Like countless interviews had started before, the reporter for a major national trade publication began this particular call with “Many of us boomers and X’ers are really having a hard time figuring out this next generation. Can you turn the lights on for us?”

It was one of those no-brainer softball questions that could have easily been answered with a standard sound bite reply out of one of my books or speeches. But for some reason, something compelled me to go down a different road.  So I answered his question with a question.

“Depends on who we’re talking about here.  Are you referring to those self-indulgent, entitled, demanding, spoiled-rotten, techno-dependant, video-game- addicted, impatient, spotlight-grabbing, saggy-pants-wearing, pierced and tattooed, disrespectful, in-your-face, know-it-alls?”

There was a long, awkward pause. I wondered if he had hung up, but then I heard him scribble something on a pad that sounded like he was taking notes.  So I continued.

“…or, are you calling to discuss these talented, techno-savvy, multi-tasking, optimistic, fearless, resilient, trend-setting, team-oriented, nondiscriminatory, environmentally vigilant, socially conscience, out-of-the-box thinkers?”

He then exclaimed, “Wow. Guess they’re not only different from us, they’re different from each other!”

“What makes you think we’re discussing two separate entities?” I asked . “ Two people could meet the same 19-year-old on the same street on the same day and each could walk away with a radically contrasting opinion of her based solely on their own personal viewpoint and prejudices, couldn’t they?” (It was kind of fun being the one asking the questions.)

“Yeah, I guess managers tend to hear—and repeat—only the negative stuff going around,” he said. “…and I’ve got to admit, as a parent of three teenagers, I’m frustrated and confused.”

“A parent of three Gen Y ’s, huh?” I pried. “Well I’ve heard all about you over-protective, smothering, doting, defensive, do-their-homework-for-them, jump in the teacher’s face, yell at the referee, give every player a trophy, be their best buddy, show up at the job interview with ‘em, helicopter parents. Can’t you just let them suffer the consequences of their own actions?”

This prompted another long pause, only this time, I heard no sounds of scribbling in the background.  I figured this interview was just about over.  So I broke the silence. 

“Oh, I’m sorry… I didn’t mean to assume.  Maybe you’re not a helicopter parent at all! Perhaps you’re one of those neglectful, unavailable, couldn’t care less, let someone else deal with ‘em, don’t have time for family dinner, let ‘em do whatever they want and have whatever they want as long as they don’t pester me, absentee kind of parents.”

“Sounds like you’re saying the parents of Gen Y are as misunderstood as the kids themselves, Mr. Chester,” he prodded…

“Stereotyping is a dangerous sport. When we rely too much on what we’ve heard or read, we can easily be thrown for a loop,” I said.

After taking a turn to delve into best practices of what leading managers and companies are doing to become relevant to Gen Why in both the workplace and the marketplace, the interview continued for another 45 minutes. I’ll remember it for being one of the more enlightening interviews I’ve had in the past 12 years. (And if I’m not learning as much as I’m sharing in an interview, I consider it a waste of time)  If we hadn’t explored new terrain in the first moments of the interview, however, I bet the finished article would have mirrored those you see and read every day about the quirkiness and deficiencies of the millennial generation. Instead, the opening moment of this conversation took the journalist—and surprisingly, myself—off the normal path, and it worked out swimmingly.

As I reflect on what prompted me to be so spirited with this particular reporter, I think my entire attitude was framed by catching the final scene of the 1980’s movie, The Breakfast Club, the night before.

In that scene, the five students ordered to serve detention in their school’s library on a Saturday are required to submit an essay on ‘who they think they are’ to the Assistant Principal, Mr. Vernon. They finally decide to let the ‘nerd’ write the essay for them. Although it’s very short, that essay sums up the attitude of youth then, and now.

“You see us as you want to see us, in the simplest terms, and the most convenient definitions…”


That is an accusation for which I must plead guilty. For the past 12 years, I’ve provided simple terms and convenient definitions to explain Gen Why, and those labels have always seemed to fit nicely and gain consensus from boomers and X’ers.  However, if I were to have provided the antonym for each of those terms and definitions instead, those labels would have also fit very nicely and I could have provided a compelling argument to win the agreement. The evidence on both sides of the discussion is abundant.

Every time you and I paint generation Y (or, for that matter, any sector of our population) with a broad brush, we miss as much ground as we cover.  As we accurately stereotype one individual, we’re describing the antithesis of his twin brother. In so doing, we alter our expectations, and that will, inevitably, alter our outcomes.

When I was a 23-year-old rookie teacher preparing to meet my very first class of students, just before I entered the classroom, a wise woman who had taught for 23 years told me, “Eric, you may or may not get what you want, and you may not get what you deserve.  But you are going to get exactly what you expect. Keep an open mind and expect only the best from each and every student.”

Sage advice I need to remember.

When we engage a young person in hopes of making a connection and influence an action or behavior, the onus is on us to lay aside our prejudices, profiles, and preconceptions. It is then when we can focus on who they are as individuals, expect the best from them, and begin to work towards getting the best out of them.

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