It’s five answers to five questions. Here we go…

1. How do I downscale our holiday celebration?

I manage a wonderful staff — they are all dedicated, responsible, mature, and get along very well with each other. They are also all, to generalize, introverts (as am I). Over the past nine years, I established a tradition for the holiday season, in which we gather during a weekday afternoon and I give them cookies and a little gift. I came up with this based on my own preferences: I don’t like being asked to leave the office, go to someone’s home, or sacrifice non-work time. And I enjoy the preparation of making cookies and coming up with a gift (everyone receives the same).

While intended to be festive and easy, this gathering often feels forced. People look to me for entertainment, as if I should be running yet another meeting, and their otherwise normal social skills abandon them. Last year it was so uncomfortable — with some perfectly lovely people uttering not one word over a 90-minute period — I swore to myself I would not put us through it again. My question is, how can I abandon the holiday gathering without seeming punitive, passive aggressive, or ungenerous? And how can I distribute the cookies/gifts, which are effectively “thank-you’s” for a year of great work and teamwork?

Could you do it at the end of a staff meeting? Or go by people’s offices individually to drop off their gifts? Or schedule individual meetings with people to thank them for their work this year and give them their gifts then?

Or, if you don’t want to kill the tradition entirely, another option is to keep it but schedule it for a much shorter time period — like 15 or 20 minutes rather than 90. Or you could make it more of a “drop-in” — where people can come and go for that hour (or however) long but aren’t expected to just sit there and stare at you if they’d rather leave. You could announce it as “cookies and gifts in my office from 4-5 on Friday — stop by and stay as little or as long as you want.”

You could also ask your staff what they prefer — you may find that they actually like the tradition, or that they’d be glad to tack it onto the end of a staff meeting, or that they want to play games this year, or so forth.

2. Bringing an on-again, off-again boyfriend to the holiday party

I am wondering what your opinion is on inviting an off and on boyfriend to a staff holiday party. My boyfriend and I have been together about three years total over four years with two break-ups in this period. I started a new job about six months ago and I’m just wondering if I should bring him to the holiday party or not. I 10000% do not see myself marrying this man and honestly, doubt we’ll be together by this time next year. Is it “wrong” to bring to a staff holiday party knowing this?

It’s not wrong to bring a date who you know you’re not serious about! The biggest question is just whether you’ll be okay with coworkers potentially asking you bout him in the future. If you’re willing to field questions like “how’s Cecil doing?” and “so is it serious with Cecil?” and so forth, then feel free to bring him! If you’d rather not deal with that, you might prefer to instead come alone.

3. Do I need to train students to answer the phone professionally?

I work at in a small academic institution, where we employ college students to do a lot of the “front-line” work for us. They sit at public desks, answer phones, and take care of a lot of day-to-day things. I am one of several people who supervises them and trains them on these operations.

I love our student workers and think many of them are more than competent and go above and beyond. So in designing their training, I did not think to include a large segment on answering the phone. We have talked to them before about a greeting, how to transfer calls, and basic things one might need showing. Have I assumed too much, or do I really need to tell people how to take messages accurately, or how to try and answer a question when someone asks for a person who isn’t in, or even to push the mute/hold button when you’re talking to me about the person who is still on the phone? I know people use the phone less (especially college students), but people call us for help with things all of the time, and even if we don’t know the answer, we try to get them to someone who does. We already train them on helping people face-to-face, so do I really need to do a separate training for how to do this same interaction on the phone?

Probably, yes! Phone usage has changed so much in recent years that some of this may be brand new to people (like taking a message, which they may never have had to do before if their family didn’t have a land line, which many people now don’t). And some of it

If you’re seeing indications that students don’t know how to do those things professionally, then yes, I’d say you need to train them on it! And some of it is stuff that students needed training on even before our phone norms changed so much. Things like how to answer a question or that you should put the caller on mute before talking about them are things that your more conscientious/mature students may know, but some of them definitely will need to be told. So, yes, I would say train them on all of it! And if you’re worried it’ll feel obvious or remedial to some of them, you can frame it at the start as, “Some of this may be obvious to you and some may not be. We’ve found that people bring different level of comfort with phone work, so I’m going to cover everything.”

4. Should I let my boss know my disorganization stemmed from ADHD?

I was diagnosed with ADHD as an adult two years ago and have been able to manage it successfully with a number of coping strategies. I started a new job a little under a year ago and everything was fine until suddenly … it wasn’t. Over a period of three months, I found my productivity way down and was struggling to get things done on time and without errors. Projects were completed, but they weren’t always done well.

It took me a while to realize that my coping strategies weren’t working and even longer to realize that I needed to give medication another shot. I’ve found one that works for me and have been getting back on track. My work and attention to detail have improved, but I am not sure if or how I should explain this to my manager. I was never reprimanded and my boss has, on the whole, praised my work. But I get the sense that I have been let off the hook because I’m new and if things had continued along the same vein, we would have had a much more serious conversation. I would like to explain why I was so distracted and unorganized but I’ve never had to have a conversation like this at work. If I’m honest, it feels like an excuse. While I work in a very supportive environment, but I am the youngest and newest person on my team and don’t want to play into the millennial stereotype. I don’t want my boss to think that I can’t handle the duties and responsibilities I have.

It’s not an excuse; it’s a medical condition. It’s an explanation, not an excuse.

And you can give your boss that context without sharing personal medical details. You could say something like, “I want to let you know that I know that my work wasn’t at my usual level for a few months over the summer. I was dealing with a medical condition, and once we found the right medication, I got back on track and don’t think it will be an issue again. I wanted to mention it in case you’d noticed and were concerned, so that you know both that I’m aware of it and that I’ve addressed it and have it under control now.”

(And I’m sorry the media seems to have given millennials a complex about your generation. Reasonable people will not think of you that way.)

5. My new job doesn’t start for six months

I’m a soon-to-be-grad who recently accepted a great job as an entry-level business analyst in a dream location, which I’m thrilled about. The problem: the job starts in June, I’m graduating in December, and I didn’t quite realize how far apart those were when on the phone with the hiring manager. I did actually ask why the start date was so late, and was told that they had filled their hiring quota for the winter, and their next entry-level start date was June.

I know I’m probably stuck with this, but is there anything I should have done differently? Is it normal for companies to hire (pretty generic) positions with such a lag?

Some companies do! (Generally you’d only see this at large companies though; smaller ones don’t as frequently do “classes” of new hires.)

You could have tried saying, “It would be difficult for me to be unemployed until June. Is there any chance of starting earlier?” But it’s possible the answer still would have been no.

You’re also not obligated to refrain from continuing to job search. If they’re leaving you unemployed for six months, they don’t have a lot of standing to be upset if you find a job you like better during that time.

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