What 19 Managers in 26 Years Taught Me
I was going through an old computer and stumbled upon a folder filled with work-related materials from my previous jobs. Most of it was made up of old performance reviews and portfolio samples I’d saved. But one text file labeled “managers” caught my attention.
When I opened it, I recognized it right away: It was a chronological list of every manager I’d ever had.
In 18 years at my first job out of grad school, I had 12 different managers—two of them twice. At my next job, I had four managers in five years. And in my last company, I had three more in three years. If you’re keeping score, that’s 19 different managers in 26 years: eight women, 11 men.
(NOTE: In that same time span, I also had 11 CEOs, but the cause and impact of that is another conversation entirely.)
It started stable enough. I had the same manager for the first five years. Then came the reorgs. And the layoffs. The era of “business transformation.” One time, I was the only person on my team not laid off—including the manager—so I floated, reporting to someone else while they figured out what to do with me. That trend never really stopped.
Here’s the breakdown on how long I reported to every manager (two people appear twice):
5+ years: 1
3–4 years: 1
1–2 years: 11
Less than 1 year: 6
One month or less: 2
More than once, because of timing, I ended up writing my own performance review. The new manager barely knew what I did, let alone whether I was any good at it. But HR deadlines wait for no one, helpful or not.
Since the employee version of the review usually came due first, and this was long before managers could lean on AI to polish their wording, it was obvious most of them were just copying and pasting what I wrote. A few didn’t even bother hiding it and simply asked me to send over a list of accomplishments.
One year, a manager admitted he’d used AI to generate mine. Not helpful if the point of evaluations is to evaluate me, but I admired the honesty.
The new norm seems to be churn over continuity. If you can avoid blame by shifting it downward, you do. And someone else becomes the problem.
How Did These Managers Stack Up?
If I were grading my managers, here’s how it would look:
Good/Great: 6
Okay/Tolerable: 6
Terrible: 7
It’s basically an even split. I’m not sure how that ratio lines up with what they teach at Harvard Business School, but I’d bet it reflects what many people have experienced, especially those who’ve spent years in the cubicle world where loyalty only flows one way.
So why is it so hard to be managed by a competent human being?
It doesn’t seem like a big ask. But somehow it is.
Management Is a Career Choice—Not a Pay Bump
Being a manager isn’t easy, and it’s more challenging than ever.
Technology disruptions, hybrid and remote work, generational shifts, the growing demand for respect across diverse perspectives, and an increased focus on short-term results over long-term strategy have all transformed the role. Add in the evolving values around what work means and why we do it, and the complexity only deepens. Some of these changes are overdue and necessary; others, less so. It doesn’t help that HR hasn’t kept pace—still operating as if it’s 1985.
But when I look back, the difference between the managers I respected and the ones who were on another page becomes pretty clear.
It starts with this: management should be a career choice—not just a pay increase opportunity.
Today, the path to a meaningful raise and input for many companies leads only through management, and that’s a flawed system. When you don’t adequately compensate and listen to the employees, they look at management openings to get some respect and financial stability.
But being a strong individual contributor doesn’t automatically translate into being an effective manager. Once that transition happens, it can be difficult to undo—especially when stepping back is viewed as a failure rather than a thoughtful realignment.
On one team I was part of, a new manager came in, and within a year, seven out of nine people were gone. Even the one person whom the manager hired quit after just two months. The manager, of course, survived.
At another company, I watched a team in my organization go through 100% turnover twice in just a few years before leadership quietly moved on from that manager.
Not all companies are like this. Silicon Valley companies used to be great at it, and some still are. These places separate well-defined managerial and IC tracks, and it is common for engineers, PMs, etc. to make more than their managers. Respect isn’t tied to headcount or title at these places—it is earned through contribution.
The best managers I had were in it by intention and investment. They wanted to lead. They took pride in helping others grow. They cared about your path as much as their own—like NFL head coaches who build deep, proud coaching trees.
One of my best managers didn’t micromanage or make grand speeches. She listened, asked sharp questions, and backed me consistently—in meetings, in emails, and in conversations with people outside our team. Then, in one-on-ones, she’d coach me directly and tell me where I needed to improve. But because she supported me publicly, I never lost face or confidence, and I trusted her feedback.
The worst manager situations are often the result of layoffs or reorganizations. It isn’t the opening or change in itself that is bad, as that can actually be a great opportunity. It is the lazy approach to resolving the gap.
Instead of a real search, these companies ask if someone on the team wants the role. If a an employee is good at their job and has vague management aspirations, what else do you need? Opening a req costs money and takes effort, and no one wants to deal with that.
Of course, when you take the lazy route, you risk ending up with a bad manager and losing a great developer, PM, or designer in the process. It’s a double loss and causes more harm to the team.
Or, worse, they bring in a “known quantity” from the CEO or VP’s past. That rarely works, because the new manager isn’t coming in to listen; they are coming in to validate the view from above.
I’ve been in that situation more than once. I always created a detailed doc listing all my responsibilities and put it on an internal shared drive for the new manager (so I can track and view metrics).
Most of the time, it was never read.
The Communication Divide
Here’s a simple rule: good managers communicate. Early and often.
They’re transparent. They give feedback when it matters, and not just at annual reviews.
Nothing frustrates employees more than getting blindsided with criticism that’s been hoarded. You hear it for the first time in the performance review and think, How long were you sitting on that?
Worse still, when the story’s vague or based on one unreliable source, the manager hits the trifecta—losing respect, trust, and hope in a single conversation.
A friend of mine recently got an email from his manager titled “chat about project X.” No agenda. No context.
He replied and asked for more details, so he could adequately prepare for this meeting (a very subtle and clever way of determining intent respectfully). The manager’s response: “It’s to discuss go/no-go for the project.”
A project he was already working on and previously approved. He was blindsided. How long were you sitting on that?
Moments like that destroy trust. And it’s surprising how common they are.
I once had a manager who didn’t schedule a single one-on-one the entire year. Instead, she’d randomly ping me on IM with, “Can you chat?”
Communication isn’t optional. It’s foundational.
The Real Superpower: Spotting Hidden Talent
According to The Wall Street Journal, the most defining trait of a great manager isn’t communication, organization, or even strategy. It’s the ability to spot and reallocate hidden talent.
They look past job titles and performance reviews. They see the potential hiding in plain sight, and they’re bold enough to put it to use.
It’s a mindset shift:
From managing performance → to developing potential
From filling vacancies → to creating opportunities
This is more important now than ever.
Skills evolve faster than org charts. It can be easier to hire from the outside than to rethink your own team. But the best managers know the greatest value usually already works there.
When someone’s strengths are truly aligned with their role, everything changes. Performance rises. Retention improves. Engagement deepens.
It’s not rocket science, but it is uncommon.
Final Thought: The Manager and the Mirror
Today I’m a freelance writer and author, so now I’m both the employee and the manager.
It’s a constant tug-of-war.
Who wins?
Not sure yet. My annual review with myself is next week, so I’ll let you know.
If this resonated with you, I’ve got a novel coming out soon that explores this world through a similar lens. You can read more and sign up for updates here.