Turns Out, My Nightmare Boss Accidentally Taught Me 4 Lessons About Great Leadership That Stuck
ahmetnkececi | ShutterstockOf the 3.5 billion working people in the world, about one in twelve are managers — that’s roughly 291,000,000 managers. Is it realistic to expect they’re all going to be great? But just like how a broken clock is still right twice a day, a bad boss can still be useful.
It’s on you to pay attention, open your mind, and apply the lessons. I’ve always learned the hard way — from mistakes, from mentors, and nowadays from the other leaders I manage and coach. Here are some of the fundamental lessons that made me the leader I am today.
My nightmare boss accidentally taught me 4 lessons about great leadership that stuck:
1. 'A title doesn’t make you a better person.'
Humans are obsessed with status. It’s baked into us from millennia of scarcity, when our tribe was our lifeline. Social status means safety, support, and a higher chance of reproducing. Fast-forward to the modern world, and this drive might seem redundant. And yet social media, office-based hierarchy, and resource-rich developed societies still trigger these urges.
I’ve seen this same pattern everywhere. From local office politics to neighborhood associations to global corporations. Give a small man a big title, and suddenly you meet the ego he’s been hiding all along.
Power doesn’t change who you are; it amplifies it. I think of Ned. A great employee and a hard worker. But also insecure and desperate to be a somebody. His promotion to middle management unleashed a monster.
He took all disagreements as disrespect. Every slight went to his heart. Every good idea became his. Every bad one, someone else’s mistake. And anyone who challenged him would find him doubling down on them.
Writer Brian Klaas describes this in Corruptible. Small, unaccountable roles in Homeowner’s Associations (HOAs) often attract people desperate to have some power. A cursory web search will reveal how common it is for those with trivial, minimal powers to let it go to their head. The tyranny of big egos with tiny power breeds a weak manager paradox.
All their lives they’ve wanted to be someone. Now, with a title and a team, they feel like they’ve ‘made it’. And worse, this new status gives them a false sense of competence. The title acts in their mind as a rubber stamp on their thoughts, ideas, and actions.
Ironically, becoming a manager should mean questioning your actions more, not less. Every decision now echoes through your people and the culture. You have impact. You’re consequential. And you’re setting an example.
You need to develop a kitbag of new skills; otherwise, you’re using yesterday’s solutions for today’s problems. And that’s about as smart as trying to perform heart surgery on a pogo stick. Fail to adjust, and you’ll fall into the Faulty Leadership Feedback Loop.
You’ll overvalue your insights. Or lean on gut instincts that are incorrectly calibrated. Or keep judging other people’s work based on what you would have done — and remembering yourself as better at the job because, hey, you got promoted, so must have been great, right? Don’t get drunk on your status.
You’re no better than anyone else. Yes, you’re more responsible for what goes on and, as a result, need to be able to make decisions and call the final shots. But save yourself a lot of red faces and mistakes, and don’t slip into thinking you know more because you’re in charge.
2. 'You’re only as good as your last mistake'
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82% of managers are ‘accidental’ managers: solid workers who got promoted and then left to sink or swim. No training. No structured onboarding. No hope? I’m lucky. My old mentor was a failure so many times that he became an expert. You learn a lot from someone who’s failed so many times that success becomes the only option left.
On top of the wealth of experience he’d accumulated from decades of errors, he also gave me this golden nugget: “You’re never as good as they say you are when you win, and never as bad when you lose.”
As a younger man, I needed to hear this. I was hungry for validation and praise, terrified of looking stupid. But you can’t calibrate taste and quality when you’re letting others decide for you.
You need to work hard on things, see them through, and reflect on what you learned. You can’t do this if you’re doing things to impress others. And you can’t take the risks you need to learn if you’re worried about looking foolish.
You don’t overcome ignorance by running away — you turn and face it. But it didn’t really sink in until I saw it embodied in a later boss. He spent his career chasing validation: avoiding blame, dodging failures, and keeping his name off mistakes. The result? Someone very good at avoidance and not much else.
Each setback, error, mistake, or failure is a building block towards a stronger, better, more agile you. You don’t grow in a comfort zone. If you only do what’s easy, you’ll crumble when things get hard — and they will get hard.
