Gen Z Guide To Understanding Millennial Managers and The Workplace

There's been an active focus on research and resources aimed at helping millennial managers understand and lead Gen Z teams. All major publications like Forbes, Harvard business review, SHRM, have written extensively on the topic.

But to my surprise, little information exists to help Gen Z understand their millennial managers—how they think, where they’re coming from, and why they work the way they do.

As a result, Gen Z is often left to rely on social media advice from creators who are rarely part of organizations and often don’t bear the consequences of their words.

So, what happens? We, Gen Z, show up at work armed with half-truths and lofty expectations of what a workplace?shouldbe—only to find that the reality is much more nuanced. And when things don’t align with those expectations, frustration builds.

While it’s easy to demand understanding, true collaboration comes from also trying to understand.

That’s the gap I want to bridge with this guide—a practical look at how we can work better with our millennial managers and the workplace in general.

Why Should You Listen To Me?

I’m not an outsider analyzing this issue from afar.

I’ve worked with millennials for over five years and now run a startup with a millennial co-founder. Together, we’re one of the rare cross-generational founding teams (seriously, let me know if you find another!)

I have fought for changes I believed were necessary, and in the process, I’ve learned invaluable lessons about working with people older than me. These insights didn’t come from theory but from real-world experience—negotiating, disagreeing, collaborating, and ultimately growing together with my millennial colleagues and leaders.

Before We Begin

Let’s set the stage with one key assumption:?both you (Gen Z) and your millennial managers are aligned with the organization’s mission and vision.

If your workplace manager fundamentally doesn’t care about the organization’s growth (or yours), then no guide is going to fix that. But if your workplace is?functional (even if imperfect)- then this guide will help you navigate these generational dynamics and set you up for success.

There will be moments when egos clash. That’s part of the human experience. But growth happens when we can step back, acknowledge those moments, and choose to move forward with mutual respect.

Why We (GenZ) Think The Way We Do?

We are the?children of the internet, social media, and COVID-19. Our lives have been shaped by an overwhelming flood of information, viral movements, and a steady stream of success stories that make everything look easy. We’ve grown up seeing stories of people going viral overnight or achieving massive success before they even turned 25.

Naturally, this shapes how we think about work:

• We believe in bold ideas because we’ve grown up watching digital success stories unfold overnight.
• We understand the internet and consumer behavior in ways that traditional organizations often don’t.
• We are adaptable to new-age skills that many millennials had to learn later in their careers.

These are all valuable traits. But they also come with a blind spot:

We are sometimes out of touch with the realities of organizational structures and long-term career growth.

Let’s be honest: social media has given us a skewed view of reality. We’re surrounded by highlight reels- perfect relationships, high-paying jobs fresh out of college, dreamy vacations, and we start to believe that’s the standard.

So when we step into the real world and get our first job offer, and the salary doesn’t match what we’ve seen online, we feel shame.

This shame manifests in different ways:

• Low self-confidence – We feel we aren’t as accomplished as our online peers.
• Resentment toward our employer – We feel the company isn’t fulfilling the criteria that social media told us a “good” job should.

But you know, not everything about the workplace is broken, and not everything online is real.

Understanding The Millennial Mindset

If Gen Z is the generation of limitless possibilities, millennials are the bridge between the old and the new. They entered the workforce at a time when opportunities were scarce, and success was often determined by persistence rather than instant innovation.

Most of your millennial leaders didn’t start their careers with the luxuries of hybrid work, mental health days, or viral LinkedIn posts that could land them a new job. Instead, they had to fight for their place in the workforce, often under rigid structures that didn’t accommodate flexibility, work-life balance, or even questioning authority.

This means that when you feel unheard at work, it’s not necessarily because your millennial boss doesn’t care—it may simply be because their professional conditioning was built in an era where they had fewer options to challenge the system.

The Evolution Of Work

If you ask a millennial mentor about how work culture has changed, you’ll hear stories of:

• Commuting for hours every day because remote work wasn’t an option.
• Staying late in the office because "face time" mattered more than output.
• Being grateful for basic workplace benefits that we now take for granted.

For many of them, the shift toward remote work was a revelation. It was the first time they could truly integrate their personal lives with their careers without having to sacrifice one for the other.

But while they welcome many of these changes, they also face an enormous challenge: the pace of transformation is faster than ever before.

What took decades to change for previous generations is now evolving within years. Millennials grew up learning a particular set of workplace values, only to find that within a decade, many of those rules had become obsolete. Now, they are expected to not only unlearn their old habits but also train the next generation while keeping up with the latest trends in tech, AI, and workplace culture.

What Millennials Bring To The Table

Millennials may not always align with our bold, fast-paced vision (rightly so! I’ll explain why at the end of this section), but they bring invaluable experience that often goes unnoticed:

1???Seeing Things Through?– Millennials excel at taking an idea from inception to execution. They’ve seen how initiatives can fail without patience and persistence.

2???Navigating Complexity?– They’ve worked on large-scale projects with shifting deadlines, multiple stakeholders, and unpredictable obstacles. They know how to manage chaos with a calm, strategic approach.

3???Mastering Core Skills?– Because they started their careers in a pre-AI, pre-automation world, millennials had to deeply understand the craft of their work. Whether it’s marketing, coding, operations, or finance, they learned the fundamentals in a way that allows them to train others (or even train AI systems that are now replacing some of those tasks).

