By Rebecca Wiessmann
Steve opens this episode from Las Vegas, on the ground at CES, where he’s stacking interviews and collecting the kind of leadership lessons that only show up when people are tired, busy, and trying to look competent on camera.
His guest is Joel Hilchey, whose career path sounds like a dare — engineer turned performer turned keynote speaker — and whose new book, The “6-and-a-Half Habits of Highly Defective Bosses,” is built around an uncomfortable truth: most bosses aren’t evil … they’re accidental.
They didn’t wake up dreaming of “leading people.” They got promoted because they were great at the work. They hit their numbers. They crushed sales. They were reliable in a crisis. And then one day someone tapped them on the shoulder and said, “Congrats — you’re in charge.” No training. No new operating system. Just a title and a team.
Joel’s big problem is the one every organization claims to care about (and then forgets to fund): losing key people. The A-players. The ones who quietly carry the place. He points out that “people don’t quit jobs, they quit bosses” is not just a meme — there’s research support behind it, and the reasons are painfully consistent: people don’t feel appreciated, challenged, recognized, or supported. Work satisfaction bleeds into life satisfaction. Leadership isn’t an HR issue; it’s a human issue.
And then Steve drops a story that makes the point in a way no slide deck ever could.
A CEO invites him to meet. Steve drives three hours. Waits. Texts. No response. The CEO finally shows up late, gives him almost no time, and moves on like it’s nothing. Steve’s conclusion is blunt and relatable: even if the company has a great product, he’ll pass. Because nobody wants to do business with jerks.
That moment ties to one of the episode’s core ideas: whether you’re selling a car, a tech solution, or asking someone to trust you with a loved one’s home, the “product” is often the people delivering the experience. You can be technically correct and still lose the relationship.
The Weirdly Perfect Leadership Lesson Hiding in Joggling
Somewhere in the middle of the conversation, Joel explains “joggling” — juggling while jogging (yes, this is a real thing; I looked it up) — and it becomes an unexpected leadership parable.
He talks about chasing a world record and discovering something that applies to careers and leadership alike: niche down far enough and the field gets smaller. You don’t have to be the best in the world at everything — you can become exceptional by leaning into what’s uniquely yours.
His punchline is absurd and memorable: he ends up setting a record for running backwards while juggling five balls. It’s ridiculous. It’s also the point. There’s power in finding your unfair advantage.
Steve immediately translates it into leadership terms: accidental leaders don’t just need competence; they need something that helps them connect — something distinctive that makes them real to their team. But Joel adds a crucial qualifier: uniqueness is great, but it doesn’t excuse being bad at the basics.
Why Leaders Stay Bad
Steve asks the question most people avoid because it’s a little too honest: why are there so many sucky leaders — and why do they stay that way?
Joel’s answer is more sympathetic than soft. Most bad bosses aren’t trying to be bad. They’re running old scripts. They lead the way they were led — by parents, teachers, authority figures — often without realizing it. So when someone misses a deadline, the default response becomes shame, lecturing, or “teaching a lesson,” even if they hated being treated that way themselves.
He shares a jaw-dropping stat from a conversation in the credit union world: it can be years between someone becoming a manager and receiving real management training. Even if that number is off, the point stands — one year is long enough to damage trust, morale, and careers.
And even when training exists, culture can sabotage it. If the organization rewards sucking up, hiding errors, and looking good instead of getting better, the wrong people rise — and stay.
The 2×2 That Explains What New Bosses Screw up First
Joel lays out a simple framework that immediately feels useful: a 2×2 matrix with time horizon (short-term vs. long-term) on one axis and focus (tasks vs. people) on the other.
New accidental bosses almost always overinvest in the quadrant that got them promoted: short-term + task-focused. Execution. Getting stuff done. Tightening screws. Making lists. Pushing harder.
Then the other quadrants show up — usually as unpleasant surprises:
- Long-term + task-focused (strategy): Are we doing the right work, not just doing work right?
- Short-term + people-focused (team dynamics): Conflict, awkward behavior, friction, performance drama—now it’s “your job.”
- Long-term + people-focused (career development): People are thinking about their future whether you ask or not. If you never talk about it, you’ll feel “blindsided” when they leave.
Joel even tells on himself: he had an assistant for two years and never once asked what she wanted next — until she quit. It wasn’t betrayal. It was normal career gravity, happening without him.
The “Nice Boss” Trap and the Feedback Fumble
Steve gets personal (and practical). He admits he often wants to be liked, and that can weaken accountability. Joel names this problem with one of his book’s habits: feedback fumbling.
He describes three ways leaders botch feedback:
- They don’t do it at all.
- They do it badly (think “annual slap in the face”).
- They demand feedback but won’t receive it.
Then he offers a simple move that changes the emotional temperature: keep conversations anchored in “what now?” rather than “who messed up.” When the focus is on repair and next steps, it feels like the same team solving the same problem.
He also connects feedback to another habit: credit stealing and finger-pointing. Teams watch closely for this. When things go well, do you share credit? When things go sideways, do you own your piece? Leaders who do both become more trusted — and ironically, more liked.
The Fastest Fix: Don’t Rely on Willpower — Build Systems
Steve asks the closing question every overwhelmed executive director is thinking: What’s the one thing to do first?
Joel’s answer is clarity before heroics: start with the self-assessment (the “Highly Defective Boss Assessment”) to identify where you’re most defective. Then — this is the real takeaway — stop trying to become a better boss through sheer intention.
Instead, build systems.
Block time for strategy and people development. Create triggers for recognition. Put “de-hassling” into the workflow so friction gets fixed before it becomes resentment. Decide what needs to be consistent and make it consistent on purpose.
Because, as Joel puts it, if you’re trying, people are surprisingly forgiving.
And that’s the best news in the whole conversation: you don’t have to become perfect. You just have to become intentional.
If you want to watch the full Foresight TV episode, here’s the link.
