Dear June,

I’m a few years out of college and was lucky enough to land a decent job in my field, publishing. Recently, a new position opened up in my department, so of course I spread the word to my friends and former classmates—and now a college buddy of mine has landed the job. While I am delighted by this news, I am also nervous because I will be his immediate supervisor. We’ve been in the same circle of friends since freshman year—how do I handle being both a supervisor and a friend? If it makes a difference (and I think it always does in the workplace), I’m female.

Of Two Minds in the Twin Cities

Dear OTM,

Yes, this situation can be tricky, and you will need to be careful. But although having a friend who becomes your coworker can create some tensions, it can also be comforting to have a work colleague who is already your “buddy,” with a shared history and circle of friends. You will have plenty to talk about, and you will both know (at this point in the game, anyway) that you like each other for your own sakes, not because your jobs force you to act as if you do. With any luck, you two will have a special trust and cohesion on the job.

Assuming you’re both reasonable people, everything should be fine so long as you clarify your role as supervisor and what that means at the outset; remain consistent; and take special care to follow your office’s procedures. When you work with a friend, especially if you’re both young and not that far apart in age or seniority, it’s tempting to keep things loose and casual. This is usually harmless, and even good for morale. Just make sure that you both understand the ground rules.

Even if your office is very informal, you should make sure to have some kind of orientation interview. A talk over coffee might set the right tone. While you are familiarizing your buddy with his job duties and the department’s policies, reassure him that you’ll make every effort not to let your work relationship affect your social one, and vice-versa. I don’t think you need to come out and say: “I’m the boss, you report to me, got a problem with that?” or: “Don’t ask for special favors from me, and I won’t make special demands on you.” But all this should be implied by the matter-of-fact, unapologetic, professional way you outline what is expected of him, and what he can expect from you and the company.
You say that gender always makes a difference in the workplace. Perhaps. But, unless your buddy is a jerk who doesn’t even know his own self-interest, you can neutralize most of the gender-related stress by taking care to project quiet, friendly authority or collegiality, as appropriate. Bite your tongue every time you feel tempted to apologize for assigning work or setting a deadline. Make every effort to avoid gratuitous self-deprecation. If you feel flustered or overwhelmed, try not to show it. I’m not saying that there will never be an assignment that really is an imposition, a deadline that is or becomes unreasonable, or mistakes and limitations of your own that you should acknowledge. But I am saying that self-confidence, decisiveness, and an air of calm should be your defaults.

Other than that, my advice overall is to do what all good supervisors do, but be extra careful. Listen. Visibly pull your own weight. Make sure your supervisee knows what to do, and help him do it well. Keep records of his achievements and challenges, and be sure to alert him as soon as any problems come up. You don’t have to be heavy-handed about this: just shoot him an email saying “Great job on the Ferrante edits! I think it really helped that you’re fluent in Italian.” Or set up a half-hour meeting about some area where he may be struggling, and document it afterward with a short, positive (if at all possible!) memo or email saying how glad you are that the two of you are working on the problem. Keep your private personnel files current and organized. All this will help you if you need to back up any unfavorable actions you or your company needs to take in the future; or, conversely, justify any promotions, perks, or awards his coworkers might otherwise see as favoritism.

It is, of course, usually far easier to supervise a good employee than a not-so-good one; and this gap can widen when the employee is also a friend. Periodic performance evaluations can be especially difficult. If your company does them – which I hope they don’t, because they tend to be counterproductive, time-consuming, bad for morale, and misleading, but that’s another story — be prepared for the possibility that your buddy may be especially sensitive to criticism if it comes from you. He may expect you to be totally positive, or to scoff at the very idea of an assessment, because he is your friend and the whole process should be pro forma. His response to anything short of a rave may be: You’re supposed to be my buddy! How could you? What right do you have? Or he may be open to honest criticism, but then take it badly and blow it all out of proportion because, coming from a friend, it seems more personal and hurts more. If your buddy’s work has been less than stellar, and if you cannot avoid doing the assessment yourself, make sure that you have already prepared him for anything negative you might have to say. Be as specific and value-neutral as possible. And if the process and format allows, write and speak in forward-looking terms: What are your buddy’s goals for next year? What new projects would he like to work on? What tools or training might help?

