Posted by Ask a Manager
https://www.askamanager.org/2025/10/socializing-on-a-week-long-work-trip-bosss-email-overload-and-more.html
https://www.askamanager.org/?p=33853
It’s five answers to five questions. Here we go…
1. How much should I expect to hang out with my coworker on a week-long work trip?
I have an upcoming work trip that I’m feeling a little anxious about, mostly because I’m unsure how to handle the social side of things.
It’s a week-long trip with just one coworker. They seem lovely, but we haven’t worked closely together before. I’ve traveled with larger groups in the past, and in those situations the unspoken norm seemed to be: do dinner together at least once or twice, and apart from that, it’s okay to stay in or go out on your own if you prefer. After all, there are others in the group they can spend time with if they’d like.
With just the two of us, though, I feel more responsible for their experience, and I’m not sure what’s expected. Should I plan for us to spend afternoons and dinners together every day, or is it okay to build in some solo time? I want this to be a positive experience for both of us, but as someone who’s neurodivergent, it’s hard for me to read the social cues. What’s the typical etiquette for a trip like this?
Dinner once or twice during the week but doing your own thing the rest of the time is a pretty typical way to handle it, even when it’s just two of you. You can set those expectations early on in a warm way by saying something on the first day like, “Do you want to do dinner together one night this week while we’re here?” That way you’re offering it! You’re being warm and friendly. But you’re also setting the expectation that it won’t be every night.
Related:
can I do my own thing in the evenings on a business trip with colleagues?
2. How do I deal with my boss’s email overload?
I work at a company that is very email-heavy, which means that we get a lot of emails and we are expected to read and respond relatively quickly. The problem is that my boss, who is a senior leader, is so inundated with emails that he regularly misses things (I would say he misses a quarter to a third of things I forward him, and at least one-third of external emails that we’re both on from new senders).
Right now, my strategy if I need a quick response is to use our chat tool to follow up. Half the time, he’ll say he didn’t see the email and I’ll need to forward it so it’s at the top of his inbox. But if it’s, for example, an email that we’ve set up a meeting to discuss, often I’ll start the meeting and realize he hasn’t read the email, and then we’ll lose 10–15 minutes while I find the thread, send it, and wait for him to receive and then read it.
It feels like there has to be a better way, and he knows this is an issue and I think would be happy to hear strategies. But I think the strategies I use (a custom priority inbox and judicious use of filters) won’t work for him, because it took me time to set it up when I started, and I do have more time in my day to keep on top of emails. Do you have any other suggestions? Or do I just accept this is how it is, and keep using strategies to work around it?
Accept that this is how he is and be proactive about working around it. That means things like assuming that there’s a good chance he won’t see emails until you specifically follow up on them, assuming he won’t have read emails before meetings (unless you chat him and specifically ask him to, which is worth trying when it’s important), using good email “hygiene” (i.e., keeping messages as short as possible and with the upshot/action needed right up top) and communicating with him in ways that aren’t email as much as possible. For example, can you save some of these items up for regular check-in meetings and not bother emailing about them at all?
That might not be ideal, but if he’s going to miss them anyway, your life will be easier if you plan for it to happen.
Related:
my boss hardly reads emails and says it’s my job to follow up with her when something’s important
my boss is impossible to reach when I need responses
my boss won’t answer my emails
3. My coworker said I look like JD Vance
I work for government, and it is obviously a professional environment. As such, comments on appearance are very rare though people will give well intentioned compliments on new haircuts, clothing etc.
Today in front of others out of nowhere, a colleague got excited and said that I look like JD Vance. I am around the same age and am a white guy with facial hair so there is some similarity but it was kind of weird and was definitely awkward with others around and with the current political environment.
Is this comment appropriate in office or am I just overreacting because I detest JD Vance and find the comparison unflattering? Also, the colleague who made the comment seemed to not think commenting on appearance that way was strange — should I try to correct them? At the time I was baffled so didn’t say much.
Eh, it’s the kind of thing that sometimes gets said. Appearance assessments shouldn’t be made at work (and if your coworker had written in asking if he should tell you that you look like JD Vance, I would have told him not to), but I don’t think it’s so egregious that you need to go back and say something about it now. (However, if you had wanted to indicate you were displeased in the moment, you could have said, “I promise you we’re quite different.”)
If he continues to harp on it, then yes, at that point you should ask him to give it a rest, but hopefully it’s not going to keep coming up.
4. We’re asked to chip in for gift cards for departing executives
I have a question about a new practice at my org (a mid-size scale-up with 500-1000 employees). Recently, several VP/C-suite executives have left, and it’s become standard to send a virtual card for all staff to sign and a virtual gift card for optional donations. The latest card had a follow-up urging everyone to sign by tomorrow, which I didn’t do on the basis I’d never met her.
There’s no guidance (other than calling it optional) on who should be gifting, but it bothers me that high-earning executives are receiving crowd-sourced gift cards. I wouldn’t be against the company seeing them off with a gift — these people have generally made an impact. Instead they’re getting around £200-£400 in donations from people almost exclusively below them. Typically, low-level employees have a gift card that has gone out to those they’ve worked with, not the entire organization.
Am I wrong to feel uncomfortable about this? Most people don’t seem to want to gift, as there are usually only about 25 donations. Isn’t it strange to ask? I want to mention it to my manager but it feels a little petty.
It’s not petty at all. It’s gross to ask lower-level employees to chip in for a goodbye gift to high-level, better paid executives (especially ones they haven’t even met, but it’s gross either way). It sounds like most of your coworkers agree, based on the low number of donations.
If the company wants to send off departing executives with a gift, they can pay for it themselves.
Whether or not it makes sense to mention to your manager depends on what your manager is like, your relationship with her, and your sense of how much capital it would take to raise it … but at a minimum you and your coworkers should feel very free to ignore these requests. If enough of you do that, hopefully whoever is organizing these will get the message.
Related:
my office wants us to chip in to send our CEO’s family on a ski trip
5. Managing my energy on days with a later start time
I work in healthcare, and my field is known for its stress levels and physical intensity. Most of my career has been spent in a consistent 8-5 schedule. However, my new job involves some days of a later start and end time, like occasional 1-8 pm days. I’ve found that I’m really used to starting my work day with a “full tank” of energy and focus at 8 am, and I’m struggling to manage my energy and focus on my 1 pm start days. I feel like my energy is peaking before I even go in to work! It’s really tough knowing that the intensity of the work day is still to come. It spikes my anxiety, and I am having trouble making that time before 1:00 either relaxing or productive, and I am also struggling to maintain all the way until 8:00.
I’d love any thoughts or ideas and how to manage this, and commiseration is welcome as well!
Let’s throw this out to readers!
The post socializing on a week-long work trip, boss’s email overload, and more appeared first on Ask a Manager.
https://www.askamanager.org/2025/10/socializing-on-a-week-long-work-trip-bosss-email-overload-and-more.html
https://www.askamanager.org/?p=33853