transcript of “The Maligned Coworker” (Ask a Manager podcast episode 7)

This is a transcription of the Ask a Manager podcast, episode 7: “The Maligned Coworker”.

Alison: This week we have a special guest and I’m so excited to introduce her. Jennifer Peepas runs the very popular website Captain Awkward, which is an advice column that specializes in helping people set boundaries and assert themselves. She gives amazing advice on romantic relationships, friendships, families, roommates, coworkers, and much more. I am a huge fan and I’m thrilled to have her here. Jennifer, welcome to the show.

Jennifer: Thank you! It’s fun to be here and I’m a big fan of your blog, I’m always sending letter writers to you. So it’s about time that we had a meeting of the minds.

Alison: It is about time, and I know a lot of Ask a Manager readers are big Captain Awkward readers as well. People often in the comment section link to your posts and send people over there for help with all sorts of things. We have a letter that we’re going to talk about together today and I’m so excited to do that. But before we do, can we talk about Captain Awkward a bit?

Jennifer: Sure, what do you want to know?

Alison: What led you to launching the site in the first place?

Jennifer: I was looking for a way to be writing regularly. I have a film background, I sometimes write and make movies, and I was looking for something that didn’t need that intense collaboration and money, and I could sort of just express myself regularly. And one of the beautiful things about advice columns, which I was totally addicted to and a fan of, is that people send you stories in your email, people email you stories. And it was such a fun way to engage with a lot of people’s stories was kind of my thinking. I was a big fan of a lot of advice things, I love Carolyn Hax at the Washington Post, and I would read a lot of other things and I was just like, “Hey, they can do that, I can do it too.”

Alison: And did you set out planning to have such a focus on boundary setting and speaking up or did it just evolve that way?

Jennifer: It kind of evolved that way. I think we’re like, we teach what we need to learn sometimes, as the aphorism goes. And it was something that I had learned as a late bloomer: that oh, the world won’t end if you say no to people and you can assert yourself and you don’t have to just constantly do what people want you to do. Oh, neat. And then realizing just through teaching – and especially as a teacher, because I teach college students – that it was a problem that a lot of students were having, that they were really afraid of conflict. And just being like, don’t be so afraid of conflict. Conflict is not the end of the world. Conflict is where the good stuff happens.

Alison: Am I remembering correctly that early on, the tagline for your site was “use your words”?

Jennifer: Yes!

Alison: That’s so perfect because it’s so much of what you teach people to do. And as someone who finds myself also pushing people to speak up and helping them figure out the words to do it with, I know people generally find it a lot harder to do than it sounds like. Do you have thoughts on why that is?

Jennifer: I think people are just really socialized to be accommodating and to try to give everyone the benefit of the doubt and try to look for reasons that it’s not people’s fault when they do bad stuff. But I think as I got older, just realizing that you can’t accommodate people into not being assholes —

Alison: Yeah.

Jennifer: You can be the most accommodating person in the world and some people don’t take that as… they don’t get the message that they should ease up, they just keep going.

Alison: Yeah.

Jennifer: So that was a lesson, but I feel like a lot of people are socialized to be very afraid of conflict, whether it’s the kind of household they grew up in, or they’re afraid, and then they get into the workplace or they get into relationships, and they don’t have those skills to be like, “No, I don’t like that. No, I don’t think that’s a good idea. Let’s do my idea.” And it’s very hard for them to say those things. And I’m not sure if there’s one reason, but I know that it’s a big thing, that a lot of people have that socialization.

Alison: Okay, I’m tempted to ask you questions all day long, but we have a letter to answer.

Jennifer: Okay, yes.

Alison: This is a letter that was sent into Captain Awkward that involves work, so we’re going to answer it together. Want to read it out?

Jennifer: Yes, sure.

Hi Captain, I have gotten myself into an uncomfortable situation at work. At first, I thought I was helping out an unfairly maligned female colleague in a male-dominated industry. Now, I feel like I’ve attached myself to a sinking ship.

Background: I started a new job in a male-dominated field – I am also a woman – and really like all of my colleagues, my manager, and the CEO. It’s possible that everyone is showing their best face for the new lady, but I genuinely think this is a good company to work for. Potentially important detail: my entire team works remotely.

