When Your Boss Is a Twenty-Something

The latest episode of New Tech City hosted at WNYC is about “young bosses”—these 22- and 24-year-old CEOs who are at the helm of companies (mostly in the tech sector), and what it’s like to work for them, and what their viewpoints are on managing people.

Brian Wong, the founder and CEO of a company called Kiip, is 22, and says, “I don’t actually view it as managing at all—I view it more as enabling, because I can’t with a straight face, tell these people that I’m more experienced than them because I’m not, nor do I know better in terms of life experience.” So Wong defers certain decisions to people who do have the kind of knowledge and life experience that he doesn’t, which sounds like a reasonable way of doing things (it reminds me of the Sandberg-Zuckerbeg relationship at Facebook).

When I was 24, I had a boss who was one or two years older than me at a tech company, and it was not exactly the best experience to say the least. It was precisely because my 25-year-old boss believed he knew everything there was to know about how to manage people. Anyone else out there worked for a young boss/is a young boss?

Photo: Paul Inkles


16 Comments / Post A Comment

Meaghano (#529)

I remember when my former boss first reached legal drinking age!

Mike Dang (#2)

@Meaghano Meaghan, that sounds like an AMAZING POST

Mike Dang (#2)

@Meaghano But I just realized you’d be writing about David.

I’m a young boss. Well technically I’m 27 year old program director who oversees compliance on a federal AmeriCorps grant that is awarded to organizations throughout my state. I guess that doesn’t technically make me young or a boss in terms of the article cited, but I’m going to give my two cents anyway.

It’s my responsibility to ensure that the organizations we fund have the opportunity to receive AmeriCorps members in the upcoming years. I manage a hefty grant, it takes a lot of work and it means that I have to tell executive directors or senior staff when they’re doing things wrong (and right!). It’s not always easy, and they often don’t want to listen to me or want to go over my head to make sure I’m not providing them incorrect information. No one wants to look up the federal regulations themselves, but no one wants to believe me when I tell them I know the answer ha!

I think my age has something to do with it. I will say, I’ve been doing this since I was 23 and now that I’m a little older, it has gotten better. Or I’m now working with more respectful people, I’m not sure which.

On another note, the other day at a compliance visit, one of the AmeriCorps members mentioned something negative about someone in the office and chocked it up to it being the product of the other, younger person’s generation. I thought that was extremely rude and insulting to me. The person in question is probably 2 years younger than me.

Kimberly Alison (#4,465)

I had this issue when I was a 23-year old supervisor of college interns. It was hard to effectively manage people who were only 1-2 years younger than myself. However, it really ended up working out because I could connect with them on a level that my older manager couldn’t and they ended up being fiercely loyal and amazing interns. I felt comfortable asking the ones who had started before I came on for help and advice because it felt like asking a friend. However, one semester I had a 67-year old (late in life returner to school) as an intern and I flat out told my boss that I was not going to tell a Vietnam war vet what he was supposed to do.

OllyOlly (#669)

@Kimberly Alison I am 24 and have two undergrad staff assistants in my department. I am decidedly not good at managing them. It is my goal to start things off on a much more authoritative foot next year when we have new staff. I actually had a staff assistant come to me and ask if she could put off the project I assigned her to finish a paper…while she was on the clock. And I rolled over on it! Maybe it was the panic in her eyes? But never again.

And in the job before this, from 22-23 I had much older admin assistants and I always felt weird even just asking them to do my busy work. It definitely can be a weird dynamic both ways.

klemay (#1,755)

@Kimberly Alison I am 23 and I manage college students, some of whom are older than I am! The way I handle it is to always ask, not tell, people to do things. They always say yes, but there isn’t some weird dynamic of a 23 year old bossing around a 30 year old. It also helps that I tend to have more knowledge in the field than our student assistants, but it’s definitely a strange dynamic!

Even weirder was when I was promoted from student assistant to my job – I went from working with two people to being their manager!

A-M (#4,317)

I’ve worked on short term projects managing other people, and it’s hard, because in many cases we could be friends and would rather chat, but I have to keep them on task. I’ve also had a manager who wasn’t drinking age, and it was strange, but he was good at what he did, so it was okay.

andnowlights (#2,902)

I’m in charge of 30 undergraduate and graduate (masters and PhDs) students and sometimes it’s a pain. We started out the semester with them thinking that because we’re slow, they could leave their shift 30 minutes early… nope, and I told them as such. I got some push back and it made me a little upset because mostly I’m really on friendly terms with my students. Managing is hard, especially when you’re younger than some of your students (I’m 27 and some of my students are 28-33)

klemay (#1,755)

@andnowlights I also manage undergraduate & grad students… I guess I’ve been lucky though. I’m accommodating when they really need me to be, so in exchange they don’t ask for said accommodations unless absolutely necessary.

andnowlights (#2,902)

@klemay I think this is the first time I’ve actually had friction with them- they really are AWESOME 99% of the time and I completely love them. We always let them do their work if they don’t have anyone to tutor so leaving early was just taking advantage of the situation.

deedee (#4,436)

I’ve had a boss who was in her 20s (younger than me by a year or two) twice. I’m not in the tech sector, and it was very odd setup in both situations.

The first time, the new boss thought she knew everything and tried to aggressively manage folks who were 60+ years old and had been at the org for 20+ years. That new boss was fired after 3 months (she was crazy and deserved it).

The second time, the situation was very similar and things also did not go well. Morale reached a new level of low and everyone tried to find new jobs. We lost a rising star to another company. This boss wasn’t really “horrible”–BUT, she also wasn’t awesome. I think if you’re a younger boss you really need to demonstrate your skill and know-how to gain people’s respect…or give your reports a ton of space to let them do whatever they want (basically, not act like a boss).

garli (#4,150)

I’m 32 and newly managing people who have kids my age. Fairly bizarre but so far everyone has been really supportive.

Kissy (#5,345)

When I was 26 I had a much older female administrative assistant. She was super cantankerous and horribly hopeless but the big boss didn’t care so I was kinda stuck. Once she actually emailed me back (email!) “f*** off” in response to being asked to do some admin work (big boss’s response – a shrug). She’d been there for so long I think the big boss was apathetic about her because he wasn’t directly affected.

Eric18 (#4,486)

I was a young boss in the military. 22 years old and commanding a platoon of soldiers. All of the NCO’s were older than me. And I took over right before we deployed to Iraq.

It worked well because I did what all good platoon leaders should do. Leverage the valuable experience that my subordinates bring to the table in order to mold an effective organization capable of taking on a wide variety of missions. I got better as time went along in delegating responsibilities because I realized that to not use my men to their full potential was a waste of resources. I also listened to my soldiers when they talked (which alot of junior officers have trouble with) but was firm and fair in my decisions.

It definitely served me well as I draw from my past experience in my current job (where I manage an even larger group of older workers).

ragazza (#4,025)

I have a boss about ten years younger than me and expect I will have bosses either my age or younger for the rest of my career. That’s because I have zero interest in managing other people–I just want to focus on my job, which is writing, and getting better at it. I think younger bosses (and probably people in general) need to realize that not everyone is interested in the traditional management route to “success.” Luckily, my boss does understand that and we have a great rapport and mutual respect.

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