Question #137: I got promoted at work, and now supervising my old friends (and lovers) is awkward.

Patty Hewes from Damages
This woman does not apologize for asking you to do your job.

Dear Captain Awkward:

I recently got a promotion (yay!) and now people I have to supervise people I’ve previously worked alongside (less yay). There’s one employee in particular who’s had a problem with taking instructions from me. He and I were hired around the same time, and he has more experience in the field. I quickly picked up on everything I needed to catch up to his experience-level, and there’s no question in my mind that I worked hard and deserve to be where I am. I just don’t know how to get him to listen to me. His work is consistently turned in late or is sloppy; when I ask him to get something done by a deadline, I often find him watching Youtube videos or Netflix movies at his desk instead of working. I’ve previously asked someone higher up the corporate chain (i.e. someone I know he respects more than me) to say something to him. This worked temporarily, but he’s slipped back into his old ways. I really don’t want to bring in a third party again, because I feel like it serves to  undercut my authority and also it looks bad to *my* boss when I can’t get my employees to listen to me.

We won’t be doing performance reviews for another seven months, so I need advice about what I can do in the meantime to get him to wake up at work. To make matters more awkward, I’ve known this person through a mutual friend long before we started working together. I’ve also slept with him (before we started working together!), but it was just sex and we were both very clear that we didn’t have feelings for each other. I know he sees this as “just a job,” but I’m looking to make a decent living and develop a niche for myself in this company – at least until I find out what I’d really like to do with my life. How do I navigate this awkward college drama while trying to become a classy adult?

-Serious Business

Congratulations on your promotion!  And for writing in with such a supremely awkward situation in such a succinct and vivid manner!

This is a “boundaries are your friend” situation.

Here’s an old post about how to handle performance reviews when you are the boss. You should never let performance issues slide until you’re at Official Review Time anyway, so I’m going to suggest that you have one of those awkward lunch or coffee meetings with this guy who is now your subordinate.

Here’s a rough script for that lunch.

Gambit:  “Hey, I wanted to sit down with you and talk about how things are going at work since we restructured things. First, it seems like you’ve had some trouble with deadlines lately – what’s going on with that?”

Then you listen and ask follow-up questions depending on what he tells you. We all hit slumps and get the blues sometimes. Maybe he’s not getting the inputs he needs in time to turn them around, and that YouTube watching is happening while he’s waiting on someone else’s work. Maybe he’s over-promising when he can get things done and needs to be more honest about how long things take.

Maybe his reasons are all bullshit – whatever, hear him out fully and don’t let on that you know it might be bullshit. It’s okay if he complains. Complaining doesn’t mean you are a bad boss or need to take anything he says personally.  Don’t interrupt to correct him or defend yourself or the company!  Giving your employees license to be really honest with you gives you information about how to motivate them. That’s all that’s going on here, even if it feels like something else. Listen and then keep directing him back toward solutions.

The main question you want to ask next is “Is there anything specific you can think of that I (or coworkers) can do to help you with this stuff?

Then you listen some more.  Maybe there isn’t anything you can do,  and if that’s the case, be honest. Maybe there is a token thing you can get for him (a faster computer, a quieter workspace, acknowledgement that x task should take longer than you guys have budgeted, a day or afternoon of sick time even though he’s not sick so he can handle some life stuff that’s stressing him out)  – if so, do it.

While we’re here, is there anything else you want to talk about?

(Listen some more).

End the conversation on a positive, but firm note.  “Thank you for being so honest with me. I’ll see what I can do about (thing you asked me).  In the meantime, I need to be honest with you – this thing with the deadlines is a big deal, and higher ups including (the person who talked to him before) have noticed. I really need you to commit to working on meeting deadlines from here on out.  Can you do that for me?

Be very clear, and direct, and use short, declarative sentences and simple questions. Don’t apologize for acting like the boss (LIKE A BOSS!) when you are the boss.  Don’t apologize, period.  Don’t over-explain or over-justify. Treat him like you expect to be taken seriously. If you have trouble with this, picture Glenn Close as Patty Hewes saying the stuff you’re saying.  Would she apologize or mince words?

