In the latest edition of the “This Is Uncomfortable” advice column, “Work Drama,” Reema digs into your trickiest workplace dilemmas – from coworkers dozing off on the job to catching feelings for your boss. And she’s joined by podcast editor Tobin Low to help break it all down.If you have any work drama going on, we want to hear about it! You can send it to us at uncomfortable@marketplace.org, leave a message at 347-RING-TIU, or fill out the form at the bottom of the page.Khrais and producer Alice Wilder shared some listener questions with Low, and here’s his advice (lightly edited for clarity and length): Question 1: “I manage a small team and one of my team members falls asleep a lot. It's not deliberate, and sometimes she doesn't even realize it's happening. There was even a time when she dozed off during an important meeting. I've tried different approaches to address it: I've had a serious conversation with her about it, and I've also gently suggested that she see a doctor, but nothing has improved. On one hand, I worry that pushing too hard on this issue might be insensitive or intrusive, especially if it's connected to something personal she's not ready to share. On the other hand, if I don't address it at all, it feels unfair to the rest of the team. Like, I'm allowing this behavior to continue. What should I do?” – Eyes Wide Open Reema Khrais: Maybe they can approach this more firmly, like, “Hey, I'm afraid your dozing off is affecting your performance. It's impacting our team. It's something that we should seriously address.” Because it would be different if like you and I were colleagues and you were falling asleep, then how much can I bring it up without it sounding like I'm just being intrusive and annoying?Tobin Low: Totally, totally. I'm also curious if they've also explored what's going on with the meetings that may be contributing? Why are they consistently falling asleep? Are we consistently having meetings after lunch when everyone's a little sleepy? Are you running the meetings in a way where you as the manager are talking the entire time and not engaging anyone, and they’re essentially coming to sit and listen to you talk? Is that contributing to an environment where someone can check out? And is a slight adjustment to just make them a little more interactive, a little more like we're talking as a group? I would say I appreciate that. Khrais: Yeah, or is this an issue with the person? Maybe they actually have a sleep disorder. At a certain point, maybe there are explicit consequences if they keep falling asleep. If they know their boss is taking this more seriously, then maybe it might lead them to go to the doctor to figure out what’s going on, if they haven’t already. Not just for their job’s sake, but for the sake of their mental health.The “Uncomfortable” verdict: Maybe try scheduling meetings at a time when everyone’s more awake and making them more interactive so all the team members can actively participate. If that doesn’t work, it might be time for a more direct conversation as a manager, because ultimately, you don’t have to solve the why behind the problem. You just need to address the behavior.Question 2: “We have a new executive at my job and he just announced that he doesn't use slack and prefers to do work communications via text message. I work at a startup. I work at a startup and have really long work hours, so I'm already struggling with work-life balance. I do not wanna add texting with our new CFO into the mix. Do I have grounds to say no to texting my boss or do I just have to adjust to his preferred method of communication?” – Not From My Work Phone Low: It feels like this is not just a tech thing, it's a control thing. Like, “you will communicate with me on my terms and when I want to.” Whereas something like Slack or work email or whatever is an agreed upon thing with coworkers. So I would prefer to handle this like: okay, let's do this on your terms and let's see how badly it goes. Fine, if they want to text, I would insist on only texting during work hours. If they text you after hours, I would try as much as you can to hold the line that that text will not be responded to until work hours hit again. And then, if something happens on Slack and they miss it, let them miss it. Do not report back to them all the stuff that's happening in Slack that's meaningful, that then they are not privy to, because that's also a dynamic that will very quickly happen. Khrais: Yeah. You can create some distance. You don't have to respond right away. And then by doing that, I think you're setting this implicit norm around your availability. Generally speaking, a lot of us enforce our boundaries at work less by what we say and more by what you consistently do. This is fundamentally a question about boundaries: how do we have a healthy work-life balance? Alice Wilder: I would refuse to text him! Because this is weird, right? I would go to my direct manager and say, “Hey, I'm not comfortable with this.” Also, you all are not paying my phone bill, so let's wake that up, or get me a work phone. But I also would ask, what is our company policy around communications? There's probably an employee handbook, and I can imagine if this got brought to HR in some way, that would be their nightmare. And so, if management thinks of it as like a liability to them, they're more likely to tell him to stop. Low: I do want to wish this person luck because they said they work at a startup, right? Startup culture, from what I know of it, is a work-fast-break-things kind of environment, and they pride themselves on small teams who work at all hours and the boundaries are non-existent. So I appreciate that this person is probably existing in a world where there might not even be an HR department yet!Khrais: Part of it is just creating some distance. I would probably move some of the more urgent stuff on the Slack channel and then frame it as, “Hey, I stay better organized if I am communicating in this way.” So it's not an issue of preference; it's more of an issue of just being able to do my work in a competent way. The “Uncomfortable” verdict: You might not be able to outright refuse to text, especially in a startup, but you can start setting some boundaries. Try redirecting conversations back to Slack when possible, and be consistent about not responding to texts outside of work hours. You can also frame it as a workflow issue, like you stay more organized when