I can’t keep helping my work BFF do her job

A reader writes:

I started working as an executive assistant at a company I love this summer, and a couple of months later, another executive assistant – we can call her Tracy – started too. We are the only two executive assistants in the company, and a lot of our work intersects; although we assist different executives, the teams that report to them overlap a lot. I am a career administrative support worker, whereas Tracy has more experience in human services/social work. I’m much more organized and detail-oriented, whereas she has great empathy and interpersonal instincts.

Day one, we mutually clocked each other as queer, and discovered throughout the following week we share a lot of other things that matter to us… we quickly developed a strong rapport which we describe as “work besties,” regularly eat lunch together, and have made plans to socialize outside of work.

But what’s becoming a problem is that Tracy’s performance isn’t up to par with mine. I came up to speed very quickly when I started, and by the time she started, I was well established and able to help her out a lot. Because of our friendship, she’s been open with me about the fact that the kind of work we do doesn’t come as naturally to her as it does to me, and I’m instinctively compelled to take up the slack so that we excel together as a team (and have been doing so), but… I can’t continue to be responsible for her. During her onboarding period, I advocated for Tracy to our shared supervisor, Kathy, and to Tracy’s executives, but as time goes on and she isn’t learning as quickly as people expected or as quickly as I did, I feel less like I can put myself on the line for her. However, I’m not sure how to pull back without it being extremely personal and hurting Tracy’s feelings. Especially since we so enthusiastically bonded. (I have a tendency, in all aspects of my life, to go full throttle and am trying to develop restraint.)

I’ve already let Kathy know that I’m invested in Tracy’s success but am having issues in deciding where to draw the boundary between us as a team versus us as individuals, and she said she is keeping an eye on the situation and asked me to let her know if I notice any problems. Tracy has also already been told, by Kathy, that she needs to depend on me less and learn how to catch/correct mistakes on her own.

I just don’t know how to navigate the nuances of our shared responsibilities, let alone how to decide when I should/shouldn’t be escalating, and am particularly concerned that Tracy might lose this job – both because having a counterpart with whom I am so comfortable and compatible is definitely an asset, and because I care about her well-being. On the other hand, it isn’t fair for me to take that on. Professionally speaking, I need to put on my own oxygen mask first! Personally speaking, I’m not sure if I should also be pulling back socially. How should I approach this?

You can read my answer to this letter at New York Magazine today. Head over there to read it.

{ 63 comments… read them below or add one }

  1. JokeyJules

    sometimes, too much help actually can hurt.

    if you’re still reteaching her aspects of the job, make sure she takes notes and tell her nicely that you’re busy with your own stuff. If it’s that she keeps forgetting the same details, thankfully you are her friend and can tell her she often forgets and help her decide a way to remind herself. Share these tricks, but start setting up that boundary of “i’m sorry but i’m super swamped over here” sooner rather than later.
    Alison is right, this might just not be a good gig for her, which isn’t something to be ashamed of, but it’s best she realize that sooner on her own.

    Reply
  2. OP

    Thank you so much, Alison.

    My biggest concern at this point is the third to the last paragraph – as I mentioned in my letter, I tend to go full throttle, and part of that is jumping in any time I see something that I can get done easily (and often, more effectively/efficiently than Tracy). I need to set boundaries as much for myself as for Tracy, and I’m going to work on coming up with something concrete.

    As far as a conversation about her happiness and success here, we’ll see where we are a bit further down the road.

    Tracy and I are going together to a Halloween function this Friday, and it’s reassuring that you don’t think I need to pull out of the friendship!

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    1. OP

      as a note, part of the problem with finding a better/more-suited-to-her gig is financial, so it isn’t as easy as “do what you love” since what we love pays significantly less than what we do; but you’ve definitely laid out convincing reasons that it’s a good idea anyways

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      1. ThankYouRoman

        If you can’t do what you love, you need to do what you’re good at. She’s not good at being an EA. So that isn’t a sustainable choice. There are other professions in offices that she may be better at. Something not so fly by the seat of your pants and ability to switch midstream.

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        1. Elle

          Exactly this. Many times we think we only have 2 options – succeed at this job, or go back to the old one. But really, there’s an option C: try a new job that relies more heavily on her natural abilities. If she’s empathetic and great with people, she might make a great manager. Or do good work in contract management, sales, etc. If you’re in manufacturing, EH&S is a wonderful place for people who want to improve the lives of those around them. And it shouldn’t be too hard for her to make a transition to that department with her background since its certificate, not degree, based.

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        2. Jen S. 2.0

          Agree with this hard. For MOST people, even if they like their job and are good at it, they are working to live. A new job doesn’t have to be 100% ideal for it to be a better fit for her. It has to be … a better fit.

