Advertise on podcast: Success Leaves Clues with Robin Bailey and Al McDonald

How do leaders create belonging at work? In Episode 310 of Success Leaves Clues, Robin Bailey joins Roy Tran, Founder of Beyond the Title and a global People and Culture executive, to explore inclusive leadership, cultural identity, and the everyday behaviours that shape a leader’s legacy. Drawing on his experience arriving in Canada as a Vietnamese refugee and working across Southeast Asia, Roy shares how cultural understanding, relationships, and a willingness to adapt build trust. He encourages leaders to recognize subtle signs of exclusion, see the people behind their roles, and make room for different ways of contributing. Roy also introduces the “human code”—the lived experiences that shape our leadership habits—and offers practical ways to create workplaces where people feel valued and free to be themselves. You’ll hear about: How Roy’s experience arriving in Canada as a Vietnamese refugee shaped his leadershipThe personal cost of hiding your identity to fit inWhat leaders can notice when employees feel invisible at workWhy organizations can lose valuable perspectives by expecting cultural assimilationHow Roy’s experience in Vietnam changed his approach to earning trustThe everyday leadership behaviours people remember and repeatWhy recognition deserves its own moment before feedbackWhat Roy means by the “human code” and how lived experience shapes behaviourHow honest feedback and small systems can support leadership growthThe legacy Roy is building through Beyond the Title and his work with leaders We talk about: 00:00 Welcome and the introduction that brought Roy to the podcast  01:01 Meet Roy Tran, Founder of Beyond the Title  01:56 Growing up feeling the need to hide your identity  07:54 Finding the confidence to stop being invisible  11:33 What leaders miss about belonging at work  16:53 Why leadership approaches need to adapt across cultures  21:57 Bringing lessons about trust and culture back to Canada  24:00 The leadership breadcrumbs people carry forward  28:02 Giving recognition room before offering feedback  30:14 Understanding your human code and changing leadership habits  35:46 Building a legacy that creates belonging for others  41:35 Connect with Roy and explore Beyond the Title Connect with Roy LinkedIn: https://www.linkedin.com/in/roytran/ Website: https://beyondthetitle.ca/about.html   Connect with Us  LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

How do you use AI for business without handing over your judgment? Start with a business problem, identify the workflow that needs to change, and keep people responsible for defining the problem and checking the results.  In Episode 309 of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Karla Congson, Founder and CEO of Agentiiv, to explore practical AI adoption, human-led leadership, and the curiosity required to reinvent your career. After more than 20 years in corporate marketing and senior leadership, Karla became an entrepreneur and later began learning AI and prompt engineering at 50. She shares why she sees reinvention as walking toward an opportunity with the expertise you already have, and why staying curious matters as much as becoming an expert. Karla explains the difference between using AI to expand your capabilities and falling into “cognitive surrender,” gradually allowing technology to take over your judgment. Her approach puts humans in the lead: asking better questions, challenging assumptions, reviewing outputs, and involving other experts when needed. Through client examples, she explores how AI agents can support research, marketing, and communications while helping teams improve quality and reduce external costs. She describes how the Canadian Marketing Association created 70 playbooks in a year through a process combining AI-generated drafts with human expertise and review.  The conversation also covers how to measure AI ROI through business outcomes, why adoption should begin with workflows, and where risk and governance belong in the process. Along the way, Karla shares why rest, relationships, and protecting your capacity to think are essential to entrepreneurial success. For entrepreneurs and business leaders exploring AI, this episode offers a practical starting point: solve a meaningful problem, preserve human judgment, and stay willing to learn. You’ll hear about: How Karla moved from corporate marketing into entrepreneurship and AIWhy experienced leaders still need the curiosity of a beginnerWhat cognitive surrender means and how it can show up at workWhy Karla advocates for humans in the lead when using AIHow expert AI agents can support teams and challenge assumptionsHow the Canadian Marketing Association combined AI with human review to create 70 playbooksWhy AI ROI should include quality, business outcomes, and employee capacityHow to identify your first AI use case through business problems and workflowsWhy AI governance and risk management belong in adoption decisionsWhat Karla hopes her entrepreneurial journey teaches her daughters We talk about: 00:00 Welcome and meet Karla Congson, Founder and CEO of Agentiiv  01:34 Moving from corporate expertise into entrepreneurship and AI  05:06 Making learning feel exciting instead of threatening  07:36 AI superpowers, cognitive surrender, and human judgment  14:32 Using AI to extend expertise and validate your thinking  17:01 Managing the pressure to do more as technology accelerates  19:13 Why rest and relationships support entrepreneurial success  23:09 Measuring AI ROI through meaningful business outcomes  23:33 How the Canadian Marketing Association uses AI and human review  25:56 AI results in an aviation and infrastructure communications team  28:39 How AI personas can challenge assumptions and support critical thinking  30:43 Where business leaders should start