training your replacement when your replacement won’t listen

A reader writes:

I work for a small, 100-person private company as a legal assistant. My boss and I were very upfront with each other about my job search, and he hired someone a few months ago to start whenever I got a new job. Well, that happened recently, and I gave two weeks’ notice. He brought my replacement in today, and I have a week from tomorrow to train her on my job functions. I found out when she started this morning that she has no legal experience, and has been an office manager and admin assistant for a number of years. I was not involved with her hiring, so I didn’t know this until today. I prioritized some things with Boss, and he told me he wanted her to learn the administrative functions I do for him, which involve various spreadsheets, and the contract development process, which is the most basic and integral part of the job.

I started training her on “small” things — how the filing system works, who gets what emails, how to answer the phones, etc. These are the more menial tasks, but I didn’t want to overwhelm her with the contract development process or the specific spreadsheets I use for data tracking right away. I’m finding it difficult, however, because she seems to be obstinate and/or disinterested about everything. For example: I tried to show her how a spreadsheet was set up, which I explained was in a specific way that my boss asked for it to be. She said, “Well, why don’t you use filters?” I said, “Because Boss asked for it to be this way.” Her response was, “Well, I use filters, so that’s going to change.” I could only shrug and tell her that this is how our department set it up, but that she was welcome to take it up with him.

Another example: I was trying to show her how to use the scan folders to scan documents because I do a lot of that for my boss, and the way it’s done in our machine is a bit complex. She stood there chatting with another coworker while I tried to show her what to do, and when I said, “Jane, do you want to try this?” her response was, “Oh… can you show me again? I’m sorry, I wasn’t really listening.” I also witnessed her telling the IT department how to set something up in Outlook, and when the network admin tried to explain that he’s been with the company for five years and knows how Outlook works, she replied, “Well I worked as the office manager to a large IT consulting firm, so I probably know it just as well as you do.” These are only a couple examples of a frustrating day.

I am trying to chalk this up to first-day jitters, but I only have one week with this person and I want to train her as well as I can so that my boss’s life is not impacted as much as possible when I’m gone. Of course, the easy answer is “It’s not your problem,” but I feel a sense of commitment and responsibility toward my job and I want to leave my company in a better place than when I found it. So maybe you could provide some insight into training a replacement for your job (whether they’re able/willing or not), and more specifically and selfishly, how to keep it from seeming like you haven’t trained your replacement “properly” even when you’ve tried — since I’d like to keep my reputation and references intact down the road.

Well, you can’t make her be someone she’s not. If she’s a bad hire, she’s a bad hire, and that’s not your fault. All you can do is try your best to train her and keep your boss in the loop about what’s going on. You can’t make her pay attention or learn things or not be arrogant.

That said, while nothing excuses her rudeness or lack of attention, it’s possible that she’s bored because you’re focusing exclusively on the small tasks. Try moving over to the substantive stuff immediately and see if that makes a difference.

But if the issues continue, be direct with her. For instance, if she’s not paying attention while you’re training her, point it out. If she’s talking to someone else while you’re trying to train her, say, “Jane, I need your attention over here right now.” If she tells you she needs something repeated because she wasn’t listening, say, “We have a lot to cover, so make sure you’re paying attention. Once I’m gone, there won’t be anyone to show you this stuff.”

Call her out on this crap. If she doesn’t care, you can’t make her care, but you can at least insist that your time be respected.

Also: If this continues on day two, you need to tell your boss about what you’re observing. Wouldn’t you want to know if you were in his shoes and not be blindsided by it once you’re gone? Besides, while you’re training someone, you’re something of a managerial figure — and part of that means reporting problems up the chain. He needs to know, and you’re the person best equipped to inform him — plus, that’ll take care of your worry about it seeming like you didn’t train her well after you’re gone.

I’d also give your boss a final wrap-up on your last day as well. Tell him how the training went, where you think she has things covered, and where you’re worried she’s weaker. If your overall impression is that she squandered most of the training time, tell him that too. (And you don’t want this to be the first time he hears that, which is another reason why you need to give him a heads-up today if the problems are continuing.)

And if you haven’t already, consider leaving behind a written manual to the things you’re trying to train her in. That way, if she doesn’t work out, at least her replacement will have the benefit of your guidance.

But that’s really all you can do. She’s responsible for her own performance and you can’t make her be a better employee than she is.

Read an update to this letter here.

{ 146 comments… read them below }

  1. moe*

    I like Alison’s advice.

    And this doesn’t help at all now, but why on earth was this replacement hired “a few months ago” but only brought in to train with one week left? Especially with her lack of experience? That’s just setting everyone up for failure and making the training process much more charged than it might otherwise be.

    It certainly sounds like the trainee is in need of a clue or two, but it’s mind-boggling that the company would fritter away the benefit of OP’s long notice period this way. I had a replacement situation turn out the same way after I gave over 4 months’ notice, and I definitely didn’t appreciate my last week being such hell. I was probably harder on my replacement than I would have been if there had been a sane time allowed for on-boarding… but hiring just wasn’t a priority until it was an emergency.

    1. The Other Dawn*

      “And this doesn’t help at all now, but why on earth was this replacement hired “a few months ago” but only brought in to train with one week left?”

      I was thinking exactly the same thing. Take advantage of that lead time!

      1. Nichole*

        I assumed they didn’t want to pay both of them for longer than necessary. Sounds like a ‘pay now or pay later’ situation…if this is how the new employee is going to act, they would have had time to figure that out, fire her, and try again before the OP left if they had brought her in as soon as she was hired.

  2. Wilton Businessman*

    Another instance of things you can’t change. Your boss says he wants her to learn X, Y, and Z before you leave, don’t waste time on filing and how to scan documents. With a week to go, your boss’ needs should take precedence.

    She’s not you and you’re not her. Your boss is going to have to work it out as to how she is going to be the most effective for his office (or not).

    And who’s to say, maybe filters are a better way to go on your spreadsheet? And believe me, just because the IT guy has been there 5 years doesn’t necessarily mean he knows how outlook works.

    1. BW*


      I have come into new jobs where I’ve been trained to do something totally painful that really doesn’t need to be that painful. Few things annoy me more than when I ask a question or share my experience and am met with “That’s the way we’ve always done it.”, end of conversation. As someone who has worked as an Admin Assistant and Office Manager spreadsheets and Outlook (and managing difficult executive types) are things she likely does have a lot of experience with. I urge the OP to not take the attitude that she just doesn’t get it or can’t do the job just because she may have a different take on things and hasn’t worked specifically in your roll.

      I agree with everyone on the focusing on the bigger things. She always knows how to use a spreadsheets. She probably knows how to scan documents. There is probably no need to go over those things in boring detail. What you want to show her are things like logistics like what and where to scan, where the spreadsheets are and what they are used for. Focus on areas where she truly doesn’t have experience. If she doesn’t know certain parts of the contract process, focus on those pieces she doesn’t know. Try AAM’s suggestion. If she’s an experienced Admin she is probably bored as heck and feels like she’s being treated like she’s inexperienced and/or stupid and “can’t learn the big things” (OP’s quote below). As an Admin/Office Manager she can likely handle learning “big things” just fine.

      1. fposte*

        Though, to be fair, it’s even less appropriate for the new hire to insist on a protocol because that’s the way she’s always done it.

        1. Samantha*

          Yes. New hire may be able to do it faster and better but changes like that need to wait until you are fully trained and settled into the job. It may seem to be faster to do it one way but there could be very specific reasons for it being done the other way. Can it be changed? Maybe, maybe not but there is a time and place for everything.