One coworker, I’ll call her Sophia, mentioned in a meeting that she is frustrated because she feels people aren’t listening to or respecting her. The rest of the team was a bit dismissive, which I felt was unfair, but I also didn’t feel confident enough to speak up in the moment. Instead, I reached out to Sophia privately and asked if she wanted some help in coming up with a list of concrete asks for our coworkers. I ran this by my manager, who thought it was a great idea and thanked me for looking out for a colleague.

I met with Sophia in-person when she was in my city for a conference, and it was bizarre. I expected her to do a bit of frustrated venting, and thought maybe we’d spend an hour coming up with a plan and then celebrate our hard work over dinner and a drink. Instead, she was incredibly negative the whole time. It was clear that she wasn’t interested in coming up with an actual plan. She showed me examples of emails and chat conversations that she considered “disrespectful” and “bullying,” but they seemed completely innocuous to me. In fact, sometimes she was the one being rude. I tried to ask questions like “Well, how would you have liked your manager to respond here?” or “Can you help me understand why you consider this to be disrespectful?” but she would change the subject and go on a rant about another person or incident.

As the evening went on, Sophia’s ranting turned into profanity-laden insults directed at the personalities and appearances of our colleagues. I tried to interject with “Wow, that’s not my experience with Dorothy at all!” or “I’m surprised to hear Arthur would handle this situation in that way,” but she wised up. She started telling stories that I would have no way of verifying or disproving, in which she was supposedly treated poorly, and then would ask questions like “Don’t you agree that that’s a horrible thing to say to someone?” Quite frankly, I was a little afraid of her and thought she might become angry and verbally abusive toward me if I pushed back or tried to leave.

In short, I feel that I was essentially tricked into agreeing to a bunch of horrible sentiments directed toward colleagues who I actually really like and respect. I could go to HR, but if this were to lead to disciplinary action for Sophia she’ll know that I was the one who brought it forward. Since I’m still new at this very small company, I don’t want to be known as a person who runs to HR as soon as she has a problem with a colleague.

I’m wondering what I should do. First, I’ll need to explain to my manager how there is no action plan as a result of this meeting. Sophia has asked me to join her in some 2-on-1 meetings with individual coworkers, and I really don’t want to participate. I said I would in the moment, but that was only because I’m afraid of her. How do I back out? How much should I tell my manager? Any advice you have would be much appreciated.

Alison: Wow, okay. This is a fascinating letter. Do you want to start us off with your thoughts?

Jennifer: Sure, and I forgot to say that the title of the email sums it up beautifully: “I tried to help someone only to discover that she is the problem.”

Alison: Yeah, perfect.

Jennifer: I agree maybe running to HR is not necessarily the best first step, but I do think this letter writer should clue their manager in a little bit. Maybe not everything about the conversation, but just like “I met with Sophia, we tried to come up with an action plan. I felt like she wasn’t really into it and that anytime I tried to make a positive suggestion she wasn’t into it. I don’t think that me coaching her or helping her facilitate this is going to work out. I just wanted to let you know what’s up.” And then maybe just leave it there and don’t continue the mentoring relationship.

Alison: Yeah. She definitely should not join in on those 2-on-1 meetings that Sophia wants her to participate in. I almost wonder – Sophia may have picked up on the fact that the letter writer doesn’t share her perspective and so she might not even come back and ask her to do those meetings. But if she does, I think the letter writer can say, “You know, I was up for being a sounding board, but I don’t think I’m well positioned to be part of those conversations. I’m so sorry you’re having a tough time and I hope it was useful to talk to some of it through with me, but I don’t have the kind of role where I would belong in those meetings.” And that’s true because even if Sophie has complaints were all very well founded, the letter writer doesn’t really belong in those meetings, especially as someone who’s pretty new and unfamiliar with the players.

Jennifer: Right. I think that’s a great script: sort of like, ” I don’t think it’s my place to be in those meetings, but I hope our conversation was productive for you and you are able to implement some of those positive action plans.” And just leave it kind of nebulous and then stay away from her, which it seems like everyone else on the team does.

Alison: Yeah. And the fact that they’re remote might work in her favor in this situation, because you won’t be running into her in the hallway, she won’t be coming by your desk. It’s easier to stay away I think, which is good.