          Please know, I took a job as an admin right out of college and SUUUUCKED at it. Those are not my skills. I was already looking for something new when I was fired — as I should have been — and I’ve since been careful to avoid jobs with a lot of admin responsibilities. Everyone is not going to excel at everything, and having a job where I sucked helped me get much better at assessing fit and figuring out where I DO excel before accepting a job.

          As others have noted, saving her situation at this job doesn’t need to be the goal here. Now, if she can, fine! Plenty of people get by for years being just-okay at their job, even if others are spectacular at it. It’s very possible that she’s a C+ and you’re an A, and it’s just in comparison to you that she’s falling short. You haven’t described her as a disaster, just not 100% ideal. But you don’t have to take that on as your problem. But if the situation can’t be saved, or, even more importantly, if her moving on elsewhere would make everyone much happier, that’s not a failure. That’s learning what jobs do and don’t work. That’s ultimately a positive.

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          1. Cercis

            I also suck at admin work. And was happy when I finally had enough experience that it wouldn’t be an option presented to me on a regular basis. Then I switched careers and found that several places only promote from within and wouldn’t I “like to start as an admin?” Saying that it isn’t my skill set seems to piss off the people making the suggestion and I get told I shouldn’t be too proud to roll up my sleeves and take a lower level position. I mean, yes, I don’t want to get paid poorly just to get my foot in the door, and I don’t think that should be a statement that pisses off people, but that’s not my main objection.

            So many people seem to think being an admin is easy. These are the people who have never done it or do have those skills naturally. I have every reason to believe that taking a job as an admin would not be in my best interest as I would not do well at it and would end up either fired or looking incompetent.

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        3. epi

          I don’t think there is any way to say from this letter that the OP’s friend is bad at being an EA.

          The OP is a career administrator who sounds like they mostly needed to get oriented to this office. Tracy is learning to *be* an EA after switching careers, and still has to get oriented to this organization herself. And she hasn’t been there as long as the OP. And she’s not getting as much practice and exposure as the OP did, because the OP is jumping in to do her work. It’s not really fair to expect Tracy to be as good as the OP, as quickly as the OP.

          While it feels helpful to jump in and do someone’s work for them, it can actually be really undermining. That person now doesn’t get to figure it out on their own, practice, and ask for help only if they are truly stuck. And the more you intermingle your work and encourage people to think they can go through either of you, the more you invite direct comparisons in which the other person is likely to be found wanting. Tracy now appears dependent on the OP, enough that their boss is involved, but at least some of that pattern was created by the OP’s assertiveness rather than Tracy’s dependence.

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          1. ThankYouRoman

            It really shouldn’t take anyone that long to get the general lay of the land if they’re going to be a decent EA.

            I have extensive history doing EA work and it’s simply not something you need months of training and life lines for if you’re going to hack it. The letter speaks volumes. Tracy isn’t the EA type.

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    2. animaniactoo

      Ah, you may find this useful. Once upon a time, I was training to take over the job my dad was leaving (typesetting). There was a project that either came in or was supposed to be mine or I don’t really remember how it happened. But I asked him about something and he sat down and started doing it, telling me that it would be quicker for him to just do it. And I said “Yes, but if you do that *I* will never learn how to do it.” He jumped right back up out of the chair, showed me how to do it and walked away and left me to work through it on my own. And he never again jumped in the seat to do it instead of either telling me the answer or pointing me towards where I could find it on my own.

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      1. animaniactoo

        For reference – I never did develop into the learned 30+ year typesetter that he was. But I did become a very competent one before the industry died.

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      2. Psyche

        Exactly this! You don’t need to leave her to flounder, but don’t do the job for her. Walk her though how to do it herself. If you see something that has to be done, flag it for her and let her know she can come to you with questions (if you are ok with that). Then you do not come across as distant or unfriendly but hopefully she will learn how to do the job.

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      3. epi

        When we were in college, one of my friends was fired from his part time job after not interrupting a similar dynamic.

        The job was food service, and there was some basic task that his shift managers *always* just handled themselves because it was easier than showing him how it was done when the store was busy. It was something crazy, like only letting him run the register while they made smoothies, so he’d never made one.

        Three months later, he was the employee who (on top of normal 19-year-old fecklessness) somehow didn’t know how to do a basic, several times a day chore. Of course it reflected badly on his managers too! But they were the ones making the decisions, and he was the one who couldn’t be counted on to do some simple tasks when they were busy.

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      4. RUKiddingMe

        I was going to mention something about this being similar to being a parent actually. As adults/parents we already (hopefully!) know how to do X, Y, or Z and a lot of times parents will jump in and do something that the child needs to learn how to do on their own simply because it’s easier/faster.

