Feeling stuck between Boomers & Gen Z? Here's why the generational divide is making your job harder as a manager

Why Generational Gaps Are a Growing Challenge for Managers in Asia

A Baby Boomer employee comes to you and says, “This new hire lacks discipline. They don’t want to stay past 6 PM.”

Meanwhile, your Gen Z employee complains, “Why do we still glorify overtime? We should be optimising productivity.”

As their manager, you’re stuck between two very different mindsets, and you can foresee conflicts between the two groups. Leading across generations is hard when team members are not on the same page. Managing generational differences in Asia is becoming increasingly complex due to rapid economic development, cultural shifts, and technological advancements.

Unlike the West, where workplace culture leans toward individualism, many Asian organisations still emphasise hierarchy, collectivism, and seniority. However, younger generations—Millennials and Gen Z—bring new expectations for flexibility, autonomy, and purpose-driven work.

These differences are rooted in Asia’s economic transformation. As societies transitioned from agrarian economies to industrialised and knowledge-based industries, values have shifted. Older generations who grew up during economic hardships prioritise stability and material success, whereas younger generations, raised in times of prosperity, emphasise work-life balance, individual expression, and purpose-driven careers.

As a result, we see misaligned values, communication breakdowns, and clashes in work styles. Senior employees expect structured workflows and formal communication, while younger employees favour digital collaboration and instant messaging. For managers, bridging these generational divides becomes a real challenge. Recognising these disconnects early is key to fostering a cohesive work environment. Here are 10 red flags that signal a generational disconnect and what you can do about them.

If you side too much with Baby Boomers & Gen X

→ Younger employees feel unheard, unappreciated, and may quit.

If you cater too much to Millennials & Gen Z

→ Older employees feel disrespected, undervalued, and may disengage.

If you avoid taking a stance altogether

→ Conflicts escalate, creating a toxic workplace culture.

So what’s the solution?

Why the ‘One-Size-Fits-All’ Approach Doesn’t Work

A common mistake managers make is assuming that all employees function the same way. However, Asia’s workforce is deeply shaped by historical, cultural and economic factors that influence generational expectations. This results in a power struggle amongst older and younger colleagues within the team. The table below illustrates how the different beliefs and values play out at work

Get the full PDF of beliefs and value systems that differ across generations by DM-ing Vivek Iyyani

Even HR leaders struggle with differing values across generations. I was once in a meeting where a HR leader from a renowned MNC shared her challenge of working with this one leader in Japan while doing a global engagement survey and focus group discussion. The leader was from the Baby Boomer generation and he was asked to include his (younger) team mates to be a part of the session. However, on the day of the session, he turned up alone. When he was asked why, he responded with, “They don’t know anything.”, implying that their presence would not add any value to the session.

Situations like these highlight the deep-rooted generational tensions that exist in many workplaces. This cultural divide has even fueled phrases like ‘Ok Boomer,’ which reflect the frustrations of younger employees. Learn more about why the ‘Ok Boomer’ phrase was born and what to do about it.

When diverse perspectives are dismissed and not entertained, it leads to a lot of conflicts within the team that up in team members having seething resentment for one another. Unchecked generational tensions can cause misunderstandings, disengagement, and productivity loss.

We see this across the globe, and more so in Asia. It becomes a tug-of-war, where one side claims their way is the right way to go about any task. The Asian values hold us strongly to our behaviours, and we see every other alternative as deviating from our roots. For example, one of the deep-rooted belief systems that we still see to this day is on working hours. Be the first to arrive and the last to leave to be noticed as a hard worker. Leaders even used to quip,

“How can you leave for home when I, your boss, am still working longer hours than you?”

The ideology behind it: “Overtime Means You’re Dedicated”

And since the promotion lies in the boss’s hands, many comply with the culture that is set within the team / organisation. I remember I was in a board meeting (prior to Covid-19) with a client and the Millennial / Gen Z employee resource group (ERG). The discussion was on experimenting with the four-day work week. In a room full of Millennials and Gen Zs that were excited about the concept, there was one Gen X manager sitting in to listen. In between their excited discussion, he interrupted them by saying,

“I think you don’t realise something. Having a four-day work week is a nightmare. Instead of working 8 hours a day for 5 days, you will need to come in for 10 hours a day for four days. You will be cramming yourself with your workload over a shorter period of time. This is a bad idea. It’s not rosy as it looks.”

Workplace expectations have evolved with time and technology. One of the main reasons for generational clashes is this evolution of workplace expectations. Baby Boomers and Gen X prioritise job security and hierarchy, while Millennials and Gen Z seek purpose, inclusivity, and digital efficiency. The challenge for managers-in-the-middle is to create a work environment where all generations feel valued and aligned with the company’s mission.

(For those leading Millennial employees, understanding their motivations and preferences is crucial. Here are the top 10 questions I’ve been asked about engaging Millennials as employees and consumers.)

