The Bosshole® Chronicles

Your leadership strength can be the very thing that’s quietly costing you trust, clarity, and results. We’re joined by Dr. Martin “Marty” Dubin, clinical psychologist, serial entrepreneur, and author of Blindspotting: How To See What’s Holding You Back As A Leader, to put language and structure around the blind spots even high performers can’t see in themselves. Click HERE for the Blindspotting we...

A “toxic leader” can sound like a fixed identity, but Dr. Kevin Sansberry II pushes us to look at something more actionable: toxic leadership behaviors and the systems that reward them. We talk about why Kevin centers on relationships, why he intentionally uses informality to reduce in-group language, and how his work blends behavioral science, applied innovation, and systems thinking to serve peo...

Bad leaders don’t always look like villains. Sometimes they look like someone who means well, loves competition, and tracks a number on a dashboard that quietly trains the team to waste time. That’s where this conversation begins: Kristen Schmitt, founder of Thrive to Lead, shares how a “Bosshole” manager pushed metrics that rewarded optics over outcomes and how those choices created predictable,...

Pressure doesn’t turn you into a different leader. It turns the lights on. John Broer sits down with Sara Best to unpack what they call “the heart of a leader,” the most elusive part of their whole person model (Head, Heart, and Briefcase, plus Baggage). The goal is practical: give managers and supervisors a way to check what’s driving their behavior before stress pulls them into control, avoidanc...

A boss pulls you aside with a quiet request: “Research this and tell me it’s fine.” Then comes the real tell: don’t put anything in writing, don’t talk to anyone else, and don’t come back with “no.” That moment is where careers bend and consciences bruise, and it’s exactly where we start with Wharton professor and negotiation scholar Dr. G. Richard Shell, author of The Conscience Code. We unpack t...

AI is moving faster than most org charts, and that speed is exposing a hard truth: buying tools is easy, but keeping culture intact is the real work. We dig into a framework created by The Predictive Index™ that names five “superpowers” HR already has to guide AI adoption without fragmenting teams, commoditizing talent, or quietly eroding trust. If you lead people, manage change, or influence stra...

You can need a license to do almost anything, yet you can become a manager with “jack squat” preparation and still have daily power over people’s health, stress, and careers. That’s the tension at the heart of our flashback conversation with leadership expert Dr. Todd Dewett, recorded as teams were clawing their way out of peak pandemic uncertainty and still painfully relevant for today’s remote w...

Promoting your best individual contributor into management might feel like a reward, but it’s often the fastest route to frustration, misalignment, and avoidable turnover. We sit down with HR leaders Tina-Marie Wolfield and Jennifer “Jen” DuPont to unpack what a robust individual contributor career path actually looks like and why modern organizations can’t afford to treat people leadership as the...

Want a team that tells you the truth before the market does? We brought back culture architect Neil Pretty to mark the launch of Leading Beyond Fear and to unpack a practical path to psychological safety that goes beyond buzzwords. We talk about how to see real-time reality, reduce unforced errors, and build a culture where dissent is data, not danger. Click HERE to order Leading Beyond Fear Click...

What if the best leadership lesson starts with hauling your own kegs? We sit down with Shorts Brewing founder Joe Short to trace the arc from a teenage homebrewer in northern Michigan to a 22-year craft mainstay known for fearless creativity, consistent quality, and a culture people want to join.  Click HERE to visit the Short's Brewing website HERE ARE MORE RESOURCES FROM REAL GOOD VENTURES:...

The lights were bright, the stakes were high, and the work felt world‑shaping. Lilly stepped into national broadcast straight out of college, scaled a tiny shop into a multi‑crew operation, and answered calls when presidents landed or crises erupted—only to realize the culture fueling those wins ran on tests, temper, and control. Click HERE to learn more about Dialectics HERE ARE MORE RESOURCES FR...

Feeling overwhelmed by AI but tired of the buzzwords? We sat down with executive coach and AI23 co‑founder Erica Ishida to reframe the moment: this isn’t about squeezing a few more percentage points of efficiency. It’s about unlocking human potential and using AI as a true partner so people can do the work that lights them up. Click HERE to visit AI23's website Click HERE for The Potential Er...