        I recall back many, many years being at a petting zoo with my then two year old son. There was a small gate that he could easily manage and I got a million and one death stares from all and sundry for standing there and telling him (and how to) do it himself…because it was a skill he would need at some point.

        I was the awful parent that made her toddler learn how to open a gate, make his own PB&J sandwich…and make his own bed. But…other than pretty much begging me to make him hamburgers (because “no one else makes them right” ::eyeroll::) and sewing on buttons for him (which he could also do, just didn’t like to do) he carried those, and many other skills that I started teaching him as soon as feasibly possible throughout his life. Tracy isn’t going to learn skills if OP keeps jumping in like Mommy-to-the-rescue.

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        1. OP

          characterizing our dynamic as “mommy to the rescue” is really demeaning to both Tracy and myself, and it’s inaccurate.

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    3. ThankYouRoman

      Especially since your supervisor is on board, I would lean on that a bit heavier. “Kathy told me she wants me to stop jumping in as much. Have you looked at your notes?” A lot of it is she’s not comfortable in her role and has found a crutch with you helping her along.

      Don’t take the entire bullet here. You’ve got others backing you stepping back. (Thank God, I’ve been punished for not carrying others who simply cannot grasp the job, argh.)

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    4. hayling

      I read something very useful recently: You don’t set boundaries with other people, you set them with yourself.

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          1. OP

            gonna keep it vague, since we work in the same office, and the original quote is good advice for all sorts of situations!

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            1. Glitsy Gus

              So I suffer from the “oh, it’s cool, I already know how to do this”-itis as well. It is really hard to stop the burning desire to ‘help’ or to just get it done.

              Remember, most of the time it really isn’t the end of the world if something takes 30 minutes longer because your friend is still figuring it out. It’s also fine if it isn’t done in the 100% most efficient way, or in a way different from how you would do it. She won’t learn the best way without finding HER best way, so you need to bite your tongue and step out of her way a bit. :)

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    5. Kes

      A couple of things that others have mentioned, but that I wanted to reinforce:
      a) Tracy’s learning involves her actually doing the things, and potentially struggling through them, which she can’t/won’t if you do things for her, so I agree that you need to restrain your urge to jump in and do things just because you can, if she really should be doing it or it’s something she needs to learn. At most, consider helping her learn only while ensuring she is the one actually doing the work
      b) As beth mentioned below, while you obviously want Tracy to succeed as a friend, it is not your responsibility (or necessarily even your ability) to make that happen – it’s really up to her.

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    6. epi

      I would actually look at pulling back as you helping her, and be honest about that. Tracy obviously wants to learn and do well, but she can’t do that without practice. She also presumably wants to stop the pattern your boss is seeing of you always helping her– but she can’t do that either if you continue to insert yourself. The last thing you want is for Tracy to appear dependent on you, when actually you are stepping up without being asked.

      So, I wouldn’t say that you need to pull out of the friendship at all. Cooperating with Tracy’s need to learn new skills and assert herself independently *is* the behavior of a true friend– someone who supports Tracy even when it feels hard. I would start giving her tasks back in a positive way. “I know you want to make sure you’ve mastered X, so I am going to try not to step on your toes starting this week. I know you’ve got this!”

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    7. Elle

      Instead of going “full throttle” at doing the job to the best of your abilities, can you rephrase it in your mind as going “full throttle” on getting your friend the best education in being an EA possible?
      Which means, actually letting her learn by doing, and being there to guide her when she gets stuck without actually taking over. Its not about doing things the most effective and efficient way possible, its about setting up your friend for long term success.

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    8. char

      Your point about setting boundaries for yourself is a great one. I also struggle with wanting to jump in and take on my team’s tasks when I know I could do them much more easily than they could. To counteract that, I’ve started explicitly assigning, say, task A to myself and task B to Fergus, and then forbidding myself from taking over B even though I could get it done in a few minutes and Fergus will take five times as long as I would. It’s better in the long run, because that way the next time a task like B comes along, Fergus will be more comfortable with it and be able to get it done faster. It’s not good for anyone if I’m the only one on the team comfortable enough with these tasks to get them done efficiently – it’s not good for me because I’ll get burnt out doing everything, and it’s not good for my team because they don’t get the chance to expand their skillsets.

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  3. animaniactoo

    If you want to help her, I would try to *broad picture* help her. These things don’t come naturally to her – okay, I am guessing they didn’t always come naturally to you and you have developed coping strategies that you have internalized to the degree that they now DO come naturally to you.

