Understanding The Different Generations With Chris De Santis


Understanding The Different Generations With Chris De Santis



Every generation thinks they’ve got it all figured out. The same kids who rebelled against their parents by listening to the “sinful” rock and roll of The Beatles later became moms and dads pleading with their offspring to “turn down that noise” as the sounds of Snoop Dogg and Dr. Dre emanated from messy, teenager-infested bedrooms.

We all think we’re the best and everyone else is wrong. As one might imagine, that’s not great for productivity, seeing as the workplace is a hodgepodge of multi-generational talent. What can be done to smooth the edges and help us all see the benefits of variety and compromise?

I recently sat down with an expert to help me find the answer. Chris De Santis has spent the last thirty years as an organizational behavior speaker, facilitator, and consultant. He’s worked with some of the world’s largest companies to improve their productivity, performance, and overall workplace harmony. Before taking over as his own boss, he was the Director of Training and Development for the American Medical Association and part of the Human Resource Development Group for Brunswick Corporation.

Our conversation was repeatedly interrupted by the sound of jets flying overhead, as the U.S. Navy Blue Angels were rehearsing for the 2022 Chicago Air and Water Show. In a world full of distractions, this was certainly an exciting one.

The title of Chris’ book, Why I Find You Irritating: Navigating Generational Friction at Work, was my first indication that Chris was the perfect person to speak to about this topic. Admittedly generalizing, he breaks down each generation as follows.

Traditionalists (Born 1922-1943)

They came of age in the 1920s and 1930s. The Great Depression meant the trauma of scarcity was deep-seated. The primary source of messaging was radio, which meant everyone heard the same programs. People were more aligned, the government was more aligned, and this made the transition to WWII easier. The people from this generation are the builders of the system in which we now reside, but we’ve transitioned from a hierarchical to a more transactional space.

Boomers (Born 1944-1964)

The last of the “covenant” generations. The early boomers lived in the “company man” society, meaning if you worked somewhere, you stayed until retirement. This is why it’s common to hear boomers complaining about other employees not being loyal. Their paradigm demanded putting up with bad boss after bad boss until finally, you got a chance to be the bad boss. The “covenant” meant that as long as you jumped through every hoop, you’d be rewarded with the promise of employment. The latter era boomers began to conclude that this no longer sufficed.

Gen X (Born 1965-1981)

Gen X saw the promise fully disappear. There’s a duality to their personalities, as they carry parts of themselves a little closer to the chest. They spent more of their childhood fending for themselves while their parents were at work, and so became more self-sufficient. Gen X feels that young millennial workers are needy but it’s fairer to frame it as Gen X’ers not being needy. In terms of finding a mate, they are the most likely to say “I can marry whomever I want.”

Millennials (Born 1982-1996)

Whereas Gen X saw the promise disappear, Millennials never had one. They get a lot of press. Despite a short window, about ten years, of an economic uptick with the dot-com boom, they have an inherent optimism. They were raised in a bubble of love, a concentration of all the attention the Gen X’ers did not get. Rather than a strict autocracy, their dynamic with their parents is a continual democratic dialogue. This can be a challenge in the workplace when they assume the boss’ instructions are more of a suggestion. The other generations slap them down for this behavior without giving them any slack for never being taught the rules. Millennials find Gen X’ers a bit aloof.

Divorce rates dip with this generation because they prefer to wait longer and be more selective about choosing a mate. They tend to marry like to like, in an assortative manner, without stepping outside their socioeconomic class. Millennials are looking for a purpose in life.

Gen Z (Born 1996-2012)

Like their predecessors, they’re looking for purpose but they go a step further to attempt the “side hustle” and monetize their interests. This partially results from being children of scarcity, as they came of age during the Great Recession, and partly derives from a desire to be influencers. Millennials are digitally fluent whereas Gen Z’ers are fully immersed in that space. They were toddlers with touchscreens.

Gen Alpha (Born 2012-?)

Gen Alpha is a placeholder label. Not much data is yet available for this latest generation but Chris worries about the potential “police state” mentality that school shootings may create.

As the title of his book would suggest, Chris isn’t shy about the fact that people can be irritating. When a coworker in the adjacent cubicle has different behaviors and norms, we often walk down the hall to find someone else. The more productive reaction, he notes, is to try to understand where each person is coming from. He believes we use preconceived judgments to see our younger coworkers as who we were at that age, not who they are now.

In my career as a financial advisor, the majority of my clients are boomers. They’ve done well financially. I wanted to know how Chris would generalize them in that sense. Using his model, he split them into older and younger boomers. The older ones worked in the “company man” model. They’re glad to be retired, away from a job they didn’t necessarily find fulfilling. Much of the younger cadre are still working because they enjoy it. He, himself, falls into this category. He calls it “pseudo-retirement” and it’s similar to what I’ve described as “The Retirement Grey Zone.”

It’s hard to get the younger boomers to fully participate in succession planning because they still see themselves as actively crucial to the job. It’s more of a gradual transition. And with so many of them still around the office, the need for communication and empathy between generational counterparts is more important than ever.

Chris asserts that with understanding comes more distribution of the wealth the older folks have accumulated. The better we see each other as valuable parts of each other’s success or failure, the more we realize that by helping others, we help ourselves. No one is an island, though I have met a few boomers who might qualify as a peninsula.

Chris feels that the key to the success of any society is more people in the middle. If you don’t have a center, he says, you don’t have cohesion. This fits with so much of the research I’ve done on happy retirees. The happiest ones are absolute masters of the middle. Having too much or too little can wreak havoc. Having just enough provides a glide path toward contentment.

There’s ample negativity in the world for any of us to justify periodic pessimism. Still, Chris believes that with the proper training, resources, support, and opportunities, everyone is capable of great things. As I listened to him make his case for embracing our differences amidst the sounds of our best and brightest fighter pilots flying overhead I’ll be damned if I didn’t start to believe him. After all, he and I are from different generations but I can say without hesitation that I don’t find him irritating.

Listen to our full conversation here:

This information is provided to you as a resource for informational purposes only and should not be viewed as investment advice or recommendations.  Investing involves risk, including the possible loss of principal. There is no guarantee offered that investment return, yield, or performance will be achieved. There will be periods of performance fluctuations, including periods of negative returns. Past performance is not indicative of future results when considering any investment vehicle. This information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and might not be suitable for all investors. This information is not intended to, and should not, form a primary basis for any investment decision that you may make. Always consult your own legal, tax, or investment advisor before making any investment/tax/estate/financial planning considerations or decisions.


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