3 Signs You’re a Bad Boss: From a Retired COO
I want to preface this by saying I am not here to be mean. I am here to be useful.
I have spent over 13 years walking into organizations and assessing what’s working and what isn’t. And I can tell you with full confidence that most bad bosses are not bad people. They are people who were promoted because they were excellent at something — a skill, a craft, a function — and then handed a team with zero training on how to actually lead one.
That’s a setup. And the people who pay for it are the ones who work for them.
So if any of these signs land close to home — good. That means you’re self-aware enough to do something about it.
Sign 1: Your Team Tells You What You Want to Hear
If every meeting goes smoothly, every idea gets enthusiastic agreement, and nobody ever pushes back on anything you say — that is not a sign that you’re a great leader. That is a sign that your team has learned it’s not safe to disagree with you.
People stop telling the truth to bosses who punish the truth. Not always with dramatic consequences — sometimes just with a tone. An eye roll. A pointed silence that makes clear the feedback wasn’t welcome. That’s all it takes. Once your team learns that honesty has a cost, they stop paying it.
And then you are making decisions based on incomplete information while genuinely believing you have the full picture. Which is one of the most dangerous places a leader can be.
The fix is not to demand honesty. You can’t demand psychological safety into existence. You build it by responding well when someone does take the risk. The first time someone tells you something you don’t want to hear and you thank them for it — genuinely, visibly — that moment matters more than any open door policy you’ve ever announced.
Sign 2: You Confuse Busyness With Productivity
Bad bosses are very good at keeping their teams busy. Meetings that could have been emails. Reports that nobody reads. Check-ins that exist to manage anxiety — theirs, not the team’s.
If your team is constantly working and constantly behind, the problem is not their work ethic. The problem is that they don’t have clarity on what actually matters. And that is a leadership problem.
Your job as a leader is not to fill your team’s calendar. It is to make sure they know what success looks like, what’s on the critical path, and what they should be working on right now versus what can wait. Without that clarity, busyness fills the void. Everyone is working. Nothing important is moving.
A good leader protects their team’s time as aggressively as they protect their own. They cut the meeting that doesn’t need to happen. They kill the project that isn’t moving the needle. They are ruthless about what deserves attention and what doesn’t.
If you can’t clearly articulate what your team’s three most important priorities are this week — that’s the work. Start there.
Sign 3: You Take Feedback Worse Than You Give It
This one is the one nobody wants to talk about.
You give feedback regularly. You call it a culture of accountability. You pride yourself on being direct. And then someone gives you feedback and suddenly it’s different. Suddenly there’s context that wasn’t considered. Suddenly the person giving the feedback has an agenda or doesn’t understand the full picture or is being too sensitive.
I have been in that room. I have watched leaders who were extraordinary at delivering feedback completely fall apart at receiving it. And I have watched what it does to a team when they see that the standard applies to everyone except the person at the top.
It destroys trust. Quietly and completely.
If you hold a leadership title — granted or self-proclaimed — you are held to the standard you set. You cannot ask your people to be accountable and then exempt yourself from that same accountability. It doesn’t work that way. And if you’re honest, you already know it doesn’t work that way.
The leaders I’ve watched earn genuine loyalty — not compliance, but loyalty — were the ones who could sit with hard feedback, thank the person for the courage it took to give it, and come back the next day having actually thought about it. That’s not weakness. That’s the whole job.
One More Thing
Your people are not going to tell you any of this to your face. Not because they don’t think it — because they’ve calculated the risk and decided it isn’t worth it.
The fact that you’re reading this and thinking about whether it applies to you puts you ahead of most. The ones who need it most will never make it this far into the post.
Your people deserve a leader who is willing to look at themselves as honestly as they look at everyone else. That’s the whole thing. That’s what separates the ones who retain great talent from the ones who keep wondering why great people keep leaving.
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