with AI adoption  34:09 Managing AI risk and governance  37:35 Building a legacy through curiosity and lifelong learning  41:15 Connect with Karla Congson Connect with Karla LinkedIn: https://www.linkedin.com/in/karlacongson/ Website: https://agentiiv.com/blog   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What happens when an investor sees an overlooked healthcare need and decides to build a business around it? In this episode of Success Leaves Clues, Robin Bailey and guest co-host Kim Seipt sit down with Lindsay Jephcott, Co-Founder of Lume Women + Health, to explore the women’s health gap and the entrepreneurial journey behind a company working to address it. Lindsay explains how her background as an investment executive helped her recognize an underserved market in women’s midlife health. Together with three physician co-founders, she set out to create a menopause clinic despite warnings that women would not want to talk about aging. As the team listened to patients, that initial concept evolved into a broader executive medical offering focused on women’s preventive care and healthy aging. She shares why menopause deserves attention from employers, how greater visibility is helping change the conversation, and why women should feel empowered to seek answers about their health. The discussion explores Lume’s approach to connecting different areas of care rather than treating each concern in isolation. Lindsay also opens up about the realities of building a company from scratch: navigating rejection, checking your ego, choosing complementary partners, and learning when to act quickly versus when to pause. With a team of 30 at the time of recording, she reflects on how founders’ responsibilities change as a business grows.  The conversation closes with her ambitions for physician education, research, advocacy, and a future where the next generation of women can find the care and answers they need. You’ll hear about: How Lindsay’s investment background led her into women’s healthcareWhy the women’s health gap represents an overlooked business opportunityHow menopause became a bigger conversation in workplaces and public lifeWhy Lume evolved from a menopause clinic into broader preventive careHow listening to patients helped shape the company’s directionWhat founders should discuss before entering a business partnershipWhy resilience, humility, and thoughtful decision-making matter when building a companyHow Lindsay hopes to create lasting change through education, research, and access We talk about: 00:00 Meet Lindsay Jephcott of Lume Women + Health  02:18 Recognizing the women’s health gap through an investor’s lens  08:03 Investment and innovation in women’s healthcare  08:42 Why the conversation about menopause is changing  12:22 Women’s midlife health and a more connected approach to care  18:41 Choosing business partners and sharing leadership  21:17 Building founder resilience and responding to patient needs  23:32 Growing a team of 30 and delegating responsibilities  24:51 Making thoughtful decisions and navigating a career transition  30:56 Creating a legacy through education, research, and access Connect with Lindsay LinkedIn: https://www.linkedin.com/in/lindsay-stollery-jephcott/ Website: https://www.lumewomenshealth.com/team/lindsay-stollery-jephcott   Connect with Us LinkedIn: Robin Bailey and Kim Seipt  Website: Aria Benefits and Caledon Hills Private Wealth

What does a people-first culture look like beyond the words on a company website? In this episode of Success Leaves Clues, Robin Bailey sits down with Sarah Pazzano, Director of People at Jarvis Consulting Group, to explore how leaders can build a workplace where employees feel safe, supported, and able to grow. Sarah explains that a people-first culture requires investment in employee development, psychological safety, and leadership grounded in transparency and empathy. She shares how employee engagement surveys, participation levels, and voluntary turnover can help reveal whether those values are showing up in everyday work. One warning sign leaders may overlook: employees who stop raising concerns. Her perspective comes from a career that began in pharmaceutical packaging operations, moved into the startup world, and led to a deliberate investment in HR education. Sarah also reflects on two years working remotely from Paris and how that experience reshaped her thinking about flexibility, connection, and work-life balance. The conversation closes with Jarvis’s mission to equalize opportunity and maximize potential. Sarah explains why hiring primarily from resumes can overlook newcomers, recent graduates, and people returning after a career break, and why curiosity, learning, and thoughtful questions deserve a closer look. You’ll hear about: How Sarah found her path from pharmaceutical packaging to people operationsWhy authentic networking can open the door to a career changeHow HR education and hands-on experience complement each otherWhat a people-first culture requires in everyday practiceWhy employee silence and low survey participation deserve attentionHow HR and managers can build psychological safety in hybrid teamsWhat working remotely from Paris taught Sarah about work-life balanceHow hiring for potential can uncover talent a resume overlooks We talk about: 00:00 Meet Sarah Pazzano of Jarvis Consulting Group  01:03 From pharmaceutical packaging to startup people operations  03:53 Networking advice for a career change  06:02 Pursuing HR education and finding meaningful work  10:16 HR designations versus hands-on experience  13:12 What a people-first culture actually looks like  16:37 Building psychological safety in hybrid teams  19:21 Working remotely from Paris and rethinking work-life balance  24:37 Hiring for potential beyond resumes and credentials  29:52 Creating pathways for Canada’s overlooked talent Connect with Sarah