Instead of seeing generational differences as roadblocks, enlightened leaders view them as opportunities. Companies that successfully bridge generational gaps foster a more cohesive, innovative, and high-performing workforce.

Strategies to Overcome Generational Challenges in Your Team

Adapt Your Communication Style

Different generations prefer different communication methods:

• Boomers & Gen X → Prefer structured meetings, emails, and phone calls.

• Millennials & Gen Z → Favour instant messaging, video calls, and collaborative platforms.

To enhance engagement, managers should use a mix of communication styles to cater to all employees. As a Manager, you can implement various communication platforms—such as emails, instant messaging, and video calls—to accommodate different preferences. This flexibility allows employees to communicate in ways that are most comfortable for them, thereby reducing misunderstandings and fostering collaboration.

Encouraging Active Listening

Active listening should be promoted across your team to ensure that all team members feel heard and valued. This practice helps to prevent assumptions and judgments based on generational stereotypes, ultimately leading to a more cohesive team dynamic [19]. This is key in team meetings, when colleagues talk over one another to get their point heard. Both want to be listened to, so structuring the meeting in a way that allows all parties to be heard will enhance relationships across generations. As basic as it might seem, many employees may not know how to actively listen…so you should model this behaviour and provide training on effective listening techniques for those who find it hard to listen actively.

Leverage Technology

Nobody likes to feel left behind, and sometimes technology has a way of infiltrating our lives so quickly it feels like too much to keep up with. In such cases, as a manger, you can help your team members who might struggle with technology by creating a session where team members can share their favourite tech tools that they are using in their personal and professional lives. Moreover, training team members on new technologies can enhance comfort levels and promote a culture of adaptability. By adopting these strategies, managers can transform potential challenges posed by a multigenerational workforce into opportunities for growth, innovation, and enhanced employee satisfaction.

Addressing Resistance to Bridging Generational Gaps

“This Is Too Much Work”

Managing a multigenerational workforce presents a unique set of challenges for today’s managers, requiring an understanding of the distinct needs, expectations, and communication styles of different age groups. One significant challenge is the resistance to change that often arises when implementing new initiatives. Older employees may prefer stability and established methods, viewing changes as threats to their job security or comfort.

In contrast, younger generations thrive in dynamic environments and may become frustrated with the slower pace of organisational changes. This dichotomy can hinder innovation and adaptation, making it essential for managers to address these differing expectations proactively. Managers often feel overwhelmed by generational conflicts. The solution? Start small. Start with communication. It could be as simple as sharing new tech tools with one another. The key is to build rapport amongst team members so that they become to work things out when things get tough.

Employee Engagement is not HR’s responsibility. It’s yours

It is also key to remember that there’s a limit to how much HR can do for you. At the end of the day, you’re managing your team and you have to take the initiative to go above and beyond – as their leader. That’s what it means to manage people. You have to ensure they work well together as a team and are productive. So if taking those few extra steps can improve productivity and efficiency, what’s bad about that? In fact, these are the small things that are easy to do and also – easy NOT to do. Taking ownership as a leader is an identity you have embrace to solve the issues within your team and organisation.

The Hidden Opportunities in Multigenerational Teams

Statistics confirm the benefits of generational diversity in your team:

• McKinsey found that companies with diverse leadership (including age diversity) are 35% more likely to outperform their peers.

• Harvard Business Review reported that firms embracing generational inclusion saw a 19% increase in innovation revenue.

• A PwC study revealed that organisations with structured mentorship programs saw a 30% increase in employee engagement.

By integrating different generational strengths, organisations can enhance collaboration, innovation, and employee retention. Generational Diversity is an opportunity, not a problem. The workforce is evolving, and managers that embrace generational diversity gain a competitive advantage. Rather than seeing generational differences as a challenge, enlightened managers leverage them as an opportunity for business growth and success.

How Will You Bridge the Generational Gap in Your Team?

Rather than forcing one generation to conform to the other, the best managers create a balance that allows both to thrive. For older employees, encourage them to see mentorship as a leadership skill and be open to modern ways of working. For younger employees, help them understand that some traditional values (like resilience and teamwork) still hold value. For Managers, start by creating a culture of mutual respect, adaptability, and shared learning between generations in your team.

About the Author

VIVEK IYYANI is a Generational Collaboration Speaker at Millennial Minds Pte Ltd. He is an award-winning author of 4 books, namely "Empowering Millennials", "Engaging Millennials", "The Millennial Leader" and "Marketing to Millennials". He has spoken at organisations like the Brunei Government, Paypal, Oracle, Booking.com, Singapore General Hospital, and many more. He has been featured by the National Population and Talent Division (NPTD) under the Prime Minister’s Office (PMO) to feature in a video of #MySingaporeStory. He has also appeared on CNBC and Channel NewsAsia as a guest on the Gen Z topic. Vivek is known in his industry to speak at conferences on topics around Generational Diversity.

This article was first published at https://vivekiyyani.com