So far I’ve only talked about your role as supervisor. Off the job — or on the job, when you are clearly interacting as friends, like having lunch or talking about your college days – you need not act all that differently from before. But err on the side of circumspection. This probably goes without saying, but don’t tell him anything about the company you wouldn’t tell a non-buddy employee. When socializing outside of work, try to avoid situations where one of you might do or say something that could spill over into your work life, like going out and getting wasted and jumping up on the bar and telling the world that James Patterson is your favorite writer.

As for your relationship outside the office, you should probably let your buddy take the lead here. He may not feel as comfortable going out and, say, getting wasted at a bar in your presence now that you are his boss. This is his call, within limits. Don’t be offended, or hold it against him, if he needs to create some distance for a while. Things will probably sort themselves out if you are patient; and years from now, when you have both moved on to other jobs, you will be able to reminisce together about the good old days, and the bad old C-suite, at Acme Publishing. In fact, your friend may be the only person with whom you end up sharing these memories: I have found that college buddies tend to last a lot longer than work buddies, even in those rare cases where work buddies are buddies at all.

Dear June,

I am a 29-year-old woman with a college degree and a secure job that pays well and has great health insurance, a 401(k) matching plan, the whole bit. I have no trouble paying the mortgage on my wonderful two-bedroom condo. I have never married — my boyfriend and I broke up in February. So I am alone again. I think this is one reason why my bossy parents think that they can still tell me how to live my life, although I am sure they have other reasons, too. Or maybe they don’t think they need a reason. Here’s the latest: my parents have just written that they are shipping me old family furniture for when I “outgrow my IKEA/Real Simple style.”  Well, I tell you, I do not want to outgrow my style, and I don’t want to be like my older sister who has one of those houses filled with a combination of new modern furniture and antiques. Sort of like Art and Antiques magazine, if you get my point. She’s rich, by the way, husband in real estate, and often agrees with my mother. She even let my mother come into her house and hang up those old fashioned heavy drapes. Well, let me tell you something. I don’t want that.

So soon I will be receiving a humongous dining room sideboard, an antique desk with bullet marks from the American Revolution, an armoire, two sets of sleigh beds, that have to be put together with special wooden screws (18th century), and even metal filing cabinets from 1900—used in my great-uncle’s law office. “We have to keep things in the family,” they say. I lied to her when I could no longer stand my great-grandmother’s stinky quilt. I said my roommate’s cat had peed all over it, and the dry cleaner said that it had had its day and I should toss it. Guess what, I walked it down to the river and let it flow by in the swift current.

My friends say that walking into my apartment and seeing my parents’ and grandparents’ furniture could be a real turnoff when I go back to dating. (By the way, I have been on sabbatical from men for six months because of my big breakup.) They also tell me that I should just accept the delivery when it comes and then sell the stuff. But then what do I do when my parents make their yearly checkup visit?

Yours sincerely,
Annoyed in Anacostia

Dear Annoyed:

When your parents write that they “are shipping” furniture, does this mean that it is already on the way? Or do they mean that they plan to ship it? If there is any chance that the furniture has not yet been shipped, jump up from your computer right now, call your folks, and tell them not to send anything until further notice, because you need to talk! If they refuse to call off the shipment, tell them that in that case you will send the furniture right back to them, and you can all talk then.

But your letter makes it sound more likely that they wrote by regular mail to inform you that the furniture was already speeding toward your condo. If so, you are not kidding that they’re “bossy.” I almost have to admire the colossal nerve of people who, over your known objections, would send you more furniture than you could possibly fit into a two-bedroom condo without removing about half of your current possessions.