LinkedIn: https://www.linkedin.com/in/sarahpazzano/Company LinkedIn: https://www.linkedin.com/company/jarvisconsulting/Website: https://www.jrvs.ca/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What does it take to turn a homemade snack into a brand stocked by more than 11,000 retailers? In this episode of Success Leaves Clues, Robin Bailey and guest co-host Christine Vigna sit down with Jake Karls, co-founder and rainmaker of Mid-Day Squares. Jake launched the company in 2018 with his sister Leslie and brother-in-law Nick, making bars in a Montreal condo kitchen and delivering orders themselves. Jake shares how inviting customers behind the scenes helped the founders build a community around the brand. He recalls an early turning point when Mid-Day Squares reached its first-year sales goal of $250,000 in just three months. Today, he says the company’s Montreal facility produces roughly 170,000 to 175,000 bars a day. The conversation explores why Jake stepped down as CMO after realizing management was not his strength. As Mid-Day Squares’ rainmaker, he now focuses on storytelling and building relationships that can lead to retail, investment, hiring, and other opportunities over time. Jake also speaks candidly about the burnout that forced him to reconsider his pace. He explains why rest is now part of how he sustains his work, and how regular therapy sessions help the three founders navigate difficult decisions while protecting their relationship as family. You’ll hear about: How Mid-Day Squares grew from hand-delivered samples to thousands of retail locations Why the founders chose to share the difficult parts of building the company What a personal response to a customer problem can mean for a brand Why Jake stepped away from the CMO role and became the company’s rainmaker How long-term relationships have helped Mid-Day Squares find partners and investors What burnout changed about Jake’s approach to work and rest How the founders use regular therapy sessions to communicate through conflict Why Jake wants the next generation to feel confident sharing their own stories We talk about: 00:00 Christine’s customer experience and Jake’s personal response  04:31 The early days of Mid-Day Squares in a Montreal condo  09:00 The founders’ belief in the business and an early sales milestone  11:47 Why the company shares its entrepreneurial journey openly  12:18 Jake’s experience with burnout and the lesson he learned about rest  21:35 Why Jake moved from CMO to the rainmaker role  23:07 Building friendships and business relationships over time  29:16 Working with family and addressing conflict  30:07 Why the founders committed to regular therapy sessions  38:14 The legacy Jake hopes to leave through Mid-Day Squares Connect with Jake LinkedIn: https://www.linkedin.com/in/jake-karls-653106ba/ Personal Instagram: https://www.instagram.com/jakekarls_ Instagram: https://www.instagram.com/middaysquare Facebook: https://www.facebook.com/MidDaySquares Website: https://www.middaysquares.com/   Connect with Us  LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What separates marketing that looks impressive from marketing that creates measurable business growth? In this episode of Success Leaves Clues, Robin and Al sit down with Alison Simpson, recently retired President and CEO of the Canadian Marketing Association, to explore marketing leadership, brand and culture alignment, business transformation, career growth, and the courage to act before certainty arrives. Alison explains why marketing leaders must speak the language of revenue, profit, customer lifetime value, and market share if they want to influence business strategy. She shares how a customer growth strategy at Holt Renfrew contributed to a 21% annual sales increase and attracted 270,000 loyalty program members in its first year. The conversation also explores the subtle language that reveals when employees no longer feel connected to a brand, why leaders build trust by taking responsibility when something fails, and how accountability can strengthen psychological safety throughout an organization. Drawing on a career that has spanned agency leadership, iconic brands, startups, corporate marketing, and the Canadian Marketing Association, Alison shares the principles that shaped her success: say yes when you are 70% ready, choose clarity over certainty, build relationships before you need them, and treat your career as a landscape rather than a ladder. She also reveals what completing 65 marathons and ultramarathons taught her about preparation, resilience, ego, and the essential difference between something that is hard and something that is harmful. You’ll hear about: How employee language reveals a growing divide between brand and culture Why customer-facing employees are critical to delivering a brand promise How leaders build trust by publicly taking responsibility for mistakes Why marketing needs more than a symbolic seat at the leadership table How to translate marketing activity into measurable business outcomes The strategy that helped generate a 21% annual sales increase at Holt Renfrew Why 70% certainty can become a competitive advantage How to distinguish relationship-building from collecting contacts What endurance racing teaches leaders about preparation and resilience Why ambition, kindness, and integrity are not competing priorities How Alison became the first female CEO in the CMA’s history Why the strongest careers are landscapes rather than ladders We talk about: 00:00 Al’s Great Cycle Challenge for SickKids  01:13 Meet Alison Simpson and her unconventional career journey  03:23 How Alison became an endurance athlete  05:01 Running 250 kilometres across the Sahara Desert  06:39 The early warning signs of brand and culture misalignment  09:00 Experiencing the customer journey before leading the team  12:45 How accountability builds trust throughout an organization  16:43 Why marketing still fights for strategic influence  18:05 Speaking the language of revenue, profit, and business growth  24:04 How businesses can measure marketing ROI  26:14 Rewirement and saying yes before you feel ready  31:08 Travel, meaningful experiences, and a priceless family memory  35:11 Is this hard, or is it harmful?  