Jennifer: Right. And I would keep things kind of friendly and neutral with her because you don’t want to antagonize her more and you don’t want to – the letter writer probably is going to go on Sophia’s, like, Arya Stark-like list of people who have wronged her at work. It just will happen. And she should keep, especially her written communications, I would keep written messages and chats with Sophia to the minimum that you need to do your work and always very positive. Always like, “Hi Sophia, so great to hear from you, here’s what we need to do on this project. Okay, great!” And just kind of keep the tone very friendly so that when Sophia starts the “and now Letter Writer is disrespecting me!” there is no trail of anything to indicate that.

Alison: Yes, very much so. Actually, that makes me think too – Sophia sounds like someone who might say things like, “well, Letter Writer agrees with me that Dorothy is horrible.” And she might say that no matter what the letter writer says, but I think it’s important for the letter writer to be studiously positive in her interactions with Sophia so that she’s not handing her words that Sophia can then twist and misrepresent later.

Jennifer: Right. I feel like everyone gossips about their coworkers. Never, never put the gossip in writing.

Alison: Yes. Oh, people make that mistake all the time.

Jennifer: Gossip away if you have to, but never ever put it in writing. You’ll never be glad that you did.

Alison: Yes, it’s so true. The other thing I think is, the way that the letter writer is defining success in this situation probably can’t be “Sophia feels positively about her and has no resentment against her,” because that probably isn’t going to happen. You’re probably right that the letter writer is going to go on Sophia’s Arya Stark-like list. And that is okay. I don’t want the letter writer to feel like the only way that she gets a good outcome here is if she can avoid that, because that’s totally out of her hands. And what we know of Sophia so far says she probably will be on that list.

Jennifer: Oh God, the thought of those 2-on-1 meetings, I cringe at it.

Alison: Yes. This sounds terrible and I think the letter writer had such good intentions here. It’s so easy when you’re new to a job and you’re just starting to see the dynamics to miss what the real dynamics are. And so I can see how she ended up making that offer and though she was doing something kind, and then have this sickening slowly dawning realization over dinner of what the dynamics really were. So I think if there’s a lesson here – I don’t want to say don’t ever help someone just because you’re new, but maybe just hang back and reserve judgment a little bit.

Jennifer: Right. And there’s another lesson here, and I’ve run into this before, is when you’re new, sometimes coworkers will be really friendly to you, the new person, but if you notice them being unfriendly to or about other people just kind of file it away that your turn is coming.

Alison: Yes, that’s right. Because sane, reasonable, rational people who have legitimate beefs with coworkers usually are not spreading them around to the new person when they first walk in the door. So that behavior in and of itself as a flag.

Jennifer: Right. If you’re their new best friend because you’re new here and everyone else is terrible, you will go on the terrible list too. So just hang back a little bit.

Alison: Yeah, I think that’s right. Any parting thoughts for this letter writer?

Jennifer: The letter writer I think is a great writer, told the story so well. It was a pleasure to read the letter. So I want to put that out there and just – yeah, you tried to help someone and it’s clearly not going to work, so give yourself permission to just kind of move on from this and use your words and your platitudes if you need to keep her at bay.

Alison: Yes, well said. Well Jennifer, thank you so much for taking the time to come on the show and talk with us. I had so much fun talking with you.

Jennifer: Yes, thank you. Any time.

Alison: You can read more of Jennifer’s work at, you can follow her on Twitter at @cawkward. For everyone who’s listening, I’ll be back next week with more advice on navigating sticky situations at work.

Alison: Thanks for listening to the Ask a Manager podcast, produced in conjunction with Penguin Random House and Anchor. If you like what you heard, please take a minute to subscribe, rate, and review the show on Apple Podcasts, Spotify, or Google Play. If you’d like to ask a question on the show, email it to And check out my new book from Ballantine Books called Ask a Manager: Clueless Coworkers, Lunch-Stealing bosses, and the Rest of Your Life at Work. It hits stores May 1st, and it’s the ultimate guide for tackling any and all workplace dilemmas. You can pre-order a copy today at or anywhere books are sold.

Thanks for listening! I’m Alison Green, and I’ll be back next week with another question.

The below was bonus content that was cut from the podcast for time and released separately.

Alison: Welcome to special bonus content for the Ask a Manager podcast. In episode 7 of the show I talked with Jennifer Peepas of the Captain Awkward advice column. Our entire conversation didn’t make it into the show because we talked for a while, so this is bonus content for people who are advice column junkies or who just like insider baseball talk about advice columns.