A brief note on “day jobs”:  A smart way to handle “just a day job” is to kick ass at it so that you can keep putting food on your table until your dreams come true.  Save this point in your arsenal for if (when) he gets defensive. “You know I’m the last person who wants to be the Internet Police, but the truth is that if you were kicking ass at your job, no one would ever notice that you went on YouTube sometimes. The fact that people are noticing means that you need to pull it together.”

I realize that asserting yourself in this way might be a big adjustment, but there is a reason your company promoted you. Should you get cold feet, remember that for an employee, one of the most annoying things is a manager who is uncomfortable with leadership or authority, so they try to pretend they are not your boss and everyone “is all friends here” (seriously, if your boss says “I think of us as a family!” RUN AWAY).  This kind of boss never tells you when things are wrong, because they’re operating on a “I like you and you like me, so why aren’t you just naturally perfectly doing what I want” assumption and they let you keep messing up until one day they explode!  And you’re fired because your boss assumed you were a mind reader. NOT COOL. Part of being a good manager is not taking an employee’s poor performance personally and laying down the law when you need to.  You are very smart to try to nip this thing in the bud.

If you get any pushback about from him, of the “Ooh, look who is management now” joking-that-isn’t-ever-really-joking (especially when it is a dude saying it to a lady who has seen his manlyjinks), say “Yup, that’s me, and I’m trying to do it right, thanks for noticing!”  If he brings up past sexytimes, he gets a mean, hostile “Really?”  If he wants to resent you, let him, as long as he uses his inside-his-head voice and takes care of business. You don’t need to beg people to respect you.

After the conversation, document it.  You can write a memo to the file, but a good way to document something is to send a follow-up email.

Dear Coworker,

Thanks for our discussion today.  I’ll plan on/look into (thing you agreed to do for him), and will count on you to be on top of deadlines going forward.

(Plus additional work thing or question – add something here so the email isn’t JUST documenting stuff for HR, especially something that he has to respond to, like “When you get a chance, can you let me know about (project)?)”

That way he has to respond to the email and you have proof he received it.

After this, you’ve got to use a combination of positive reinforcement (sincere thanks when he does meet deadlines, sincere recognition of improvement) and staying on top of him.  If he starts messing around when things are due, you’re going to have to be the one who says “Can you please close YouTube and get to work on that thing you promised me you’d have today?” (Document) and “Is there something I need to know about why you’re struggling with deadlines again?  How should we solve this?” (Document) and “This is sloppy and needs another edit. Can you get me the final version in an hour?” (Document).  Hopefully he’ll turn it around by performance review time. If not, you’ll have the unfortunate paper trail you need to relieve him of this crappy day job that he only does when he feels like it.

16 thoughts on “Question #137: I got promoted at work, and now supervising my old friends (and lovers) is awkward.

  1. She also needs to go and peruse the archives of the Ask A Manager blog. There is a lot of advice around this topic. I would also suggest being very clear that there are consequences if his work performance does not improve, including probation and termination of employment.

    That’s not to threaten your employee at all but you have to be clear that it could be the end result if his work product does not improve.

  2. Absolutely, Ask a Manager is very helpful.

    I’d save potential consequences for a follow-up conversation (if the behavior doesn’t improve). This is the putting the cards on the table meeting (“Hey, knock it off!”) where you sincerely try to get to the bottom of what’s going on with the employee and try to motivate him to do what’s right positively. The second conversation is the “We need to talk….about how we talked about this a month ago and you agreed to improve and you didn’t. Now I have to write you up and it could lead to probation, firing. Please take this very seriously.”

  3. Yes – document, document, document. And you do not have to wait until formal performance review time to give someone an indication of how well you feel they are performing. In fact, one’s performance review results should never be a surprise. If things are still going downhill after the “I’m your boss, I need you to rejoin the team” talk recommended by Capt Awkward, you need to be pulling them in and give them the straight talk where you say, “look, I know you can do better than this. You can’t keep going down this road. Example: documented item, Example: documented item. I’m here to help you succeed and I want to give you time before formal performance review time to pull it together. We’ve tried X and X (things you said you were going to help him with in the first conversation); is there something else that you need.”