41:22 Ambition, integrity, and building a career without a ladder Connect with Alison LinkedIn: https://www.linkedin.com/in/alisonksimpson/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What if the greatest thing a leader could give their team was not an answer, but the space to discover one? In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Christine Vigna, Chief People Officer at Dejero, to explore leadership coaching, employee empowerment, workplace culture, governance, and the connection between employee experience and business performance. Christine explains why Dejero developed its leaders to become better coaches instead of simply better managers. By moving decisions away from leadership bottlenecks and empowering employees to solve problems, the company has strengthened engagement, accelerated development, improved customer experiences, and achieved employee retention two to three times longer than the average stay in the technology sector. She also shares why culture cannot be separated from business performance, how ego quietly erodes psychological safety, and why confident leaders create space for other people’s ideas rather than needing to be the smartest person in the room. This conversation offers a human-centered approach to leadership that does not sacrifice accountability or results. It shows how thoughtful coaching, consistent governance, and trust can help people perform at their best while building a stronger, more scalable organization. You’ll hear about: How employee experience influences customer experience and revenue Why governance supports scalable, consistent decision-making The question leaders should ask before sacrificing long-term capability How coaching became a driver of business performance at Dejero Why managers become bottlenecks when every decision flows upward How leadership coaching improves autonomy, engagement, and retention Why performance challenges should never surprise an employee How Dejero achieved retention two to three times the technology-sector averageThe difference between confidence and ego in leadership How executive behaviour shapes psychological safety and workplace culture Why coaches help people uncover answers instead of supplying them How to move forward without perfect information or perfect conditions We talk about: 00:00 Intro  01:13 Meet Christine Vigna, Chief People Officer at Dejero  02:26 Connecting people, customer support, and corporate governance  05:00 Are you solving today’s problem at tomorrow’s expense?  06:16 A customer experience lesson from Mid-Day Squares  09:34 Why governance becomes easier when people see progress  12:41 Aligning business strategy with human-centered practices  14:02 Developing better coaches instead of better managers  15:38 How coaching improved engagement, performance, and retention  21:21 Why every leader can benefit from coaching  24:46 How managers unintentionally become decision-making bottlenecks  28:57 Why ego quietly destroys culture and psychological safety  32:49 Moving forward without perfect conditions or complete information Connect with Christina LinkedIn: https://www.linkedin.com/in/christinemvigna/ Website: https://www.dejero.com/leadership/christine-vigna/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

Do successful leaders need to be ruthless, or can kindness, character, and high performance coexist? In this episode of Success Leaves Clues, Robin and Al sit down with Scott Vanderwel, CEO of PointsBet Canada, for a candid conversation about people-first leadership, strategic growth, employee empowerment, and building a successful company without compromising who you are. Scott was brought in to build PointsBet Canada before Ontario’s regulated online gaming market officially opened. Starting with a team of three, an emerging industry, and no established Canadian brand presence, he had to determine where the company could compete, how it would earn trust, and which opportunities were worth pursuing. He shares how PointsBet used strategic partnerships with organizations including Maple Leaf Sports & Entertainment, Curling Canada, the NHL Players’ Association, the NBA, and the NFL to establish credibility in a rapidly evolving market. Scott also explains why being ready on day one, controlling the company’s technology, and focusing on in-play betting gave PointsBet a meaningful point of differentiation. But the heart of this conversation is not betting. It is leadership. Whether you are a CEO, entrepreneur, people leader, executive, or emerging leader, this conversation is a powerful reminder that success is not only measured by what you build. It is also measured by how you treat people while building it. You’ll hear about: How Scott Vanderwel built PointsBet Canada from the ground up What leaders learn inside a startup that established businesses cannot teach them How strategic partnerships helped an unfamiliar brand earn trust Why choosing what not to pursue is essential to business strategy How PointsBet differentiated itself through proprietary technology Why geographic focus helped the company concentrate its resources Why strategy means little if you cannot move people toward it Why Scott’s team believes he should run a CEO school How leaders can inspire people to contribute their “extra 25%”  Scott’s personal definition of success and stakeholder balance Why you do not have to be ruthless to become successful How to make difficult people decisions while preserving dignity How regulated gaming can create greater