Hi Zee. Tell me, just how much of a jerk is your boss?
Do they micromanage and send emails at 11:43 PM? Schedule meetings that could have been a Slack message? Ask for your thoughts and then ignore them completely?
Dear Zee. I think I might have been a shitty boss once.
Confession time. I spent years managing teams and I can look back now and see moments where I was operating from stress or "fight mode" instead of leadership. At the time, I thought I was being supportive, but in reality I’m pretty sure I was hovering. I can now admit I’m guilty of expecting people to work the way I worked, instead of recognizing they were different humans with different needs, priorities and motivations.
The uncomfortable truth is that a lot of Millennial managers aren't particularly good at managing people.
Now before we throw every Millennial manager into the corporate dumpster, it's worth understanding how they got here. I can promise you that most Millennials didn't wake up one day and decide to become difficult. We, like you, inherited our own mess.
Let's look at where me (and your shitty Boss Mel) came from
Millennials were raised primarily by our friends the Boomers who taught us that hard work would be rewarded. It was a period of economic optimism. Success wasn't just encouraged, it became intertwined with identity. Being productive meant being responsible and being busy meant being valuable. We had a formula to follow that worked very well for Mom and Dad.
Get good grades.
Go to university.
Climb the corporate ladder.
Buy a house.
Build a career.
Retire comfortably.
When the economy shifted and many of those promises stopped materializing, Millennials didn't necessarily abandon those beliefs. Most simply worked harder.
Many Millennials entered the workforce around the time of the 2008 financial crisis, when jobs vanished, salaries stagnated and housing prices began what seems to be a never ending climb to totally unattainable. The ladder we had been told to climb didn't completely disappear, but it certainly became a lot shakier and a lot harder to access.
We also happened to be the last generation to remember a world before constant connectivity. We learned to work before smartphones, but we built our careers after them. As a result, we became the generation that answered emails on vacation, skipped lunch, took conference calls from soccer practices, and somehow managed to convince ourselves that burnout was a personality trait rather than a warning sign. (And for all of that Zee, I would like to formally apologize. We really screwed that one up.)
Then one day we became managers. The problem here was that nobody really taught us how to lead. We were promoted because we were good individual contributors, not because we understood psychology, coaching, conflict resolution, communication or organizational design. I’m not making this up, I swear. A recent Gallup report found that only 44% of managers have ever received any formal management training.
More than half of the people responsible for leading teams are essentially figuring it out as they go. I know I certainly was.
At the same time, Millennials were stepping into management during one of the biggest workplace transitions in modern history. They experienced the rise of hustle culture, the collapse of traditional job security, remote work, hybrid work, AI, constant digital connectivity and a global pandemic that fundamentally changed how many people think about work altogether.
To make matters more interesting, many Millennial managers are no longer career executives. They're actually founders. They built something from scratch, hired a few people, then hired a few more… and suddenly found themselves leading teams of twenty, fifty or a hundred people. The business grew faster than their leadership skills had a chance to develop and suddenly they’re responsible for managing huge teams without ever having developed the skills to do so. We spend a lot of time celebrating entrepreneurship, but very little time talking about what happens when a talented founder suddenly becomes responsible for the wellbeing, development and performance of dozens of people. Business growth can happen quickly but leadership growth usually takes longer.
Today, Millennials, like Mel and I, represent the largest managerial cohort in the workforce, which means many of your bosses are trying to navigate a workplace that looks nothing like the one they were trained for. Above them sit executives who built their careers in a world where face time mattered, loyalty was rewarded, and productivity was often measured by how many hours you were willing to sacrifice. Below them arrived you, Zee, asking many of the questions Millennials probably should have asked years ago:
Why are we doing it this way?
Why is being busy considered a virtue?
Why am I expected to answer emails after work?
Why are we measuring hours instead of outcomes?
They're fair questions. In fact, they're excellent questions.
The challenge is that Millennial managers ended up stuck in the middle. On one side are demands for bigger targets, faster growth and greater efficiency. On the other are demands for healthier boundaries, more flexibility and workplaces that recognized employees as human beings first and workers second. Neither side is wrong. Where Millennials got into trouble is that they tried to satisfy both sides using leadership tools we were never taught.
So what happens when someone is overwhelmed, undertrained, and squeezed from both directions? (cough… burnout) They fall back on what they know and start to micromanage, hover, work too much and send those really annoying emails at midnight. They mistake control for leadership and urgency for importance. Believe it or not, they aren't intentionally trying to make your life difficult. (Okay not all of them. Some bosses are genuinely jerks) For many Millennial managers, these behaviours are less about power and more about survival. They're operating from the only playbook they've ever been given.
Understanding your boss doesn’t mean excusing your boss. Plenty of managers have done the work to become better leaders, and plenty haven’t. But if we want better workplaces, we can’t keep pretending leaders appear fully formed. We have to understand how they were built.