        2. Ariancita*

          Actually, it really depends. I interviewed for a job where they told me they did one large integral piece basically by painstaking rudimentary way because the last time the boss, who didn’t specialize in that area and wasn’t tasked to even do that job, looked at the software for it years ago and decided he didn’t like the software (and again, he wouldn’t even be tasked to do the job). It was an appalling lack of best practices. I asked why they didn’t use it anyway or push for it and they just sort of shrugged and said they really hadn’t looked at the software themselves to make an independent judgement. I mean, it was basically the equivalent of saying you do all your stats by hand and calculator because you think SAS is a little buggy.

          1. fposte*

            I think it’s okay to ask if you can do the procedure in a way that you think would be more efficient, but I don’t think it’s okay to insist, or to prefer it because it’s the way you’re used to. The workplace default trumps the new employee default.

            1. Ariancita*

              Well in my example, I disagree. The boss would receive the end product and how I did that had no effect on him whatsoever. And yet, no one in the office thought it was ridiculous that he insisted on them doing something the hard way that everyone else in the industry uses specialized software for. To me, that’s bad practices and it was a huge deterrent for me to seriously consider the position. Maybe in OPs case, it doesn’t affect the boss one way or the other if the spreadsheets are filtered but would make the assistant’s job a lot easier. I think if the process is in your domain where anyone else only needs the end product, you absolutely have a right to insist on utilizing best practices (or not take a job where they don’t encourage best practices in such a fundamental way).

              1. fposte*

                Yeah, we may just disagree on this. I’m fine with having a new practice proposed, but there’s a good chance my staff might not realize the reasons why something seemingly illogical is actually the situational best practice. Of course, in reality there are tons of decisions and updates they do on their own, so maybe you and I are thinking of different kinds of things. But the OP is talking about something that the boss specifically has stated a dislike for and will actually see, and I think it’s tough to make a case for it to be good new employee practice to go ahead and make that change anyway.

                1. Ariancita*

                  I think we’re talking separate things. In my situation, I’m really talking the equivalent of doing stats by hand vs using SAS or SPSS because the boss looked at the program once a couple of years ago and found it buggy (even though the boss wouldn’t be in charge of doing the actual stats, just receiving the analysis). If a company isn’t using best practices and can’t explain why they aren’t, beyond this-is-just-how-it’s-done, then it’s not a company I’m interested in working for. And that is something I ask when I interview (i.e., “Why have you chosen to use this process? What alternatives have you tried? How open are you to seeing that process made more efficient?”).

                  If the boss isn’t working directly on spreadsheets, but only receiving the end result and the admin assistant is the only one working on them, I don’t see why filtering would be an issue.

                2. Ariancita*

                  Which is not to say that the OP’s trainee wasn’t rude with her approach. I do think the trainee handled it wrong, if she did so in the way the OP is describing.

              2. B*

                I think it’s very common for new people to come in and want to do things a different way, but it’s smart to hold back and build rapport with your coworkers before you suggest changes that may cause more work for everyone else, at least in the beginning. Don’t start making demands until you have established mutual trust and get your bearings at the new company. Sometimes, what you think is really important is not important to other people, and you may just have to respect that if you are lower down on the hierachy.

            2. Kelly O*

              I think the bigger picture is, you shouldn’t just automatically assume that your way is the best way, or that there is not merit or reason for the way things are being done.

              It’s okay to make suggestions about improving processes, but you really need to use the existing processes first and find out what the real end results are (or what the desired results are) before you start flat saying no to things or insisting on changing.

              1. Elizabeth West*

                Yes. This. Once you’ve used them and can see how much time they take, or whether they involve extra, unnecessary steps, then you’ll be in a much better place to streamline or update the process.

                Exjob used handwritten material request sheets, despite an existing Access database set up specifically for sample shipping. Once I discovered it, I implemented it and everything became much smoother. It even printed packing lists. :) I was so proud of my process there I include it in cover letters.

              2. Kimberlee*

                I totally agree. In many cases, there are complications that you just don’t know about the first day on the job… things that are theoretically easy become much more complicated because of an extenuating factor that is out of your position’s control. I see examples of this all the time in my job, and I learned pretty fast after I started that I needed to stop having the hubris of thinking my previous experience is always the best way of doing things.

                Not to mention that the boss is… well, the boss. Good alternatives should always be proposed, but if she/he wants you to spend 3 times as long to pull info, then that’s what you do.

          2. Flynn*

            Yes! The boss being slightly technically illiterate was my first thought, too.

            For example, my manager is NOT good with IT, but recently got very excited over an Excel spreadsheet someone sent them and asked me to do all my data exactly like that and sent it to me in case I needed to figure out how to do it (it was pretty ugly, basically just used borders and background fill, nothing complicated, and NOT set up to produce graphs, but it was more readable than my figuring-stuff-out documents). I managed to interpret her request as ‘make my stuff more readable’ and did something else, which she was perfectly happy with.

      2. Samantha*

        When I trained for this job (2 weeks training time) I was told how the alphabet works. I’m not kidding.

        1. JT*

          The 26 letters, or alphabetization?

          Depending on the material you are alphabetized, the latter is not obvious without specific guidelines, and different people are likely to do it differently, resulting in big filing problems.

          1. Anonymous*

            And do accented characters sort
            As the unaccented version
            Immediately after the unaccented version
            At the end of the alphabet

          2. Samantha*

            both. And it was filing invoices. By the alphabet. Which apparently had to be explained to me. There’s only one way to do this. And no it didn’t have to be explained to me. I’m not sure how there is more than one way to file by alphabet.

            1. S*

              There are various systems that are considered alphabetical but have different rules. A friend was telling me the other day that her office files by first two letters of last name, then first four letters of first name. So Smythe, Adam would be before Smith, Wesley. So while A before B doesn’t change, the actual rule to follow do.

              Add in numbers vs. letters (are they always first, or does your company put numbers last?), Mc, Mac, and just plain M, accented/foreign characters, etc., and it can get even more complicated, even without truncating as in my first example.

              But yes, I completely agree that I would be highly irritated if someone explained that the alphabet goes A, B, C, and so on. :-)

            2. Anonymous*

              I once had a temp assignment where I had to do *lots* of filing. (I was temping after my freshman year of college.) The staff kept telling me how I was doing an awesome job. After awhile, I told them that I’m glad they appreciated my efforts, but they didn’t need to go overboard. After all, I learned these skills in second grade, and it’s really no that hard.

              They told me they understood, but what I didn’t know was that the temp agency sent over some pretty lousy people who couldn’t even do that. So they really were appreciative of my ability to do that job.

            3. Natalie*

              You’d think there’s only one way, but you could be wrong. :)

              I inherited a filing system from someone who filed items start with “The” under T and filed things that start with numbers under the first letter of the first number, if it was spelled out. So an invoice from 360Design was filed under T. I learned filing in a library, where numbers get their own section and articles are ignored.

          3. Flynn*

            Yes! I used to be a library shelver and it’s amazing the odd ones that you run into. For example, is Ursula Le Guin under L or G? If it’s L, does it come before or after John Legend?

            And it’s really, really obvious when a new person has been shelving.

      3. Piper*

        Agreed. Perhaps she is very bored and frustrated with the “training.” Most people with any kind of office experience at all (especially admins) understand Outlook, filing, and scanning. I’d be a little peeved as well if someone assumed I couldn’t figure such things out.

