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Intergenerational Battle at 30,000 Feet

Every once in a while, you sit next to a stranger on a plane and have a conversation that sticks with you. This just happened to me with a successful 75-year-old Baby Boomer CEO of a small healthcare company. I felt like sharing it as it does help explain what I do for a living.

Ray – thanks for the flight!


The conversation began…

“So what do you do for a living?” I think he was surprised that I was in first class and looking like I had just come from the gym.

Knowing that the generational topic typically sparks lots of conversations ranging from Pet Rocks to the pandemic, I was prepared for a longer conversation. What I wasn’t prepared for was an argument. 

“I study the different generations and how differences impact the workplace, marketplace, and nonprofits.”

“Oh. You’re one of them.”

“What’s that supposed to mean?”

“Putting people in a box and labeling them.”

“Actually – I think I take the lid off the box and help people understand their employees, customers, students, donors and more.”

“So I’m one of those Boomers. And you’re younger than me…”

“I’m a Gen Xer.”

“OK. We both work hard. Raise families. Hope to retire. Are we really that different?”

I was irritated and wanted to point out that we were very different, put on my headphones and watch a move. But I was too into the conversation to pull out. 

“You are right. We definitely hit the same life stages. But here is the trick, we approach them with our own generational biases.”

“That seems ridiculous! Just because of the year I was born?”

“It’s way beyond birth years… it’s the events and conditions that take place during our formative years. I’ll give you an example since we are flying at 10,000 feet. When you were a kid, what was it like to watch air and space travel? Do you have a favorite memory?”

“Oh. I remember like yesterday where I was when we landed on the moon. My friends and I had been talking about it non-stop and then we saw it live. The whole country stopped. It was one of our country’s finest moments.”

“Hmmm.” I replied. “I don’t have any memories like that. In fact, all I remember is writing letters to a school teacher, Krista Mccalluf who had been chosen to go in space. She wrote back to our class too. I also remember talking to my friends about it, but on the day of the launch – we watched her explode inside the Challenger. I still can feel the silence in the room. I was in 11th grade.”

And speaking of silence. My travel buddy seemed to suddenly be searching for words.

“OK. I see how we might have some different viewpoints. But just because we may see space travel differently, how does that impact my business. I work in healthcare.”

“Well every industry is impacted by these differences. Space travel was just one example. I would be willing to bet if we kept talking (not that I was suggesting we do) about topics such as applying for a job, asking for feedback, whether to do a meeting on Zoom or in person, dress code, work hours and so much more – we might not be looking through the same lens.”

He was nodding slowly – he was getting it. I think. I continued…

“If you assume we are looking at the workplace the same way – that’s when costly gaps can occur.” 

“You know – I’ve always thought those Millennial kids today at work are way too entitled… don’t you agree?”

He was hoping I would.

“Not at all, actually. Millennials are the most collaborative generation I have studied and have brought more meaning into jobs than my generation or yours. And by the way, they are not kids. They are having kids of their own.”

“I guess right,” he said…but still looked troubled.

“You see, just because another generation is looking through a different lens, doesn’t mean they are doing something wrong or even worse than you. It’s just different.”

“Oh please!” I clearly annoyed him. “When I was younger you got to the office before your boss and you stayed no matter what time until he left. You didn’t leave early for yoga. And you for sure didn’t get a participation trophy just for showing up!”

“I bet that’s frustrating. But I do have to ask, how did that work-a-holic mentality work for you and your peers? Many in the younger generation would say you paid too big of a price. They have figured out a way to get the job done AND go to yoga.”

“That’s my point! They leave at 5pm when there is still things to do!”

“But did you ever think that maybe they went to yoga, got home for dinner with the family, and then logged on before bed and finished the work. If the work is still getting done – which I’m not hearing otherwise… then maybe they aren’t doing anything wrong.”

“I suppose you’re right. Maybe I’m just an old fart stuck in his ways. I really don’t like how the new hires show up so casual and put those earbuds in. But they do good work – I’ll give them that. I suppose I just need to adapt.”

I felt like I had won the lottery… major breakthrough and so excited I could hit the play button on the movie. But he continued…

“I was thinking… how are all these Millennial college graduates today ever going to pay off their loans?”

Hmmmm. Do I shrug it off and put the headphones on and hit play… or do I give him the answer I think is so critical.

“Well. That is a very good question…but if you really want to tap into these insights, then I have to tell you that these graduates are not Millennials.”

“Millennials have a new name?”

Deep breath…

“Well, we actually have a whole new generation called Gen Z. Believe it or not, there is life after the Millennials!”

“What are you talking about? There’s a whole new generation?”

Now he was annoyed again.

“It’s not a bad thing. Relax. The good news is that now it can be on your radar. And you’ll be happy to know they put the participation trophy to bed. Listen, I can’t tell you how many leaders in every industry I meet are just assuming everyone under 30 is the same and is a Millennial.”

“What makes them different?”

“Well, I’m sure if we had a Gen Zer sitting with us, he wouldn’t be talking about the Moon landing or the Challenger. He would be all abuzz about Elon Musk or Jeff Bezos hopefully taking him into space.”

Phew – I got a chuckle. I then went on to explain that history was actually repeating itself. I even put it into language he would understand. I took him back to the 90s when he and his 80 million other Boomer cohorts were clawing their way to the top. He reflected on how many policies there were to do everything – even joking – “I think we needed a policy or procedure to go to the bathroom.”

I then talked about what it was like when my generation, Gen X, showed up. I very quickly reminded him of all the frustrations he had with me and my colleagues. They hated how we dressed, our lack of interest in all the policies, our straight to the point communication style and so much more. We even both agreed that it was some of businesses most costly collisions. 

It didn’t take long for him to start making the connection I was going for. 

“You’re telling me that Gen Z is radically different than Millennials? 

I wanted to take the opportunity for a shameless plug to read my latest book on Gen Z or have me speak at their next company function, but I resisted.

“Hard to believe that not enough senior leaders are waking up to the fact that we have a whole new generation. The leading edge of Gen Z is already 28!”

He was sitting up and even pulled out a notebook from his bag. I assured him – 

“Look, I do believe that leaders can be proactive, and not quite be reactive just yet. The time to get to know Gen Z is today! And if you treat Gen Z like the Millennials it will be no different than what went down between our two generations in the 90s when we tried to treat Gen X like the Boomers.”

“I have so many questions! What are their key events that shape them? What are their vales? How are they different from Millennials? Will they actually be able to pay off their student loans?”

“Who said they are going to college? In fact, 75% of Gen Z says there are ways of getting a good education other than by going to college. I’m curious, does your company require a 4-year degree to work there?”

“Well of course!”


“Well… ummm…”

I finished the sentence for him… “Do you think every position you hire for needs a degree to work there?”

“I suppose not. In fact, we hired a kid over the summer who was taking a gap year and man, he could do circles around us. Especially for our social media strategy.”

And without even having to say more… my point was made, and my guess was a new policy at his company would be made as well. Progress.

The announcement came on to put our seats and tray tables up. Clearly I would catch my movie on the next flight. My co passenger seemed a little rattled as he looked at me.

“So where do you think the best place is to start if we want to get our heads around Gen Z?”

This time I couldn’t resist. I reached into my bag, pulled out a copy of my book, grabbed a Sharpie and wrote…

Enjoy getting to know Gen Z!

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