consumer protection The example Scott hopes to leave for the next generation of leaders We talk about: 00:00 Al McDonald’s Great Cycle Challenge for SickKids  00:56 Meet Scott Vanderwel, CEO of PointsBet Canada  02:23 Building PointsBet Canada before Ontario’s market opened  05:02 Creating a market-entry strategy in a brand-new industry  06:08 Earning trust through major Canadian sports partnerships  08:13 The skills Scott carried from Rogers into the CEO role  13:09 Choosing where to compete and where not to play  16:00 How in-play betting became a competitive advantage  18:27 Why starting with Ontario gave PointsBet greater focus  21:08 Why Scott’s team says he should run a CEO school  23:24 Creating the conditions for people to do their best work  28:18 Scott’s personal definition of success  33:12 The mentors who shaped Scott’s leadership  35:13 Why successful leaders do not have to be ruthless  40:56 Making difficult decisions with consistency and humanity Connect with Scott LinkedIn: https://www.linkedin.com/in/scottyvanderwel/ Website: https://join.pointsbet.ca/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

Will AI replace recruiters, or will it make the best recruiters even more valuable? In this episode of Success Leaves Clues, Robin and Al sit down with Andrew Tai, Co-Founder at Deeply Talented and creator of Detra, an AI recruiting teammate helping enterprise recruiting teams work more efficiently without losing the human connection at the heart of hiring. After building, scaling, and exiting his first company, Andrew returned to entrepreneurship with a different perspective. Success, he explains, is rarely an overnight event. It is a collection of hard-earned repetitions, difficult seasons, imperfect decisions, and the willingness to keep moving when the outcome is uncertain. Andrew shares why AI will not replace the judgment, chemistry, trust, and connection required to hire great people. Instead, it can handle the repetitive work recruiters often have too little time to perform properly, from reviewing large volumes of applications to identifying qualified candidates who fall outside a rigid checklist. Whether you are a recruiter, HR leader, entrepreneur, hiring manager, or business leader navigating the future of work, this conversation offers a practical and optimistic perspective on using AI to strengthen human judgment, not replace it. You’ll hear about: The leadership lesson Andrew learned after building and exiting his first companyWhy most overnight successes are actually ten-year journeys How to appreciate the good old days while you are still living them Navigating the storms and sunshine of entrepreneurship Why AI will never replace human connection in recruiting The recruiting tasks AI can perform faster and more consistently How overwhelmed recruiters can overlook excellent applicants Why rigid job requirements can eliminate people capable of doing the work How AI can help companies take a Moneyball approach to recruiting The difference between demographic bias and recruiting shorthand How AI can challenge assumptions and expose gaps in hiring criteria Why recruiters remain responsible for judgment and final decisions What Andrew learned from hiring people who did not check every box How to make peace with decisions made using the information available at the time The danger of waiting for perfect conditions before beginning We talk about: 00:00 Introduction to Andrew Tai and the future of AI in recruiting  03:00 Leadership lessons from building and exiting a company  06:23 Why most overnight successes take ten years  08:09 Surviving the storms and sunshine of entrepreneurship  10:02 Will AI replace recruiters?  13:34 Human connection as recruiting’s enduring advantage  17:09 The hiring mistakes successful companies continue to make  19:00 How AI rediscovered a rejected candidate who was later hired  21:17 Why the best candidate may not meet every requirement  23:00 The Moneyball approach to finding overlooked talent  27:12 Recruiting bias, merit-based screening, and responsible AI  32:19 How an AI teammate can challenge a recruiter’s assumptions  35:21 Taking chances on candidates with potential  39:43 The proverbial trees Andrew is planting through entrepreneurship  42:06 Building a company to model resilience for his daughters  43:13 Why waiting for perfect usually means never beginning  46:12 How to connect with Andrew Tai and Deeply Talented Connect with Andrew LinkedIn: https://www.linkedin.com/in/ahytai/ Website: https://www.deeplytalented.com/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What if the most meaningful chapter of your life hasn’t happened yet?  In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Brenda Benard, COO at Benard + Associates, to explore midlife reinvention, overcoming self-doubt, and finding the courage to create a life that reflects who you are becoming. Brenda never planned to become a business leader. After turning down an opportunity to study theatre, struggling with low confidence, and believing her happiness would come from other people, she spent years moving through life without a clear sense of what she wanted. But a quiet voice continued reminding her that she was capable of more. Brenda shares why walking into a room filled with CEOs changed how she saw her own value, what her professional-athlete daughter taught her about self-belief, and how perimenopause affected her confidence, identity, and mental health. She also explains why asking “What’s the worst that could happen?” can make intimidating decisions feel possible. Robin, Al, and Brenda discuss intentional aging, protecting your health, listening to the whispers that tell you something needs to change, and refusing to postpone meaningful experiences until someday. Whether you’re questioning your career, navigating midlife, rebuilding your confidence, or wondering