4?? The Hidden Skill of Delegation – Gen Z often perceives their bosses as “not doing anything” while passing tasks down the chain. But in reality, delegation is a skill that they have made active effort to master over years.

Millennials have seen trends come and go. What they actually do(often without us realizing) is help us think harder about our bold ideas and filter out the noise from fleeting trends.

Victims Or Change Makers?

When our ideas meet resistance, it’s frustrating. You might think,?“Why don’t they get it? Why is my manager so stuck in their ways?”?Over time, this can make you feel like a victim of the system. You feel criticized for who you are—your bold ideas, your ambition, your way of working.

But let’s zoom out for a moment.

Every bold idea in history—whether it was a political reform, a revolutionary product, or a social movement—faced its fair share of backlash. Take any significant change, and you’ll find that the people driving it weren’t met with open arms. They were challenged, questioned, and, at times, outright rejected.

The Nature Of Bold Moves

Think about the fight for environmental sustainability. Climate activists spent years pushing for change, advocating for businesses to adopt greener practices. At first, they were dismissed as “idealistic” and “unrealistic.” Today, concepts like ESG (Environmental, Social, and Governance) are mainstream in corporate boardrooms. But this shift didn’t happen overnight.

The activists had to show?why?change was necessary. They built coalitions, presented data, appealed to emotions, and addressed every stakeholder’s concerns. It wasn’t easy, and it wasn’t quick—and it is still work in progress.

This is the lesson for us in the workplace: If we truly believe in a change, we can’t just demand it. We have to?convince.

The Work Behind Change

Think about building consensus as a long game.

Imagine it like this: you’re presenting an idea to your manager or team, but instead of one big presentation that wins everyone over, you need to have multiple conversations.

You have to listen first. Understand their concerns. Address their objections. And, most importantly, make them feel like this change benefits?them, not just you.

A forced solution, no matter how brilliant, won’t stick. People need to feel invested in the outcome.

Let’s revisit the?Ram Mandir resolution, one of the most sensitive and polarizing issues in Indian history. For decades, there was gridlock, with no resolution in sight. When Sri Sri Ravi Shankar stepped in, he didn’t demand an immediate fix. Instead, he brought opposing parties to the table, facilitated dialogues, and worked toward an agreement that all stakeholders could live with.

In your workplace, the stakes may not be as high, but the principle is the same:?lasting change comes from collaboration, not coercion.

A Workplace Case Study

You’re a marketing executive working at a small startup, and you report directly to the founder, who’s in their 40s. You notice that the company has little to no presence on social media, and you feel strongly that building a personal brand for the founder could transform your growth trajectory.

So, in your first week, you tell them:

"We need to be active on social media! If you’re not building your personal brand, the company will fall behind.”

Now, let’s break down how the founder might really feel (even if they don’t say it out loud):

• “We’ve built our company through network effects and one-on-one sales—we’re still getting clients this way.”
• “I’m not comfortable making reels online.”
• “Kids these days are so quick to judge. They don’t understand the realities of business.”
• “I don’t disagree, but we don’t have the bandwidth to implement this right now.”

Your idea may be spot-on, but the way you’ve presented it feels like an attack on their current strategy- a strategy that’s worked for them so far. Instead of opening a door for collaboration, you’ve unintentionally triggered defensiveness.

Flipping The Script

Instead of making a sweeping statement, try approaching the conversation with curiosity rather than certainty. Ask questions that invite discussion rather than triggering defensiveness.

For example:

1?? “What are our current growth channels? Which ones are performing best?”

2?? “I’ve noticed some companies in our industry using LinkedIn to attract talent and clients. Have we ever explored that?”

3?? “Would you be open to experimenting with social media in a low-effort way, like repurposing blog posts?”

This approach does three things:

?? It acknowledges the existing growth channels instead of dismissing them.

?? It makes the founder feel in control of the decision instead of being forced into it.

?? It opens the door for collaboration rather than confrontation.

Taking Ownership

Finally, your boss needs to feel that you’re not just making suggestions—you’re ready to execute. Many leaders resist change not because they dislike the idea but because they fear it will become another abandoned initiative.

So instead of saying "We should do this," try saying:

"If you're open to it, I can take the lead on this. Let me run a small pilot for 30 days and track the impact."

Take them on an adventure, and help them see the world upside down

This is me and Henna Vij (my millennial co-founder) on one of our adventures, exploring lost stories and finding inspiration in the most unexpected places.

This article is just an attempt to bridge the gap. By itself, it can’t create the change we need, but my hope is that it sparks conversations in the right direction and helps us move away from a space of resentment.

I urge millennial leaders, fellow Gen Z founders, and new joinees to take active steps toward building understanding and collaboration. Real change will take effort from all of us, and I’m excited to see where we can go together.

P.S. We’re hiring marketing fresher! At Cosmofynd , we’re on a mission to help people live in alignment with their soul through the timeless wisdom of ancient India. If you dream of a world that doesn’t exist yet, but are ready to roll up your sleeves and make it happen, apply here- https://parallel-howler-c73.notion.site/Growth-Marketing-Executive-JD-196bed739ce68030b7e2e1c26dc19213