The Bad Assistant: When To Switch, When to Fire

When to Fire a Bad Assistant | CorporetteWhat should you do when you’re stuck with a bad assistant, secretary or subordinate — and your assistant doesn’t assist? When is just time to switch assistants, or even fire the person? Reader K wonders:

We are a small (12 people) conservative professional investment firm serving high net worth clients. I recently moved from front office to portfolio assistant. The young woman who replaced me thinks she is doing a great job even though she was told by management that she needs to work on skills. She says she has a photographic memory and doesn’t take notes on anything I try to explain. I prepared “how to'” notes for her, but have had to print them for her repeatedly. She makes “to do” lists but rarely does items on the list. When I try to explain something, she has gotten up and walked off or continues to stare at computer screen. Her history shows that she is constantly on the Internet. I was told to monitor these things, but feel uncomfortable. I am working an extra 15 hours a week trying to do my new job and picking up slack on hers. Needless to say, I am stressed. Management is aware of issues, but not that I am really stressed out over this. How should I handle this?

Wow — I’m sorry, K, that sounds like it really stinks. You say she’s been warned; you say management is already aware of these issues. That all leads me to the following advice:

  • Talk with management about switching assistants — or firing her and hiring someone new. This person isn’t working for you, and it’s anyone’s guess why. Maybe she’s incompetent, but maybe she’s just young — or there’s a clash between your general generational work styles. (Pictured: SNL just had a pretty amusing skit on point, “The Millennials.”) Bottom line: things aren’t working between you and her. Management needs to know that they need to make a switch. If that means firing her, ask management what they need from you to make that happen — it may be a written record of times she’s failed you, it may be a formal warning to her in writing, or more.
  • Assess what she is actually doing, if anything. You’re going to need to prepare to absorb that work during the transition. Maybe you can outsource it to a VA or contractor; maybe you can give her a lot of it to do before the transition to get things in the bank. (If you can, hiring an intern to overlap a bit between your bad assistant and the future assistant might help.)
  • Try to learn from the situation. Figure out why this person got hired: Did she look great on paper? Was the wrong skill set advertised? Wherever the disconnect was, you need to put some real thought into what went wrong and how you can do it better next time. There are things to be learned about your own managerial style, as well as institutionally for the company, the office, and the job.

My advice might be different if things weren’t at this level (my older advice to a reader with a bad secretary might be of interest; the reader there shared an assistant with a partner in a large firm, and the assistant continually prioritized other things above the OP’s work) — but it sounds like everyone is aware that this worker is a problem, and no one is there to white-knight her. Good luck to you, K…

Readers, what are your thoughts — what should you do when saddled with a bad assistant? How much work can you do yourself before it becomes time to fire? How many chances do you give someone to improve? If you do think this comes back to a generational divide, what are your tips for Reader K?


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  1. Anon Worker Bee :

    The “this girl” in Kat’s advice (“This girl isn’t working for you”, “How did this girl get hired”) is really rubbing me the wrong way. It sounds really sexist and dismissive and the kind of talk that women on this s!te have to fight against all the time.

  2. The focus on the assistant’s age seems strange for many reasons, not the least of which that Reader K is only a step ahead of the assistant in her career, so it’s very possible that they’re actually from the same generation. Also, I am tired of people conflating “millennial” with “young” (I’m a millennial. I’m also 32) and with “flaky” (good thing no one born before 1982 was ever feckless at their job!)

    • Co-signing, as a fellow 32-year-old. The assistant sounds both confident and incompetent, which is a dangerous combination at any age. Time for a formal improvement plan leading to termination.

    • I completely agree. I’m 28 and have worked with my fare share of flaky people or worse, people with very little work ethic, who are older than me.

      I also have beef with the term millenial, since it’s used to lump everyone who is early 20s (sometimes they even go younger!) to early/mid 30s. I think there’s a huge generational gap in the middle of this, especially considering many people on the older side of that range still remember a time when technology was not prevalent.

      • Pancakes, did you read this?

        I thought it summed up the early vs. late millennial differences quite well.

      • Agree with the notion of a gap generation, of which I am part.

        I salute your Oregon Trail and add a Jordan Catalano:

    • lucy stone :

      Also 32 and really rubbed the wrong way here.

    • At 29, I agree with the other women in this comment thread. I felt like this was particularly demeaning coming from a blog I have followed for a while and trust for advice.

