The Bosshole® Chronicles

Sunday shouldn’t feel like a countdown to dread. In Part 2 we dig into the real drivers of the “Sunday Scaries” with Lisa Walden, co-author of The Future of Work Is Human, and get practical about what actually changes how teams feel and perform: human-centered leadership, clear communication, and thoughtful hybrid rituals that spark connection instead of compliance. Click HERE to order The Future...

The ground beneath work has shifted, and many leaders are still wearing shoes from another era. We dig into the “great chasm” between how managers were taught to lead and what today’s teams actually need, with guest Lisa Walden bringing sharp insight from her book The Future of Work Is Human . This first part of our three-part series tackles the return-to-office debate without clichés, showing why...

Want a culture that actually improves performance instead of living on a poster? We sat down with Heather Haas, CEO at Advisa and Predictive Index Certified Partner, to explore a clear, practical path to compassionate leadership that drives real results. The conversation centers on four levels of connection—job, manager, team, and culture—and how leaders can use each to reduce friction, boost enga...

What happens when a beloved company purpose stops landing the way it used to? We sit down with Biggby Coffee co-founder Mike McFall (and Bosshole Chronicles alum) to unpack a rare level of candor: why he let go of an identity he helped build, how a new president brought fresh focus, and what it takes to rewrite purpose, vision, and values without losing the soul of the brand.  Click HERE for Mike&...

A battlefield can teach you more about leadership than a bookshelf ever will. We sit down with retired U.S. Army Colonel Jeffrey McCausland—former Dean of Academics at the U.S. Army War College and CEO of Diamond 6 Leadership and Strategy—to translate Gettysburg’s hard lessons into everyday decisions leaders face right now. Click HERE to order Battle Tested Click HERE for the Diamond 6 website HER...

A battlefield can teach you more about leadership than a bookshelf ever will. We sit down with retired U.S. Army Colonel Jeffrey McCausland—former Dean of Academics at the U.S. Army War College and CEO of Diamond 6 Leadership and Strategy—to translate Gettysburg’s hard lessons into everyday decisions leaders face right now. Click HERE to order Battle Tested Click HERE for the Diamond 6 website HER...

Why is it so difficult for managers to simply say "I'm sorry"? This fascinating episode dives deep into the psychology behind leadership vulnerability and the barriers that prevent authentic connection in the workplace. HERE ARE MORE RESOURCES FROM REAL GOOD VENTURES: Never miss a good opportunity to learn from a bad boss... Click HERE to get your very own Reference Profile .  We us...

The Venturer stands as one of the rarest profiles in the workforce - representing only 3.31% of the population. These self-starting risk-takers bring a unique combination of analytical thinking and bold action that can transform organizations when properly understood and positioned. Click HERE to get your very own Reference Profile Related TBC Episodes: Head, Heart, and Briefcase The Collaborator...

Dive into the fascinating world of the Individualist manager. Making up just 3.66% of the population, Individualists bring a unique combination of independence, persistence, and results-orientation that can transform teams when properly understood and leveraged. Click HERE to get your very own Reference Profile Related TBC Episodes: Head, Heart, and Briefcase The Collaborator Manager The Operator...

Representing just 2.95% of the human population, Analyzers are the rarest personality type measured by the Predictive Index assessment. This scarcity creates unique challenges for hiring managers and team leaders trying to optimize job fit for roles where the Analyzer profile excels. Click HERE to get your very own Reference Profile Related TBC Episodes: Head, Heart, and Briefcase The Collaborator...

The hybrid work revolution isn't coming—it's already here. This revealing conversation with Jenny Mobius, Senior VP at SKEDDA and host of the Heroes of Hybrid Work podcast, cuts through the noise with hard data confirming what forward-thinking leaders already know: hybrid work delivers better results for both employees and organizations. Click HERE for Part 2 of our interview with Jenny...

Mark Ostach takes us on a fascinating journey through the psychology of technology and reveals how our digital behaviors profoundly shape our emotions, relationships, and workplace cultures. Drawing from his unique background in psychology and over a decade in the tech industry, Mark shares the pivotal moments that led him from bootstrapping a technology company to becoming a sought-after keynote...