        1. KayDay*

          “I’d be a little peeved as well if someone assumed I couldn’t figure such things out.”

          That’s exactly what I was thinking. On the one hand, the Trainee does seem rather arrogant to me, but on the other hand, it really sounds like the OP is seriously doubting the Trainee’s ability to do the job, right from the start. I really wonder if the OP is coming across as rather condescending to the Trainee.

          1. Piper*

            Yeah, in my mind, it’s sort of the equivalent of a web developer starting a job and having the trainer ask if he knows how to code and trying to train him to do it. Or asking a graphic designer if they know Photoshop. These are basic tools and skills for these types of jobs.

        2. The Other Dawn*

          “I’d be a little peeved as well if someone assumed I couldn’t figure such things out.”

          I’ve found through the years that one can never assume anything, no matter how small or routine the tasks seems and no matter how much experience one has. Some people show really well during an interview, but when they get on site it’s a different story.

      4. Sam*

        I agree that the new hire might just be getting bored with training in rudimentary office functions. However, having been in that situation myself in the past, I’d say her attitude is all wrong. She should accept the training with good grace, polite smiles and nods. She’ll probably learn something about the way the office works, the various quirks and ways that different offices use huniversal software. If she is really bored or irritated, the new hire should say something to the OP, asking to be trained on the more complex stuff. She shouldn’t be ignoring the training and have such an arrogant attitude.

        On the flip side, the OP as a trainer should be constantly evaluating how well the new hire is taking on the information and be responsive to boredom cues and the like. She should be asking the new hire if the training is OK, if there’s anything in particular she’d like to focus on (within the priorities set by the boss).

        Ultimately, 1 weeks worth of training isn’t really a great deal time, and the training is going to suffer. There will be things that the OP can’t pass on, and things that the new hire simply won’t be able to pick up in the time given. I like the idea that the OP should (if she hasn’t already) write a manual for her primary job functions – to either help the new hire or their replacement.

        I agree with posters who have said that the company should have taken advantage of the generous notice period, rather than waiting to the last minute to hire the replacement.

    2. Jamie*

      “And believe me, just because the IT guy has been there 5 years doesn’t necessarily mean he knows how outlook works.”

      Someone should stitch this on a sampler.

      Office applications are not IT.

  3. Student*

    While I can understand your frustration, OP, as an outsider it sounds like you are focusing on a poor choice of things to quibble about. Let her and your boss hash out trivial details like spreadsheet functionality. Understand that she is going to want to put her own mark on “your” job, and understand that her interactions with other co-workers are simply not your problem. Let these things go, they are inevitable.

    Focus on teaching her the important, big points of the job. Like AAM said, write stuff down if you think she’s not paying attention to what you say. But please don’t waste another minute of your short time left to argue about form when you should be talking about function. Prioritize! If contract development is the most important thing to teach her, then focus on that. Things like how to answer the phone and who emails go to are things she can learn after you’re gone, if necessary. Then you’ll have done the best you can for this company as you head out the door. Whether she makes good use of the info you give her is, though you don’t want to hear it, her problem.

  4. AD*

    I really don’t see anything that egregious in the examples presented, at least not for one day. I think it’s pretty natural that someone coming into a position would have some interest in changing things for the better, so pushing back on a “we’ve always done it this way” is a good thing. She’s being a bit rude, both to the trainer and to the IT person, but nothing (yet) signals to me that she is incompetent or a bad hire.

    1. moe*

      I agree… seems more like bad form than anything else. Trainee should just be making mental notes of what she’d like to see changed down the road, when she knows the needs and can better assess what’s required or not, rather than bringing it up now.

      But bad judgment and talking out of turn is a big problem for an admin role, so red flags would be raised for me, too.

    2. Ask a Manager* Post author

      Assuming that they were just two examples out of more, I can see why the OP feels it indicates arrogance. Even if the new employee is absolutely right, those aren’t the kind of comments you’d normally make on your first day — if nothing else, it indicates a lack of awareness (or care) about how she’s coming across.

      I do think it’s normal and fine for a new person to make some changes and the OP needs to be okay with that, but this replacement does sound like someone who I’d be getting alarmed about too. Especially the talking to someone else while she’s in the middle of being trained — it signals rudeness and short-sightedness. (Unless the other person approached her and she was trying to be polite.)

      1. AD*

        I’m wondering if the root cause is that one week is not adequate for training, so it puts both the OP and her replacement in a stressful spot. I was thinking that one day is far too quick to judge someone, but the OP has very little time. On the other hand, if the new person was expecting her “first day of work” to be mostly paperwork, HR stuff, meeting the team, etc., she could be overwhelmed with everything being thrown at her.

        As you mention, it’s hard to know who initiated the “talking while being trained” conversation…but a training schedule should not be so tight it doesn’t allow for someone to come by and introduce herself to the new person in the department.

        1. fposte*

          First off, sometimes they just are that tight; you can get introduced to people when the departing employee leaves in a few days, but this is your one chance to get trained. And while I think the OP could probably have told her coworker to hold off while the training is happening, it’s still significant if the trainee wanted to hang out and talk about baseball or whatever while the trainer was in the middle of training.

          OP, I’m also thinking you could be direct: “We hired you because you’re good at stuff, but the reason they’re willing to fund my taking a week to train you is that it’s important that you be good at the way our office needs our stuff. Is there a way I can teach you that that would work better for you?”

  5. Julie*

    Given that you’ve been job hunting for a while, with the full knowledge of your boss, have you written up a set of SOPs (standard operating procedures) for your replacement? It might be too late to start now, but it might be something to think about if you’re caught in this situation again.

    1. OP*

      Oh yeah, I’ve done that at every job I’ve been in, including this one. I started the SOP book when I got the job, and updated it with every new task I was given. It’s always helpful to me when I come into a job with something like this, and where there isn’t one in place, I always make sure to create it. :)

      1. K.*

        I do that too! I make a “procedures” folder and update it with every new task or project. At my last job, there was no such documentation so when I started creating it on my own, I earned major points and kudos from my boss. I’m not an admin so the projects might be different (at my last job, for example, it was more of a calendar of our recurring marketing events and campaigns, what we do for each – and of course that changes as the marketing landscape changes – and who on staff generally does what), but it’s good practice in general, I’ve found.

        1. Piper*

          Why do more people not do this? I have done this at every job I’ve had as well. Two of those jobs were brand new positions, so obviously no one preceded me to make any kind of SOPs, so I understand the lack of them there.

          However, in jobs where I’m replacing someone, I have never, ever received any kind of training documentation or SOPs from my predecessor. I find this very strange because it’s just a no-brainer for me to leave something like this behind (and my previous bosses love me for it).

          1. Sydney*

            Some people don’t do it because they don’t think about it or weren’t told to do it. Some people don’t do it for job security. Some people do it for other reasons.

            I’m the website person for a small start-up and I don’t have SOP documentation for most of my tasks because if someone needs directions (and not just login info), they shouldn’t be doing it. I’ve had to fix enough problems my coworkers created when they were doing their own things. But for easy stuff like sending email campaigns, or updating our blog, I created documentation. Just not for things like how to FTP files to our website or how to change our SEO strategy.

            1. Piper*

              Just to clarify, I’ve never used an SOP to explain to give directions to someone for something they shouldn’t be doing and that is my job. I create SOPs specific to my job and keep them on file (and generally don’t advertise that I have them) until I’ve given my notice somewhere. Then I compile and create all the documentation I possibly can so the person who replaces me has some kind of a road map to follow.

