employee is missing the mark with our dress code, manager keeps delaying our team off-site, and more — Ask a Manager
It’s five answers to five questions. Here we go…
1. My employee is missing the mark with our dress code
My direct report has been very open about being on the autism spectrum and having some learning disabilities. I’ve been working with him closely to provide regular feedback and coaching on a few performance issues. He is eager to improve, and I want to provide as much support as is reasonable.
One area where I’m struggling is his appearance. We’re a professional service firm, so we regularly interact with clients. We’re not overly formal, but it’s important that we look put together. He’s come to client calls looking disheveled, with hair all over the place and a t-shirt with small holes in the neck. I’ve told him a few times that the expectation is business casual on calls, like a button-down or sweater.
The problem is he’s following that advice now, but the shirts are often wrinkly, or a bit too small, or he’s not wearing an undershirt and he’s showing a lot of chest hair. He’s technically following my recommendations, but still doesn’t look client-ready.
How direct should I be with feedback moving forward? I have no problem continuing to remind him that the expectation is a neat and clean appearance. However, it feels overly personal to spell out everything I’ve said above. Of course, I also want to be respectful of the fact that some of this might not be obvious to him. As his supervisor, how much coaching do I owe him on this?
Please be direct with him! I think your initial feedback — that the expectation is business casual — assumed he’d have access to a sort of cultural playbook about what that means, but a lot of people were never given that playbook and you’re more likely to get your message across if you spell out exactly what it means. (Notably, this is the case for most people, not just people with autism, and so many problems would get solved if managers would do more of it.)
So spell it out! “We’ve talked in the past about our dress code being business casual, and I’ve realized I should be clearer about what that means. Especially when you’re going to be interacting with clients, you should (fill in details of exactly what you want to see from him that you’re currently not).” I suspect you haven’t done that yet because you feel awkward about dictating this stuff at such a micro level — like it’s somehow insulting or overly micromanagery — but the reality is, you have expectations that he’s currently not meeting, he’d probably like to meet them, and you’ll be helping him out by telling him exactly what they are.
2. How to get coworkers to stop asking how I’m doing
For the first time in my life, I’m facing health issues that are impacting my work. I’m pregnant and this pregnancy is wreaking havoc on my body in myriad ways. My boss knows the full details and is incredibly respectful and supportive, and it’s getting to the point where my coworkers — and even coworkers I don’t know — can visibly tell that something is wrong. I can barely walk most days and am increasingly working from home in a very in-person office, so when I’m not there it’s noticed.
My coworkers are lovely and they mean well, but every day they ask how I’m doing. I just want to yell, how do you think I’m doing? I’m shuffling around the office like I’m 80 and am clearly in pain! I don’t like talking pregnancy in detail, both because it’s my private medical information and also out of sensitivity to a coworker experiencing infertility, so I usually just brush it off with a casual “oh, you know.” Because the truth is I’m NOT doing well and I’m not going to get better until I have the baby, five months from now.
Any tips for respectfully getting people to stop asking how I’m doing, even though I know they’re asking out of concern?
“You’re kind to ask, but it’s easier on me if we can skip talking about it until I’m through it. Ask me in five months!”
Or, “You’re kind to ask, but it’s been rough and it’s easier for me not to get that question at work. I’d be so grateful if no one asked me that for the next five months!”
3. Manager keeps delaying our team off-site and I’m frustrated
I’ve been working at my company for one year, and my manager started working here around the same time. We have a small team (two other coworkers) and are all remote, but all teams at this company are allocated a travel budget for multiple team off-sites per year. Our team has never had an off-site yet, despite repeated promises from our manager and constant pleas to him from our team.
When I first started, the plan was that we were going to meet in September, then that changed to October, then for sure December, then definitely January or February, then April or May (we even put together a google sheet with everyone’s availability so our manager could pick the week), then 100% June and now it’s certainly happening in July or over the summer. I can’t take this anymore! We’ve tried everything — we bring it up to him nearly every week and he acts like he’s taking it very seriously but then he’ll delay it again.
