How to Bridge the Gap Between Gen X, Gen Y and Millennials

Opinion: A dose of empathy can go a long way

Different generations tend to butt heads, but approaching each other with empathy can reduce that unnecessary tension. Getty Images
Headshot of Michael Ventura

I was born in Hackensack, New Jersey, in 1980. Depending on who you ask, that makes me part of Gen X, a millennial or part of the oft-debated, rarely-remembered label, Gen Y.

We don’t hear much about Gen Y for a few reasons. First, it’s relatively small when compared to the vast size of the baby boomers, Gen X, millennial and the newly-minted Gen Z. In addition, Gen Y is hard to categorize because it’s a blend of a few different mentalities. We were born with analog between 1977 and 1982. We grew up with encyclopedias on our bookshelves and typewriters in our schools. But at some point, computers appeared. We were the first generation in history to be given a formal technology education. And while that education was certainly a rudimentary MVP of today’s digital curricula, it gave us a unique understanding of two distinct worlds: a world pre- and post-digital.

Growing up watching Gen Xers enter the workforce ahead of us, my peers and I shared a sense of empathy for their mindset and rebellious nature. While baby boomers scoffed at them and called them “slackers,” we understood that their perceived malaise was really more of a disaffected middle finger to “the man.” It wasn’t that Gen Xers didn’t carethey just didn’t care to follow the path of the generation before them.

Today, in conference rooms and corporate offices, a new rift is playing out. Many of those same baby boomers now sit side-by-side with Gen X executives, their differences harder to discern in the light of today. These groups often malign the entitlement and haughty expectations of millennials, citing their lack of understanding for how the world really works. Having sat in many of these rooms and heard these conversations firsthand, it initially astounded me to realize how common this issue had becomeand how similar it was to the boomer/Gen X rift of 20 years ago.

But like the baby boomer/Gen X differences, millennials (by and large) are being misinterpreted. Their goals and expectations for the modern workplace aren’t wrong so much as they are challenging. They are forcing companies to consider different ways of operating that break from convention and put the employee experience first.

Offering more flexible ways of working (open PTO, flexible hours), creating more overt feedback loops (town halls, two-way reviews) and emphasizing the importance of culture (skills development, wellness programs) are just a few of the efforts cropping up in virtually every company geared toward recruiting and retaining young talent.

Shifting culture through organizational design is iterative, conversational and, most importantly, must be empathic.

Amidst these changing times, the empathic abilities of Gen Y are needed more than ever. Our odd place in the timeline of history affords us the ability to genuinely understand the views of both sides and often gives us an opportunity to be the much-needed mortar that holds these critical generations together.

In working to help bridge the gap between these generations, there are a few key insights I’ve uncovered that can help teams bolster their empathy for each other.

Practice deep listening

Too often, our personal biases or opinions on a topic have concretized the more we’ve been in the workforce. It takes effort to suspend your views in these critical moments but doing so can greatly improve your ability to listen deeply to the other voices in the room. Don’t feign listening while planning your rebuttal. Listen to hear your colleagues, going so far as to even project yourself into their shoes and see the topic from their vantage.

Ask orienting questions

An orienting question can help steer the conversation toward alignment by helping to reveal an aspect of the issue that might be getting overlooked. For example, a millennial team member might be debating the benefits of a flexible work schedule because it fits their lifestyle and wouldn’t inhibit their productivity. A manager might ask if they had considered how a flexible schedule might impact the overall ability for teams to work together and be more collaborative. This type of question pulls the altitude of the conversation up from personal to organizational and can often reveal the challenges that need to be overcome in order to shift policy or culture.

Accept imperfection

This sort of mediation can be messy work. A single conversation doesn’t often do it justice, nor does it typically include enough participants to make a new policy or decision well-rounded. The value that different individuals place on culture is highly personal. When both sides debate an issue, they can quickly become impatient with the other, frustrated with their inability to empathize and align. In order for things to progress, sometimes we need to make incremental efforts that can feel clunky and inelegant but may be necessary to move forward. Remember the old adage about negotiations: If both sides feel like they lost the debate, the deal is probably fair.

Generational divides are not new things. There’s always been a bit of an “us and them” that permeates companies as they evolve. But it doesn’t have to be fixed or rigid. Shifting culture through organizational design is iterative, conversational and, most importantly, must be empathic. But by making an effort to truly understand the views of each stakeholder, we can begin to build a pattern of empathy that helps us move through differences quickly while still maintaining our humanity.

After all, if there’s one thing every generation can agree on it’s that we want to feel understood.

Michael Ventura is CEO and founder of Sub Rosa.