    Rather than helping pick up her slack, I would focus on saying that you are going to limit yourself to trying to help her figure out how to manage the details for herself. Sit down, break down what details you pick up and why, what are key words for you that let you know that X Y or Z needs to be followed up or watched or whatever? How do you note the need to do, remind yourself, etc.?* Granted, some of your systems may not work for her. But helping her figure out what she’s missing regularly and helping her think through what might help her to be more on top of that could still be valuable.

    *I’m assuming that you are probably doing some of this already but possibly not in as explicit a way as you may think you are, the same way that people keep saying they’ve let someone know something and then it turns out they’ve never said the exact thing in words that are direct and clear.

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    1. JokeyJules

      this is great advice. teach her the skills you have developed that make you better at the job, rather than talking her through the tasks. that will be immensely more helpful to her throughout her career.

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        1. Lynn P

          The advise is good AND is dependent on whether your friend at work wants this type of specific coaching from you. This is also time consuming — and could also hurt your friendship.

          1) I would offer to show her — and then see if she then initiates asking. 2) I would work hard on not jumping in to fill the gaps and try to be honest/kind with your friend that you need to refrain from helping as much — for your performance, not for hers 3) I would definitely let her know what Kathy shared with you – and say that you need to pull back. If you keep filling the gap, it will trip up your friend and it will trip up your job too.

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          1. animaniactoo

            Good point about offering vs just doing. I wouldn’t necessarily wait to see if she initiates asking, but rather if she accepts, offer up a plan for doing some of it such as “Tomorrow, during lunch, let’s go over X, okay?” and keep it in that vein as the person who is willing to offer those things as your time allows, but pulling back from jumping to be other kinds of help. While being clear that if she’s struggling with anything. she can ask you for direction on figuring out how to handle it in the moment.

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  4. Greg NY

    This isn’t even really about Kathy. Kathy merely gave you a suggestion that happens to be correct, she didn’t give you any kind of order (which only bad managers do) and said she’s aware of what’s happening and you can come to her to help solve any other issues with Tracy. So this is about what you need to do with Tracy.

    It’s not good, unless you can’t stand a colleague, to use your manager as any type of excuse. It’s not good for their development. You should, as a friend, explain to her that success in any job is eventually being able to perform its basic functions competently and without a ton of assistance. Depending on you and not being able to gradually wean herself off your helping her is going to leave her floundering when you can’t be there for her (and like Alison said, it can be your own workload, a vacation, or an illness). The reality is that you aren’t going to have time to constantly help her, not every day, and she needs to know whether she can transition into being able to do these tasks herself or whether this job isn’t a good fit for her.

    The very first job I ever had, at age 22, didn’t work out. As hard as I tried, I simply couldn’t get the hang of it. Sometimes the fit just isn’t there, and that’s not a horrible thing.

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    1. LarsTheRealGirl

      “You should, as a friend, explain to her that success in any job is eventually being able to perform its basic functions competently and without a lot of assistance.”

      I don’t see any way of having that specific conversation without coming off extremely condescending. This woman presumably knows that doing a job well requires….doing the job well? And it’s not OP’s job (or appropriate) to coach or manage a peer at that extent – that’s her manager’s job.

      In fact, the whole point of using the manager as “an excuse”(?) is because it’s not OP’s place to have these types of work discussions with a peer. You don’t often have detailed “this is what it takes to succeed here” conversations and coaching by same-level colleagues.

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      1. serenity

        Agreed.

        If a one-on-one conversation is the way OP chooses to go, there are much better ways to go about it. She could say “I feel like I’m picking up a lot of the slack here, and I’m going to need to cut back.” Or any other number of ways. But lecturing Tracy on basic job norms is really patronizing.

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        1. J.B.

          I mostly agree, would just modify your statement slightly instead of “picking up the slack” to say she has been doing too much herself. My managers are notorious about doing things themselves then dropping the ball and being surprised that you didn’t know you were responsible for the next step.

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    2. MK

      I disagree that only had managers give orders; all managers give orders, you can’t be a boss by suggesting things and leave it to your employees to choose whether to do it or not. What they don’t do is bark them like an army sergeant, but that’s a matter of civility.

      If Kathy is Tracy’s boss, she has every right to forbid the OP to do her job for her.

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    3. Barbara Lander

      Actually, I think Kathy deserves kudos for being aware of the situation and wanting Tracy to stand on her own two feet. A lot of managers would figure that as long as the work is getting done, who cares how that happens.

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  5. beth

    I think you need to let go of the idea that you have any control over whether Tracy loses this job. I know you didn’t outright use the word ‘control’ in your letter, but that’s the tone here–you have the feeling that if you just find the right balance of helping and supporting, you’ll be able to make it so she succeeds and won’t get fired, and you’re trying to figure out exactly where that sweet spot is.