Teams are a reflection of their manager. If you treat failure with shame, people will hide their mistakes. If you treat it like data, they’ll grow. Breaking free from the chains of other people’s opinions, I was able to integrate my failures and upgrade myself. And this set a great example for the team.
My mistakes are the real trophies. I’m proud of what they showed me, forced me to confront, and shocked me into fixing. Expose your weaknesses and learn from them. Integrate your failures and grow.
3. 'Do your job — and motivate people to do theirs'
What most people get wrong about leadership is exactly why it’s so necessary. Getting people to do things is hard — really hard. Many managers try to micromanage their way out of this. Because control feels like leadership. Until it kills motivation or infantilizes your team.
Angela was a solid editor. In a previous life, she’d run an online magazine and done freelance editing for notable publishers. Joining this company, she had found her niche in the team. She had a hawkish eye for detail, and so people often wanted her help checking their work.
And her feedback was detailed — multi-page reports with color-coded screenshots and rewrites for ‘clarity’. People were busy. The advice (née corrections) was seen as a shortcut to quality. And few would challenge the advice from someone confident and demonstrably competent.
Inevitably, she got a promotion. Leading her former colleagues, she leaned on what had gotten her here — more control masquerading as help.
She was quickly demonstrating her vision of ‘management’: nitpicking with a fine-tooth comb while the house burned down. Like, yeah, thanks for getting the nits in my hair, but there’s a fire, man. Is this really the time?!
Micromanagement is like a cheese knife. For very specific purposes, it’s a great tool. Maybe the best. But you don’t eat your soup with it. Or try to play the drums. Doing someone else’s job isn’t leadership. It’s avoidance disguised as diligence. The truth is, Angela wasn’t confident managing people, so she fell back on what she did know: doing the work herself. The problem was that she was calling this leadership.
Scratch the surface, and you see it’s all just turning on the hairdryer and saying there’s a hurricane. See, management is about managing. People, workloads, projects. Your job as a leader is to consistently produce high-quality output, ideally while making your team better. And this was Angela’s job too.
But all that time spent on micro-edits to emails and documents was so time-intensive, she dropped the ball on the big-ticket items. Y’know, the things she was actually paid to do. Every bad boss I’ve met thought they were raising standards. In truth, they were just shrinking the world to the size of their comfort zone.
“It is better to do your own duty badly than to perfectly do another’s” — Bhagavad Gita. Do that which only you can do. Do your job.
4. 'Authority is an illusion — influence is real power'
The hardest lessons come when you see yourself turning into what you once criticized. So for this final lesson, the terrible boss was me. Summer, 2007. I’m a newly promoted assistant bar manager, eager to prove myself. So I’ve brought in a bunch of new rules to ‘raise standards’.
Staff don’t seem to be keen on these. I take this as disrespect, and so I’m strict to enforce them. Soon, everyone is doing as I asked. Great, right? Then one night, everything falls apart.
No limes. Clogged urinals. A dead ice machine. The team is following all my rules, but showing no initiative. People were doing exactly what I’d asked without taking things on for themselves. I’ve gained compliance but lost commitment. Eddie, a friend I was now managing, takes me for a beer the next day to tell me straight.
“You’ve become a little tyrant.” And he’s right. Authority doesn’t really exist. But influence does. If you’re controlling, you’ll probably get compliance. But you’ll likely lose creativity, community, and care.
People don’t want to feel controlled. They want to feel part of something, like they contribute to it, and that they have the space to be themselves. Every manager crosses that line at some point — mistaking control for respect. The trick is noticing it before your team does, or acting quickly when they do.
Everything you need to improve at anything in life is hidden in the world around you. But it’s up to you to pay attention and gather these insights. Effective leadership requires building a healthy collection of these. And then the humility to use them. Every mistake I’ve seen — mine or another’s — is beneficial. Each one whispers the same truth.
Leadership isn’t about being perfect. It’s about staying teachable. You don’t need the perfect mentor, the best corporate training, or the most expensive coach.
Everything you need to improve is already around you. Collect the lessons, and unlock the leader within.
Tobias C. Shaw is a writer, leadership coach, and corporate executive. He's had articles featured in Medium and Business Insider, as well as many other sites, and has been working in and around leadership for the best part of two decades.
