Why Your Boss Thinks That Way: A generational breakdown of leadership

COMMENT | Daisy Ariho Kansiime | It’s a dull Monday morning. 7:30 a.m. sharp. The boardroom door swings open, and in walks Mr. Kato, the boss and personal human alarm clock, carrying a thick stack of printed agendas. Nothing screams “urgent” like murdered trees. He arrives with the energy of a motivational WhatsApp quote: “Rise and grind, champions!” Meanwhile, the air-con blasts like a US base in Antarctica. You drag yourself in, barely awake, silently asking the question on every junior staffer’s mind: Couldn’t this have been a voice note?

After six years navigating the modern workplace while dodging vague policies, haunted printers, and “a quick one” that stretches into a half-day marathon. As a corporate youngin, I’ve made peace with a simple truth: leadership styles are generational. Every boss, mentor, or middle manager has been shaped by a distinct mix of world events, economic climates, and cultural expectations. And while it’s tempting to roll your eyes during yet another printed agenda meeting,

It’s far more interesting to then ask: Why does leadership feel so different across generations? And how do we work with it instead of around it?

Take the Baby Boomers. Born between 1946 and 1964, they’re the boardroom veterans and are the “we built this company” legends who wear legacy like a tailored suit. They came of age in post-war optimism and independence movements. In their universe, loyalty was gold, structure was sacred, and questioning the boss bordered on career suicide. To them, authority wasn’t just respected; it was revered. They didn’t ping anyone on Slack; they waited their turn in boardroom queues.

Then came Generation X, born between 1965 and 1980, commonly termed “the silent fixers.” These are your stealthy middle managers, the ones who type like machine guns and solve everything from broken printers to broken HR policies without breaking a sweat. Raised during political instability and public service meltdowns, they turned candle-lit homework into careers. Gen Xers were told that education would save them, hence shaping their belief in it. They became the first-degree holders in their families and the invisible backbone of every office. No fluff. No chaos. Just systems that work and strong coffee.

And then we met the Millennials, born from 1981 to 1996. The dreamy-eyed idealists who dragged soft skills into boardrooms and transformed LinkedIn into a battlefield of motivational posts. They’re the generation that grew up on “you can be anything” messaging, only to graduate into a job market that demanded five years’ experience for entry-level roles. They hustle through burnout, juggle side gigs, and keep HR busy with wellness suggestions. They want meaning, balance, and mental health days even though they’re also expected to lead, innovate, and smile through performance reviews. They’re part rebel, part role model, often both in the same meeting.

And then there’s my peers, the Gen Z. Born into Wi-Fi, raised on YouTube tutorials, and shaped by pandemics, protests, and productivity hacks. We’re not here for titles; we’re here for impact. We don’t ask “why” to defy; we ask to improve. We crave feedback, reject busywork, and question tradition, not because we’re entitled, but because we’re efficiency addicts. We run on multiple browser tabs and coffee that’s more milk than bean. Our mentors might call us impatient. We prefer “strategically allergic to time wastage.”

Of course, it’s not just about the age difference, rather, it’s about what each generation carries to work. Boomers arrive with decades of experience and a growing sense of being sidelined by the digital revolution. Gen X walks in holding the weight of two generations: helping Boomers transition and managing Millennials who want purpose, not just paychecks. Millennials clock in, juggling babies, burnout, and bad internet. And Gen Z? We show up already multitasking, expecting Slack replies in 5 minutes and asking why we still need to print things in 2025.

So what really keeps everyone up at night?

Boomers are still trying to understand why printers seem moody while quietly fighting ageism and wondering when decades of loyalty stopped being valuable. Gen Xers remain the quiet workers who fix everything, get thanked rarely, get promoted slowly, and are constantly told they’re “too experienced” or “too quiet.” Millennials are stuck in the middle, expected to lead, inspire, and innovate while still paying rent during tough economic times. And Gen Z? We’re supposed to change the world, but first, we need our logins.

The result? Meetings where Boomers request hard copies, Millennials want to align with values, Gen Xers say “let’s just finish,” and Gen Z asks if it can be an email instead. These are not conflicts but rather code switches. And when we stop seeing each other as “the problem” and start seeing ourselves as interlocking puzzle pieces, that’s when the workplace gets interesting.

So how do we move forward?

It starts with making room for humility. Saying “I don’t get this” shouldn’t be career suicide—it should be normal.

Communication can be a bridge, not a battleground. Boomers can learn Slack. Gen Z can learn patience. Millennials can teach EQ. Gen X can teach resilience. And we all can stop pretending that tenure automatically translates to relevance, further highlighting that youth equals insight.

Because here’s the truth: Mr. Kato isn’t the enemy. He’s just from a time when “filing” meant actual files. So the next time he walks in with a stapled agenda and a sermon on professionalism, don’t roll your eyes. Roll with it. Leadership isn’t about one generation calling the shots anymore. It’s about how we move forward together.

Preferably with a working Wi-Fi connection, mutual respect, and a shared Google Calendar.

*****

Daisy Ariho Kansiime is an observant (and occasionally over-caffeinated) Gen Z.