    I want to take some of that pressure off you. You have no control over this. Tracy has some control (she’s the one who has the power to dig in and really force herself to learn things better and get up to speed) and Kathy does (she’s Tracy’s supervisor and probably has a say in how Tracy’s performance is viewed), but you are neither Tracy nor Kathy. You can’t make Tracy perform better, and you can’t decide that Tracy’s current performance is acceptable–those are the two biggest factors in whether Tracy stays, and you have control over neither of them.

    Your role here is only supportive. As a coworker, you can help train Tracy to the extent that your workload allows–and no more, because as you say, you need to put on your own oxygen mask first. When you hit that limit, it’s OK (and in fact necessary) to say, “I really need to go to X right now, can you handle Y on your own?” You want to make sure the work is done successfully to the best of your ability, but doing her job for her isn’t going to be good for either of you in the long run.

    And as a friend, you can help Tracy with the emotional side of not doing well in a job. Assuming she recognizes that she’s not doing well, she’s probably feeling bad about that and also nervous about her job prospects; you can give her space to talk through those feelings to a friendly, caring ear that understands the context. You don’t have to fix the problem for her–listening and offering comfort is enough. (This would be true even if the problem wasn’t your mutual workplace! People underestimate how valuable and helpful just listening to a friend can be.)

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    1. OP

      Thank you for this. I really am a fixer/the quintessential type A, and try to make sure everything has an optimal outcome, often even if it’s bad for me. Control is something I need to learn to let go of (which can be counter-intuitive in this line of work, as well).

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      1. beth

        It’s totally understandable! Lots of people are ‘fixers’, and it’s not a bad first instinct in a lot of situations. But don’t let it overwhelm you–sometimes you can’t fix something, and sometimes fixing the problem isn’t really what your friend needs from you in the first place. I know you want to do your best for your friend, but that will work better if you take a step back and recognize what ‘your best’ actually means in this situation.

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        1. valentine

          OP, reframe optimal outcome to include your well-being. It doesn’t help anyone, not even Tracy, if you burn out doing her job. That may actually hide her issues because you’ll look like a controlling person who wouldn’t let her learn by doing/shine.

          While my instinct is to help, I am wary of being the only one doing the work on the group project and I want my counterpart to be as capable and competent as I am at our tasks, regardless of our strengths. Are you a team or do you do the same job for different entities? Draw a line between helping and carrying or, especially, taking over from. Tracy has to get out a mailing and do some scanning in the next five minutes? You could do the scanning. Tracy asks you for instructions each time and you just do all the scanning, perhaps while she uselessly watches? Stop. Tracy is inefficient and still has a 10-item to-do list while yours is down to three and you need her number 9 to do your number 3? You don’t have to do her number 9. If your 3 is more important, she can reorder her list or someone, possibly someone who isn’t you, can make the decision. It’s possible your rush to take up for her has disguised that it’s okay to let someone else sort some issues. Maybe you can reschedule your 3.

          The business and you need someone closer to your level in Tracy’s role. She can look for a job she can excel at that pays more than what she needs to get by on, and find other ways to do social work.

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      2. Hey Karma, Over here.

        And think about this part. What if Tracy knew how much mental energy you are putting into her succeeding, not because you want to have her around as a friend, but because you see her failing? You need to separate yourself from her professional life, and just be work buddies.

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    2. PM Punk

      Totally agree with beth’s assessment. I fell into a similar pattern with a coworker in my previous role (also an assistant role) and realized a little too late that I couldn’t make the job be more “right” for coworker, and our friendship suffered for it. I wish I had Alison’s advice back then!

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  6. Ama

    I think it is good that the OP has recognized she needs to dial back her level of support. I have been in several work situations where I know I have to be the person to catch any errors (not always because my coworkers are struggling, sometimes because they are still training or because I’m the only one with the proper context/background info) and it is extremely draining to feel like you can never make a mistake and also have to catch everyone else’s — it can make you resent a job you otherwise like.

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  7. Clay on my Apron

    OP, you seem pretty empathetic yourself, as well as detail oriented and analytical.

    If you can see what’s causing her to fail, perhaps you can help with the *way* she works rather than by fixing the problems as they arise. For example if you see that she forgets things because she doesn’t take notes in meetings or doesn’t use to-do lists, you could suggest that she tries those things, and finds a way to make them work (sometimes they don’t work on the first few attempts).

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  8. ThankYouRoman

    I think so much of it is accepting that a job that’s intuitive and easy for you is often a nightmare to others. You simply cannot mold someone into a great EA who is struggling at this level.

    I’ve been in this boat but without management backing me at all. “Oh, they’ll catch on, keep working with them! Nevermind that you’re buried in both jobs now.”