(Or did you make your objections known? On rereading your letter, I see that this is unclear. Might your folks have simply assumed that you’d prefer their family antiques to the furniture you have now? If so, this is still overbearing of them, and I presume your response will be the same – you don’t want it — but you should, perhaps, let them down a bit more easily. The situation might also be simpler to resolve in this case: maybe your sister would be happy to take “your” furniture now that you have renounced your claim, and maybe your parents would be happy to give it to the daughter who truly appreciates it now that both of you have made your preferences clear.)

I confess that I know little or nothing about the logistics of shipping and taking delivery of large and valuable items. I suppose that much depends on the carrier your parents hired. What happens if you refuse delivery – does the stuff get sent safely back to your folks, or does it sit on the street until it is ruined or stolen? How do the delivery people let you know they are coming? If your parents used a moving and storage company, do you get a price break if you tell them not to unpack the stuff, but to send it along to some third party or to a storage facility? So let’s just ignore these practical aspects for now, and assume that we can will the furniture to go where you want it to go.

So where should it go? It sounds as if you do not want the furniture because it is simply not your style, and does not represent the way you want to live. If this is true, I advise you to stick to your guns. Refuse the furniture, and be open about it. The only way to stand up to your parents is, well, to stand up to your parents. You are almost 30, self-sufficient, and a homeowner. They have every right to offer you furniture and even to suggest why you should accept it, but they can’t force you to take it, or indeed to do anything at all. If you do not want the furniture, tell them that you are going to send it back to them, and do so. Or send it to your sister or to a reseller or to some museum, if you and your parents and/or sister can agree on any of those options. Your parents might actually like to see their treasured possessions in some museum or historic house. They might even have fun planning this. If you are open with your parents about what you plan to do, you won’t have to quake in your boots until their next inspection visit.

Your friends’ suggestion, that you take delivery and then sell everything, is not a good one. It borders on dishonesty: although it is usually fine for the recipient of a gift to do whatever she wants with it, the gift here is clearly conditional – if your parents thought you would sell the furniture instead of using it while holding it for the next generation, they would not have sent it. Sure, selling it off without telling them would serve them right, kind of, especially if they were fully aware of your objections to owning it. But it would be mean not to give them a chance to consult on where the furniture should go, if not to you. And you would have to lie to them while awaiting the day of reckoning. If your parents say that they’re done with the furniture and you can do whatever the hell you want with it, you are of course free to sell it, although it might still be a nice gesture to give your sister first dibs.

One caveat: at the risk of sounding like your parents, are you positive that you will never want any of this furniture? I fully understand why you want to assert your own style. On the other hand, some of the stuff you’re being sent sounds as if it’s not really all that huge and ghastly – well, the desk does, anyway – and all of it, even the filing cabinets, holds generations of history. If you plan on having children some day, they might want some of it: we’re talking serious antiques here, not just old furniture. I can see why your parents think of some these pieces as family heirlooms, with each generation stewards for the next. You do not have to agree with them on this – a condo in Anacostia is not Blenheim Palace – but the concept is worth a moment’s thought. Compromise may be possible. You could keep one or two pieces, and sell or return or donate or store the rest. You could even store it all for a while – who knows, you make take up with a fellow who owns a big country house that seems made for sleigh beds.

I also noticed that you seem struck by your friends’ bizarre opinion that your family’s furniture might be a “turnoff” to future dates. This sounds a little as if you are still basing your decisions on what other people think, just not the same people. Make sure you know your own mind.

I hope that your parents learn to dial down the officiousness a bit, and that the furniture gets resettled with a minimum of fuss.

A note to my more curious readers: The ferret is safe and apparently unharmed.

Cleaver’s in-house advice columnist opines on matters punctuational, interpersonal, and philosophical, spinning wit and literary wisdom in response to your ethical quandaries. Write to her at [email protected]. Find more columns by June in her attic.