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22 Stories And Confessions From Gen X'ers About Working With Millennials And Gen Z

"Some millennials and Zoomers will think you're mad at them if you use periods at the end of sentences in emails."

Recently on Reddit, u/biishep1230 shared their experience working with a new coworker, writing, "Today I was training a new person at work who just transferred to a team that I lead, and she was shocked that I had worked for the company for 25 years and exclaimed, 'I’m only 25 years old!' I gave her a pro tip that that might not be the best thing to point out. Everyone had a good laugh."

"I reminded everyone that I converted a PowerPoint to PDF without asking anyone on the team (all younger than me) for help. I ended the day with the Gen X saying, 'Now, go have fun, just don’t get hurt.'"

They finished their story with, "They seem to like having a Gen X boss. Anyone else have a team of millennials and Gen Z?" In the comments, other Gen X'ers shared their stories about working with younger generations, and it was really fascinating to see. Here's some of what they had to say:

1. "My boss is 20 years younger than me, and the youngest person on our team is 35 years younger than me. I have to say, I’m so glad I get to work with this younger generation before I leave the workforce. As an always LGBTQ ally, I still remember rolling my eyes at the cis/trans/pronouns conversation for a hot minute, then realizing I was being that kind of older person. Yuck."

Person in a yellow top working on a computer, with a pride flag in the background

2. "The topic of the Y2K bug came up. My team wasn’t even born."

u/cspinelive

3. "I have a newish thirtysomething on my team, and he has asked about my experience, and not in an ass-kissing way. It’s such a shame that people today don’t receive the training we did. I feel it is my responsibility to pass on what I know."

"He has stated many times that he appreciates the extra time I spend with him to get him up to speed. I think he is sincere, and I have to admit it feels good to be appreciated."

u/AlexVlahos

4. "Management isn't anything like it was in the '80s, when we were young and wouldn't have dreamed of expecting the kind of fairness demanded now. I'm not ripping on gens Y and Z. Just saying it would have been nice to be able to expect respect when we were baby workers. We didn't get it."

Woman sitting at a desk, working with papers, surrounded by office equipment of the past era

5. "My boss is a millennial and doesn't grasp that I don't know how to use Excel as if it's my second language, the way she does. First of all, my job never required using Excel before. When I went to high school, we had two Macintosh computers that you had to sign up for, hoping the other 3,000 students didn't need to use them at the same time."

"Second, if she wants me to be proficient, don't sign me up for an Excel class and wait a year to assign me a project, then wonder why I don't remember how to use it and get frustrated."

u/Various-General-8610

6. "We have a Gen Z administrative assistant for a team of Gen X cops who work Internet Crimes Against Children (among other things). For a while, she was in a near-perpetual state of shock between the cases we work and just us in general. Seeing her wander around with a VHS tape trying to figure out what it is was one of the most hilarious things that has happened at work."

"She's on board now and loves us. We got her to perfect her eyeroll, say 'whatever' with the proper inflection, and become very liberal with the middle finger. We may have been a bit too successful with the Gen X conversion therapy."

u/Experiment_262

7. "Some millennials and Zoomers will think you're mad at them if you use periods at the end of sentences in emails."

Woman in glasses using smartphone and laptop at desk, with flowers in background

8. "This is not true of most of the under-30 crowd; I've worked with plenty of great kids. However, in the last eight years, I've had to train several young adults who just cannot take direction without assuming you're trying to change them on some fundamental level."

"I've been in supervisory and training positions for 25 years and had never heard someone tell me, 'I don't like doing it that way,' and when I tell them they have to, they accuse me of trying to make them do things my way.

"It ain't my way, kid, it's the way it's done here, it's the way I was also taught to do it. It's as if they have no concept that work isn't free time and that they're a part of a team (or what being part of a team even means). It blows my mind, and I still haven't figured out a way to train these kids. They often end up feeling oppressed and out of place and end up leaving or just getting fired for not learning how to do work."

u/TheReal8symbols

9. "I'm in a supervisory role with mostly millennials on my team, and I’m here to tell you that it has been a learning process. Let me say that I’m not a person who thinks millennials or even Gen Z sucks; quite the opposite. I love that they have priorities that differ from my own; it keeps some of my quasi-boomer tendencies in check. That being said, I have had to continue to change my expectations drastically from what was expected of me on my way up."

"I’ve tried so many different ways to get and keep people engaged, from sharing revenue to paid time off, and have been met with disappointment along the way. We as a generation have been accused of creating a sense of entitlement in our children because we overcompensated for our free-range upbringing by being helicopter parents who never missed a child’s activity, and that may be a fair assessment. 

"A balance has to be found through the tried-and-true method of trial and error, strikes and gutter balls, to put it in Lebowski terms. Regardless, I find that I have had to temper certain expectations. The point is, I love my team, and they work their asses off, but it’s a challenge to maintain the push and pull of generational expectations. 

"I will say I have benefited greatly in my own personal life by adapting to their expectations, and I truly feel that they’ve gained a little more appreciation for how I approach things in the process. There is no black and white in management, IMO, just ever-changing values of gray."

u/PhotonWranglers

10. "My favorite team I ever managed was nearly all millennials. I realized how lucky I was to have managed them when I ended up at a large company and temporarily managed a group with an average age of 50-plus (this was in the mid-2000s). I’m still friends with a couple of the millennials all these years later. We had a great team environment where we all helped one another and had a lot of fun in the process. Never felt that with the older group I managed later."