  3. Is it truly your job to make sure this woman succeeds or you pick up her slack? I’d back off and let her fail…hard. Sounds like you’ve already tried to help and she’s not getting it. Sometimes hiring the right person is better than attempting to fix the wrong one….

  4. I think it is important to ALWAYS give assistant’s a chance to suceed, b/c sometimes, they come into law offices WITHOUT the necessary background, and it is up to US, as seasoned profesionals, to bring them up to speed as to the intracicies of our jobs and what it means to be a legal assistant, and their ethical obligations to our cleint’s.

    When Lynn first joined, she would share WC storie’s she heard at work with her family and I did NOT think this was appropriate. So I spoke with her and talked about confidentieality and priviledge, and she VERY much apreciated my advice. Now she does NOT disclose anything outside of the office. I hope this will continue AFTER Mason leaves (at the end of the week). She I think will still be dateing him, as the firm does NOT have a policy stating NOT to date with ex-associate’s or ex-partners. I will speak to the manageing partner about establisheing such a policy, tho I guess I will have to Grandfather her if she continue’s to date Mason.

  5. How does a message of “monitor” these things equate with the writer even having the responsibility (yet alone authority) to switch or fire assistants? She was just in that assistant role herself a short time ago. I also don’t see how it’s fair to dump her new role’s work in on the “extra 15 hours” calculation. If that’s the case, too, shouldn’t it be more than 15?

    Here’s an alternate view: The poster is not letting go enough of the old role and it’s turned into micromanaging. Since the new assistant doesn’t report to the poster (supposedly “management” has talked to her, so that’s where authority lies). It kind of explains why getting notes ignored and the tuning out is happening. The “photographic memory” is a clear signal that she wants the lecture to end. Time to let this one sink or swim on her own. Management can do its own “monitoring.” Since it has talked with the assistant in the past it must be doing this to some degree already. Better for the poster just to focus on her new role and stay out of the fray.

    I’m 42. And no, I don’t think it was fair to dump in age comments.

    • I don’t appreciate the age comments either. Maybe the person is incompetent and and maybe she isn’t. Either way, the issue is about her work performance, not what is on her birth certificate. I suppose that ageism will be one of the last isms to go away – if ever.

  6. Anon lawyer :

    Man I can relate to this. My assistant is incredibly incompetent but doesn’t realize it. I’m an associate in a highly dysfunctional firm so I know she’ll never be fired. I’ve just stopped giving her things to do, unless its copying/faxing/couriering.

    Probably not the best solution but I’m tired of having to redo her job after she messes it up the first time.

  7. Has the situation been discussed with this person in a very direct way? Sometimes people don’t pick up on subtleties…they need to be told exactly what is expected of them, and that if they don’t do those things, they are on the brink of losing their job. Is she that bad of an assistant, or is she just not challenged? Sometimes people spend a lot of time on the internet when they feel like their work doesn’t matter, or if they don’t appear to have enough work on their plates, or if they feel like they’re being “pushed” to work instead of “allowed” to handle it on their own. Set very clear deadlines with this person and don’t print out any more “how to” lists for them. They should know how to do things by now, and if not, they should have the “how to” list saved on their own computer.

    I also can agree with Si’s comment above about micromanaging. If she wants the work done, she needs to give it to her assistant in a kind, non-micromanagerial way. Those are the best managers – the ones who let people decide how to do their work their own way, as long as the end result gets done how and when it needs to. Most (not all, but MOST) people want to do a good job for their company. Perhaps she is getting no praise (no even a “thank you”) and feels unimportant? Or perhaps she feels worthless?

    Open up a very direct, but NOT angry, conversation and allow her to talk as well and work toward a common goal of mutual respect. If you stop thinking of this person as an assistant, and instead think of her as a colleague, and I think things will get better.

    • I whole heartedly support this option — being direct and making sure assistants have things to do. I once worked as an assistant/runner at a law firm for a little under 3 months and nothing was ever direct, including when I got fired, and it was a miserable experience. It took about one month for the other women to warm up to me and then another for them to start gossiping behind my back. The password to the computer at my assigned work station had been changed one morning and ‘no one knew why’ nor did they know the new password. I had checked my e-mail a few times, read the news during little breaks, while the rest of the office was consistently on Facebook. I NEVER used social media while on the clock or on any of their computers. I was blamed often for missing files, when eventually they would be found in the ‘absent-minded’ attorney’s office. Eventually I was fired to make room for his son. I am a ‘millennial’ AND I take work very seriously. I know there are ways I could have improved my performance, but I also know that I was not set up for success nor supported in any sort of training. Maybe they knew they didn’t want to keep me there? Nonetheless, a lot of these ‘subtleties’ were open for interpretation, as is all non-direct communication, and I guess I didn’t ‘get the memo’ soon enough.

