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A lot of people spend plenty of time thinking about how to succeed in their jobs, but far less time thinking about how to choose the right jobs in the first place. In this episode of Career Sessions, J.R. Lowry sits down with Kelly O. Kay, managing partner at executive search firm Heidrick & Struggles and co-author of Show Up to Win: How to Land the Leadership Role You Want. Drawing on decades of experience advising executives and companies, Kelly shares an insider’s perspective on how to manage your career more deliberately. He explains why you should take the recruiter call even when you’re happy where you are, how to test your value in the market, what makes a candidate’s story compelling, and how to evaluate whether an opportunity is actually right for you. J.R. and Kelly also discuss why internal candidates sometimes struggle against outsiders, how to recover professionally after being fired, the subtle ways candidates sabotage themselves during the hiring process, and why your reputation can follow you for decades. Whether you’re actively considering a move or perfectly happy in your current role, the message is simple: the best time to manage your career is before you need to. Check out the full series of “Career Sessions” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/kelly-kay/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

You may not think of yourself as a salesperson, but every day at work, you’re selling something—an idea, a proposal, your capabilities, or even yourself.   In this episode of Career Sessions, J.R. Lowry sits down with sales expert, author, and longtime podcast host Andy Paul to explore what the rest of us can learn from great salespeople about influence, curiosity, and human connection.   Andy explains why the best way to persuade someone isn’t to push harder, but to understand what matters to them. He shares how asking better questions and truly listening can strengthen relationships, why curiosity is often trained out of us as we move through school and work, and how to avoid making conversations about ourselves.   The conversation also moves beyond sales to a bigger career question: Are you building the career you actually want—or simply following someone else’s playbook? Andy discusses why success is situational, how to find environments where you can be yourself, the importance of choosing the right boss, and why it’s sometimes better to leave a bad fit rather than keep trying to make it work.   Along the way, Andy shares lessons from nearly five decades in business—and a reminder that there’s no age limit on taking on new challenges.   In this episode, you’ll learn: Why everyone is selling, whether they realize it or notHow curiosity can make you more influentialThe difference between listening to understand and listening to respondWhy great questions create stronger relationshipsHow to find work environments that fit your strengths and valuesWhy you should define success on your own terms Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/andy-paul/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

What if you achieve everything you thought you wanted in your career, and still find yourself wondering if that's really all there is? Former Vertex CEO Jeff Westphal joins host J.R. Lowry to discuss how you can build a Work Life Worth Living when traditional status isn't enough. Jeff Westphal spent two decades as CEO of Vertex, helping grow the company from roughly 75 employees to more than 1,000 and increasing its value fortyfold. Along the way, he started asking deeper questions about purpose and why listening can be far more powerful than having all the answers. He shares how an intense focus on reflection transformed his leadership and helped him create an environment where employees felt truly invested. They also examine how rapid changes in AI mean distinctly human qualities like empathy, judgment, and connection will define our professional future. Whether you're rethinking your path or leading a team, this conversation will help you reflect on what truly makes your career meaningful. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/jeff-westphal/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

Most professionals assume great work speaks for itself, but solid Product Positioning proves that value never communicates automatically. When competitors offer flashy feature checklists or when crowded markets blur real differentiation, buyers and hiring managers get confused quickly. Host JR Lowry sits down with April Dunford, leading positioning expert and bestselling author of Obviously Awesome and Sales Pitch, to unpack why building something valuable is only half the battle. They walk through actionable frameworks to move past surface features, clarify unique value themes, and align internal teams before ever pitching external buyers. Together, they break down how individuals can treat their career journeys like high-stakes B2B products by narrowing focus, embracing natural strengths, and knowing exactly when to walk away from poor-fit opportunities. Finally, they tackle the rise of artificial intelligence, outlining why automated tools raise the bar for genuine business strategy rather than replacing it. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/april-dunford/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

