Turning Dysfunction Into Your Leadership Edge
We’ve all had that moment—the kind where your manager says something so off-base you have to pause and ask yourself, “Did that really just happen?” Maybe you're left biting your tongue, feeling frustrated, or silently questioning your own sanity. But what if I told you that those moments of dysfunction—yes, even the frustrating, chaotic ones—could actually become the very soil in which your leadership potential takes root?
In this episode of Tim Stating the Obvious, I sit down with Eric Charran, author of Have You Ever Had a Boss? to explore this very idea. Eric has walked through the fires of corporate dysfunction—and not only lived to tell about it, but used it to become a better, wiser leader.
With over 25 years of experience as a technology executive and thought leader, Eric has led major initiatives at companies like Microsoft and Capital One. He knows what it takes to manage complexity, innovate through chaos, and lead with clarity—even when the system is anything but clear.
At the heart of workplace dysfunction is something very simple: imbalance. Eric shares that many leaders, especially new ones, walk into the role without a complete toolkit. They lead the way they were led. That might mean outdated, reactive, or emotionally unaware behaviors that don’t serve anyone well.
In fact, according to a 2023 SHRM study, 84% of workers said poor leadership directly causes unnecessary stress and work. But here’s the kicker—those behaviors aren’t always malicious. Often, they’re inherited patterns. And unless we break the cycle, we pass them on.
One of the most important distinctions Eric makes is between being a “manager” and being a true leader. We’ve all seen it—someone is a rockstar individual contributor, so they get promoted… and suddenly, they’re managing people without the training or self-awareness to lead well.
Eric lived this. Early in his career, he was promoted as a high-performing developer, only to find himself buried in performance reviews and admin tasks he didn’t sign up for. He pulled back for over a decade to refine his skills before stepping into leadership again—with purpose this time.
The takeaway? Organizations should start leadership development at the entry level. Let’s give our new leaders the tools before they start mimicking bad habits.
During the episode, we dive into different “manager archetypes” Eric identifies in his book. Some cause damage, some are misunderstood—but all are real.
One that hit home for Eric was the “Attack Sub Manager.” This type runs silent, runs deep. They stay quiet for days or weeks… until the last possible moment. Right before your flight or major presentation, they surface with a list of last-minute demands, only to vanish again. It’s exhausting, frustrating, and disruptive.
Then there’s the “Amnesiac Manager”—a confusing archetype who seems to forget entire conversations and agreements. You bring data, logic, and alignment… and they ask, “Why are we doing this again?” Eric admits he’s been on both sides of this one. It’s a call for grace and better systems, not judgment.
Here’s where things get personal. Eric shares a story about navigating a “LIFO” manager—Last In, First Out. These leaders chase whatever’s newest, causing “priority whiplash” for the team. The solution wasn’t rebellion. It was empathy and coaching.
Instead of resisting the leader, Eric helped them see how constant changes were hurting the mission. He equipped them with language to push back in meetings and helped reframe priorities. That’s real leadership—serving upward to strengthen the team’s foundation.
Eric is big on EQ. And in toxic environments, emotional intelligence and empathy aren’t soft skills—they’re survival tools. When your manager drops a stress bomb or forgets your entire proposal, it’s easy to take it personally. But nine times out of ten, it’s not about you. It’s about what they’re carrying.
By understanding the emotional state behind the behavior, you create space to lead—even when you’re not in charge. That’s how you influence outcomes and stay grounded.
Two of Eric’s most practical tools? Conversation and documentation.
He encourages employees to talk things through and follow up in writing. Not as a way to “cover yourself” but as a way to bring clarity and collaboration into the chaos. And when your boss resists that clarity? Stay curious. Stay flexible. Keep showing up.
Because the real win isn’t being right—it’s being heard.
We’ve all been in a meeting where we had to face a difficult manager or executive. Eric’s advice? Sit on your hands—literally, if you need to. Pause the urge to assert. Start with understanding.
Say, “If I were in your shoes, this would probably feel overwhelming.” Then ask, “Is that right?” That simple move opens the door to real connection. It flips the power dynamic from adversarial to collaborative. It makes space for solutions.
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