This post was written by Alison Green and published on Ask a Manager.
It’s five answers to five questions. Here we go…
1. How can I help an awkward new employee connect better with coworkers?
I am a senior team member. Reporting to me are Bill (mid-level — seven years of experience), and three people at the junior level (one to three years of experience). Bill is the newest hire on my team, hired because we really needed someone to take some stuff off my plate and also hopefully act as a resource and mentor to the more junior staff.
Bill’s work is good and I am happy with the hire, but without fail, he says the perfectly wrong thing. It is harmless, socially awkward stuff: trying to join a joke but the delivery is loud and the reference is obscure, or unknowingly suggesting something that is a pain point. Think of Michael Scott’s cringiest social moments and you will have an idea.
This is compounded by the fact that two of my junior level staff applied for this role when I announced we were hiring. I discussed with each of them that the move just was not right, they were too junior for the responsibilities, and they understood, I think … but it for sure makes interacting with Bill extra grating. Bill has noted to me that it is hard to join a new team where there are established relationships so I know he is picking up on it. The two staff members will text and grab coffee together sometimes, though they are certainly cordial to everyone. I have organized a weekly lunch, but it winds up just adding to the awkwardness because Bill kills the conversation with a disconnected statement about a topic we all finished talking about 10 minutes ago.
I think Bill’s attempts to make social strides, especially with everyone but especially with these two is just adding to the pressure and awkwardness of it all. It is painful to watch! Any suggestions of how to coach someone on connecting with coworkers, but to just the right degree? Should I be taking any other action to make everyone like each other more?
It’s not really your role to coach Bill socially. And he may just be an awkward guy, which is okay — people are allowed to be awkward! There are probably some places where you can coach around the edges (“when you made that reference to X, people were confused because X is pretty obscure and most people don’t know what it is”), but I wouldn’t count on it making a significant difference. I’d also lay off the weekly team lunches, or at least do them much less frequently — they don’t sound like they’re working and might be making things worse, and either way that’s a lot of organized togetherness.
What I do think is your role, though, is looking for ways to set up Bill where he can do better. What’s he good at? Can you look for opportunities where it would be logical to pair him with one of your junior people to collaborate, in an area where he has expertise and is comfortable? Can you keep an eye out for times where a junior employee is struggling with something and you can genuinely suggest Bill as a resource? And then set Bill up for success there as much as you can — for example, letting him know that he’s great at X specific nuance of Y and asking him to collaborate with Jane on that specific element of it. You’ll need to keep an eye on how those interactions go — you don’t want to increase everyone’s aggravation if he doesn’t handle those well — but the hope would be that if people have more positive interactions with him, it might change their comfort with him and he might start feeling less awkward too.
The goal should be less about revamping Bill’s personality — some awkwardness and quirkiness is totally okay in most roles — and more about getting everyone more familiar with each other through the work itself and helping the rest of your team see Bill’s value.
2. My boss asked me to talk to a coworker about her cleavage
I am the office coordinator for the school where I work, and my boss asked me to talk to a coworker/friend of mine about showing cleavage at work. My boss has been approached my parents as well as other staff members about this coworker’s clothing. I don’t know how to approach this. She’s an educational assistant and most of the EA’s here are fairly dressed down, as it can be a pretty physical job. She does have a large chest and I know that that can be an issue when buying clothing, as I have the same issue.
I just feel uncomfortable speaking to her. I think the reason my boss asked me to speak to her is because I am friends with her and so that it’s not an “official” reprimand and could be dealt with discreetly.
Her direct supervisor is a man, but the principal (the one who asked me) is a woman. I do have some authority within the school but it’s mostly organizational; I have some administrative responsibilities and have been asked to sit in on these types of meetings in the past with other employees, but I am in no way a supervisor of anyone and I am not in HR.
You should decline to do this. It’s not your job to give dress code feedback, and it sounds like you’re being asked to do it so someone else can avoid an awkward conversation, which is not a good enough reason. And if it’s really true that they want to avoid it being an official reprimand, they can easily accomplish that by … not making it an official reprimand. Managers can give feedback without it being memorialized as formal discipline; it can simply be a conversation/reminder about the dress code.
If your coworker isn’t in compliance with the dress code, that needs to be handled the same way your employer would handle any other dress code problem — which presumably means a reminder by someone with the authority to issue that kind of reminder, not asking a friend to pass along a message.
I’d go back to your boss and say this: “I thought more about your request that I talk to Jane about her clothing, and I don’t feel comfortable doing that. It should come from someone with the authority to discuss the dress code and answer questions if she has any. I think she’d feel very awkward hearing that from a peer, and I’m not comfortable delivering that feedback to a peer.”
