The Technological Divide: Leap or Fall?

By Tom Hubler • May 20, 2014

Tom Hubler
Tom Hubler

For the first time in history, four distinct generations of adults are now socializing, communicating and actively participating in the workplace. Countless theories, articles and study courses have been devoted to analyzing and understanding these dynamics. Marketers and demographers have defined these issues. Sociologists and psychologists have proposed each generation’s psychographic (behavioral) characteristics. You’ve likely heard some of them and probably identify with at least one of these groups below.


  • Four distinct generations of adults are now socializing, communicating and actively participating in the workplace. It doesn’t always go smoothly.
  • What one side may see as common sense, the other may see as naiveté or a comment from someone with a condescending or marginalizing attitude.
  • Working in a small to midsize organization, like working in a family business, requires each generation to make regular contributions to the common good.

Four generations

Here is a matrix you can use to compare generational differences.

Baby Boomers
Generation X
Gen Y or Millennials
Loyal Optimistic Skeptical Collaborative
Born 1945 and before Born 1946-1964 Born 1965-1980 Born 1981-1999
Grew up with radio Grew up with TV Grew up with all media (including cable, VCR, video) Are technically saavy and grew up with the Internet
Believe in “chain of command” Believe in “change of command” Believe in collaboration (“self command”) Believe in collaboration (“all command”)
Rewarded by satisfaction of a job well done Rewarded by money and recognition Freedom is the ultimate reward Expect more than one career and rewarded by it; expect these careers to be meaningful to them
Shaped by events of Pearl Harbor, Great Depression, WWI & WWII, GI bill Shaped by events of Vietnam, Watergate, Kent State, Cold War, Civil Rights Movement Shaped by AIDs, divorce, PC, MTV, crack, being latchkey kids, Sesame Street Shaped by Internet, digital tech, pop culture, fall of Berlin Wall, drugs, gangs
Influential people such as Joe DiMaggio, Alfred Hitchcock, FDR, Charles Lindberg, John Wayne, Bob Hope Influential people such as Martin Luther King Jr., Kingston Trio, Richard Nixon, JFK, The Osmonds, The Beatles Influential people such as Ronald Reagan, Bill Clinton, PacMan, Madonna, Motley Crue, the deaths of Elvis and John Lennon Influential people such as Prince William, Chelsea Clinton, Tinky Winky, Claire Danes, Leonardo DiCaprio, Barney, The Backstreet Boys, Buffy
How to communicate with them …
Express appreciation for their efforts; acknowledge their value
Emphasize the need for their input for team success; discuss actions and plans together Be straightforward and focus on results rather than process; avoid “back in my day…” Emphasize reasons for change and let them know you’re there to help; act on that promise

Copyright 2014 Hubler for Business Families. All Rights Reserved.

The oldest of the next (fifth) generation are already in their teens and will soon be entering the workforce. They haven’t been named yet, but I imagine them as Gen Wii or Gen 9-11, based on the world events that influenced them. We’ll see.

I spent extra time identifying the generations because in family businesses, like in government, corporate and not-for-profit organizations, many mistakenly believe that generational differences are exceptionally disruptive. It’s common in my practice to hear one generation complain that a co-worker from a different era isn’t doing something right or taking constructive criticism. Why? Because the constructive criticism is coming from a colleague they perceive as way too young (or too old) to be giving it.

Differences become irritants that can lead to battles that engulf a family business or work team and can ruin their social as well as business life.

I suggest that the more you understand those who are younger than you (and older than you), the more rewarding your work experience will be. Granted, that’s easier said than done. Each of us brings a generational perspective and bias to life and to work. That generational perspective is natural to us in our generation. It represents not only how we see the world, but also how we think others should see the world. It is a kind of “truth.”

Reverse mentoring

In spite of how smart I think I am, it has taken me a long time to adjust to all the technology inventions. In order to make the leap into the 21st century, I’ve had to work with several Gen X technology consultants. I truly appreciate their patience, as it eventually gave me the confidence to work with and understand social media.

While I am still not quite there, I am beginning to see the results of the new systems, and it is easier for me to encourage my father-generation clients (those from the traditional and boomer generations) to work with their younger-generation sons and daughters to integrate these new technologies into their lives.

Right now, early baby boomers are beginning to enter their mid-60s, and as late traditionalists who started a business, they are well aware of the prospect of retirement. Many of your organization’s vendor and supplier members may fall into this category.

Within business families and organizational work teams, there seems to be increasing friction between those planning to retire and their children who expect to take the lead.

Boomers formed ideas that cause them to be prone to workaholism and to need more balance between work and family. They tend to base authority on tenure or seniority. And, central to this article, they are often uncomfortable with technology and slow to adjust to it.

On the other hand, boomers’ Gen Y/millennial children formed perceptions that cause them essentially to “work to live,” and they are much more aware of work-life balance than their parents tend to be. They think workaholics “waste life.” Gen Y/millennials grew up with computers, cellphones, iPads and notebooks, and they expect tech companies to innovate even more than they already do.

Based on my training as a psychologist and my experience with thousands of business-family clients, I see that technology has caused a major gap between boomers and their Gen Y children. The technological dynamic of instant and ubiquitous access to the Internet has caused what I would call a great technological divide. More than an issue of access, understanding, training or even accommodation, the generations see this technological gap as a personality issue rather than as an informational issue. The generations are blaming each other, losing trust in each other and even undercutting each other over feelings about the state and use of technology in the world.


The boomer entrepreneur looks at his or her Gen Y adult child and thinks, “Technology has ruined our capacity to reason and communicate.” Meanwhile, the Gen Y daughter or son looks at the parents thinks, “They are totally out of touch with how the world works today.” Each generation feels disrespected, underutilized, in touch but unrecognized, and misunderstood. Each questions the other’s capability as a personal competency rather than as a technological preference.

In my next installment, we’ll look at ways to resolve this crisis.

Tom Hubler is president of Hubler for Business Families and a founding member and Fellow of the Family Firm Institute in Boston, a professional organization serving the needs of family-owned businesses. He also serves as an adjunct professor at the University of St. Thomas.