              That said, I have created standard, company-wide SOPs that everyone followed for certain things. These are different from training documentation for a predecessor.

              1. Piper*

                Sorry, last sentence should say replacement not predecessor. Clearly, it’s Friday afternoon and my brain has checked out for the weekend.

      2. Anonymous*

        Can I just say I love SOP manuals?

        Its not always simple to write but Its nice to be able to say “you need to know how to do X? Read this – it even has screen caps of every step!”.

        1. Rana*

          I love them too, and make them whenever I’m working at something where they’re appropriate.

          They’re not just for one’s co-workers and replacements, after all. They benefit you too, both as an example of what you’ve been doing (and how well you understand) and as a reference for infrequent tasks. Who wants to waste brain space trying to remember how that once-a-year report is formatted, when you can just flip open your procedures book and see exactly how you handled it last time, what improvements need to be made, etc.?

  6. OP*

    I do feel the need to point out that I have to focus on the small things because without the small things, she CAN’T learn the big things. The spreadsheets and scanning details ARE part of the contract process, they’re just a smaller part. I felt the need to start there because she was saying yesterday that she felt overwhelmed by the amount of information she’d been given during her morning session with HR, my boss, and myself.

    The small spreadsheets are part of the structure of the overall process, and my boss – even when I’ve suggested better ways to do things – does NOT respond well to change. I am trying to train her to perform well for him, which basically means doing things the way that he wants them done, which is how he has ALWAYS done them. Change is not an option working for this person, and if it is, she’ll have to hash that out with him later. I can’t train her AND let her change things in only a week. I realize that’s an issue with him and not her, but I can only train her to function within the parameters of what our employer will be happy with. If she wants to change things, she’s more than welcome to do so – in a week, after I’m gone. For now, I can only train her the way I know how to do my job, which is the way I was told to do it.

    That said, I’m going to try Alison’s suggestion this morning of moving to the more substantive work and seeing if that makes a difference. I do wish my employer had brought her in with more than a week to go, particularly in light of her inexperience with contracts and legals, but there’s nothing I can do there. I can only work with what I’ve got. I’ll keep y’all posted as developments occur. :)

    1. AD*

      A great technique I learned from a manager early in my career was to start with the high level, and then subsequently drill down to the details, so when you are showing someone a seemingly menial task, they have context for why it is important.

      For example:

      “We’re going to make lunch, because that will allow us to stop being hungry. Now, to make lunch, we need to make a sandwich, soup, and lemonade. A sandwich is made up of bread, meat, cheese, and tomato. Let’s get out the knife and cutting board so I can show you how to chop a tomato.”

      Rather than “Get out the knife and cutting board so I can show you how to chop a tomato, because we’re going to need that, as you’ll see later.”

      1. Julie*

        This is great. The only way it would have been better is if it had been a chocolate teapot analogy. *grin*

        (“Okay, we’re going to make a chocolate teapot. To do that, we need to get a mold, melt some chocolate, pour it in, and chill it. Here’s where the molds are stored; you’ll know which one to use based on the work order. Now let me show you where you’ll find the premium chocolates…”)

      2. Ariancita*

        Really agree with this. I need to know the big picture first so that I know how subsequent pieces fit. I need contextualization. I had a small job a long time ago where my boss started with the small things and I had to interrupt him (very politely) and ask the bigger picture questions first. He was sheepish and admitted something like, “Right, it probably helps to know why you’re doing this first.”

        1. Piper*

          Also, without the bigger picture context or any indication that bigger responsibilities exist, the new hire may think that the “little things” are all that are involved in her new job and may think the job was misrepresented. And that breeds frustration, too.

          1. Ask a Manager* Post author

            But on the first day? And when she’s already told the OP that she’s feeling overwhelmed (per the OP’s earlier comment here)? That seems like jumping the gun.

            1. Piper*

              I guess it depends on the person’s previous experiences. Rightly or wrongly, those past experiences project onto new experiences, and if the new employee has experienced a bait and switch in the past, she could be fearing that it’s happening again.

              Also, I’m not sure that her indicated that she was overwhelmed with information means that she doesn’t want to get a bigger picture of her training. She may have been overwhelmed by tons of company info, benefits, corporate policies, etc., but that doesn’t means she’s not eager to jump in and do her actual job.

              1. Ask a Manager* Post author

                Even if she’s had bad experiences before, I’m still going to argue that behaving this way as a result of that on her first day shows problematic judgment, at best.

          2. Indie_Rachael*

            I agree with Piper. For some reason, people always want to train as though a job is composed of isolated mini-tasks, when the reality is that everything is interrelated. Maybe it’s because I’m an accountant, but I want an information flow chart that goes beyond just my duties so I can see how my work affects others, too. And yes, I want this from the very first day.

            I still have some tasks that I’m having to teach myself the inner workings of because the person who trained me wanted to take a “first you push this button, then you push that one” approach rather than explaining the reasoning behind the task.

            1. Ask a Manager* Post author

              Sure — but to be thinking on the first day that the job isn’t what you signed up for just because the initial focus is on smaller tasks seems a bit premature.

              That said, I totally agree that it’s more effective to train by starting with the big picture and then drilling down. I used to tell people that it’s like a tree — you have to give them the trunk and structure before you give them the branches and leaves, or the branches and leaves will have nothing to hold on to.

      3. Rana*

        Agreed. I do much better remembering things when I understand the logic of why I need to do them, and how they fit in with other tasks. If you just show me something, without context, I have to brute-force memorize it, or take notes (which I’d be doing anyway), and then it’s harder to remember later.

    2. Stells*

      As a former legal assistant who now works in another industry – lawyers are notorious for wanting things done THEIR WAY, and not open to change. Since she has no legal experience, you might want to go over this point with her as well. In every other industry I’ve worked in, people are willing to let you have some freedom over the administrative stuff as long as they can read it and it’s user friendly. Not with lawyers. I once had a partner who was very strict on both the font name and size (and not a standard font, btw) for EVERY document on a specific case. The case was a 4 year long SEC investigation, so that was 5 or so file rooms of folders, boxes, letters, contracts, etc, and they were all in the same font chosen by the partner.

    3. ruby*

      I appreciate your commitment to making sure that everything functions well after yolu leave and all goes smoothly but I think you have to accept that your ability to do that is limited. You have time limitations and you have limitations based on how the new person is handling the training process. This new person will work out her own relationship with the boss – she may have some success changign him or she may not, but either way, that’s up to them and is out of your hands. You can tell her that your boss has distinct preferences for small details and that’s why you are sharing them with her and she can either choose to accept that or vow to change him – again, that’s out of your hands (thankfully!)

      I know you’re feeling like how well she performs in the job is a direct reflection of how well you trained her and is going to impact your reputation there, but I think your reputation and how people there view your job performance will be based on your time there and not hers.

      I do agree if this persists, you many want to mention it to the boss in a benign way: “Jane has a lot of ideas on how to change the XYZ process and mentioned that she thinks we should do A instead of B”. Basically give him the head’s up on how she approached things and let him worry abotu how to deal with it.

      My approach to starting a new job has always been to learn how they do what they do and why. Then once I have that down, to look for places where improvements can be made. I see others approach it differently – they want to make a big splash right off the bat and come in with lots of new ideas and shake things up. Different strokes and all but I’d not be happy training someone like this either.