The mysterious Scholar Reference Profile – analytical, reserved, imaginative, and technically-minded – takes center stage in this deep dive from The Bosshhole® Chronicles. Host John Broer unpacks the unique behavioral DNA that makes Scholars tick: their moderately high dominance, low extroversion, moderately high patience, and notably high formality create professionals who crave independence, ref...

What does it really take to become a CEO – and how do you prepare to eventually step away? In this remarkably candid conversation, Vince DiPofi, CEO of SSOE Group, peels back the curtain on his leadership journey from drafting board to corner office, revealing the personal transformation required to lead a global engineering firm. "You don't know what it's like until you're act...

Ever found yourself searching for that perfect candidate who can somehow be innovative and detail-oriented, people-focused and results-driven, all at once? Stop right there. This eye-opening episode debunks the myth of the "unicorn employee" – that mythical 18th reference profile that simply doesn't exist. Click HERE to get your very own Reference Profile . Related TBC Episodes: Hea...

What if the secret to transforming toxic workplaces wasn't just about removing bad bosses, but teaching good ones how to balance caring deeply with challenging directly? In this profound flashback conversation with Kim Scott, author of "Radical Candor" and "Just Work" , we explore the frameworks that can revolutionize workplace dynamics and eliminate the harm caused by poo...

Marcel Schwantes joins us to share the harrowing experience that inspired his new book "Humane Leadership: Lead with Radical Love, Be a Kick-Ass Boss." In a powerful testament to the physical impact of toxic workplaces, Marcel recounts how workplace stress caused his body to literally shut down—leaving him temporarily paralyzed and unable to walk for a month. This life-changing event bec...

What transforms a caring manager into someone their employees fear? According to executive coach Sabina Nawaz, it's not a personality defect—it's pressure. Drawing from her own jarring experience of returning from maternity leave to find herself snapping at her team, Nawaz reveals the hidden forces that push good people into problematic leadership behaviors. This eye-opening conversation...

Are your management practices stuck in the 1800s? They might be if you're still operating with conventional management approaches. In this eye-opening episode, Jason Lauritsen reveals why so many workplaces struggle with engagement, retention, and performance — our management methods were designed during the industrial revolution to make humans behave like machines. Jason introduces his groun...

Ever wondered about those colleagues who seem to change their approach depending on the situation? The ones who are harder to pin down, yet somehow able to work effectively with almost anyone? Our latest episode dives deep into the mysterious world of the Adapter Reference Profile. Click HERE for a short video about the Adapter. Click HERE to get your very own Reference Profile . Related TBC Episo...

Ever wonder why someone with a stellar resume struggles in their new role? Or why another employee with modest credentials becomes your top performer? The answer lies in understanding that people are more than their professional history. The Bosshole Chronicles takes you on a journey through the powerful "Head, Heart, and Briefcase" model—a framework that transforms how leaders view, sel...

Monica Challingsworth takes us behind the scenes of her entrepreneurial journey, revealing how conscious leadership principles transformed her hospitality career and led to the founding of multiple thriving businesses. With remarkable candor, she shares her path from college graduate to founder of Eustress and Demeter restaurant consulting and co-creator of Dink and Dine Pickle Park—an innovative...

Ever witnessed a manager publicly humiliate a colleague and felt that collective cringe spread through the room? The latest Bosshole® Chronicles episode tackles the destructive impact of sarcasm and public embarrassment in the workplace—common leadership behaviors that instantly qualify someone as a "Bosshole." HERE ARE MORE RESOURCES FROM REAL GOOD VENTURES: Never miss a good opportunit...

The modern mental health conversation has taken a concerning turn, according to clinical therapist Jonelle Massey. Rather than building resilience, we've defined wellbeing as the absence of discomfort and the avoidance of challenges—a definition that ultimately leaves us ill-equipped for life's inevitable difficulties.  Drawing from her experiences as a former D1 athlete and her work wit...

Freedom isn't free. This simple yet profound truth anchors our special Memorial Day episode as we explore the origins, evolution, and significance of this solemn American holiday that honors those who made the ultimate sacrifice for our nation. Did you know that approximately 43% of Americans, primarily younger generations, don't fully understand Memorial Day's origins? Beyond barbe...