What's the real job of a leader? According to Dave Ulrich, it isn’t having all the answers, building your own reputation, or even telling a compelling story about where you’re going. Great leaders help the people around them build their stories—and create value for others. In this episode of Career Sessions, J.R. Lowry sits down with Dave, one of the world’s most influential thinkers on leadership, talent, and organizational effectiveness, for a wide-ranging conversation about what great leadership looks like in a rapidly changing world. They explore why many of the fundamentals of leadership are timeless, even as technology and workplace expectations change dramatically. Dave explains the critical distinction between values—what matters to you—and value—what your actions create for someone else. He also shares a simple question leaders can use to rethink how they spend their time: What will happen in someone else's life because of what I do today? Dave and J.R. also discuss the choices and trade-offs that come with ambition, why our definition of success should change at different stages of life, and what Dave learned from deliberately stepping back from his own career while raising his children. And, inevitably, they tackle AI. Dave argues that AI makes distinctly human capabilities more important, not less. As information becomes ubiquitous, leaders will increasingly differentiate themselves through vision, innovation, emotion, judgment, and wisdom. The conversation also explores learning agility, navigating uncertainty, admitting when you don’t know the answer, and becoming comfortable figuring things out alongside the people you lead. Whether you’re a first-time manager or an experienced executive, this episode is a reminder that leadership ultimately isn’t about you. It’s about what becomes possible for other people because you were there. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/dave-ulrich/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

Finding a job has never been easy, but today’s hiring process can feel particularly frustrating. Hundreds of applicants compete for a single role, AI is reshaping how candidates are screened, and qualified people often struggle to get noticed. At the same time, employers insist they can’t find the talent they need. So what’s really going on? In this episode of Career Sessions, J.R. Lowry talks with Lorena Prego, founder and CEO of Prometeo Talent, who has spent two decades in recruiting and helped companies make more than 5,000 hiring decisions. Lorena takes us behind the scenes of the hiring process to explain what recruiters and hiring managers actually look for—and what separates candidates who consistently land opportunities from those who struggle to break through. They discuss why applying to hundreds of jobs may actually hurt your search, how to take more control of an interview, what recruiters notice when comparing your resume and LinkedIn profile, and how to build productive relationships with search firms. They also explore how AI and remote work are transforming recruiting and why communication, critical thinking, adaptability, and the ability to keep learning will become even more important. Whether you’re actively looking for a job or simply want to position yourself for your next opportunity, this episode offers a practical insider’s guide to getting noticed, telling your story, and managing your career for the long term. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/lorena-prego-ojeda/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

AI can already draft, summarize, analyze data, write code, and find patterns faster than most of us. So as these capabilities become increasingly commonplace, what will make you valuable? In this episode of Career Sessions, J.R. Lowry talks with Liat Ben-Zur, former senior executive at Microsoft, Qualcomm, and Philips and author of The Bias Advantage, about how AI is changing the skills that matter most—and why some of the experiences that once made your career harder may actually have prepared you for what's coming next. Liat argues that the answer isn't trying to compete with AI at what it does best. Instead, we need to double down on capabilities machines struggle to replicate: judgment, adaptability, empathy, ethical decision-making, creativity, influence, and the ability to see what others miss. They also discuss why hard work alone isn't enough to advance your career, how to make your impact visible without becoming overly self-promotional, why nonlinear careers may become increasingly valuable, and how to use AI to strengthen your thinking rather than replace it. In this episode, you'll learn: Which human capabilities will become more valuable as AI gets betterWhy career setbacks and being an outsider can build unexpected advantagesHow to make sure your contributions are recognized—not just deliveredWhy career range may be more valuable than narrow specializationHow to use AI as a thinking partner without weakening your own judgmentWhat leaders will need to do differently as AI reshapes organizations If you're wondering how to remain relevant, differentiated, and valuable as AI transforms the workplace, this conversation offers a practical roadmap. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/liat-ben-zur/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

AI can write, analyze, summarize, code, and create—and its capabilities are advancing at a remarkable pace. So as machines become more intelligent, what will keep humans indispensable?   Johan Roos believes the answer lies in what he calls “human magic”: the distinctly human capabilities that technology can support, but never replace. Johan is an internationally recognized strategy scholar, former business school dean, co-creator of LEGO Serious Play, and author of Human Magic.   In this episode of Career Sessions, Johan and J.R. explore why our advantage in an AI-powered world comes not from trying to compete with machines, but from becoming more human as AI gets smarter.   They discuss the five capabilities at the heart of human magic—curiosity, creativity, critical thinking, communication, and collaboration—and why practical wisdom and sound judgment are becoming increasingly valuable. They also examine the danger of “cognitive offloading”: relying so heavily on AI that the very skills that differentiate us begin to atrophy.   Johan shares what leaders should be doing differently in the AI era, including asking better questions, creating the conditions for their teams to think deeply, and focusing the AI conversation on transforming tasks rather than eliminating jobs.   The conversation also revisits the origins of LEGO Serious Play and what Johan learned about creativity, collaboration, and better decision-making by getting people out of conventional meetings and thinking with their hands. Those lessons may be even more relevant as organizations figure out how humans and AI should work together.   The takeaway: use AI intensely to prepare—but when the room is watching, show up as a human. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/johan-roos/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

