The Question

What’s the worst boss you’ve ever had, and what did they teach you about leadership?

Story time: I once had a marketing manager who turned every meeting into a minefield. Any idea that wasn’t theirs was immediately dismissed. Not just disagreed with, shot down in a way that left you feeling small. I’d share a suggestion, and instead of debating it, they’d roll their eyes or cut me off mid-sentence.

After a few weeks of this, I stopped raising ideas altogether. I’d sit in meetings, keep my head down, and wait for instructions. Me, the guy who had built programs, raised money, and thrived on innovation, reduced to silence. I remember walking out of one meeting, taking a long lap around the block, just to breathe out the frustration.

I lasted four months in that role. And here’s the kicker: six months after I quit, they implemented the exact marketing strategy I had pitched on day one.

That job showed me exactly who I didn’t want to become as a leader. And sometimes, that’s the clearest mirror we’ll ever get. Here’s what it taught me.

The Research 🔍

Bad bosses leave scars, but they also leave lessons. Research shows that toxic leadership behaviours aren’t rare; they’re surprisingly common. 

Gallup’s State of the American Manager report found that one in two employees have left a job to escape a manager at some point in their career. According to further Gallup analysis, 52% of exiting employees say their manager or organization could have taken steps to prevent them from leaving. People don’t quit companies, they quit leaders.

The cost of that leadership gap is massive. Replacing an employee can cost anywhere from 50% to 200% of their annual salary when you factor in recruitment, onboarding, and lost productivity. It’s not just money leaving, it’s experience, relationships, and momentum.

And recognition matters more than most leaders realize. Gallup’s workplace research shows that employees who strongly agree they receive meaningful feedback and recognition are five times more likely to be engaged at work. That’s not about praise for praise’s sake, it’s about showing people that their effort has impact. Without that signal, the message is clear: stay quiet, stay safe, don’t bother.

The bottom line: bad bosses drive people out the door and silence the ones who stay. Great leaders flip that script by keeping people engaged, valued, and willing to go all in.

Some Advice 💬

The worst boss I ever had showed me exactly how quickly a team can shut down when ideas are dismissed or people feel undervalued. Within weeks, I went from motivated and brimming with ideas to silent and disengaged. And that’s the danger: bad bosses don’t always “break” people, they slowly condition them to stop trying.

As a leader, you have to remember that people are constantly reading the signals you send. Every time you dismiss an idea, ignore effort, or fail to follow through on recognition, you’re not just making a one-off mistake; you’re training people to pull back. Over time, that compounds into turnover, apathy, and wasted talent.

The flip side is also true. Leaders who make space for input, acknowledge contributions, and show they care about growth send the opposite message: “you matter here.” Those teams don’t just work harder, they work with more creativity, ownership, and resilience.

If you want to avoid being that boss, the one people quietly disengage from or actively leave, here are some quick hacks you can start applying right away:

1. Respond, don’t react.
   When an idea lands on your desk, your first words matter more than you think. A quick dismissal teaches people to hold back next time. Instead, pause and ask: “What problem are you trying to solve with this?” This shifts the conversation from judgment to exploration. Over time, it builds a culture where people bring you more ideas, and better ones.

2. Make recognition a system, not a mood.
   Recognition isn’t about grand gestures; it’s about consistency. Create a simple ritual: in every team meeting, highlight one contribution or learning, no matter how small. Tie recognition back to impact (“your prep helped us close that deal” versus “good job”). This does two things: it shows you’re paying attention, and it reinforces the behaviours you want repeated.

3. Close the loop.
   One of the fastest ways to erode trust is to let ideas vanish into a black hole. If someone brings you a suggestion, circle back, even if it’s just to say “we’re not acting on this now, but here’s why.” People can handle a “no.” What they can’t handle is silence, because silence feels like they don’t matter. Closing the loop shows respect, and respect is the currency of engagement.

4. Shift from control to ownership.
   Instead of giving instructions, frame problems. Say: “We need to improve customer response time. How would you approach it?” This gives your team space to take ownership. When people feel trusted to solve, they stretch their thinking, experiment, and feel more invested in outcomes. The best part? Ownership creates accountability; you’ll spend less time chasing and more time coaching.

5. Audit your leadership signals.
   Every few weeks, step back and ask: “What are my behaviours teaching my team right now?” If meetings are quiet, if ideas aren’t flowing, if people are only doing the minimum, those are signals. Don’t brush them off. They’re mirrors. Invite feedback, even if it stings, and adjust. Great leaders aren’t perfect; they’re tuned in.

Parting Thoughts 💭

That short, painful job taught me something priceless: people rarely leave companies, they leave bosses. And the ones who stay under poor leadership often stop bringing their best.

As leaders, our responsibility isn’t just to direct work; it’s to create an environment where people want to give their full selves. The way you listen, recognize, and empower doesn’t just shape the week, it shapes whether people stick around for the long haul.

So here’s the question worth asking yourself: if your team had the chance to describe you to someone else, would they call you the leader who made them smaller, or the one who helped them grow?

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