The Bosshole® Chronicles

Fear is expensive, and not just emotionally. It slows decisions, kills creativity, and quietly trains good people to play it safe. In this TBC Flashback, we sit down with Rich Sheridan, CEO and Chief Storyteller at Menlo Innovations and author of Joy Inc. and Chief Joy Officer, to unpack what it really takes to build a joyful workplace culture that performs without burning people out. Click HERE t...

Power is easy to grab. The harder move is refusing it, and that’s where George Washington still teaches modern leaders the most. With America on the eve of its 250th anniversary, we take a close look at why Washington became the unanimous choice to lead the Continental Army and later serve as the first President of the United States, then translate those qualities into practical leadership lessons...

Nobody tells you the hardest part of becoming a manager: the job changes overnight, but your skill set doesn’t. I rewind to the early 1990s, when I stepped out of individual contributor sales and into leading sales and marketing with almost no real mentoring. I was frustrated, second-guessing myself, and running into old-school management habits that looked normal on paper but felt wrong in practi...

Your attention isn’t just getting interrupted, it’s getting retrained. We sit down with digital wellness guide and speaker Mark Ostach to unpack why so many of us feel rushed, reactive, and oddly disconnected even when we’re “caught up.” Mark joins us to share the heart behind his new book, The Gift of Connection: Reclaiming Presence in the Age of Distraction , and to make a clear case that presen...

A dusty box in the basement turns into a full-on leadership time machine. I stumble onto a stack of handwritten memos from my old manager “Fred,” the same boss from our early “Don’t Bring Him Back” story, and reading them instantly brings back the stress of being managed by metrics instead of being led by insight. Don't Bring Him Back HERE ARE MORE RESOURCES FROM REAL GOOD VENTURES: Never mis...

“We only promote from within” sounds like a values-driven promise, but what happens when that promise puts the wrong person in a critical seat? John Broer and Karen Shulman dig into the uncomfortable reality: internal promotions can fail, sometimes spectacularly, when organizations rely on seniority, loyalty, or gut feel instead of clear evidence of job fit. Head, Heart, and Briefcase The Individu...

Memorial Day asks for more than a moment of silence, so we take a different path this week and sit with the words Americans once used when the stakes were life and death. I’m recording on Memorial Day weekend, thinking about the more than 1.3 million Americans who have died in service, and the debt that number represents: families, futures, and everyday people who never got to come home. If we wan...

Introspection feels like the responsible thing to do, but what if it’s quietly making you less self-aware and more stressed? We sit down with organizational psychologist and author Dr. Tasha Eurich to unpack what the science actually says about self-awareness, why so many high-achieving leaders get stuck in rumination, and how a few small shifts can change the way you lead. Click HERE to purchase...

PowerPoint may be the most common management tool on Earth, but it might also be the fastest way to lose the room. We sit down with Eric Harris, creator of The Campfire Method, to rethink how leaders communicate when the stakes are high and change is constant. Instead of treating presentations as a deck you “run,” Eric argues for a more human approach where we earn belief, reduce anxiety, and help...

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...