communication happens in one place.Question 3: “I've been with my company for over 10 years. As the company's grown, we've needed to hire more staff, and I've been primarily responsible for training them. But there's this coworker, but there's this one coworker who's extremely harsh on new hires. Whenever a new hire runs into a problem, this coworker immediately criticizes them. Then they'll go to the manager and complain that the new hire isn't trying hard enough. In the past two years, we've had at least four new hires and every single one of them have left because they can't deal with this one coworker. No one has stayed longer than a year, and our workload never gets lighter. I've been stuck in this cycle of constantly training new people over and over for the past two years, and I'm honestly exhausted.” – OverworkedLow: Honestly, this coworker sounds like a real nightmare. I can remember the times that I've been a new hire and feeling like I'm all alone and everyone else likes each other, gets along and agrees with how things are going – that can be kind of the vibe you feel right when you walk in the door. And so then, when someone comes at you hard like this, it can feel like everyone agrees with them. I would say to the advice asker in this case, is there anything you can do for these new hires to talk to them and signal like, “I see it too, and we know it's not ideal.” Because when I've been in that situation, if someone just acknowledges, “yes, this is the dynamic, it’s unfair.” Or like, “This person is weird and we see it too,” then that helps make me feel less crazy. It helps me understand what’s going on here and know that I have allies. That said, I'm saying all of this as a solution that doesn't involve actually calling out this person, which is actually the answer! Khrais: I think so. Right? These new hires are leaving over this problematic coworker, so I would go to the manager and say, “Hey, after the last two years, we've had X number of new hires and I've noticed this pattern where like, you know, their experience with this coworker played a role and it's creating this bad cycle because I'm constantly retraining them and it's impacting both the team morale and our productivity.” It gets at this larger problem that I think can happen in a workplace, which is when one person's behavior starts shaping so much of the culture, and everyone else is forced to adjust around it. At first, it's easy to just dismiss that person's behavior, but then over time, that behavior comes at a real cost – in this case, people start leaving, and you're dealing with the same problems. And then people like this listener end up being the ones who absorb that fallout and feel like they have to fix these problems.Tobin: Yeah. I do feel bad for the advice asker, who seems to be really taking this on as their problem, when it's really their coworkers problem, or the company’s problem! Wilder: I'm on board with that. Let it play out: you should stop taking on the fact that they can't retain staff as your problem. You should not work extra to make up for that. Stop going above and beyond, because that's kind of enabling this behavior. The “Uncomfortable” verdict: You’ve been carrying a problem that isn’t actually yours to solve. You can support new hires and make them feel less alone, but you can’t fix a coworker whose behavior is driving people out the door. At this point, it might be time to name the pattern as a business issue to your manager. And remember, try to stop overcompensating and let the consequences of this coworker’s behavior be visible.Question 4: “I just started a new job and right away I developed a pretty serious crush on one of my coworkers. I didn't even think he'd be my type. He's 15 years older than me. At first, I thought, okay, maybe I can send him some signals I'm interested, maybe flirt a little during happy hour, because I can at least tell that he enjoys my company. But then out of nowhere, my office had a reorg, and now he's my boss. I wish I could just turn my feelings off, but I get giddy every time I talk with him and still find myself daydreaming about what it would be like if we started dating. I've been single for a bit and haven't felt like this about someone in a while. Do I just try to get over it now that he's my boss? Or is there any version of this where it's not a terrible idea to find out if the feeling is mutual?” – Head Over Heels Low: Personally, the fact that this person is now your boss, I think unfortunately, let's just take it off the table. I don't know that there's really any way to navigate this that isn't weird or bad, or gross. Khrais: Well, that's a thing with workplace relationships: it either goes really well – people are getting married, they're having kids, they become a success story – or it goes miserably wrong! It can become so messy: you're seeing them every day, getting into fights, it's awkward, people are talking about it, so it is tricky. But also, this person just started this job, so how well can they know them? Wilder: I've heard it said that a crush is a lack of information. Maybe hold off for six months: get on the apps, start dating people who are not your coworkers, and if six months goes by and you still feel this way, then you can revisit trying to get moved to another department. And if you two decide you like each other, you could go to HR together and say, “Hey, I need to be assigned to a different supervisor, because like we’re seeing each other.”Low: Yeah. It reminds me of another saying, which is: “what it's meant for you will not pass you by.” And so we are saying you should take your time, fight against this as much as you can, and if in a year's time, you have that more information and the feelings are still there, then maybe you revisit this question, but it feels like there's a lack of information right now perhaps. The “Uncomfortable” verdict: This is one of those situations where the timing really matters, so for now, you might want to give yourself more time and space. See how you feel after a few months, maybe date other people, and let things settle a bit. And if the feelings are still there down the line, then you can revisit it, like switching teams or no longer having them as your direct manager.Got a work problem you want some advice on? Email us at uncomfortable@marketplace.org, leave a message at 347-RING-TIU, or fill out the form below:Support “This Is Uncomfortable” with your donation today.