whether it’s too late to make a change, this episode is a powerful reminder that today is the youngest you will ever be again. You’ll hear about: Why Brenda calls herself the “reluctant COO”How self-doubt shaped Brenda’s early life and career decisionsWhy she turned down her dream of studying theatreBecoming a police officer at 33 while raising two young daughtersHow to recognize the quiet signs that you are capable of moreThe question that changed Brenda’s outlook on time and opportunityWhy taking responsibility can be more empowering than assigning blameThe moment Brenda realized she deserved to have her success celebratedHow other people may see strengths you cannot yet recognize in yourselfOvercoming feelings of inferiority around senior leaders and executivesWhy even the most accomplished leaders are still figuring things outHow perimenopause can affect confidence, identity, and mental healthWhat Brenda’s daughter taught her about making her younger self proudHow evaluating the worst-case scenario can help you move through fearWhy health and longevity have become central to Brenda’s next chapterThe power of trading expectation for appreciation We talk about: 00:00 Introduction to Brenda Benard and rethinking success in midlife 03:43 Self-doubt, abandoned dreams, and expecting happiness from others 05:02 Listening to life’s whispers and becoming a police officer at 33 08:41 “If not now, then when?” and why someday may never arrive 11:31 The moment Brenda decided she deserved to have her success celebrated 13:53 How Brenda’s employees saw strengths she couldn’t recognize in herself 21:06 Walking into a room of CEOs and overcoming feelings of inferiority 26:00 Perimenopause, self-confidence, and navigating the dark years 27:52 What Brenda’s daughter taught her about honouring her younger self 29:42 Using the worst-case scenario to move through fear 31:02 Raising courageous daughters and refusing to waste more time 33:10 Intentional aging, protecting your health, and living while you can 38:57 Trading expectation for appreciation Connect with Brenda LinkedIn: https://www.linkedin.com/in/brenda-benard-4a259188Website: www.benardinc.com   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What if people strategy was treated as a driver of growth rather than an HR cost centre? For the milestone **300th** episode of Success Leaves Clues, Robin Bailey and Al McDonald welcome back Joanna Kmiec, Chief People Officer at Loopio and one of the people who helped shape the direction of the podcast. Joanna challenges the idea that a Chief People Officer’s job is simply to keep employees happy. The real mandate is to build an organization that can grow, perform, and endure, without losing the humans inside the org chart. That requires business fluency, empathy, accountability, systems thinking, and the courage to speak up when everyone else in the room agrees. She explains how a strong people strategy reduces organizational drag, improves time to productivity, strengthens manager effectiveness, and allows senior leaders to spend more time building instead of repairing. Joanna also shares which workforce metrics matter, how people leaders can connect their work to business performance, and why the story behind the data is often more valuable than the number itself. Whether you are a CEO, founder, people leader, HR professional, or executive scaling a growing company, this episode offers a candid look at what strategic people leadership requires and how it can become a genuine lever for organizational growth. You’ll hear about: What a Chief People Officer is actually responsible for Why people strategy should be treated as a growth lever How culture can accelerate or obstruct business strategy Why people outcomes belong to managers, not only HR How to be bold without sacrificing kindness Measuring time to productivity and manager effectiveness Identifying and reducing organizational drag Why responsibility without authority causes leadership burnout How HR leaders can protect themselves during periods of chaos The quieter strengths that define exceptional leadership Why great employees sometimes leave great companies How former employees can become lifelong brand ambassadors Why creating other leaders is one of leadership’s greatest successes Using persistence and setbacks to move closer to a breakthrough We talk about: 00:00 Celebrating 300 episodes of Success Leaves Clues  03:02 The real role of a Chief People Officer  06:16 How strategic HR leadership has evolved  09:47 Becoming comfortable with tension as a leader  14:33 Why people strategy is a growth lever  18:14 Measuring the impact of people initiatives  22:23 What causes burnout among HR leaders  28:00 Staying calm and healthy during organizational chaos  34:38 The quieter qualities of exceptional leaders  38:00 Why great employees leave great companies  42:02 Why real leaders create other leaders  44:33 The advice that shaped Joanna’s leadership Connect with Joanna LinkedIn: https://www.linkedin.com/in/joanna-kmiec-chrl/ Website: https://loopio.com/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What if one of the most effective ways to improve employee engagement, workplace culture, and business performance costs nothing more than a thoughtful thank you? In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Kristian Gaetano, Chief Operating Officer at Achievers, to explore why employee recognition is far more powerful than an annual award or expensive incentive. Since joining Achievers nearly 15 years ago, Kristian has progressed from customer success into the C-suite by volunteering to solve the complex problems others avoided. He shares how leaning into his strengths, embracing challenges before he felt fully qualified, and becoming known as a dependable problem-solver shaped his leadership journey. The conversation also explores how leaders can balance