How it works:
- Bad bosses break feedback loops
- Great bosses deliberately manufacture them
I’ve worked for both. I’ve been both. The framing above is how I try to not be the boss people warn their friends about.
Early in my career, I assumed bad bosses must be immature, unskilled, or morally compromised. I now believe all it takes to be a bad boss is to break feedback loops about your own behavior.
Specifically, a bad boss is someone who can’t metabolize critical feedback about themselves. Respond poorly to feedback just once, and the feedback stops permanently.
People learn very quickly what is safe to say to their leadership. When telling the truth comes with consequences, the truth disappears. From that point on, the leader can’t tell whether problems come from weak execution, strategy, or themselves. They’ve lost the ability to diagnose anything else.
Disagree with me? Here’s a pull-quote. You can’t argue with a pull-quote.
The moment a leader loses feedback about themselves, they’re still steering, but they’re flying blind.
I once onboarded a new executive to lead my org. Me peers and I were excited at first — this new person said all the right things about leadership. Then, in their first weekly meeting with us, they spent the entire hour explaining their personal definition of KTLO.
The backchannel snickered. New leader, nerves, it’ll be okay.
The following week, they did it again. Another full hour. No work happened.
This could have stayed funny and temporary. But when people gently tried to redirect — “The company already has a formal KTLO definition?” or “Uh, what are our quarterly goals?” — those people got their hands slapped.
That’s the moment feedback dies. Not because the leader is wrong, but because being right becomes unsafe.
Keeping your job can depend on knowing exactly how much truth your leader is willing to hear — and respecting it.
A friend of mine once had a boss tell her, “Never correct me in a meeting, even if I’m wrong.”
Alright. The line is clear. It’s unhinged, but it’s clear.
Once that line is visible, behavior adapts instantly. People stop offering signal and start managing their exposure. The work doesn’t necessarily get worse, but the leader’s access to it does.
From there, the organization slowly fills with second-order behavior: agreement instead of insight, alignment theater instead of problem-solving, silence where judgment should be. The leader is still making decisions, but now they’re doing it without access to reality.
I got into management partly to replace leaders I thought weren’t doing it well. Becoming another version of the problem would be the most ironic career failure for me.
Avoiding that outcome is a low bar: don’t destroy your access to feedback.
So what if I do the opposite and maximize feedback?
What Great Bosses Do Differently
Great bosses take the same idea — protecting feedback loops — and apply it deliberately and at scale.
A year ago, I hired two managers to report to me who were each significantly stronger than I am, in different ways. One is the strongest line manager I’d ever worked with. The other was exceptional at product leadership.
This is a great problem to have; I highly recommend it. It’s still a problem1.
I became responsible for supporting people whose abilities outstrip mine. I needed to help them grow but couldn’t just hand them my job as a promotion (there are two of them, so I very literally could not).
I made a decision then to maximize their success — at the company and in their careers — without letting my own limitations be the bottleneck. To do that, my job had to change.
My management stopped being about my judgment, my advice, or my answers. It became about crafting opportunities, building durable communication channels, and creating structures that exposed them to feedback they would otherwise never receive.
I’m going to say that again in a pull-quote, because then it’s definitely true:
Management stops being about judgment the moment your report becomes better than you.
I can protect my reports from turning into bad bosses by making systems that expose them to feedback. And, because I have positional authority, I can crank up the volume on that feedback really high and combine it with my own coaching and emotional support.
The job becomes a form of environmental design.
Tactically, here’s my process:
- Identify their strengths (and the inherent weaknesses that come with each)
- Set goals that are meaningful to the company and crafted to their strengths
- Construct feedback loops that connect their work to its impact
- Give a damn about them (so your feedback is trusted)
- Pay attention and give direct personal feedback on the work
Identifying strengths
This is not just skills — it’s the overlap of ability, knowledge, and genuine interest. Interest matters more than we admit. People don’t just perform better at what they enjoy; they learn faster. When someone grows in a direction that excites them, they’re happier, and we get more for every dollar of salary spent.
It also requires honesty about weaknesses — treating weaknesses not as personal flaws, but as design constraints. The goal isn’t to turn everyone into a generalist, but to build a team whose strengths cover for one another so no one is forced to lean on their weakest reflexes.
Setting real goals
This is where strong managers earn their keep. There’s just no shortcut; we gotta dig in and work the problem. Assigning goals and forcing someone to commit is easy and flimsy. That’s how we manage a vendor. Leading a team means shaping work around people, adjusting plans when the fit is wrong, and sometimes even applying backpressure on the roadmap.
Feedback loops and visibility
People need to see whether they’re winning. We set (or help them set) clear, achievable goals that deliver incremental wins.
Progress should be legible without a status update (I hate status updates — nobody is listening, people). When the signal is clear, teams self-correct. When it isn’t, you end up managing narratives instead of results.
Give a damn
Hopefully you got into management because this is the part you like. Awesome. One important note: If you feel positive vibes toward someone and you do not interfere when they’re working below their max potential, you don’t give a damn about them. You just give a damn about them thinking you do.
So not just vibes. Not performative vulnerability. Actually respecting someone’s experience. Remembering they are a human being whose life does not begin or end at work. Then tracking them toward success, even if they don’t love all of how you do that.
Pay attention
Great bosses give feedback on the work itself—especially when the person doing the work is more capable than they are. In those moments, feedback must be just that. Not advice. Not judgment. Not control.
If you hesitate to give feedback, use a trick to strip your interpretation out of it. Start your sentence with “From where I was standing, it looked like …” and then say what it looked like.
Yes, you are greedy for pull-quotes. Fine. One more.
When you lead people stronger than you, feedback should feel like a mirror, not a steering wheel.
Why This Actually Works
One last thing that should be obvious, but often isn’t: your reports are optimizing, just like you are.
Every day, they allocate time and energy to maximize personal return. Founders work brutal hours because they have autonomy and massive upside. Employees work hard when the work helps them grow, when they’re improving at something that matters to them, and when the feedback loop is tight enough to feel progress.
They are not working harder because they believe extra effort magically turns into company success and then into personal gain. That math doesn’t work, and they know it.
The process I’ve outlined above reliably leads strong people to the same conclusion: that working hard with you, here is the fastest way to grow and have impact.