one built on adaptability, resilience, and courage in the face of uncertainty. 

From starting her own firm to advising Fortune 500 companies on transformation and performance, Suzanne shares powerful insights on how to navigate setbacks, maintain culture during upheaval, and find opportunity in crisis. Her philosophy? Something will always go wrong, but the best leaders turn those moments into growth. 

You’ll hear about: 

• Future-Proof Leadership: Why adaptability has replaced collaboration as the most critical leadership skill. 
• Embracing Disruption: How to anticipate change, stay calm, and lead teams through uncertainty. 
• Crisis as Catalyst: How setbacks can strengthen strategy, innovation, and resilience. 
• Workforce Trends: Why leaders need to plan for shorter career cycles, automation, and evolving skill sets. 
• Culture & Retention: How to preserve trust, clarity, and engagement during mass change or return-to-office mandates. 
• Start Less, Finish More: Why prioritization and focus drive stronger results than multitasking ever could. 
• Wellness & Leadership: Why sustainable success depends on treating leadership like a marathon, not a sprint. 
• Never Waste a Good Crisis: How to turn breakdowns into breakthroughs. 

If you’re a business leader, HR professional, or entrepreneur looking to lead with purpose and stability in a rapidly changing world, this conversation is a must-listen. 

We talk about: 

• 00:00 Introduction   
• 04:00 Why adaptability defines the modern leader 
• 09:00 Turning setbacks into strategy 
• 14:00 Future-proofing your team and organization 
• 18:00 Building culture in times of change 
• 24:00 The art of prioritization and focus 
• 31:00 Wellness, leadership, and long-term performance 
• 35:00 The trees Suzanne is planting for future leaders 

Connect with Suzanne 

• LinkedIn: https://www.linkedin.com/in/skknight/ 
• Website: https://suzanneknight.com/  

Connect with Us 

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

Jennifer shares her journey from early career challenges to leading one of Canada’s most impactful not-for-profit organizations. She opens up about how living her values, fostering inclusion, and empowering her team have helped ACCES Employment transform thousands of lives every year. 

From overcoming fear and finding her voice to building mentorship programs that cultivate tomorrow’s leaders, Jennifer’s story is a masterclass in how courage, humility, and purpose-driven leadership create lasting impact. 

You’ll hear about: 

• Purpose-Driven Leadership: How ACCES Employment empowers underserved communities through meaningful employment opportunities. 
• Values in Action: Why aligning personal values with organizational mission drives engagement and fulfillment. 
• Culture and Collaboration: How HR can partner with leaders to co-create healthier, high-performing workplaces. 
• From Fear to Fearless: How saying yes — and raising your hand — can transform your confidence and career trajectory. 
• The Power of Mentorship: Why mentorship is the ultimate investment in organizational success and human growth. 
• Work Ethic and Impact: What Jennifer learned from her toughest early jobs — and how those lessons shaped her leadership style. 
• Planting Seeds for the Future: How generosity, inclusion, and mentorship build the leaders of tomorrow. 

If you are an HR leader, business owner, or aspiring change-maker seeking to build engaged teams, elevate culture, and lead with both head and heart, this episode offers the clarity and inspiration you’ve been looking for. 

We talk about: 

• 00:00 Introduction   
• 02:00 Meet Jennifer Hall and the Mission Behind ACCES Employment 
• 04:00 How ACCES Empowers Underserved Communities Across Canada 
• 06:00 Finding Purpose in Nonprofit Work 
• 07:00 The Art of “Getting to Yes” in the Nonprofit World 
• 08:00 Measuring Impact in HR: Culture, Engagement, and Results 
• 10:00 Building Leadership Buy-In and Inclusive Culture 
• 13:00 Overcoming Fear and Finding Your Voice 
• 15:00 The Turning Point: Taking Ownership and Speaking Up 
• 18:00 Why Raising Your Hand Changes Everything 
• 19:00 Leading with Humility and Silencing the Ego 
• 21:00 Building Teams That Trust and Thrive 
• 23:00 Where Work Ethic Comes From (and How It Lasts a Lifetime) 
• 27:00 Mentorship That Builds Future Leaders 
• 30:00 How to Be an Effective First-Time Mentor 
• 34:00 Planting the Seeds of Leadership and Inclusion 

Connect with Jennifer 

• LinkedIn: https://www.linkedin.com/in/hrjenniferhall  
• Website: https://accesemployment.ca/people/jennifer-hall   

Connect with Us 

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

Devin shares candid insights from his journey as a corporate and competition lawyer, advocate, and changemaker – from building sustainable firm cultures and balancing family life to driving greater representation and equity within the legal system. 