data with instinct, why information requires human context, and how Kristian uses a “worry list” and trusted truth tellers to manage high-stakes decisions. As AI reshapes the workplace, he offers an important reminder that technology remains a tool. Critical thinking, community, empathy, and human connection are still what move organizations forward. Whether you are a CEO, founder, people leader, customer success professional, or executive navigating the future of work, this episode offers a human-centred approach to building stronger teams, customer relationships, and organizations. You’ll hear about: How Kristian grew from customer success into the COO role Why tackling difficult problems can accelerate leadership growth How customer success has become a strategic partnership Balancing data, instinct, empathy, and human context Why senior leaders need trusted truth tellers How to stop late-night worries from controlling your thinking The biggest misconception about employee recognition Why everyday recognition can influence workplace behaviour The connection between employee engagement and customer experience Why AI must support people, not replace critical thinking How organizations can remain human during workplace transformation Helping other people recognize and reach their potential We talk about: 00:00 Welcome and introduction to Kristian Gaetano  03:02 Growing from customer success into the COO role  04:00 Solving the problems nobody else wants  06:13 Leaning into your strengths as a leader  12:00 Why the customer is not always right, but is never wrong  13:19 Using empathy and constructive tension with customers  15:17 Balancing data with instinct and experience  18:09 The weight of making high-stakes leadership decisions  19:19 Kristian’s late-night “worry list” strategy  20:14 Why leaders need trusted truth tellers  22:15 Adding human context to data and AI  25:53 The biggest misconceptions about employee recognition  27:20 Recognizing everyday behaviours, not only major achievements  29:00 How employee engagement affects business performance  30:53 When AI transformation makes employees feel disposable  32:52 Attracting, engaging, and retaining talent in the future  34:20 Why the future of work requires community and humanity  36:24 Planting trees by helping people reach their potential Connect with Kristian LinkedIn: https://www.linkedin.com/in/kristiangaetano/ Website: https://www.achievers.com/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What makes people genuinely love where they work? In this episode of Success Leaves Clues, Robin Bailey is joined by special guest co-host Ashlea DesRoches for an inspiring conversation with Stephanie Crombie, Employee Experience Manager at HeyOrca, about the power of creating workplaces where people truly feel they belong. Drawing from a career that began in hospitality and took her around the world aboard cruise ships, Stephanie shares how memorable experiences, intentional leadership, and personalized employee journeys can transform workplace culture, especially in fully remote organizations. Rather than relying on generic perks or one-size-fits-all programs, Stephanie explains why today's most successful organizations create meaningful moments that help employees feel seen, valued, and connected from their very first day. From onboarding new hires to recognizing everyday contributions, she reveals practical strategies leaders can implement to improve engagement, retention, and long-term business success. Robin, Ashlea, and Stephanie also discuss remote culture, personalization, employee recognition, onboarding, belonging, leadership, workplace happiness, and why the way leaders make people feel will always matter more than any KPI. Whether you're a CEO, founder, HR leader, people manager, or someone passionate about building stronger workplace cultures, this episode offers actionable ideas for creating organizations where people thrive. You’ll hear about: Why employee experience extends far beyond perks and benefits Creating meaningful workplace moments that employees remember Building a culture of belonging in fully remote teams The connection between employee happiness and business success Why personalized recognition outperforms generic rewards How intentional onboarding increases engagement and retention Practical ways leaders can make employees feel seen and valued Recognizing effort throughout the journey, not just outcomes Voice and choice as the foundation of great employee experiences How small moments create lasting workplace cultures Why human connection remains leadership's greatest advantage We talk about: 00:00 Welcome and introduction to Stephanie Crombie 02:00 From hospitality to employee experience leadership 05:45 Why people remember how work made them feel 10:20 Building belonging in fully remote organizations 15:30 Spotting culture shifts before they become problems 17:30 Creating unforgettable onboarding experiences 22:20 Personalization versus automation in employee experience 27:00 Why generic perks no longer create engagement 28:15 The power of "Voice and Choice" 30:00 Happiness, belonging, and leadership culture 32:00 Planting trees for future employees 35:00 Final leadership lessons and closing thoughts Connect with Stephanie LinkedIn: https://www.linkedin.com/in/stephanie-crombie14/ Website: https://www.heyorca.com/   Connect with Us LinkedIn: Robin Bailey and Al McDonald Website: Aria Benefits and Life & Legacy Advisory Group