    Spoiler: Each time that’s happened, I’ve left. Within 1-2 weeks of being gone (2 days in one case!) the person has been let go. So she’s on borrowed time if you ever take a vacation or get sick for more than a day or two.

    I share this only in hopes you can let go of the pressure you feel to save someone’s job. It’s the classic “You can lead a horse to water.” situation.

    I really hope she clicks when you step back. My instinct is also to always jump in when things are going all wrong, it’s a terrible feeling to have to watch a person crash and burn but we put ourselves at so much risk putting out constant flames.

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  9. Meteor

    Hey OP! Alison & the other commenters have really sound advice. If you do continue to be socially close, I would caution that you don’t fall into a trap of complaining about the situation. She may develop some bitterness as she understands that her job is in jeopardy. Since you continue to excel, you don’t want to say anything (or even participate in conversation) that is very negative about your company/boss, even if you’re just trying to commiserate and make Tracy feel better.

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    1. OP

      This is actually something that has come up – not about the company or anyone who manages me, but one of her executives. I think that she has valid points but is a little less prudent than she should be about avoiding saying stuff that could come back to bite her; and I agree with her, but it does make me uncomfortable and I’m not sure how to opt out of those conversations since on some level, it is a friend venting.

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      1. ThankYouRoman

        I would say something like “Miranda is difficult and demanding at times. I’ve found responding immediately to her helps take the grouchiness down a bit.” or something like that (of course some people are just prickly and my response is “yeah she’s got a cranky streak, it’s not personal.” Anything to squash the hardship of being in the middle of idle gossip that can hurt you.

        I’ve had bosses who were frankly, jerkbags, at times. My response has always been “If you keep butting heads…maybe swerve out of the way next time, you can’t change them but you can change how you react to them!”

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      2. animaniactoo

        “I hear that you’re struggling with this, and while the point may be valid, my experience is that focusing on X piece is not useful and actually hinders my ability to get the job done.”

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      3. beth

        Being friends with someone doesn’t mean you have to be open to anything from them at any time. Why not try something like, “Hey Tracy, I understand your frustration with Executive, but since I also work with them sometimes, it puts me in a really awkward position to be your vent-ee on this topic. Can you save that particular subject for another friend?”

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  10. NicoleK

    One thing to remember is that she may begin to resent you for not helping her. You’ve been keeping her afloat. She may not appreciate you withdrawing your assistance.

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  11. bopper

    First, someone looking for money/help will review their options from most convenient to least convenient. When you’re asked by someone in a hard position, it may feel like you’re the difference between their chance to succeed and their chance to fail. But you’re really just the next stop on the list…there was an easier one before you and there will be a harder one after you.

    Second, “What appears to be a crisis is often the end of the illusion that things were working.” It’s rare that someone is actually in a situation where they were OK before and they’ll be OK after, if they can just resolve one immediate issue.

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  12. Oxford Comma

    Can you start by delineating responsibilities where those overlap?

    And while I think it’s great to be concerned for a work friend, it’s not your job to make sure she succeeds. That’s her job. And if your friend is falling short, that’s up to the supervisor, not you, to address. In the long run, you’re not doing anyone favors by getting involved or doing her work for her.

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  13. Cassandra

    Alison, this is such kind advice. I learned so much just from how you arranged and wrote it that I will use as I advise and mentor students.

    OP, one thing that doesn’t seem to have been mentioned yet: At some point during all this, Tracy is going to drop a ball. Seems inevitable. As a fixer, the hard thing for you will be to let it happen. I think your boss is prepared for it to happen, which is good, but you also need that mental preparation. (If you haven’t had an explicit conversation with your boss about what you should do in such a situation… it might not be a bad idea?)

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  14. Elle

    Oof. I had this happen once. Actually, my ‘work bestie’ was a great person but poorly equipped to perform a role that wasn’t what she expected or in line with her strengths. She ended up getting fired for performance (somewhat unfairly). It was super hard on both of us.

    So I feel you. And I was lucky enough that we did the same job, but they didn’t overlap to the point where I could *actually* help her get hers done. One thing I tried to do was help her in ways that actually developed her own abilities. Which, really takes more patience and time than just doing the work for her. I’d ask questions like “OK, well what do you think you should do? Why is that? Have you considered coming at it from this angle?” Those questions help guide her to self-sufficiency rather than relying on you. And by helping her with that approach, you aren’t just hanging her out to dry.
    Also, I had to be really careful about separating our friendship from our work relationship. When people talked about her poor performance, I couldn’t just be jumping to her aid and defending her every single time because that would me look like I was, professionally speaking, ill equipped to evaluate employees and unaware of what a good job looked like. So instead I focused on acknowledging performance gaps and presenting my plan to assist her in overcoming them.
    Then, I went and had those hard, honest conversations with her where I told her I suspected her job was in jeopardy and we needed to work overtime to get her up to speed. I think being honest is the best thing you can do for a friend in this situation.