      1. KayDay*

        Ditto to Ruby’s entire last paragraph. I would also add that sometimes doing things differently might be more efficient for you (the worker bee), but your boss and the other people who utilize your work might not like it.

    4. Student*

      While I’m sure that you have a good read of your boss, realize that things change. The boss clearly does not care nearly as much as you do that this transition go smoothly. He does not care that the new hire get every detail right immediately. If he did, then he would’ve prioritized that and given you more time to train her on all those details. He didn’t. He wants you to teach her core business functions so the office keeps running. That may be a bad decision on his part if he is very fussy about details, but the decision has been made and you should respect it.

      So let go of the details and accept that this will not be a perfectly smooth transition. Focus on teaching her the big picture; let her suffer through the minor details on her own. You said you provided SOPs, so have some faith that you did those well. If you’re just worried about your reputation, then tell the boss that there won’t be enough time to get every detail exactly perfect, but you’re focused on the most important business functions. Then hand him your new contact info and encourage him (or the new hire) to contact you if anything comes up that can be handled via an email or a quick phone conversation.

      1. Ask a Manager* Post author

        It’s also possible that the boss doesn’t understand that the details can’t be taught in a week. That doesn’t make it the OP’s problem, but it sounds like she likes the boss and cares about her job and wants to leave things as well-settled as possible, and she’s dealing with a situation where the boss thinks a week is sufficient when in fact it’s not.

    5. TheSnarkyB*

      I think you could tell her exactly what you said above. Maybe if your stated goals for the week are clearer, she’ll have more info with which to adjust hers. Honestly, this sounds like someone who might have a little bit of natural arrogance, but is also nervous and has gotten bad advice in the past about “hitting the ground running” and “always be engaging in process optimization.” She might feel that she won’t be valued as much if she doesn’t show, right away, that she knows how to suggest improvements and make everyone’s life “easier” (By her yardstick).

    6. Mishsmom*

      OP, a week is pretty good compared to where i work. there was someone retiring a few years ago, so it wasn’t a surprise that they were leaving. by the time they got around to hiring someone and bringing her in for training, they had one whole afternoon together… it’s just not a priority for some people, and i know in this case it was because they thought there wasn’t much to the job so it shouldn’t need more than an afternoon. lovely…

      hey – i totally get what you are saying. it IS important to learn a few basics before the big stuff. i see it like dating – if she has this kind of attitude on her first day at this job, which is exactly when one should be at the very least pretending to be nice and amenable, and for sure they should be listening, then it’s not going anywhere good. i’d trust your gut on this one.

      BUT, you can only do what you can do. the rest is up to her. people like that weed themselves out and show their true colors. your boss will figure it out. you’re not responsible for her.

      i also agree with AAM, tell him now and before you leave exactly what you see. that way he knows you did your all.

      good luck!

    7. Anon.*

      OP, I’m so glad you explained this in more detail – I feel like I understood what you said in the original post but that the commenter did not and so were piling on you a bit.

      Good luck in the continued training and in y0ur new job!

      Btw, it would be really interesting to hear back from you in a few months regarding this new hire – if you keep in touch with your boss or coworkers – as to how this new person works out (or doesn’t work out).

  7. Charles*

    AAM, you once told me that you didn’t know much about training – I’m am now officially calling you out on that claim!

    Your response is everything that I would have done as a trainer:

    1 – tell her to pay attention. Most folks don’t realize that the education they received in K-12 and higher ed is not the way to train adults; that may be part of the problem. OP, you should have had her doing the hands on from the start instead of telling her to watch you. Did you continue to show her while the two were talking? If so, what were you thinking?
    2 – create written instructions (something that the OP should have considered doing months ago, BTW, since she knew this day was coming)
    3 – reconsider the training method/agenda (related to number 1; but, is it kind of late to do anything about it now?)
    4 – report to the boss how training is going. Yes, let the boss know how the training priorities are going. I find it kind of unbelievable that everything will be covered in one week. You will find that priorities will change as you discover what can and cannot be covered in one week’s time.
    5 – not your problem (okay, not exactly what you said; but, yea there is only so much the “trainer” can do – you can lead a horse to water but you cannot make it drink)

    One thing that I will add that I think you overlooked, AAM, it is key to me that the OP mentions that she was not involved in hiring and has found experience lacking. That really isn’t her call to make. I’m projecting a bit here; but, perhaps, the OP doesn’t want this to work and so is looking for fault? A sort of “no one can replace me” attitude. (OP, I don’t mean to offend and I am certainly not saying this is the case; but, I have seen it happen too many times to not wonder)

    Lastly, OP, why don’t you use filters? The answer you gave is NOT acceptable to me. That may be part of the problem as well. No two people work the same way – accept that – she will not be your clone. Instead of focusing on what-to-do, focus on the goal.

    1. Natasha*

      If the boss doesn’t want to use filters, why is that an unacceptable answer? Particularly since the OP mentioned in a later comment that she has tried to approach the boss about change and he didn’t want to go for it.

      1. Charles*

        Because she did NOT say the boss doesn’t want filters; she just said this is the way it is. An explanation of why filters won’t work would be the better answer.

        1. moe*

          From OP:

          “She said, ‘Well, why don’t you use filters?’ I said, ‘Because Boss asked for it to be this way.'”

          1. Flynn*

            Yeah, that’s not really an answer. WHY does the Boss want it that way? Because they’re incompetent? Because it’s a small cog that will have flow on effects? Because they hate fiddly data sheets, even if they know how to use them? It does matter, because it tells the person a) the Boss is not going to negotiate based on preference, or b) an alternative would actually be great, just figure out how to present or c) there’s a really really good reason.

            This has the benefit of actually answering the question (whether they were showing off, or they genuinely cared, or they were just trying to contribute they still benefit from a real answer). It tells them what the boss is like, heads off a rampage of arbitrary changes, or shows them that hey, this is an area to engage your brain in and maybe find a better way. And this is probably going to be a common theme across the various tasks – They Are That Way Because…

            “Because the Boss has to read these and finds this way easier to work with”

            “Because the Boss can’t figure filters out”

            “Because we have to keep these consistent across…”

            “Because we haven’t had time/training to work out an alternative that the Boss can also use, and it isn’t worth the effort otherwise”

            “I don’t actually know, but the Boss has expressed a very strong preference and I haven’t needed to change it”.

            1. Charles*

              Yes, it does indeed help. It seems like the new person is not being trained; but, rather is just being brain dumped on. As a result this new person is looking for a way to process the information in an easier way and looking for a new (in her mind that reads “better”) way of doing the job.

            2. Ariancita*

              Yes, exactly. To my ears, ‘the boss wants it done this way’ with no further explanation is about the same as, ‘it’s the way we’ve always done it.’ For me, it would be crucial to know the whether it’s because no one’s made the change to best practices for various reasons (as you provided above) or if it’s because of a weird micro-managing boss who makes my work unproductive and is not open to innovation. It’s crucial to know this because there can be a culture fit issue. And if you’re already hired, it’s crucial to know how much wiggle room you have for suggesting change, when to suggest it if possible, and how. The non-answer is not at all helpful.

    2. Another Ellie*

      I think that you are a little over the top here. The OP might just be frustrated because of the reasons that were given: a week to train a new employee in something that employee has no experience in, the employee isn’t paying attention to the small details that will build up into a challenging new job, and is being a bit rude about it to boot.

      Also, it’s nice that you find “my boss wants a spreadsheet that I manage for him set up a certain way” NOT acceptable. But you aren’t the OP’s boss, are you?

