What Is It Like to Work Under a Millennial or Gen Z Boss? My Take on Navigating the New Workplace Dynamics

Scrolling through Reddit, I stumbled upon an intriguing thread in r/askSingapore, where users were sharing their experiences of working under Millennial and Gen Z bosses. This got me thinking: Millennials are truly the game-changers in the workplace, aren’t they? And I don’t say this just because I’m a Millennial myself. I say it because of the shift I’ve witnessed—and lived—between the way we were managed and the way we now manage others.

Growing up in a work environment led by Gen X or even Baby Boomers, I found myself navigating the murky waters of questionable ethics and values. Trust was a currency rarely spent. I still remember my earlier days on the job, where inclusivity was more of a buzzword than a reality. I’ve been in meetings where conversations with clients took place entirely in Mandarin. As the Malay minority guy in the room, my role was to nod, smile, and pretend I understood every word, even though I was mentally adrift. It was a kind of micro-discrimination that silently screamed, "You don’t belong here." And trust me, that sentiment wasn’t just whispered behind closed doors. When I was working as a flight attendant for an international airline, the idea that "Malays need to work doubly hard than the Chinese to be visible to our superiors" wasn’t just an unspoken truth; it was openly acknowledged.

These experiences left a mark. They shaped how I see leadership and how I wanted to be seen as a leader. I made a promise to myself: If I ever found myself in a position to manage people, I’d do it differently. No one should feel invisible in the workplace, especially not because of their ethnicity, language, or background. I wanted to create a space where inclusivity wasn’t just a policy but a lived reality, where trust wasn’t earned through silent compliance but fostered through open dialogue.

However, here’s where things get complicated. Millennials like me, who have climbed the career ladder only to find ourselves in senior positions, often overcompensate. We stretch ourselves thin, trying to undo years of toxic culture, striving to be the “cool,” empathetic bosses who care about their team's mental health, personal growth, and work-life balance. But this comes at a cost: our own mental overload. We carry the burden of not wanting to become the managers we loathed, of trying to ensure everyone feels heard and respected.

Enter Gen Z, the new kids on the block. They bring with them a different mentality, one that is both refreshing and daunting. Gen Z employees are empowered in ways we never were. They’re more likely to set boundaries, demand inclusivity, and walk away from toxic workplaces without a second thought. They are unapologetically comfortable in their own skin, championing their identities. And why shouldn’t they be? Millennials have been the ones to pave this way, to challenge the old guard and break from generational toxic workplace culture.

Yet, this creates an interesting conundrum. While Millennials try to fix what’s broken, Gen Z expects nothing less than perfection in workplace culture. They are quick to call out microaggressions, push back against unnecessary hierarchies, and demand spaces that are genuinely inclusive. It’s a powerful stance, one that Millennials often admire and aspire to, but it can also feel like navigating a tightrope. We’re caught between wanting to change things fast and realising that systemic change is slow, gradual, and sometimes, painfully tedious.

So where does that leave us? Despite generational differences, one thing is clear: we’re all in this together. Millennials and Gen Z alike need to recognise that we’re working towards the same goal—a more inclusive, empathetic, and balanced workplace. We might have different approaches and expectations, but at the end of the day, it’s just work. And work is something we do, not who we are.

In navigating these generational shifts, we must remember to be patient with each other. Change is a process, not an event. And while Millennials may have started the fight, Gen Z is here to carry the torch. Our collective strength lies in our diversity and our ability to learn from each other. After all, it’s not about whether you’re a Millennial, Gen Z, or even Gen Alpha. It’s about creating a workplace where everyone, regardless of generation, feels seen, valued, and respected.

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