    One thing I will say is that she was miserable doing a job she wasn’t naturally good at, and getting fired was the best thing to ever happen to her. She now works at a job shes amazing at and everyone loves her, she’s been promoted multiple times. Sometimes jobs just aren’t the job for us, and that’s ok. Perhaps now, before her performance starts to be a problem, would be a good time for her to negotiate a move to an internal role that’s a better fit for her – like HR. Not that she can’t learn the new role, but its worth bringing up that maybe something else would be a better fit.

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  15. Narwhal

    I think OP could also use her tendency to jump in as a starting point in the conversation with Tracy. The re-framing might make it less awkward and more positive.
    Something like “You know Kathy wants me to help you less with your tasks. I realize that I sometimes jump right in to help and maybe not give you a chance to practice and learn to do these tasks on your own. I will try to reel that back in and please let me know if I’m still doing it too much. I am happy to help you figure out how to do these tasks so you can become more independent and confident in them.”
    If you want to go an extra mile, ask Tracy which tasks she thinks she needs most help in and what she think she needs to get better at them. Then celebrate with her when she successfully masters a task. Maybe you two could come up with a list of the tasks that Tracy should do on her own and check in with her in a month to see how confident she is with them. I would have loved for someone to have a competency checklist and then semi-officially be told that I am now good enough in those tasks to not require help/review/oversight.

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  16. JulieCanCan

    I can’t tell how many months Tracy has been with the company by your letter but it sounds like she’s been there about 1-2 months if you started this summer. Often there’s a 2-3 month window at the start of any job to really understand not only HOW to the job, but WHY you’re doing the various aspects involved in the job – how everything is connected. A person can do parts A, B, and C of a job perfectly yet may not know *why* she’s doing A, B, or C. It takes longer to understand that doing A + B = C, and to really grasp why things need to happen a certain way or within a certain timeframe. So if you’re jumping in every time she’s getting flustered or when she seems tentative about the next move, she’ll never learn the job (or she won’t learn more than the fundamental aspects of the job).

    It can be truly painful to observe a new person struggling to do what you know how to do (and what seems so obvious to you), but a person needs to actually DO the work, (possibly make mistakes, and learn from subsequent mistakes) before she truly “gets” it.

    I totally understand the stress involved when you’re watching someone attempting to complete a task that to you is so simple and is already part of your brain’s wiring, it is incredibly frustrating (for both parties). But until she’s made to do things on her own, she’s not getting a fair shot of learning the job. I’m a huge believer in being thrown into a job to truly learn how to do it, because while training can help you with the position’s key areas and help you understand why the job is necessary within the company’s functions and systems, there’s no better way to learn something than just DOING it. With your set-up it’s hard since you’re sitting with each other and she knows you’re there as her safety net. And with your inclination to help (which is 100% normal) she hasn’t needed to learn from mistakes or really figure out things on her own. It totally sucks – I’ve been on both sides (as the trainER and the trainEE); being new and knowing the person training you (who knows all the answers) is 3 feet away, it’s natural to ask if what you’re doing is correct or to ask for help when a problem arises. I was always happy when training was over and the person training me wasn’t nearby – there’s a sort of “freedom” to figure things out and take a little longer to go through your notes or training manual. Then yes, you might make mistakes, but you’re forced to really THINK THINGS THROUGH and get a better understanding of every concept involved. And ideally, she’ll learn from her mistakes and will never ever make the same mistake twice. (Don’t get me wrong- making mistakes SUCK and can be embarrassing and frustrating, but they really are a good way to ensure you do the right thing in the future.)

    At the start of a new week, I would say something like “Let’s go through the entire week as if I’m not here. I really want you to thrive here and in order to do that you’ll need to understand how things work, from A to Z. I’m afraid that with me acting as your safety net, I’m preventing that from happening. If there’s something that you TRULY cannot figure out after going through your notes, reading the training manuals, and everything we’ve discussed, then you should ask me to point you in the right direction. But if you just get stuck and know I’d be able to give you the quick answer, do everything in your power to figure it out on your own. There will be days/weeks when I’ll take vacations and you’ll be on your own, so we should start thinking in terms of both of us being able to successfully cover all responsibilities involved in our jobs.”