        1. Charles*

          And just what is that “reputation”?

          Hey, if you want to debate the issue; then debate the ISSUE; Not the person.

          My point is that the OP should have given a better explanation as to why filters were not acceptable – not just a “Because Boss asked for it to be this way.” Which, BTW, doesn’t tell me that filters will not work. Without details neither you nor I really know if filters will or will not work.

          1. moe*

            I’m debating the role and dogma of the trainer, not you personally.

            It’s consistently been my experience that when a trainer’s expertise is in training/pedagogy rather than the content of a subject area, the actual content owners bristle at working with him/her. There’s a certain arrogance and dogmatic approach that seems to go along with these roles.

            I don’t see the value in having to explain “why” every little thing is the best or entertain disagreement about everything when you have *one week* to train someone on your job. I consistently see trainers do things like this–get bogged down on the details and miss that the point is to train effectively in a reasonable period of time, not to satisfy some pedagogical theory. It’s how we end up with bloated masses of training sessions everyone dreads.

            The OP is the expert in her job.

          2. fposte*

            Charles, I think you’ve just gotten stuck on the take that you got from initially misreading. If you’re starting out new in an office and the boss likes an absence of filters, or green pens, or Adobe Garamond, you don’t start by prioritizing your way over his and insisting he deal with filters, purple pens, and Calibri, no matter how good your reasons are.

            I’m not even a lawyer, but I can tell you as an editor that I need my eye to be drawn to the differences that I have to correct, and I expect my staff to be able to keep to the formatting that we’ve established. If somebody has a suggestion as to why we should change it, then they need to talk to me, but not just present me with the way they like to do it instead.

              1. Jamie*

                What’s wrong with calibri? It’s clean like arial, but smaller. It’s my favorite font :).

                Times New Roman…now that would be worth quitting a job over!

                1. Ivy*

                  +1.. I use Calibri for everything… The new Microsoft Office has it set as its default which gives me the liberty to use it on work documents (that’s my excuse and I’m sticking to it!)… oh and lol at the Times New Roman comment (+1 to that too :P)

        1. Liz*

          I don’t mean to be hard on the OP – I have a tendency to tease that I need to watch.

          I do still think, though, that the OP keeps saying, in effect, “I need to DO SOMETHING about this” and it seems over the top, as well as raised my suspicions. I know legal types, too, so maybe I am projecting my experiences. But “I have found a moral requirement to do something that, oh what a conincidence, feeds my ego in the most dramatic way possible!” It just seems to happen a lot with legal types and after a while it is just an eye roll anytime anyone says something along the lines of “but I can’t let her get away with it!”

          The legal profession attracts self-serving wolf criers, basically, and the OP hit my warning bells, possibly thru no fault of her own.

    3. Anonymous*

      “Instead of focusing on what-to-do, focus on the goal.”

      The goal is to work with the boss appropriately. If the boss wants it THAT way and doesn’t want to use filters then ultimately he is the boss!

      An instant dismissal of “well I use filters” is rude – especially on the first day. A more suitable comment would have been “have you discussed using filters with him in the past then? I do prefer to use them…”

      A note for people being trained: Ask questions, don’t give “well that isn’t good enough” ultimatums!

      1. Elizabeth West*


        Once New Person is settled in the job, then she can approach Boss with a more efficient (if indeed it is) way to set up the spreadsheets. There’s no point in arguing about it now. Once the OP leaves, unless she has an agreement that the replacement can contact her for a period of time, it is no longer her problem.

  8. Long Time Admin*

    OP, it’s NOT your problem if you can’t train your replacement in one week. It’s your stupid boss’s problem, since he’s the one who wouldn’t bring her in earlier.

    Let it go. Show her as much as you can, explain your SOP book to her, and leave with a clean conscience. Your responsibility ends when you leave.

    A bit more: You’re not Superwoman. Your boss gave you an almost impossible task. A normal person cannot train a replacement for a job such as yours in one week, and a normal person cannot learn a job such as yours in one week.

    Whatever happens after you leave on your last day is not your responsibility. Frankly, I wouldn’t give it another thought.

    Go in peace, and enjoy your new job.

  9. KayDay*

    I have a few comments, as I understand where the OP is coming from, but I also think I get where the trainee is coming from as well.

    1. Don’t discount the fact that the Trainee has no legal assistant experience and has only been an office manager. From what I understand, the two jobs have a lot of overlap in the types of skills needed, so I think it’s reasonable to expect her to learn to do your job. Also, your boss my have hired her because of the new skills she is bring to the table.

    2. Unfortunately, the Trainee is very rude/arrogant. I can’t imagine not paying attention to my trainer on the first few days on the job, even if it was incredibly boring. In any job, the first few things you will learn are usually pretty boring, but that’s part of starting a job.

    3. That said, it would probably be best to get into the more substantive tasks soon, because as a former executive assistant and office manager, she certainly has plenty of experience answering phones, filing, etc. After all, she has been a admin assistant and office manger “for a number of years” ! She should definitely learn these sorts of tasks really quickly! It sounds like, from her (rude) comment about the spreadsheets and Outlook, she might be a bit insulted that you are spending so much time on these basic things. It sounds like when she’s paying attention, she understands things pretty quickly, so maybe you need to get on to the more complex items. Leave written notes for the basics, and demonstrate the complex things.

    4. While, it’s reasonable that the trainee might want to change things when she starts, utilizing the knowledge that she brings to the table, she also needs to be willing to learn how things are done. Sometimes “the-way-we-do-things” is for a very good reason, and it’s also important for a new hire to understand how the current systems work. Also, a lot of those basic admin functions are really different at different offices, so she needs to learn your procedures. And sometimes, when your boss wants something one way, it needs to be done that way even if there are better ways to do it.

    Now, I’m not really sure if her arrogance is backed up by actual skills from your email. So, to CYA, I would strongly recommend leaving behind a training manual. In addition to being available for trainee’s replacement, if it comes to that, the manual will demonstrate that you did everything you could to ensure a smooth transition. And as AAM said, keep your boss in the loop if she continues to be rude, arrogant, and/or completely uninterested in learning about the job.

    (p.s. sorry for the novel)

  10. Phyllis*

    The OP didn’t mention if the trainee was doing this or not, but I have a feeling based on the description of her behavior that she isn’t, and that’s taking her own notes. I’d be furiously scribbling my own copious notes on everything the trainer was telling me, even if I *thought* I already knew how to do or had an idea of how to improve the process. I don’t care how much you know about anything, and how good your memory is, you aren’t going to remember all of those things.

      1. Chocolate Teapot*

        I find that my instructions notebook is one of my most important pieces of kit!

    1. mh_76*


      Also, as other commenters said, focus on the big picture and on why she is doing the scanning, the filter-less spreadsheet, the other menial-seeming things. Without knowing where those things fit into the big picture, those things are pointless. It’s OK to show her once, then talk her through it, then let her try it on her own, asking questions as needed. You know what she needs to learn but she knows what her learning pace is and what prior but overlapping knowledge she brings to the job.

      As for the filter-less spreadsheet, that would make me crazy…I’d be looking for Access on the computer or figuring out macros to streamline the work (which I know is a piece of junk but I know how to use it) or taking a couple of cracks at convincing the boss that using filters will be more efficient…but that is your successor’s battle to fight.

      1. mh_76*

        D’oh! I reread this as it passed through my Google Reader feed & realized that I messed up a sentence move…

        Access is a piece of junk (or so I’ve been told by real IT people) that I know how to use. Thought I’d clarify.