Why do some teams consistently outperform while others—with equally talented people—struggle with endless meetings, constant interruptions, and burnout? In this episode of Career Sessions, JR Lowry sits down with organizational psychologist and bestselling author Ron Friedman to explore what separates exceptional teams from average ones. Drawing on research involving more than 6,000 workers for his new book, Super Teams, Ron reveals that only about 8% of teams qualified as “super teams”—and that what distinguishes them often runs counter to conventional wisdom about productivity, collaboration, and where work should happen. Their conversation covers: Why how a team works matters more than where it works—and what that means for the ongoing debate over remote, hybrid, and in-office work How excessive meetings and always-on communication undermine productivity—and why great teams establish clear meeting guidelines Why individual productivity hacks can actually create bottlenecks for the rest of the team The importance of protecting focused work and why “brainwriting” can produce better ideas than traditional brainstorming How active recovery outside of work can improve performance—and why leaders’ recovery habits can affect their teams The three ingredients of workplace trust: competence, caring, and consistency Why shared goals, role clarity, and interdependence are essential for creating a true team mentality Practical ways to take control of your workday by looking forward, looking backward, and staying present Why working longer hours eventually produces diminishing—and even negative—returns How high-performing teams are approaching AI differently, including openly sharing prompts and learning from one another rather than hiding their AI use The central message is simple: great teams aren't built by assembling the smartest people or forcing more collaboration. They're built intentionally, by creating the conditions that allow talented people to do their best work—both individually and together. Whether you lead a team or work as part of one, this conversation offers practical, research-backed ideas for reducing friction, building trust, protecting people's time, and creating a team that performs at a higher level. Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly conversations on careers, leadership, and the changing world of work. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/ron-friedman/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

For decades, a good job meant stability, career development, and a long-term relationship between employers and employees. But according to MIT Sloan professor Paul Osterman, that social contract has fundamentally changed. In this episode of Career Sessions, JR Lowry sits down with Osterman to discuss the ideas behind his new book, Disposable Workers, and why more than one-third of today's workforce now falls into employment arrangements designed for flexibility rather than long-term investment.   Together, they explore what's driving this shift, why it extends well beyond the gig economy, how AI may accelerate the trend, and what individuals, leaders, and policymakers can do to build a future of work that benefits both organizations and employees. Whether you're just starting your career or leading an organization through change, this conversation will challenge the way you think about job security, career development, and the future of work.   Key topics covered: Why Paul Osterman believes over one-third of workers are now "disposable workers"The difference between contractors, freelancers, marginal workers, and traditional employeesWhat's driving organizations toward more flexible—and less committed—workforcesHow AI is likely to accelerate the trend toward workforce disposabilityThe costs of disposable work for employees, organizations, and societyPractical advice for building career resilience through skills, networks, and smart career choicesWhat business leaders and policymakers can do to improve the quality of work Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/paul-osterman/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

Most people were never taught how to manage money. Yet they're expected to navigate rising housing costs, student debt, investing, retirement planning, and an economy that often feels stacked against them.   In this episode of Career Sessions, Career Lessons, JR Lowry sits down with Carrie Joy Grimes, founder of WorkMoney and author of the USA Today bestselling book The Joy of Money, to explore why financial success has far more to do with psychology than spreadsheets.   Carrie explains why shame and avoidance keep so many people financially stuck, how small behavioral changes compound into long-term wealth, and why the biggest obstacle to financial security often isn't a lack of knowledge—it's the stories we tell ourselves about money.   They also discuss:   Why "I'm just bad with money" is one of the most damaging beliefs you can have The surprising connection between money habits and career success Why budgeting should create freedom—not guilt How to overcome financial avoidance and build confidence one small step at a time Why chasing the next hot investment rarely beats mastering the fundamentals How to think about raises, retirement savings, and building wealth in today's challenging economy   Whether you're just starting your career or trying to gain greater financial confidence after years in the workforce, this conversation offers practical, encouraging advice that can help you take control of both your money and your future. Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly episodes like this.  Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/carrie-joy-grimes/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