There’s never any good reason for his delays. He doesn’t claim to be too busy, and he wouldn’t have to plan any itinerary himself — he just needs to pick the date so we can be authorized to book plane tickets and hotel rooms, then we can take care of the rest. He does have a history of not really caring about things that we care about unless it’s something he’s personally invested in, so my guess is he just doesn’t care that much and therefore it’s not a priority to him.
There’s nothing work-related that isn’t happening because of this. It’s mainly about team connection and getting to spend time together in person. The company allocates every team a travel budget for a trip each quarter, to get to visit the offices and meet other colleagues but also to have fun team events. It’s been tough seeing everyone else get to experience this multiple times and we’ve never done it once.
I mentioned this issue in a “listening session” that our broader org was holding for smaller groups to discuss any problems they’re facing and everyone seemed horrified, but that didn’t result in any changes either. It seems too whiny and petty to mention to my skip level but I don’t know what else to do. I know this sounds like a very minor problem but seeing other teams have two or three off-sites over the last year while we have zero has been really demoralizing and upsetting. Any advice?
A lot of people hate off-sites, and your manager may be one of them. Or he might have things going on outside of work that make it hard for him to commit (caring for a family member, health issues of his own, or who knows what).
If you and your coworkers haven’t already told him very clearly that this is important to you, try that. Say it’s important to you for X reasons, you’re disappointed by the delays, and it’s frustrating watching other teams having off-sites while you don’t. Ask point-blank what needs to happen to commit to a date, or whether it’s not something you should plan on at all for the foreseeable future. But if you’ve already done that, or you do it and nothing changes … well, I think you’re not going to have an off-site anytime soon. It’s really his call to make, as the head of your team.
If your sense is that the organization is committed to these to such a degree that his boss would overrule him if she knew about it, then in theory you could raise it with someone above him … but I suspect there are things more worth saving your capital for (and realistically, forcing him to lead an off-site that he actively doesn’t want to do might not produce the type of event you see others having anyway).
4. My boss asked how things are going … and I didn’t tell him I’m planning to leave
I am the only full-time employee for a super small business. Everyone else is contracted workers or family members of my boss, the owner. I’m the executive assistant.
I don’t have horrible complaints, but I am currently looking for a new gig for more pay. He is also an older man, and he is often irritable and forgetful.
My boss really appreciates me and tells me so. He has given me a holiday bonus and a birthday bonus ($500 and $250). Just now he called me to say he realized he hasn’t asked me how I am in a bit and how I feel the work is going. I said, “Pretty good.” Then he asked, “What would make you feel great?”
I really didn’t know what to say. Obviously more pay would make me feel great, but I wasn’t ready to say that. So I just said, “I am great, no complaints.” He said that’s good and again he stated how much he appreciates me and how he couldn’t do everything without me.
I just worry that I will be blindsiding him if and when I get a new job and put in my notice. Is it right to say everything is going well, even though I am currently job searching?
You’re fine. You don’t owe your boss full transparency that you’re thinking about leaving just because he happened to ask how you’re doing. If you end up resigning soon and feel weird about the timing, you can say the new opportunity fell in your lap and was too good to pass up.
That said, for the rest of your career, a good answer to have ready to pull out in response to the question he asked is, “More money would always make me happier!”
5. Asking about AI in an interview
I have an interview coming up soon for a marketing position, and while I feel fairly prepared and confident I’m a good candidate for the job, I’m curious about bringing up something during the “what questions do you have for us” portion of the conversation.
Specifically, this position would require a bit of copywriting and promotion of the works they put out, and while I don’t believe this particular company would ever push someone out of a job just to use a trendy new technology, I would like to broach the topic of AI just out of curiosity and an abundance of caution. I’m thinking of framing it as “what conversations are you having as a company about the rise of AI use in writing, and do you have any screening tools in place to prevent AI-created pieces from being submitted?”
Is that an off-base thing to ask about in the interview process? Like I said, I’m not exactly worried about this company fully embracing AI like techbros, but I don’t think AI is going away anytime soon, and I’d like to know sooner rather than later if this is going to be something that will impact the job.
Totally reasonable, and your wording is great.