Ever wish tough conversations didn’t spiral into stress and silence? We bring peace psychologist Dr. Jeremy Pollack back in this TBC Flashback to explore how leaders can turn friction into trust with a simple shift: care before solution. Instead of jumping to fixes, we practice reflective listening, validate what we hear, and slow our nervous systems so better options can emerge. Click HERE to acc...

What if your next meeting didn’t start with, “Let’s wait for a few more to join,” and end with, “Sorry, we’re out of time”? We sat down with Chad Littlefield, co-founder and Chief Experience Officer at We and Me, to unpack a practical, repeatable way to turn passive rooms into engaged teams. The Contribution Method replaces consumption with involvement, helping leaders design moments where people...

Trust is thinning across today’s workplaces, and the cracks aren’t coming from the usual suspects alone. We dive into Glassdoor’s 2026 worklife trends and unpack what managers and teams are actually feeling: a power swing back to employers, a rise in “forever layoffs,” remote work turning into a career trade-off, and AI anxiety that’s more about leadership choices than the tools themselves. Along...

Change feels relentless right now—faster cycles, noisier feeds, and fewer chances to catch our breath - and we're just 20 days into the new year! We take you inside what’s actually happening in your brain and body when uncertainty spikes, then show how small, deliberate actions can flip you from reactivity to leadership. No fluff, no platitudes—just clear science, real talk, and tools you can...

Change isn’t new, but the pile-up is real. Between shifting budgets, reorgs, tech churn, and personal life turns, even strong teams feel their vitality drop. We open up a practical, empathetic way to navigate uncertainty using the change curve: status quo, disruption, exploration, and rebuilding. Instead of pretending the dip doesn’t exist, we name it, normalize it, and use simple moves to climb o...

Click HERE for Amy's LinkedIn profile Click HERE to purchase The Fearless Organization Click HERE to purchase Teaming Click HERE to download "What is a Fearless Organization." Check out these other episodes on Psychological Safety: Aaron Dignan - Brave New Work John and Sara - Psychological Safety John and Sara - Above the Line, Below the Line HERE ARE MORE RESOURCES FROM REAL GOOD...

The final Tuesday of the year is the perfect moment to trade vague goals for practices that actually change teams. We share five manager resolutions for 2026 that cut through noise and target what matters most: self-reflection, psychological safety, emotional intelligence, a whole-person approach, and eliminating destructive behaviors that erode trust. HERE ARE MORE RESOURCES FROM REAL GOOD VENTUR...

Something for the holidays. Merry Christmas and Happy New Year to The Bosshole Transformation Nation! Send us Fan Mail

A fifth anniversary deserves a true origin story, and ours begins with a manager who meant well and nearly torched hard-won credibility. We rewind to the first Bosshole Chronicles episode and unpack two moments that shaped our mission: a plant visit where a leader faked fluency and a high-stakes client dinner that turned into a monologue. The details are uncomfortable on purpose—because every lead...

What if the most dangerous person in your company is also your top performer on paper? We bring Dean and Professor Emeritus Dr. George Reed to unpack toxic leadership with a definition that cuts through opinion, ego, and excuses: it’s a sustained pattern of behavior that damages team climate over time. Not a bad day. Not a tough conversation. A measurable, persistent drag on safety, trust, retenti...

Most promotions celebrate your past performance; leadership demands a different future. We’re pulling back the curtain on what it really takes to move from star individual contributor to effective first-time manager, with candid stories from Karen Schulman and sharp, field-tested tactics you can use today. If you’ve ever been “tapped on the shoulder” and told you’ll be great at managing because yo...

Gratitude gets real when work gets hard. We mark Thanksgiving by leaning into the uncomfortable truth that thankfulness isn’t just for cozy moments—it’s a practical, biological, and leadership-level tool for moving from fight or flight into calm, focus, and connection. John and Sara reflect on why gratitude helps leaders navigate tough feedback, toxic dynamics, and the wider “emotional recession”...

Forget the lazy Gen Z cliché. We asked RGV's young pro to share what bias looks like on the ground, then brought in author and generational sociologist Lisa X. Walden to unpack the real forces shaping how the newest cohort works, learns, and leads. The conversation moves from stereotypes to systems, showing how curiosity disarms conflict, how digital native skills accelerate adoption of AI an...