What if the biggest financial risk in your life isn't the stock market—but your paycheck?   Most professionals spend years building successful careers, yet their entire financial future depends on a single employer. In today's world of layoffs, AI disruption, and economic uncertainty, that's becoming an increasingly fragile strategy.   In this episode, JR Lowry sits down with Jon Ostenson, founder of FranBridge Consulting and author of Non-Food Franchising, to explore an alternative that more professionals are beginning to consider: business ownership through franchising.   Forget fast food. Jon explains why many of today's fastest-growing franchise opportunities are in service businesses—from home services and senior care to B2B consulting—and why they're attracting professionals looking for additional income, long-term wealth, and greater control over their future.   Together they discuss: Why relying on one paycheck may be riskier than owning a businessThe biggest myths about franchising—and what it's really likeHow professionals can own businesses while keeping their day jobsThe difference between entrepreneurship and buying into a proven systemWhat makes some businesses more recession-resistant than othersHow business ownership fits into a broader wealth-building strategy  Whether you're dreaming of leaving corporate life, looking for a second source of income, or simply thinking more strategically about your financial future, this conversation will challenge how you think about work, risk, and ownership. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/jon-ostenson/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

Most careers stall because professionals wait for permission, confidence, or the right timing rather than taking action. In this episode, host J.R. Lowry sits down with former professional athlete and entrepreneur Dre Baldwin to dissect why professional discipline outperforms raw motivation every time. Baldwin reveals how he translated lessons from overseas sports courts into scalable business frameworks centered on mindset, strategy, systems, and execution. They explore actionable ways to build true executive presence before you get the promotion, navigate career reinvention, and develop the human judgment skills AI can't replace. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/dre-baldwin. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

What if becoming a better leader has less to do with learning new management techniques and more to do with becoming more yourself? In this episode, former RBC executive and HomeEquity Bank CEO Katherine Dudtschak shares a deeply personal journey that transformed not only her life, but also her philosophy of leadership. After publicly affirming her gender while leading thousands of employees, Katherine discovered that vulnerability, compassion, and authenticity weren't leadership liabilities. In fact, they became her greatest strengths. In this episode, you'll learn: Why success and fulfillment aren't always the same thingHow fear-based leadership limits both people and performanceWhy vulnerability builds trust faster than authorityHow curiosity and compassion can outperform command-and-control managementWhy doing the inner work is one of the most important responsibilities of a leaderPractical ways to lead with greater authenticity without sacrificing resultsWhether you're leading a team, navigating your own career, or simply questioning whether the life you've built truly reflects who you are, this conversation will challenge the way you think about leadership and yourself. If you’re interested in the impact of capitalism on leadership and innovation, make sure you tune in. Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly episodes like this.  Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/katherine-dudtschak/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

Everyone talks about AI as the future of work. But what if the bigger story is something we're overlooking? In this episode, JR speaks with leadership strategist and author Dan Pontefract about why experience—not youth—may become one of the most valuable assets in tomorrow's workplace. As workforces age and labor shortages grow, Dan argues that organizations must rethink how they hire, develop, and retain talent—or risk losing decades of knowledge and expertise. In this episode, you'll learn: Why demographic change may have a bigger impact on work than AI What "age debt" is—and why organizations aren't prepared for it How ageism affects professionals at every stage of their careers Why traditional generational labels may be doing more harm than good Dan's "Rivers, Rocks, and Rubies" framework for understanding career growth How organizations can turn experience into a competitive advantage instead of treating it as a cost What professionals can do to build careers that remain relevant and rewarding for decades Whether you're just starting your career, leading a team, or thinking about what's next in your 50s, 60s, and beyond, this conversation will challenge many of the assumptions we've long held about work, careers, and retirement. You'll come away with a new perspective on why experience may be one of the greatest advantages you can build—and why the organizations that recognize its value will be the ones best positioned to succeed in the years ahead. Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/dan-pontefract/. For more career guidance and resources, subscribe to my member community at https://community/pathwise.io