      I now work with almost exclusively women at the university where I am pursuing my Master’s. They are all supportive, uplifting, positive, and influential women I look up to. I’ve been trained and am even encouraged to look into more technical trainings for my specific job, and they actively work with me when I have hit a road block or am seeking new projects to work on. If something isn’t working, we are all direct about it! I love working there :)

  8. So so so anon for this.... :

    Yesterday, one of the assistants in my office was fired for incompetence. She used to be my assistant.

    A few years ago I told my boss that I would like to change assistants. She was on probation, for the second time, at that time.

    Eventually I got my wish, but my boss told me that I “couldn’t get along with her” (we got along just fine, she just could not do the job), because “sometimes women can’t work together”.

    But NOW she is incompetent. Right.

  9. Anonymous BigLaw Associate :

    This isn’t really that applicable to the reader’s situation, but maybe for others. I have worked at different law firms, and at one assistants had a lot of responsibility with things like maintaining ShareRooms, preparing shells for pleadings, doing filings, cleaning up formatting on documents, running tables, etc. But at another law firm, all my assistant could really do to help me was submit expenses and deliver my mail. I found that it was just a result of the way the firm was set-up, and my assistant basically had no training. So if new to an organization, it’s good to figure out if it is YOUR assistant or ALL assistants….

  10. Performance plan.

  11. Two things based on being an admin:

    First, if no one has directly told her that she’s not doing a good enough job AND that her internet use is excessive AND that this is putting her job in peril, this needs to happen. In my first office job (okay, admittedly, it was a student job at college) I really didn’t understand how to handle office work and I’m sure everyone thought I was lazy and absolutely the worst….but it was really just the transition from very, very structured service industry work to more self-directed work that confused me. I too spent too much time on the internet and didn’t understand that I needed to take notes.

    Second, it may be that because the LW was formerly in the assistant’s position, the assistant isn’t taking her seriously enough – seeing her more as a peer than a supervisor. This might be reinforced if the LW is relating to her in a more “peer” way, or is the same age, or has the same general social style. It’s possible that a meeting with the LW and the LW’s supervisor and the assistant might help.

    I would suggest having a real come-to-Jesus meeting with the assistant, with clear expectations of incremental improvement. She’s not going to change 100% overnight, but you’ll be able to tell a lot about her character if she genuinely tries.

    I also suggest that the senior person and the LW together provide some practices for the LW that they expect to see implemented – for instance, they expect an email at the start of the day detailing what needs to be done and an email at the end of the day listing what was done (including any new/urgent work that came in). This may help her focus. (I usually send myself an email at the end of every day so that I don’t forget anything overnight.)

    I think it’s worth giving this woman another shot at succeeding – firing and hiring will be a bit of a nuisance and you never know who you’ll end up with next.

    A third thought, or perhaps a fourth: how routinized is her work? One thing I’ve struggled with over the years is getting my work into shape so that I can manage all of it. I find it helpful to set aside chunks of the day (or a set time each week, depending) for recurring tasks so that I can clean them up. It might help her if she were encouraged to set up her own schedule so that 9am – 11am every Monday, Wednesday and Friday is for Task X, and every Thursday from 1pm to 3pm she takes care of Task Y.

  12. Maybe she (“this girl”) also feels under a lot of pressure and does not know how to handle the situation.
    Maybe it’s not like that, but if it is – this can really stop you from working efficiently.
    I don’t know what has been going on before, but I’d try a “friendly” approach first – setting up a work schedule with her and having “regular” meetups, checking the progress, asking her what she had problems with, what went fine etc.
    I would not just fire or exchange anyone without actually asking her for her perspective and telling her that I am open for her answer whatever it is and want that we’re both ok with the outcome.
    If you just need a “functioning” assistant, maybe she was the wrong choice for the job (too unexperienced or other reasons). Maybe this “girl” can switch jobs in your company to some different job and some other person knowing about what’s going on there can take her job. That’s a solution we used in my group, where one girl just could not handle job A (strategical), and is not perfectly fine with job B(organizational).

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