OK Boomer, Call Me Karen. Millennials Can Teach Us A Thing Or Two.

Millennials, currently aged 22 – 37, have been thought of by some as entitled “kids” who expected their careers to be handed to them. Now, with so many millennials in their 30’s, not only are they not kids anymore, they may actually be your boss.

Today, more than one in three people in the U.S. labor force is a millennial. If you’re a Gen Xer like me, and lucky enough to still be working in a creative or innovative field, likely you have someone younger than you for a boss and many more someones younger than you on your team. 

I’m well aware that stereotypes are lazy and wrong, but still I approached cautiously. What could my boss, over a decade younger, offer me? 

Turns out, a lot.

Here’s what I learned from my millennial boss. 

  1. Trophies For Everyone!
  2. Tell
  3. Cheat
  4. Use emojis
  5. Hug, Don’t Push

Trophies For Everyone! 

One of the stereotypes of millennials is that because they took home a trophy for showing up at soccer practice in grade school, they expect praise and raises for showing up to work and doing their job. 

Here’s the thing. I don’t think people deserve a raise just for coming to work. But is regular praise really a bad thing? 

Here’s a story. A whole gaggle of us are in a meeting in a glass-walled conference room. One millennial guy, I’ll call him Tyler, glances through the wall into the open office space as another millennial guy, I’ll call him Brandon, is arriving for the day. 

Tyler, taking in Brandon’s dress and manner mutters, “fucking Brandon.”

We all turn. 

Brandon is resplendent. His full beard is oiled and trimmed, his Burberry suit is slim cut, pressed, and a daring shade of blue gray. Brandon looks like Justine Timberlake’s woke younger brother. Brandon’s hair is perfect. 

This story is a lesson in noticing people and giving praise.  

In my day, in my industry, especially among same sex het males, jealousy surfaced in blocked work, in eye rolling, in publicly dismissing the contribution of another. 

This lesson is attributable to our changing culture in addition to generational differences. Today, praise for one does not mean shame for another. And today, we understand the power of recognizing another’s charms. Still, as emerging leaders in the workplace, millennial leaders are teaching up and down that it’s not only safe, it’s cool—to praise loudly, generously, frequently. 


This one runs deep. As a child during the ‘70s, it was us kids against the adults, who were distracted by life, divorce, gin. As such, coming into the professional world, we didn’t have a language for the, sometimes gross, injustices that happened during even mundane workplace encounters. During this earlier era when I came of age, feelings, both at work and at home, were things to get past, or around, not share. 

Things have changed. While, ‘don’t be a complainer,’ still holds as an important construct of corporate culture, more and more, it’s okay to ask for help, discuss feelings. More and more, it’s okay to tell. 

My millennial boss told me early on that if I were working with someone who is being a jerk, not accountable to the team, dragging their feet on deliverables, or simply creating too much drama, that I should tell. “Take your grievance to the right higherup—me,” he said, “and blab.”

This was an epiphany as well as a relief. Twenty years into my career my millennial boss taught me I don’t have solve it alone. I am not a hero for suffering in silence. I am not a ‘good team player,’ when I keep quiet. 


People in the business world read a lot of books. We’re supposed to. We have to. There’s a constant onslaught of things we should read. My millennial boss taught me this—buy the book, display the book conspicuously on my desk, and read the article about the book. Then, if you really want to, listen to the audiobook. Or part of it. Gen Xers, please, you can still honor your analogue roots and covet your LPs, but you don’t have to read the whole book from start to finish to say you read the book.

Use emojis

Gen Xers, and I’m especially talking to you, the liberal arts snobs among us, you may use an exclamation point every now and then. No one will think less of you. 

For context on this lesson please recall, I am a 50-year-old woman. For years I packed a 90 pound Dell laptop and reams of paper into a Jones New York tote bag that I slung onto my right shoulder and carried it all over the country. And please know, today, I have two teen-aged children who just might be trying to kill me and an aging mother who needs more care than I am able to provide. In short, I drink coffee by the gallon, I have too much on my plate, I am a very close to being overwhelmed by life. As such, my brow has a natural furrow, my shoulder may freeze any minute and my teeth are more patina than pearl. 

Every morning I march this glory into work and take center stage in an open-concept office where all this damage and distraction is on display for all to see. 

Surrounded by my moonfaced millennial and Gen Z colleagues, I frown at my computer and mumble to myself as I sort through the stacks of paper on my desk. I pause my hunchbacked scrutiny of my computer screen to pinch at the crook in my neck and to leer at them over my magnifiers. In the midst of all these aches and grimaces, a smiley face goes a long way. So too an exclamation point. 

The workplace is about communication. Today, we should feel free to use every widget in the expression toolkit to make ourselves understood. There’s no hierarchy for communication, so we shouldn’t feel like a smiley face is below us if it helps us to be more fully understood. Just. Keep. Talking. Sharing. Expressing. 

This means, shrug, basically.

Hug, Don’t Push

This is a big one, because it’s reflective of a systematic shift in how we get things done in teams today compared to years past. My millennial boss and peers, because they are products of their upbringing, are patient, flexible consensus-builders. I came up in an era when every person in the meeting was competing to be the smartest person in the room. Today, being the most collaborative person in the room is the surest way to win. 

Yes, they’re a smidge precious. Yes, they’re a wee vain. But that preciousness of self-identity allows them also to meet others in their onlyness. By meeting others in their onlyness, that spot in the world where only they stand, they are able to shift the power dynamics of the meeting, culture or organization, from bullying to seeing, or, from push to hug. 

It’s a freeing dynamic, I find. 

So. If you’re lucky enough to work long enough to have a boss who is younger than you, you’re likely also self-aware and flexible enough to learn a thing or two along the way. It’s much easier to navigate the transition from Gen X boss to Gen X employee if you don’t believe the stereotypes and are open to meeting people where they are. 

Decades in, keep the lessons coming.