      2. Really?*

        Its possible to use filters for your own updating and then removing them before the ‘final’ spreadsheet. Or just remove them before saving.

        I had do this for certain reporting in an old job as filters are useful for me but not for one of my bosses who can’t get his head around a lot of the data “going missing” when he opened the spreadsheet and it had been saved with a filter on it. The spreadsheet was 5000 lines approx…

        AS TO mh76 about Access… yeah, I’ve never found access able to do something that Excel can’t do better if you’ve got decent knowledge of the program.

        1. mh_76*

          re: Access – it is more useful than Excel for database tasks like comparing data from multiple sources, manipulating / adding to large amounts of data using queries and macros that run multiple queries (and nested macros etc), and generating reports/other spreadsheets to be emailed/archived.
          Excel is more useful for lists, pivot tables, visual representations (graphs, charts), and a few other things.

          Example: old master list vs. new master list, both including a field [last-updated-date] and a primary key field (ID#).
          Need: compare (using primary key) entries on both lists – which data has fallen off of the old list and which has been added to the new list -and- which data has changed on the on the new list (for the same entry). Also need to update changed data any other lists that are generated using the master list and record the most recent date updated.
          Excel: lots and lots of manual labor, helpful to have multiple monitors.
          Access: queries & macros (that can run both queries and other macros) – sit there clicking “OK” for a few minutes.

          Having typed all of that, there are much better database programs out there, some of them open source (like open office)…but I haven’t needed to use them…yet.

    2. Rana*

      YES. Notes are particularly crucial if you are, like me, a visual and kinesthetic learner. If someone merely tells me how to do something, it’s an enormous struggle for me to remember it later, especially if I’m nervous or don’t have a clear sense of the context for the information.

      It’s sometimes feels a bit awkward to be taking notes while someone’s talking to me, but it’s the best way I have of paying attention. If I could get away with it in social situations as well as professional ones, I would.

      1. Ariancita*

        Me too! I am never without my notebook..even when I go out to bars with my friends. You never know when inspiration will strike and I’ll never remember it if I don’t write it down.

  11. Max*

    Certainly, a newly-hired legal assistant spending her first training day telling the IT department how to do their jobs is a definite warning sign. It reflects poorly on her judgment, casts doubt on her ability to work with others and to cooperate with other departments, and suggests that she doesn’t really understand her role in the company yet. And from the IT side of things, I’ve got to wonder: if her computer breaks, is she going to take it to IT or is she going to waste time trying to fix it herself (and risk breaking it further)? It’s not her job to give IT explanations…

    …and the OP, being in a supervisory role should be letting her know about that. The fact that she could have a whole conversation without you noticing that she was disengaged from your demonstration suggests that you’re not really paying much attention to the training process either, OP – you’re just going through the motions and expecting her to maintain interest on her own. While it’s reasonable to expect a professional to pay attention to training without any prodding on your part, the fact of the matter is that if you want to do right by your employer, you have to be just as engaged in the training process as you expect her to be. It’s not really fair to you, but if you care about the training, then that means asserting yourself when the trainee is clearly not paying attention. When I read the OP, I see a rude new hire who has trouble listening to others…but I also see a timid OP who’s letting the new hire walk all over her.

  12. Kimmie Sue*

    I agree with AAM all the way, but have one possibly contrary point.

    How long has the OP been with the company and doing the role? Is it possible that perhaps they are hesitant to let go? I have had to train my replacement at two different companies. I left them both in a very amicable way and agreed to provide a smooth transition and training. I must admit though, my feathers were a bit ruffled each time. It bruised my ego somewhat to train someone new on a job that I had held for a long time. Having lived and survived the reasons “why we did things the way we did” made it difficult not to be taken aback when the trainees suggested an alternate way of doing things. They didn’t have the history that I had.

    That said, their contributions, questions and suggestions for improvement were ALSO valid.

    1. Anonymous*

      Agreed, it’s not easy to let go of ownership of a task, even when you think you have and are headed for a new job. I’ve been in both sets of shoes! It’s hard when you think your replacement isn’t going to do it the “right” way. But after all, what is really “right”? Your replacement will put her own stamp on this position, just as you will in your new one. Let it go, enjoy your last week, and prepare for your next challenge.

  13. J*

    Writing a manual (if you don’t mind, have the time, and can be clear and organized) is probably one of the most helpful things I’ve done (and received from the person I was temping for) at one of my previous jobs — I’d recommend that in general for anyone leaving an office job!

    At the very least, a list of common terms that you deal with (like “instead of chocolate teapots, we call them cocoa-flavored tea-carrying devices”), or people you have to contact a lot (individual names, or at least positions, if they change a lot). I filled in for three months for an admissions assistant at a high school (after filling in as registrar) after an unexpected booting of a staff member…

    Person A left with two weeks notice in November, right as admissions season was starting. They hired Person B in two weeks, who wasn’t a great fit, who left in March. I filled in from March to June, and overlapped for only one week with the new person, Person C. (Who they actually hired intelligently, yay!)

    I knew that Person C would have to do the whole year cycle from start to finish with basically no guidance, so I made as many manuals as I could for her common tasks that she was expected to do by default that had nothing to do with admissions — such as organizing massive week-long field trips for each grade level, and tracking health forms each family had to send in every year. By making sample packets for each different task, explaining what each piece was and where the files on the computer were, and naming the people she would have to hunt down for information, I hope it wasn’t quite as mystifying. Fingers crossed…

  14. Anon*

    I am wondering if this new person’s first name starts with the letter “J” because she sounds EXACTLY like an admin that my company hired a couple of years ago. That person was extremely argumentative and defiant from the beginning. She was always telling everyone that she had a better way to do things, and would flat out refuse to do tasks that were her responsibility. We all suffered for months with this lady. In her case, she was bitter because she had been laid off and this new job had a lot lower salary than she was accustomed to.

    Finally, she either quit or was fired. All I know is she was there one morning with the usual scowl on her face and a few hours later, an email went out saying “J is not longer an employee at X company.”

    We all cried Hallelujah!!!

    1. anon*

      It’s sad when people are so angry and self-absorbed they don’t realize that their actions are effecting everyone around them. I also worked with a defiant co-worker who wanted to reinvent the way our organization created products. She ended up quitting, and my last year has been so much more peaceful and productive without her around. Sometimes people infict incredible negativity on others in their quest to “improve” things. Being right doesn’t always make you a winner if you ruin the relationships you have with everyone you work with in the process.

  15. OP*

    OP here. Just to give a quick update (since I’m on break!) – the comments herein have been largely reflective of potential for boredom with minute tasks, since she is, as many of you pointed out, an experienced admin if nothing else. I took that into account and gave her some bigger things, which also involved the scanning/spreadsheets. I asked her to scan and email a document to me when I went to lunch, and asked her to update a spreadsheet with the information, and that said I would review it all when I got back.

    I came back to find her at the scanner, and asked her what was wrong. She said she couldn’t remember how to scan to her folder. She also said she wasn’t sure how to update the spreadsheet, despite my SOP manual giving instructions (which I had pointed out to her prior to leaving for lunch). I did notice, however, that she isn’t taking notes, and politely suggested she start doing so.