A little bit of context to ensure that you can follow along. At one point in this conversation, Jennifer and I talk about an especially memorable letter from her site. She printed a letter at Captain Awkward back in 2012 from someone whose live-in boyfriend would hog the bathroom for literally hours, two to three hours in the morning and in the evenings – and it wasn’t a medical situation, he was just locked in there sitting on the toilet, reading on his iPad – and it was their only bathroom and it meant she didn’t have any access to it. At one point, she peed in the sink out of desperation and he still wouldn’t alter his habits. It was pretty horrifying. Jennifer, of course, gave her the very good advice that this was not okay and that she needs to be able to use the bathroom in her own home and not to have to pee in the sink. But as you can imagine, people have really remembered this letter because it was such a ridiculous situation. In the conversation you’re about to hear, that letter comes up and I wanted you to have context for it. So here we go – let’s dive straight into the conversation.

Alison: One of the many reasons I was excited to talk to you is because writing an advice column is weird and there’s not a huge community of other people doing the same work to talk to you about things like moderating a comment section or screening reader mail or knowing if a letter is fake. And I’m curious, is there anything that has really surprised you about writing an advice column or that you think would surprise others?

Jennifer: I’ve been doing this now for seven years, so I think the biggest surprise is that people will still send things in, that it just became self-sustaining. People get very invested in certain stories, and sometimes like the level of investment surprises me. People start sharing their stories and the comments and it’s just the common experiences – sometimes I get letters that I think are very strange and then the commenters are like, “Oh, this totally happened to me too.” And I’m surprised.

Alison: I have the same thing happen. I’ve run things before where I’ve thought, “I’m pretty sure this is real,” but there’s part of me in the back of my head that thinks, “This is so unusual-sounding that maybe it’s not.” And then five or six people in the comments will say, “Oh, the same thing happened.”

Jennifer: Yeah, I think that I’ve definitely read some like, “Who behaves like that?” on your site. Like, who would do that?

Alison: Yes, yeah. There’s an endless variety of human weirdness out there, which is great for us (laughs), for advice columns.

Jennifer: The one I always think back to from your site is the person who, their coworker was stealing their lunch and then they made their lunch real spicy, and the coworker still stole it and then got sick. And then the person whose lunch was stolen was accused of poisoning the coworker.

Alison: Yes. It was a crazy story. The person actually got temporarily fired for making their own lunch spicy because it sickened the person who was stealing it. It didn’t sicken them, just caused some mouth pain.

Jennifer: (Laughs) Very spicy food.

Alison: But then got their job back when the CEO of the company came back and heard what had happened, and then there was all this intrigue that came out. It turned out that the lunch thief had been having an affair with the HR person who fired the letter writer. It was a lot of drama.

Jennifer: I guess I missed the affair. That’s amazing.

Alison: Yeah, I’ll send you the update. The updates often have so much interesting additional information in there. I love it when people send in updates.

Jennifer: Yeah. That’s one of the things I love about your site is that you have a lot of updates. I sometimes post updates when they come in, but I don’t ever want to create the expectation that you have to update.

Alison: Yeah, that was my sense because people are writing to you about very personal, intimate, often painful things. Whereas with my people, I feel more comfortable pressuring them to update.

Jennifer: Right, and I don’t want people to ever feel pressure that they have to do it.

Alison: Yeah, I mean, I want to pressure mine (laughs).

Jennifer: We can get very invested in their story, but like it’s still their story to update if they want to, and they don’t owe us. Although, everyone always asks about the letter writer whose boyfriend would hug the bathroom.

Alison: Yes. That’s one of the first letters I read on your site.

Jennifer: I did get through the grapevine update that she eventually broke up with him and she’s fine and she can now pee. And everyone who got that information – I think I tweeted it out – was like, “Yes, I’ve been holding my breath for four years to know that.”

Alison: Oh, that’s great to know. That letter stayed with me.

Jennifer: It stays with people. He’s denying you your basic human rights! Maybe he’s not a great boyfriend?

Alison: Advice columns are the best.

Alison: So there you have it. Some additional bonus content for you from the Ask a Manager podcast. Thanks for listening.

Thanks for listening! I’m Alison Green, and I’ll be back next week with another question.

Transcript provided by MJ Brodie.

You can see past podcast transcripts here.