Success Leaves Clues with Robin Bailey and Al McDonald

A Starting with One Podcast
  • 5.0 (15)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

"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: Ep 293 - The Leadership Behaviours that Shape Culture with Jessica Lewis of PointsBet

    1D AGO

    Success Leaves Clues: Ep 293 - The Leadership Behaviours that Shape Culture with Jessica Lewis of PointsBet

    What actually creates a great company culture? 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 statementsWhat leaders reveal about culture behind closed doorsThe hiring mistake that quietly damages organizations over timeWhy technical skill alone is never enough for leadership successHow mentorship changes careers and builds long-term confidenceThe importance of giving feedback early and with kindnessWhy trust and transparency are critical for strong workplace culturesHow AI is reshaping HR and the employee experienceThe role frontline managers play in reinforcing company valuesWhy creating more women leaders matters for the future of business We talk about: 00:00 Introduction to Jessica Lewis and PointsBet02:00 From executive assistant to people leadership04:30 Why HR became Jessica’s purpose and passion06:30 Staying ahead in leadership through mentorship and community08:30 The connection between leadership and company culture10:00 What actually causes workplace culture to break down11:30 Why culture is revealed behind closed doors13:00 Hiring for values, not just technical competence15:30 How fast-growing companies redefine leadership needs17:00 Giving feedback early and building accountability19:00 Technical skill vs cultural alignment, which matters more?21:30 The leadership lessons mentorship creates23:30 Building confidence as a woman in leadership25:00 Why representation and equity in leadership matter26:30 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

    28 min
  2. Success Leaves Clues: Ep 292 - The Power of Bold Decisions and Relentless Persistence with Dan Turner, CEO at Xperigo

    MAY 14

    Success Leaves Clues: Ep 292 - The Power of Bold Decisions and Relentless Persistence with Dan Turner, CEO at Xperigo

    What if the only thing standing between where you are… and where you want to be… is one bold decision you haven’t made yet? 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 lifeHow Dan Turner turned a bold hunch into a multi-million dollar opportunityThe real reason most people stay stuck in their comfort zoneWhy risk is required if you want to reach your full potentialHow confidence is built through action, not certaintyThe mindset shift that turns “failure” into growthWhy opportunity rarely announces itself, and how to spot it earlyHow proactive thinking separates top performers from everyone elseThe role persistence plays in long-term successWhy stepping outside your comfort zone is non-negotiable for growth We talk about: 00:00 Introduction to Dan Turner and Xperigo02:30 From tow truck driver to CEO, the origin story05:00 The moment that sparked a bold, long-term vision08:00 Why big goals feel overwhelming, and how to start anyway11:00 Comfort zones vs. growth, why staying safe keeps you stuck14:00 The Apple iPhone story, spotting opportunity before the world sees it17:30 Turning a bold idea into a multi-million dollar deal20:00 Risk, doubt, and why the upside is always worth it23:00 The mindset that separates leaders from followers25:30 Culture vs performance, why they fuel each other28:00 Building trust, transparency, and high-performing teams31:00 Leadership today, why vulnerability is a strength, not a weakness34:00 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

    38 min
  3. Success Leaves Clues: Ep 291 - Stop Hiring for Resume. Start Hiring for Impact with Alison Kaizer, Partner at Golden Ventures

    APR 30

    Success Leaves Clues: Ep 291 - Stop Hiring for Resume. Start Hiring for Impact with Alison Kaizer, Partner at Golden Ventures

    What if the reason your company isn’t scaling… has nothing to do with your product, and everything to do with who you hire? 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 Ventures02:00 From consulting to recruiting, the unexpected career path05:30 Scaling talent functions inside high-growth startups08:30 The moment pattern recognition becomes a superpower11:00 The biggest hiring mistake founders make (resume bias)14:00 Why aptitude beats experience in early-stage companies17:30 How to build structured interviews that actually predict success20:30 The truth about “culture fit” and how to assess values properly23:30 Scaling hiring without lowering the bar26:00 Compensation transparency and building trust with candidates29:00 Hiring in startups vs. enterprise environments31:30 How AI is reshaping hiring and talent evaluation33:30 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

    32 min
  4. Success Leaves Clues Ep. 290 - The Leadership Shift That Builds Companies That Last with Sarah O’Brien, Chief Operating Officer at SMS Security

    APR 23

    Success Leaves Clues Ep. 290 - The Leadership Shift That Builds Companies That Last with Sarah O’Brien, Chief Operating Officer at SMS Security

    What happens when you inherit a legacy… but need to evolve it to survive? 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 Security02:00 Transitioning from corporate to a family business04:30 The reality of stepping into leadership and earning trust07:00 Navigating legacy, expectations, and comparison to previous leadership10:00 Resistance, accountability, and evolving company culture13:00 Building support systems as a leader and overcoming isolation16:00 Leading in a high-stakes, reactive industry19:00 Customer trust, vulnerability, and service under pressure22:00 The power of listening and creating space in leadership25:00 Developing people and leading in a 24/7 environment28:00 Preventing burnout while maintaining high performance30:00 The shift from problem-solver to system builder33:00 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

    29 min
  5. Success Leaves Clues Ep. 289 - The Employee Experience Strategy with Alisha Patel, VP People & Culture at CanadaHelps

    APR 9

    Success Leaves Clues Ep. 289 - The Employee Experience Strategy with Alisha Patel, VP People & Culture at CanadaHelps

    What if your employee experience strategy is the reason your business is either scaling… or stalling?  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

    28 min
  6. Success Leaves Clues: Ep288 - Why Culture Is Your Only Real Competitive Advantage with Ashlea Desroches, People & Culture Leader at Elastic Path

    APR 2

    Success Leaves Clues: Ep288 - Why Culture Is Your Only Real Competitive Advantage with Ashlea Desroches, People & Culture Leader at Elastic Path

    What if employee experience isn’t an HR initiative… but the system your entire business runs on?  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

    37 min
  7. Success Leaves Clues Ep. 287 - Redefining Leadership, Operations, and Culture with Michelle Brooks, Chief People Officer & Head of Operations at Security Compass

    MAR 26

    Success Leaves Clues Ep. 287 - Redefining Leadership, Operations, and Culture with Michelle Brooks, Chief People Officer & Head of Operations at Security Compass

    What if the Chief People Officer is no longer just responsible for people… but for how the entire business operates?  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

    31 min
  8. Success Leaves Clues Ep. 286 - Inclusive Leadership Isn’t What You Think with Stewart Whittingham, Director of Culture and Belonging at Miller Thomson

    MAR 19

    Success Leaves Clues Ep. 286 - Inclusive Leadership Isn’t What You Think with Stewart Whittingham, Director of Culture and Belonging at Miller Thomson

    In this episode of Success Leaves Clues, Robin and Al sit down with Stewart Whittingham, Director of Culture and Belonging at Miller Thomson, to explore one of the most overlooked challenges in leadership today: the gap between the culture leaders believe they are creating and what employees actually experience.  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

    29 min
See All (324)

Ratings & Reviews

5
out of 5
15 Ratings

About

"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

Information

You Might Also Like