    Sometimes, they can’t just get it together and you will have to fire them. And it will feel awful. It is ok to go for a drink with your management mentor or a close friend and tell them how awful you feel and they will help you get through it. But work is not a daycare for grown ups and if he can’t do the job – for whatever reason – sometimes they have got to go. What you don’t want to do is to keep coddling him along after he has used up all his chances for improvement. Your bosses will notice and it will reflect badly on you.

  4. Be very clear, and direct, and use short, declarative sentences and simple questions. Don’t apologize for acting like the boss (LIKE A BOSS!) when you are the boss. Don’t apologize, period. Don’t over-explain or over-justify. Treat him like you expect to be taken seriously.

    i second the succinct – you don’t need to justify your requests. it doesn’t matter why you are asking for something, and it opens you up to arguments that you just don’t need to have.

  5. Great advice, Captain. I’ve been on both sides of that conversation and it usually ends well. It is more likely to end well if the listening is genuine.
    I’ve also worked for the ‘we’re all a family here’ manager and it was one of the worst work situations of my career. Look for that nonsense attitude in an interview and don’t work for this guy (woman). You have a family-what you need is a manager who will manage and coworkers you can trust and respect.

  6. Never feel bad about telling a subordinate his/her performance is unsatisfactory if it is — but do be clear about what good performance would look like *first,* and give them an opportunity to give you that before criticizing. One of the worst employers I’ve ever had was lousy about communicating what expectations were, even when directly asked — until the performance review, when they invariably said the employee had not met expectations. (Gotcha!) (I actually found out later that reviewers were specifically told to give unsatisfactory reviews, so underlings would never imagine they were entitled to advancement…. on a scale of 1-4 they were literally not allowed to give 4s and had to write a memo justifying any 3s. Screwed up, or what??)

    The sympathetic conversation can be along the lines of “you’ve seemed a little off your game lately,” and then those questions about whether there is anything he needs from you to get back on track.

    But you should also take the opportunity to “clarify expectations,” to make sure you’re not judging him adversely for failing to meet expectations he’s not aware you have, a) because you *should* want to be sure of that and b) because it is a good, non-confrontational way to get those expectations out there.

    That part of the conversation should definitely be documented. What “documented” means is that you write a memo (or e-mail, depending on culture — as long as you print a copy for your records) that says “to make sure we are all on the same page, I wanted to summarize what we discussed this afternoon. Then set forth the expectations as you discussed them and anything you discussed in terms of “metrics” (concrete ways to measure whether the expectations are being met) and agreements on his part. Finish by saying “The purpose of our conversation being to make sure we are on the same page, please let me know right away if you believe this is not an accurate summary of what we discussed.”

    If he acts like “yeah, well this is a stupid job anyway I can’t believe you’re taking it/yourself so seriously just because you got a piddly-ass promotion,” I would say “I know this is not your dream job. But I assume that you would still like to be the one who decides when you move on, and that you would like to take positive references when you go. That being the case, you really need to step up your performance.”

    If he acts like you’re being a bad friend, you can tell him “I realized that if I had to write a performance evaluation for you today, I could not honestly write a very good one. I wanted to give you a chance to change that before performance review time actually rolls around.”

    If he gets nasty in any way, “You do realize this is a meeting with your boss, where she’s telling you your work performance is unsatisfactory, right? Surely you don’t think lashing out at that boss is going to *help*! If you ever do that again, do *not* expect me to let it slide.”

    Oh, and just as an aside, surely you can make sure he always has some less-time-sensitive work that he can do at odd moments when his main projects are in someone else’s hands. I don’t think there’s anything wrong with saying “I do not ever want to see you watching Youtube or Netflix videos on company time.”

  7. I’ve also stopped saying, “Would you please?” or “Can you please”.

    No I say “Do it beeyatch!”. No, just kidding, I say, “Please do ***. Thank you”

  8. As much as I hate to admit to watching a lot of the Office, I think it does a good job at showing why your advice is so helpful. Michael Scott sucked at being a boss, and would rarely criticize his employees when they needed it, and never demanded their respect as their boss (or even acted like he deserved it). In comparison, the new boss, Andy Bernard, got an employee motivated on doing better by telling him (when he was prompted several times) just why that employee wasn’t promoted, and reminding him that he is expected to do his job, that people will notice when he doesn’t, and that if he does he will be rewarded. Not to say that you want to be like Andy, but that acting like a boss is actually a good thing. It’s now your job to manage your employees, and they’ll benefit from it!

