Rethinking Generations: What CEOs Need to Know from the Expert on Leading and Selling to Multiple Generations

 Rethinking Generations: What CEOs Need to Know from the Expert on Leading and Selling to Multiple Generations

Leading Across Five Generations in a Remote-Work Era

For the first time in recent history, Texas CEOs face a daunting task: leading, communicating, motivating, and engaging five different generations of employees, trendsetters, and customers. This has never happened before, and it is creating all kinds of challenges. Solving these challenges was important before the pandemic. Doing so now has become absolutely critical in a newly remote-work landscape alongside the emergence of unexpected purchasing habits that vary dramatically by generation.

As President and Lead Researcher at The Center for Generational Kinetics (CGK), I—along with my cofounder and our CEO, Dr. Denise Villa—am on a mission to separate myth from truth about generations. Our goal is to educate leaders so they can make fast, accurate, and more effective decisions that drive measurable results. This mission is not easy because of the tremendous amount of misinformation about generations—including how to accurately define a generation.

The Old Generational Myths Are Just That—Myths

We’ve all heard the stories and seen the memes about Millennials being lazy and not working, yet prior to COVID-19, Millennials were the largest generation in the US workforce. In fact, for many of our 700 corporate clients, Millennials are also the largest generation in management roles.

At the same time, myths about generations affect not just the youngest employees and customers, but also the most experienced ones. Ironically, the “OK, Boomer” retort used so frequently on social media discounts the fact that Baby Boomers invented much of the technology that younger generations now rely on to poke fun at them.

All too often, people overlook or don’t talk enough about Gen X, yet so often, Gen X is the glue of the workforce. In fact, Gen X is now at a difficult life stage, where they are often taking care of their kids, helping their parents, and trying to make key career decisions.

Next up: Gen Z. They don’t remember 9/11 and think Millennials are old, and our research shows that they value employer stability and benefits. In a way, they are most similar to . . . Baby Boomers.  

And on and on it goes.

Replacing Guesses with Research

As a Millennial myself, I got into my work with CEOs because I was frustrated by the lack of actual research into generations to help leaders make the right decisions. Thirteen years ago, Dr. Villa and I founded CGK to solve this research challenge with a focus on behavioral insights into each generation.

We chose to focus on research and insights because CEOs didn’t need more data—what they needed was to know:

1. why the data they had is important, and

2. what actions to take based on that data.

In my work speaking to and advising CEOs, boards, investors, and founders, I found a lot of data and cheap generational headlines, but no actual research. By adding the missing generational “why” to a company’s data, we could unlock tremendous value and give them a competitive advantage.

A CEO of a financial services firm might know their own client numbers inside and out, or a CHRO would know the recruiting and retention stats every month, but there was no research on why sales went up, down, or why employee retention varied so much by generation. My partner and I went on a mission to fix that for companies around the world. What we uncovered was surprising and has led to research for clients on four continents, and to me speaking to leaders from over 100 countries.

We’ve now led more than 65 generational studies that uncover and explore the hidden behavioral drivers of each generation. The studies account for not just birth year, but also gender, geography, ethnicity, and many more factors—such as education level, household income, specific job roles, industries, and customers’ experiences. What we found opened our eyes to how to serve CEOs best, and showed us what leaders needed to know about generations at a strategic level to be more effective and make better decisions.

5 Key Insights for Understanding Generations—and Driving Results

To help you lead multiple generations at this pivotal time, I want to share five key insights that any leader can use to start rethinking generations now—and that will help you drive measurable results:

