Career Sessions

Are today's managers too nice? In our efforts to create more compassionate workplaces, have we gone too far in avoiding difficult conversations, lowering expectations, and letting poor performance slide?

In this episode of Career Sessions, J.R. Lowry sits down with Matt Hunter, executive coach and co-author of Tough Enough: How to Lead a Team to Greatness Without Being a Jerk, to explore why great leadership requires more than kindness. It also demands candor, accountability, high standards, and the willingness to make uncomfortable decisions.

Matt argues that many organizations have fallen into what he calls the "Mirage of Compassion"—creating the appearance of caring for employees while failing to challenge them to grow and perform at their best. But there's a fine line between being appropriately tough and becoming the kind of boss nobody wants to work for.

Together, J.R. and Matt discuss how to find that balance, including:

Why managers often confuse compassion with avoiding discomfort

How to establish clear expectations and hold people accountable without being unfair

Why psychological safety should encourage honest disagreement, not suppress it

How leaders can become more comfortable giving—and receiving—difficult feedback

Why the right level of toughness depends on your ambitions, circumstances, and stage of life

They also explore the risks of taking toughness too far, drawing lessons from high-profile business leaders and Matt's own experiences as an entrepreneur and executive coach.

Whether you're managing a team, aspiring to leadership, or simply trying to navigate a demanding workplace, this conversation offers a thought-provoking perspective on what it really takes to achieve high performance without sacrificing humanity.

The takeaway: Being a people-first leader doesn't mean making everyone comfortable. It means caring enough to tell the truth, set meaningful expectations, and help people become their best.

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/matt-hunter.

For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

What happens when your commitment to putting others first comes at the expense of your own well-being?

Kristen Hadeed built Student Made into a successful business known for its people-first culture. But after years of prioritizing her team and company above herself, she reached a breaking point. She had lost her passion, felt disconnected from herself, and realized that the leadership philosophy she believed in had become a source of burnout and resentment.

In this episode of Career Sessions, host J.R. Lowry sits down with Kristen, author of Permission to Screw Up and Human Leadership, to explore her journey from people-pleasing entrepreneur to a leader who understands that caring for others shouldn't mean abandoning yourself.

Kristen shares why she made the difficult decision to close the business she'd spent years building, how deeply held beliefs from childhood shaped her leadership style, and why avoiding uncomfortable conversations can actually damage the relationships we're trying to protect.

They also discuss practical ways to become a more effective and authentic leader, including how to recognize the beliefs holding you back, make time for self-reflection, give meaningful feedback, and have difficult conversations with courage and compassion.

Whether you're leading a team, navigating burnout, or questioning whether you've outgrown your current role, this conversation offers a powerful reminder: great leadership isn't about being perfect or keeping everyone happy. It's about having the self-awareness and courage to lead yourself as well as others.

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/kristen-hadeed/.

For more career guidance and resources, subscribe to my member community at https://community/pathwise.io

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 not
• How curiosity can make you more influential
• The difference between listening to understand and listening to respond
• Why great questions create stronger relationships
• How to find work environments that fit your strengths and values
• Why 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 better
• Why career setbacks and being an outsider can build unexpected advantages
• How to make sure your contributions are recognized—not just delivered
• Why career range may be more valuable than narrow specialization
• How to use AI as a thinking partner without weakening your own judgment
• What 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