He discusses how mentorship, advocacy, and a collaborative mindset are reshaping the future of law in Canada, and why creating win-win outcomes is the ultimate mark of professional success. 

You’ll hear about: 

• Balancing High Performance and Humanity: How large firms can promote sustainability and mental health in high-pressure careers. 
• Culture and Connection: Why authenticity and family time are non-negotiables for long-term success. 
• The Future of Law: How AI, globalization, and protectionism are reshaping Canadian business and legal practice. 
• Representation Matters: The evolution of the South Asian Bar Association (SABA) and its role in driving diversity and equity. 
• Mentorship and Legacy: How sending the elevator back down builds stronger communities and future leaders. 
• Redefining Success: Why true leadership means uplifting others while balancing professional excellence and personal joy. 

If you are an HR leader, founder, or law student who wants to build healthier teams and a more inclusive profession, this episode shows how mentorship, balanced culture, and practical policy can shape a more competitive and humane legal landscape in Canada. 

We talk about: 

• 00:00 Introduction   
• 03:00 The Realities of Law Firm Culture and Burnout 
• 06:00 How COVID Changed the Legal Landscape 
• 08:00 Gender Equity and Sustainable Career Paths 
• 09:00 Protecting Mental Health and Family Time 
• 12:00 The Future of Law: AI, Globalization, and Protectionism 
• 16:00 Building Canada’s Talent Pipeline: Education and Immigration 
• 18:00 What “Winning” Really Means for a Lawyer 
• 21:00 Redefining Success Beyond the Office 
• 23:00 The South Asian Bar Association: History and Impact 
• 27:00 Representation, Mentorship, and Equity in Law 
• 31:00 Creating Access Through TMU’s Law School 
• 33:00 Progress and Challenges in Legal Leadership Diversity 
• 35:00 What Needs to Change to Advance Inclusion 
• 38:00 Planting Trees: Devin’s Vision for Mentorship and Legacy 

Connect with Devin 

• LinkedIn: https://www.linkedin.com/in/devin-persaud/  
• Website: https://www.millerthomson.com/en/your-team/devin-persaud/  

Connect with Us 

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

With over 25 years of experience in healthcare innovation, Carl shares how Optimal U is bridging the gap between public and private care – empowering individuals to take charge of their health through data-driven assessments, personalized care plans, and actionable lifestyle changes. 

Carl discusses how small, daily habits create measurable, long-term health outcomes, and how wearables, genetic testing, and AI are helping Canadians stay healthier longer. He also explains how employers can integrate lifestyle medicine into benefits programs to boost productivity, reduce absenteeism, and lower healthcare costs. 

This episode is a wake-up call for anyone who believes “ignorance is bliss” when it comes to their health, and an invitation to start planting the seeds of wellness today. 

You’ll hear about: 

• From Sick Care to Preventive Care: Why Canada’s public system focuses on treatment, and how Optimal U fills the prevention gap. 
• The Six Pillars of Lifestyle Medicine: Nutrition, exercise, sleep, stress, social connection, and avoiding risky substances. 
• Data-Driven Health: How bloodwork, genetic screening, and wearables reveal what your body truly needs. 
• Ignorance Isn’t Bliss: Why knowing your health risks early empowers better choices and longer vitality. 
• Employers and Well-Being: How companies can use lifestyle medicine to reduce costs and build healthier, more engaged teams. 
• The Future of Personalized Care: How AI and continuous monitoring are making wellness more accessible and actionable than ever.