  9. I have sort of the reverse perspective – I’m an employee who tends toward slacking and becoming disorganized, bad time management, too much time on youtube, etc. etc. etc.

    I agree with all the advice and I want to reemphasize – the worst, most anxiety-producing thing for an employee like myself is a boss who is not consistent and firm about expectations and deadlines. If my boss says “I need this by Monday” and then doesn’t call me on it ON MONDAY it creates a really dysfunctional dynamic because then I’m thinking “hmm, well I wonder what the real deadline is. or maybe this isn’t that important after all? i’m sure she’ll say something when she really needs it.”

    This may seem unfair, and it probably is – you’re not the guy’s mom. But if he’s promising work Monday and then avoiding you, that’s two problems – you need to train him not only to deliver on time but to seek you out and explain himself. The only way to do that is to call him on his deadlines right away.

    I think one way of bringing up the “other stuff” in a productive way is to say “hey, with our history I think it’s my responsibility to show you total respect and professionalism. The reason I’m holding you to these deadlines is because they’re serious and missing them isn’t OK. It wouldn’t be fair to you if I pretended otherwise and then you get blindsided at your employee review.”

    Or, you could just ignore the history because it really isn’t relevant (beyond the fact that it does indeed create an added urgency to the need for honesty, respect and professionalism in your relationship.)

    1. Thanks for this comment. Especially when I was younger, I struggled with creating structure for myself, and was helped by bosses and teachers who could help me create it by being clear about what they expected and clear when it wasn’t happening.

      The longer you wait to tell someone they are messing up, the weirder and more personal it gets, where the sooner you do it the more it’s like “Please get that on my desk today, thanks.”

      1. On a bit of a tangent, but has anyone got any good links* on creating your own structure and the motivation to maintain it when your boss isn’t chasing you? It’s something I’m finding tough right now.

        * aka, aids to further procrastination? 😉

        1. NessieMonster:

          I don’t want to leave your question unanswered, but really, I’m the wrong guy to ask. The way I “handled” it was I became a stay at home dad. Kids are pretty good at calling you on deadlines. As in “can I finish this scene before I get your snack for you?” “NO I WANT IT RIGHT NOW!!!!”

          I still struggle with it, though. One thing to remember is the cycle of shame and catharsis, followed by a burst of energy as you clean up the mess, is actually part of the dysfunction. If you set down some of the shame and self-flagellation that comes with always feeling behind on everything, you may find you reach that crisis point of “Everything is falling apart WHAT DO IT DO?!?!?!” less and less often.

          I’d also encourage you to pursue some creative work that really interests and excites you in your spare time. It’s a great way to build habits that are based on intrinsic motivation instead of appeasing others, and you’ll have fun and learn a lot about yourself along the way.

          Through amateur filmmaking I learned that I don’t ask people for what I need, I like to ask them for like half of what I need and hope to scramble to make up the difference. This doesn’t work very well when you’re directing a cast and crew of 20 – you don’t have enough hands, and can’t be in enough places at once.

  10. This is so amazing. I just moved from a “Aren’t we all just the best of friends” job because I couldn’t stand it. I found out three months after my performance review that my boss and the other woman in my department had been covering on some stuff for me because I wasn’t doing it correctly. They did this rather than EVER tell me, even ONE time that the way I was doing it was unacceptable.

    Don’t be like that. Constructive criticism and pushing is important. Also, definitely don’t wait until everything sucks and you are overwhelmed to send a “why aren’t you doing a better job?” e-mail.

  11. “for an employee, one of the most annoying things is a manager who is uncomfortable with leadership or authority, so they try to pretend they are not your boss and everyone “is all friends here””

    This is so so true. The last time I had an excellent boss was when I was in college working at a sandwich shop. The assistant manager there had a knack for knowing when to get involved and when to let his employees work things out on their own, for nipping certain behaviors in the bud, for knowing when someone was having a rough time versus just slacking off. I miss that. In my entire adult professional life, I have had mostly bosses who have no managerial skills or training. They have been fine people, good at their profession, but not necessarily good with the people management needed to be in charge.

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