Four people in a casual office meeting, one with a laptop, engaging in a discussion

11. "I've noticed that any level of directness is often perceived as a personal attack and the height of aggression. No, I'm just not bullshitting you, out of basic human respect."

u/Up2Eleven

12. "At 50, I'm at the very top tier of old farts in my workplace. We're mostly hiring Gen Z now. They are almost universally respectful, but my line of work strongly preselects for respect regarding seniority and rank. I hope to be viewed as a mentor, father figure, or at least an uncle figure. It seems as if I am."

u/testingground171

13. "I’m a 47-year-old lawyer. Been practicing for 20 years. Solo attorney the entire time. I have two employees, both in their late 20s. The difference between us is sometimes minimal and sometimes huge. My 20 years of experience over them is a huge factor, but we’re ultimately into the same things, watch the same shows, and listen to the same music. The biggest difference is literally my 20 years of experience. I’ve been there and done that. They haven’t. Things I take for granted are new to them. Once I realized that, it made me a better boss, teacher, and mentor."

Two women, one older and one younger, looking at a laptop screen together

14. "Got 30 undergrads who are constantly rotating because undergrads tend to graduate, even today. I know all of the language, all of the memes, all of the Discord, all of the Twitch, all of the culture. I am immersed in it and completely empowered to constantly embarrass my Gen Z/Alpha children because I know all of the things they know, and it makes them very upset."

u/hibbledyhey

15. "I work with all millennials, and I can honestly say that they are a pleasure to work with! Kind, empathetic, and I get ~90% of their references without feeling old. I just grew up playing different video games and listening to different music. Maybe it’s just a matter of maturity. It doesn’t matter what generation you are — the ones who are 19 to 25 will never fail to mention how young they are until they start feeling old themselves! Those 26 and up start getting much more humble and relatable."

u/dotnetgirl

16. "As a Gen X'er in a management position, I unfortunately feel like I have to train my parents in the digital world and also Gen Z'ers regarding office politics, workplace socializing, and just basically everything, including using a freaking printer. I have no kids, but boomer parents are like teenagers who are lazy or angry about technology and the way the world works right now."

Woman appears frustrated with a jammed printer in an office setting

17. "My boss is an elder millennial and loves having me on his team because he can point me in a direction, and I just go do the thing that needs doing, while everyone else needs some level of hand-holding and babysitting."

"They keep trying to put me into management, but I have zero desire. I'm totally cool with where I am and with what I do. The big joke is that since I'm Gen X, I'm happy working a job where I'm ignored — just as long as they don't ignore me when it comes to my pay.

"I've been with my company for 23 years, and that longevity blows a lot of younger folks' minds. It also blows their minds that I'm NOT in management and don't want to be — because that's what they've been told they're supposed to do in order to be successful in life; otherwise, they're failing. I love watching that little part of their brain light up when I tell them it's perfectly OK to be comfortable where you're at and not have to climb the corporate ladder if you don't want to. No one will care what your work title was when you're dead."

u/PrincessBuzzkill

18. "I have coworkers born in 1995 — the year I bought my current Jeep. They love riding around in it because it’s an 'antique' to them. I have to remind them that I was an adult when I bought it."

u/supershinythings

19. "We have a few Gen Z'ers on the team, and we drop random pop culture facts like Will Smith used to be a rapper and Mark Wahlberg used to be Marky Mark. It blows their young minds. And when one of them started, she would talk about her mom a lot; then one day she said, 'I can't believe my mom is almost 50. That's so old.' We told her maybe next time, we'll invite her mom out instead of her for beer."

Will Smith posing with DJ Jazzy Jeff in the early 1990s

20. "Generally, the millennials and Gen Z'ers I've worked with have been fine. The only thing that annoys me a bit is when they complain or poke fun at each other about being 'old' or make condescending comments about anyone over 30 being 'old.' Anyone pushing 50 is 'really old.'"

"I get it, but it's a rude thing to go on about within earshot of other older coworkers unless you've established some kind of rapport and know that everyone can take a joke.

"Generally, I just roll my eyes, but in 20 years, they'll be screaming bloody murder when the Gen Alphas arrive and make the same remarks."

u/LittleMoonBoot

21. "To be honest, it's exhausting watching them take on more work than they can handle, hoard the work until the last minute, and then ask for last-minute help. I get the unfinished work and wonder what they've been doing all this time besides bemoaning how much work they have. Rinse and repeat. As a manager, I actually try to help them with time management and pacing, but other managers just let them fall on their faces and help them pick up the pieces like a helicopter parent, to the detriment of the entire team."

u/ArtisticBrilliant491

22. "I have four teams rolling up to me, consisting of Gen X, millennials, and Gen Z, or whatever they call the young people entering the workforce over the last five years or so. I don't think of them as 'generation anything,' and frankly, I don't care and don't want to know how old any of them are. I only care that they do their jobs in reasonable and responsible ways and demonstrate growth so that I have the data I need to pay them more and promote them."

Three colleagues in an office, one standing talking, another listening attentively, third working at a desk

Are you a Gen X'er? Share your opinions about working with the younger generations in the comments!

Note: Some responses have been edited for length and/or clarity.