Related:
my employee’s clothes accentuate her chest — how do I talk to her about it?
3. Left out of a group chat
I work in an office of eight (one manager, me, and my six coworkers), which is then part of a larger division. For the past week or so, my coworkers have all been discussing different New York Times games. I normally play Wordle myself, so I jump into these conversations too. It’s been a fun thing to chat about in the mornings.
However, my coworkers will also discuss these games in a Teams chat that I’m not a part of. I was out sick one day earlier this month, and I’m thinking that might have been the day they started it. I guess I’m just confused by the fact that I’m part of these regular conversations, and for some reason all six of my coworkers (even the guy who started three weeks ago!) have not thought to add me? My coworkers are all very nice people who treat me well, respect my time, etc. — my point being that I have no reason to think they’re purposely excluding me as some sort of schoolyard bullying tactic.
Do I bring this up to them? Do I bring it up to my manager? Thinking about it, I don’t think I care, but it does seem a little hurtful. I mean, what would my manager even do? Wag his finger and tell them to add me?
It sounds like there’s every reason to believe it was unintentional — it’s likely they did start it on the day you were out and then haven’t thought very deeply about it since. You can just say, “Hey, can I get in on the games chat on Teams?” and that shouldn’t be weird (particularly if they’ve talked about it in front of you) and should take care of it. The only way this would be weird is if your coworkers were a bunch of exclusionary asses and it doesn’t sound like that’s the case.
Note: the New York Times tech union is currently on strike and asking people to honor their picket line by not playing Wordle and other NYT games during the strike.
4. My organization doesn’t post job openings until the old person has already left
My organization seems to have a policy of not posting a staff member’s position until that person has left. Is there any way that this makes sense? I don’t know why they want four weeks notice if they don’t use that time to find the replacement. Hiring is slow anyway, so this routinely means that positions are open for months, which I cynically think maybe they like because they are saving money while everyone scrambles to cover the workload. Anything I’m missing here?
I’m curious whether this is actually their policy, or whether it’s just what happens in practice because they’re slow and/or disorganized. If it’s their policy, it’s a bizarre one! Generally a notice period (even a four-week one) isn’t long enough to hire a replacement and have them start while the departing person is still there to train them, but there’s no reason to squander that time; generally you want to move forward on filling soon-to-be vacancies with some sense of urgency. (There are some exceptions to this, of course, like if questions need to be worked out about the position before you post it, but typically you’d want to begin recruiting pretty quickly.)
By the way, four weeks notice is two weeks longer than the standard in most industries, and you might consider whether you really need to stick to that:
can I give 2 weeks notice when my employer says they “expect” 4 weeks?
5. I’m ready to retire young but don’t want to burn bridges
I’m a mid-career manager of a small team of experienced individual contributors involved with fairly high-profile projects for my organization. The organization consistently struggles to prioritize work and provide the appropriate resources; we often are trying to do too much, all at once, with too little. Despite this, my team is well-respected and gets things done. However, I’m tired and have been vacillating in and out of burnout for years. Vacations offer only a short-term fix. I suspect that I have undiagnosed neurodivergence that makes my set working conditions especially challenging.
My company does not offer sabbaticals. I have been focused on FIRE (Financial Independence, Retire Early) for years and I’m finally at a point where I feel like I’ve accumulated enough that I can take an indefinite break and am planning on resigning within the next six months. I’ve worked for this organization for a long time and, as I’m still relatively young, I’m sure my resignation will come as something of a surprise. I don’t want to leave my small team and my manager in a bind, but for the sake of my own best interests, I’m not comfortable giving more than a couple of weeks notice.
I have not yet determined if my mini-retirement will turn into full-blown retirement and mark the end of my corporate career. How do I frame my resignation and deal with questions from colleagues during my notice period when I’m not leaving for another job? I want to leave on good terms, but I’m not open to being convinced to stay with the organization while they figure things out. I want a clean break on my terms.
You’re overthinking it! You’re allowed to resign any time you want. It’s true that people might be surprised to hear that you’re not going to another job but you can say, “I’m taking some time off before deciding what I want to do next.” That’s true! “What I want to do next” doesn’t need to mean a job, necessarily. Or if you’re up for sharing more, you could say, “I’ve worked for a while to be able to take a long break from work, and now I’m able to do that.”
If you’re pushed to stay longer since you don’t have the deadline of a start date somewhere else, just hold firm: “I do need to stick with X as my last day because I have some immovable plans for right after that.”
This isn’t bridge-burning! You’re not an indentured servant; you get to decide when you’re ready to leave a job. And leaving a job for any reason nearly always creates some inconvenience for the team you’re leaving; that’s just part of the deal with resigning, not a reason not to do it.