  1. Generations are not boxes that each of us fit neatly inside. Too often, speakers and experts present generations as a series of boxes based on people’s birth years. That is not accurate. It’s important to reframe generations not as boxes but rather as research-based clues we can use to faster connect with, influence, and drive results with different age groups. These clues can be incredibly powerful and predictive—which is why we use them to develop sales and employment strategies for clients—but generations still only give you clues, not definitive guide.
  • Every generation brings value as employees, customers, trendsetters, and community members. Every. Single. One. No generation is more or less important than the others. The spotlight tends to shine brightest on whichever new generation is emerging, which is reasonable because the new generation is often the least understood and researched. The new mindset and behaviors they bring create both challenges as well as tremendous opportunities for leaders who adapt to engage them using data. That’s why people have focused on Millennials so much in the past ten or fifteen years, but also why at CGK we are now extensively focusing on Gen Z, including in our new book, Zconomy: How Gen Z Will Change the Future of Business—and What to Do About It.
  • When talking about generations within your organization, it’s important to not talk about a single generation in a vacuum. Always talk about a generation in the context of other generations. As a strategic advisor to CEOs, this is a costly mistake I frequently see leaders make. Rather than talking only about Millennials, Gen Z, or any other one generation by itself, always bring a multigenerational perspective. If you’re going to talk about a characteristic of one generational group, then you should talk about that characteristic as it pertains to the other groups as well, as part of a larger conversation. At CGK, we call this Generational Context™. It’s incredibly important for every generation to feel valued and included as part of the conversation, innovation, and solution.
  • Geography has a massive role in shaping generations, and in how we research and understand them—and this is not talked about enough. As strategists for companies, we view generations as a group of people born about the same time and raised in about the same place. The importance of geography on shaping generations is rarely discussed, but it is critical to accurately understand how to lead, market, and sell to different generations. Within our great state of Texas, leaders will see differences in the same generation based on the part of the state the person is from and whether they were raised in an urban or rural environment. They will also see intragenerational differences between native Texans and people born and raised outside Texas. And, of course, those members of the generation will be different from people who live elsewhere in the United States. Even in our work in Europe, Asia, and other countries of the Americas, we have to look at generations based on the region to understand them and find the hidden drivers that lead to the outcomes our clients want to create.
  • You stay in the same generation, but as you get older, you pass through different life stages. This insight is easy to overlook, but it enables leaders to better appreciate generational change and new norms. For example, the term “Millennials” is too often applied to all young people today, yet the youngest Millennials are 25 years old, and the oldest is around age 40! Gen Z, the generation after Millennials, are now the emerging workers, consumers, and trendsetters—and they’re very different from Millennials. Our research shows that Gen Z does not remember 9/11, that many don’t remember a time before smartphones, and that their expectations for work, education, communication, and life will create a new normal as they gain more influence. In the same way that Baby Boomers were once teenagers, Millennials have aged up and are often now the parents of children today.

What can you do with these five insights about generations?

In my work speaking and advising CEOs, I’ve found that the best approach is to start with these five insights and then dive deeper into what you need to know about each generation. The best starting place for an executive team is to create an accurate generational snapshot of their organization. This process involves creating a pie chart that shows the percentage of each generation in your workforce or customer base. A generational snapshot is always eye-opening, as many leaders don’t have a generational view of their current employees and customers.

With this generational snapshot, you can then create strategies, address challenges, and find opportunities to drive results in the organization. The snapshot will also help you see what is—and is not—working to attract and retain different generations of employees and customers. Going deeper, you can then explore key performance drivers by generation, such as sales and marketing results, as well as retention and engagement information you’re already collecting but is often not viewed by generation. Using this as an initial approach, you can start to separate myth from truth using your own data and then add expert insight to bring a results-driven approach to leading and driving results across generations.

Now More Than Ever, CEOs Must Unlock the Potential of Every Generation

Intentionally seeking to unlock the talent, perspective, and energy of each generation drives better performance without adding cost. To be clear, this is not about catering to or coddling a specific generation—we have a lot of data showing that doesn’t work. Instead, this is about recognizing that there are generational differences, and what works for one may not work for another.

In our work with clients around the world, we repeatedly see that CEOs who learn how to understand, engage, and lead multiple generations have a distinct advantage in driving trust, communication, innovation, sales—and most importantly, results. This has never been more important or urgent than in our current business climate, where unlocking the potential of every generation is a necessity for delivering results through uncertainty.

And, as a Millennial, I want to thank you for bringing your own generational lens to this article. Thank you for being interested in rethinking not just my own generation but every generation. We all add value when you’re open to seeing it.

Jason Dorsey

Jason Dorsey works with CEOs and leaders to solve generational challenges and drive growth. He is a global keynote speaker, researcher, and strategic advisor. Jason has served on public and private company boards, cofounded The Center for Generational Kinetics, and received over 1,000 standing ovations. Learn more at or check out his new book, Zconomy: How Gen Z Will Change the Future of Business—and What to Do About It.

Related post

Leave a Reply

Your email address will not be published. Required fields are marked *

Sign-Up For Our NewsletterIt is free and can be opted out of at any time.

Like what you are reading? Don't miss out and sign up for our eNewsletter and get more leadership resources right to your inbox.