Has AI made hiring easier, or has it simply made recruiting more complicated? In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Kristin Condon, Chief Talent Officer at Sales Talent Agency, to explore how artificial intelligence is reshaping recruitment, leadership, and the future of work. With more than 25 years of experience advising founders, CEOs, CHROs, and executive teams across North America and the UK, Kristin has helped organizations make more than 4,000 successful hires. She explains why the companies winning today's talent market aren't relying on AI alone. They're building authentic leadership, investing in employer branding, and creating cultures where people want to stay. The conversation dives into the growing disconnect between AI-generated applications and the highly sought-after passive candidates companies actually want to hire. Kristin shares why attracting top performers now requires stronger leadership, greater transparency, and a talent strategy that's every bit as intentional as a company's revenue strategy. Robin, Al, and Kristin also discuss employer branding, succession planning, leadership development, candidate experience, and why curiosity, adaptability, and human connection are becoming even more valuable in an AI-driven world. Whether you're a CEO, founder, HR leader, hiring manager, or professional navigating today's evolving workplace, this episode offers practical insights into building organizations where both businesses and people thrive. You’ll hear about: How AI is transforming recruitment and hiring Why more applications don't necessarily mean better candidates The growing importance of employer branding Why passive candidates are today's most competitive talent How leaders can retain high performers in an evolving workplace The leadership qualities employees are looking for today Why authenticity and transparency build stronger teams Helping junior talent succeed in an AI-driven economy Why curiosity and adaptability matter more than ever Building succession plans for long-term business success The connection between talent strategy and business growth Why CEOs should treat talent strategy like revenue strategy Creating candidate experiences that attract top performers How human connection remains a competitive advantage We talk about: 00:00 Introduction to Kristin Condon and Sales Talent Agency 02:00 How AI is changing recruitment and talent acquisition 06:00 Why hiring has become more competitive, not easier 09:15 What employers should look for in future talent 13:45 Why employer branding matters more than ever 17:30 The founder's role in attracting top candidates 20:00 Leadership qualities that retain exceptional people 23:40 Why employees quietly disengage and leave 27:00 The power of vulnerability and transparency in leadership 31:00 Why talent strategy deserves the same focus as revenue strategy 33:00 Building a legacy through connection, contribution, and community Connect with Kristin LinkedIn: https://www.linkedin.com/in/kristincondon00/ Website: https://www.salestalentagency.com/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

What happens when life-saving medications exist, but patients still can't access them? In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with John Leombruno, CEO of OkRx, healthcare entrepreneur, pharmacist, and former founder of Patient Direct Pharmacy and GMD Distribution, to explore one of healthcare's biggest hidden challenges: helping patients get the medications they need without being buried in paperwork, outdated systems, and administrative delays. John shares how witnessing breakthrough treatments transform children's lives at SickKids Hospital shaped his career and inspired him to focus on improving patient access rather than simply developing new therapies. That experience became the foundation for building businesses that simplify specialty medication access for patients, physicians, insurers, and pharmaceutical companies. The conversation explores why healthcare still relies heavily on manual processes, how digitizing prior authorization can dramatically reduce administrative burden, and why trust, relationships, and patient-first thinking remain essential when introducing innovation into one of the world's most complex industries. John also discusses entrepreneurship in healthcare, balancing innovation with patient safety, the realities of building trust across healthcare systems, and why lasting business success begins with solving meaningful problems. You’ll hear about: How a life-changing experience at SickKids Hospital shaped John's entrepreneurial journey Why patient access remains one of healthcare's biggest challenges The hidden barriers preventing patients from receiving specialty medications Why healthcare still relies on outdated administrative systems How digital prior authorization can transform patient care The importance of building trust before driving innovation Why patient-first thinking leads to better business decisions Balancing innovation with patient safety The role technology plays in reducing healthcare administration Building successful healthcare companies by solving real problems Lessons from multiple healthcare exits and entrepreneurial ventures Why relationships matter more than speed in healthcare innovation How healthcare technology can improve outcomes for patients and providers Creating meaningful impact through purpose-driven entrepreneurship We talk about: 00:00 Introduction to John Leombruno and OkRx 02:10 The experience at SickKids that changed John's career forever 05:15 Why breakthrough medications still don't guarantee patient access 07:00 What a truly patient-centered healthcare system should look like 10:20 Why specialty medications are becoming mainstream healthcare 11:00 Building OkRx to simplify specialty medication access 14:20 Balancing scientific thinking with entrepreneurial leadership 16:10 Why trust is healthcare's most valuable currency 18:00 How innovation succeeds one relationship at a time 21:00 Planting seeds that improve healthcare for future generations Connect with John: LinkedIn: https://www.linkedin.com/in/john-leombruno-4bb1777/ Website: https://www.okrx.ca/   Connect with Us: LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group