Ask a Boss: I’m an Introvert and It’s Holding Me Back!

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Photo: H. Armstrong Roberts

Dear Boss,

I work in the legal field. I am not a lawyer, and I love the work I do. Legal practice is a great outlet for my extremely detail-oriented tendencies. Leave me in a room with reams of paper, a laptop, and five hard drives of disorganized electronic files, and I’m happy as a clam analyzing and organizing and researching and reporting on what I find. What other workers would find isolating and boring is my nirvana. 

I’m definitely an introvert and I find social interaction taxing. I can perform it if I have to, for a while, like a stage role. I interview really well because I’m able to turn it on for a period of time. But Chatty Cathy social nattering is definitely not my default state. Sometimes I feel like I misrepresent myself in interviews because I can manage it for an hour or two, but not 40 hours a week.

On a day-to-day basis it just doesn’t occur to me to babble at people about their dogs, or spouse, or my new cappuccino maker, or my funny weekend. I hear other people having these conversations with each other with a vague feeling of amazement, as if they all got a memo I never received, written in a language I wouldn’t have been able to read. When people try to start these conversations with me, it fizzles out because I don’t have the knack. 

My managers, who are all lawyers, are all intimidatingly good at this kind of thing because business development is an ever-present fact of legal life. They eventually figure out that I’m an introvert who is really good at what she does and produces great work product, but who isn’t going to natter unnecessarily. 

At least, I hope that’s the conclusion they come to. Honestly though, for some of them it’s not. At least one attorney has come to the conclusion that I’m disagreeable or I just don’t like him. Which isn’t true! I just don’t have anything in common with him other than the work we do, and it’s exhausting to try to pretend that I do on a regular basis. 

I interact best with the attorneys who talk to me about work, probably because I know I have a sure footing there, and I feel confident in what I’m saying. Which is all well and good, but it doesn’t build a relationship. And the subtle laughing and joking and one-upmanship strong male personalities do with each other, and with women colleagues who can handle it, leaves me unsettled and sometimes deeply uncomfortable. 

This is just Über-educated, type-A men who like to think they’ll one day own the world jostling shoulders and elbows verbally with other men of the same type. They play this game with each other, and I don’t know how to play. Which is fine, I’m not one of them. But I also don’t know how to play the witty-banter supporting roles either. Or even just have a work conversation about which coffee shop down the street is better than the other. I end up sidelining myself and sitting like a deer in headlights before retreating to my office and getting back to blessed work. 

I’ve noticed it affecting my career prospects, and it probably goes without saying, my standing in the world of office politics. Several times I’ve dealt with a situation where I’m right in what I’m saying, but I don’t have the backing of a decision-making attorney, or I’m not able to win the backing, in part because I don’t have those witty social relationships with them, and someone who is factually wrong or otherwise wrongheaded takes the day. In the long view, it’s backfired both times, but that’s cold comfort six months to a year later. And by then my cause is dead in the water.

Do you have any advice for how I can get more comfortable with social work conversations? I’m tired of feeling like the artsy-fartsy nutty-professor introvert trapped in a building of chatterboxes who sometimes act to maneuver over my job boundaries when they realize they can. 

Hello, fellow introvert! Yes, as someone who similarly has been wishing people would leave me alone ever since I emerged from the womb, this part of work can really suck when you’re someone who wants to do your work in peace and then go home.

When you’re an introvert in an office dominated by extroverts, I think you have two ways to go: You can find ways to “perform” relationship-building that look like the methods your co-workers use but which will probably never feel totally natural to you, or you do things that feel true to you.

But I think you’re more likely to be happy in the long term if you figure out your own ways to build rapport with people, even if those ways don’t look anything like the methods your colleagues are using. One of the most straightforward ways to do that — and one that a lot of introverts find easier to pull off — is just to take a genuine interest in people. You probably have a natural curiosity about people somewhere in you, even if you don’t typically indulge it at work, and this is the time to let it out.

For example: Wondering where the guy down the hall got all those interesting art prints on his wall? Ask. Thinking about taking a vacation to Iceland and remember that your co-worker went there last year? Ask what she did, what she liked, and what she’d recommend against. Always been interested in how your other co-worker switched from art school to law? Ask about it. I don’t mean that you should just pepper people with questions like some sort of crazed interrogator, of course; the idea is just to use things that genuinely intrigue you as ways to build more of a connection with people over time.

If you’re struggling to find anything terribly interesting about the people around you, then you can fall back on simply being kind — which can often just mean checking in on people’s lives. Ask about their kids or their marathon training or how their binge-watching of The Americans is going. Most people so enjoy having someone take an interest in them that they may never realize that you’re not sharing much about yourself (although you will probably get more comfortable doing that too once this method makes people more of a known quantity to you).

Also! Try finding the person in your office who’s most like you but who manages to hold her own in these conversations, and watch how she does it. There’s probably someone who’s a bit less polished in these conversations than everyone else but who jumps in anyway; see if you can figure out what works for her. You might find that she has three topics she mainly sticks to, or that she just speaks her mind without worrying about how it’s perceived and people like her for it, or who knows what — but there are probably interesting data points in there for you if you pay attention.

And keep in mind that you don’t need to do this for 40 hours a week. You only need to do it for five to ten minutes at a time, a handful of times a week. That time commitment is pretty small but can take you from “Jane, whom I never see or speak with” to “Jane, who talked with me about Game of Thrones when we were both microwaving things in the kitchen last week.”

One other thing to remember: People probably care less than you think. Most people are probably pretty okay with you being the quiet person who does good work. They’re probably well aware that their jobs require them to have schmoozing skills and that yours doesn’t, and they probably primarily appreciate that you’re good at your job. Yes, that one guy decided you don’t like him, but he’s just one person and he might have concluded that even if you were the world’s loudest extrovert. If everyone else seems reasonably happy with you, don’t be thrown by one person.

Of course, that isn’t much comfort when you’re worried that a lack of relationships is putting you at a disadvantage when it comes to work decisions. So, to get at that piece of it specifically, is there someone at work you have decent rapport with and who’s well-positioned enough to have seen some of this happen? If so, talk to that person and share what you’re worried about. It’s possible that you’ll hear that those decisions didn’t go your way not because you had inadequate social relationships but because of other things entirely (like politics or differing and opaque priorities above you). Or it’s possible that you’ll hear that it’s not that you needed better social relationships but that you needed to be more assertive or frame your argument differently or that you weren’t voicing your concerns to the right person. I see a lot of people frustrated that work decisions don’t go their way, and there are so many explanations for it that aren’t about relationships; it’s often that they’re just getting one of these other elements wrong.

But if you try all of this and you still feel like you don’t fit in well enough to give you a baseline level of happiness at work, nothing says that you need to stay in this particular environment forever. Certainly when you’re working in law, you’re going to encounter more of these types of offices than in other fields, but even in law not every office functions this way. It’s legitimate to decide that this is a quality-of-life issue like any other you might screen for when evaluating jobs in the future, like hours or location.

Alternately, in some cases you can get yourself to the point where you’re so good at your job that people don’t really care that you’re in your office by yourself all the time, because you save their asses when it comes to work stuff. That won’t necessarily work in every office, but it works in the functional ones and it’s not an unreasonable game plan if you love what you do.

Got something to Ask a Boss? Send your questions to askaboss@nymag.com.