    (Obviously there are things in the above statement that you’d want to tweak/revise based on your particular situation. And I want to underscore that when she does ask you for help *after doing everything possible to figure it out on her own first*, you should only help her enough so she can continue the work, but don’t complete the task for her. You’ll need to break her habit of depending on you, so while you should definitely still help her, don’t do her job for her. Also – I don’t remember if you mentioned her taking notes while you train her, but if she’s repeatedly asking for help about things she’s responsible for doing, you should have her write down the information- taking good notes is crucial and I believe it can be the difference between doing well and failing in a new job. I am a major note-taker and like to have *everything* in my notes – literally things like “click on “Open” then in first line enter Last name, second line enter First name. Then click on “next page” to start with patient details.” I mean, I write down every single step and word that comes out of the trainer’s mouth, so if that person isn’t around I can refer to my notes and rest assured that somewhere in my Mead 5-subject notebook, every answer to every question about every possible responsibility of mine is available. If she’s not taking good notes, make sure that starts immediately.)

    You’ll need to make a concerted effort to NOT jump in when you see her struggling – it will be difficult, but in the long run it’s for everyone’s benefit. If she isn’t made to at least attempt it on her own, you’ll both be stuck in this scenario and your resentment will grow stronger every day. This way you’ll find out if she can even do the job – because right now you can’t be sure either way. After a month of her doing everything on her own (and performing as if you’re not there to help every single time she gets stuck) you will know if this job is one she’s a good fit for. Who knows, maybe once she’s really made to work on things and figure problems out, she’ll prove to be a great executive assistant. Or, on the flip side, you’ll learn that she really shouldn’t be in this position and she’s better suited for a job like the ones she’s held in the past. But at least you let her figure it out either way.

    Good luck OP – congratulations on finding a position you thrive in and that you’re really good at! I hope this sorts itself out soon and both you and Tracy can continue your friendship without the stress and frustration involved at the moment. Ideally, if Tracy realizes this isn’t the place for her, you two can move beyond this and maintain the close bond you’ve formed. Good friends add a lot to life.

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  17. Martina

    I am a person who tends to get overly dependent on other people in new environments. I had jobs where this turned into a problem. It’s not that I can’t master the task, it’s that I am not very confident and due to being an aspergrian I have a hard time with how most people explain stuff.

    Many people, seeing my confidence levels and seeing me puzzling over their explanation (I tend to get there in the end), just jump in and take over. In the moment, I am grateful, because they removed a piece of stress and uncertainty from my life. I also feel guilty for taking up their time. Therefore I am overtly thankful. That, I think, makes them see their help as more necessary than it really is. And I didn’t really learn the task so next time I will ask again. Plus, if this goes on long enough, I’ll be under the impression that this is how things are done.

    What was a huge help, though, was when I befriended a colleague in a new job and I felt safe enough with her to discuss to discuss the job honestly outside of work, where there was enough time, no task pressing to be completed – and I could ask all the questions and I wasn’t ashamed to ask for clarification if I didn’t understand something. It’s maybe due to how my brain works, but most of what people do seems really arbitrary (up there is, of course, social conduct, but there are other things). I am used to doing things that don’t make sense and not asking many questions because doing so flags me as “different”. With this un-logic I can arrive at outcomes that seem bizarre to people, but there’s less repercussions to being “useless” than to being “different” in my experience, however counter-intuitive it seems. What my friend did was give me a bird’s eye view of the type of logic that is expected at work, answered all my why’s and if’s, even those legitimately out of line, and helped me see how everything ties together. That set of information made all the difference in the world to me.

    Maybe instead of helping with her work, you could help Tracy get better at her work.

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  18. KK

    The next time she asks for help on something, give her your assistance & make her take clear and concise notes. Make sure they are perfect. It may be time-consuming but in the end, it’s less time you will spend with her in the future. Review the notes with her & make sure she understands and be willing to field any questions in the moment.

    Then the next time she asks for help after you’ve trained her with notes, tell her that you’re swamped and she will need to refer to the notes. No need to be harsh but she needs a bit of tough love.

    And I would then have a heart to heart with her that you care that she is fully equipped to do her job without your help as it’s been brought to your attention she leans on you too much. It’s helping her be fully trained while you are able to do your own work uninterrupted.

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  19. GreenDoor

    If Friend needs to keep this job, she’ll need to excel at it, and the only way for her to do that is to grow into the role. Which means, OP, you’ve got to stop with the full throttle, which it sounds like you are aware of. For that to work, dont’ take any work from her. Instead, be the “sage on the stage” and offer verbal or written guidance (whichever is better in the moment) then….let her at it. Even if she still does it wrong, or slower, or sloppier. It’s super hard to stand back and watch someone you think highly of or care about make a mistake, but it’s the only way to grow. I know I had to sit through a few embarrasing conversations and scoldings in my career before but, doing so, is a big part of what helped me became a pro at what I do. I wouldn’t have gotten as far as I have if someone was holding my hand the whole time.

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