    One other oddity: the CEO introduced himself to her today, and while he was walking away, she turned to me and said (rather loudly, enough for him to be in earshot), “He’s a whackjob.” Literally two seconds after meeting him. I didn’t really know how to respond, but it leads me to believe this is less an issue of arrogance and more an issue of social skills… which, in any admin (legal or otherwise) is going to be a problem. It’s not good practice to call the CEO a “whackjob” on your second day, particularly when it’s loud enough to be heard by others.

    I’m keeping notes, and will review them with my boss later in the day, but for now, you guys have been very helpful – keep the thoughts coming if you want – I have a week to go and am more than happy to continue implementing suggestions here.

    1. Charles*

      Within earshot or not, CEO or someone lower on the totem pole – I would report that to you manager pronto. There is not excuse for such rude behaviour!

    2. khilde*

      I don’t think there’s anything else I can add for constructive suggestions other than to echo what a few have said earlier: do your best (which it sounds like you are more than doing) and let it go. Enjoy your new ventures and don’t assume too much responsibility for how things turn out after you leave. That’s a yoke you’ll never get off your neck. Sounds like you are more than being reasonable and fair – the additional observations you’ve shared here demonstrate the type of judgment the trainee has and I think most would agree that she’s the one with issues, not you.

    3. Student*

      I’d say, let go of the whackjob comment. Yes, it’s bad and stupid of her, but you are LEAVING. The decision to hire this woman is already made and you cannot do anything about that. Trying to get her fired has the potential to make you look bad right now even if you are 100% correct that this is, as they say, a “bad fit.” It’d be a completely different matter if you were staying, but you aren’t.

      Just go over everything that you reasonably can, focusing on priority tasks. Tell your boss what you’ve covered with her (in writing, with links to that set of SOPs), and tell your boss if she’s still struggling at the end of the week. Offer your contact info to your boss for brief questions via email or phone after you are gone, if you want to be a “nice guy” and leave the door open to help with the transition further.

      I can understand your dismay that she doesn’t seem able to replace you, but it is really not your problem. Your boss has opted to learn an important management lesson the hard way, and there is nothing you can do to fix that, so please try to let it go. I know it’s hard to watch people you like make mistakes, but that’s an important part of the learning process.

      1. Ask a Manager* Post author

        I know opinions will differ on this, but personally I’d mention the “whackjob” comment to the boss when giving the overview. It’s not about trying to get her fired; it’s about making sure the boss has the lay of the land and is able to watch out for issues himself (that he otherwise might not pay close attention to) and can give the new employee some guidance on what is and isn’t appropriate, etc. I’d sure as hell want to know about that comment if I were in his shoes.

        1. OP*

          Particularly because she’ll be dealing personally with clients, I’m inclined to agree with you. If she’s willing to say that to the CEO, what happens when an irate customer calls for the legal department and she’s answering the phone? My boss left early today but I plan to go over this with him on Monday, for sure.

        2. AMG*

          +1! Within earshot, no less. She will be doing right by her company to let the boss know. I think any of us would want some situational awareness if we were the boss. Boss may have to re-hire and re-train someone at the last minute, but it’s better than having her hang around stirring up trouble.

    4. Really?*

      One other oddity: the CEO introduced himself to her today, and while he was walking away, she turned to me and said (rather loudly, enough for him to be in earshot), “He’s a whackjob.” Literally two seconds after meeting him. I didn’t really know how to respond, but it leads me to believe this is less an issue of arrogance and more an issue of social skills…

      I disagree that there is no arrogance involved – Even the most non-social skilled person I know would draw the line at saying something like that. Its arrogant to have that perspective within seconds of meeting someone unless they were dressed like the mad hatter, talking to their invisible friend in weird voices and juggling Chocolate Teapots at the same time.

      Either way management have to know before she is let loose on clients. If she has that little of a filter around management then I’d give her less than 5 conversations before she says something to (or about and is overheard) a client that looses the company the account and upsets them.

      1. Ariancita*

        “Its arrogant to have that perspective within seconds of meeting someone unless they were dressed like the mad hatter, talking to their invisible friend in weird voices and juggling Chocolate Teapots at the same time. ”

        Even then, I’d just find him charmingly eccentric (as long as he does his job well).

          1. Charles*

            Yea, Mad-hatter juggling chocolate teapots would be fun to work with; but, I bet his invisible friend is a total slacker!

      2. Liz*

        Are you sure she wasn’t being sarcastic? I say this as someone who once freaked out a room of fellow grad students on the first day of classes by saying brightly, “Oh yeah, I’m excited to start school, but I didn’t study for the pop quiz, did you?”

        I still don’t know why I did that. I was just nervous and it popped into my head as a jokey thing to say. I didn’t think anyone would BELIEVE it. Years later people still thought it was some Machiavellian attempt on my part to psych out my classmates.

        1. Ariancita*

          See, I love that kind of dry humor! I would have followed up with something like, “no, because I was more focused on preparing for arm wrestling portion of today’s exam.”

          1. Liz*

            We would have had fun in grad school. Where we’re you for three years I’ll never get back?

    5. The Other Dawn*

      I hate to say it, but if it were me I would be looking for a replacement already. I’ve seen enough of these people come through my place that I can spot them a mile away. The whack-job comment, within earshot of the CEO no less, tells me she lacks judgment and may be a bit too loosey-goosey for this job. I say if she doesn’t come in tomorrow with a new attitude, ready to learn, take notes, etc., look for a replacement.

  16. Anon.*

    One thing that came to mind about the employee talking to someone else during training – I wonder if she got an office org chart showing who reports to who, etc? It can be confusing to have to figure out on the fly who the important people are. If the other person did indeed come up and interrupt your training to introduce themselves, the new person may have assumed they were important enough to do that.

    That said, it sounds like she has other attitude problems, so this may not be the case – but it’s something to generally keep in mind while training!

  17. Lisa*

    Interesting comments/advice! As some have commented, I like knowing the big picture as well. It gives me more meaning and a better understanding as to WHY something is being done a particular way. Along those lines, how about having the Trainee “shadow” the Trainer for a day with the Trainer explaining how and why it fits into the big picture. Then the Trainer and the Trainee can assess the areas where the Trainee needs the most training or has the most questions.

    As for the Trainee asking questions about how come you do it this way…I think that’s legit question. Because the Boss likes it this way is an answer. I don’t think it’s the Trainee’s position to challenge the Trainer at this point. It’s “a learn as much as you can” about how things fit into the big picture. When the Trainer takes on her new job, and the Trainee becomes acclimated to the job/environment, perhaps “style” and “enhancements” can come later on. But I think as a Trainee I would certainly not be telling the Trainer how to do something better. As a Trainee, my focus would becoming acclimated quickly. As the Trainer, my focus would be on detailing the aspects of the job the Trainee isn’t experienced in. Shadow, find out where the training is needed most.

    I once had to train for particular task and I asked why do you do it this way? The answer was “Because this is how I was taught.” That’s an answer I’m not going to challenge with the Trainer! :)

    In any event, I am wishing both the OP and the Trainee the best!

    1. Really?*

      Lovely story here that is the other side of the coin about accepting everything at face value (I’m not sure where but I came across it years ago):

      a mother is showing her daughter how to cook the Sunday Roast. She tells her that you cut off the end portion of the joint and then put it in the pan etc. Daughter asks why. Mother doesn’t know, says Grandmother taught her to do it that way.

      Daughter asks Grandmother next time she sees her and Grandmother says “We had to cut the end off…. it didn’t fit in the pan otherwise.”

      1. Lisa*

        It’s about accepting the co-worker. To find the real answer one has to go a little deeper than that because the answer isn’t going to come from the person who says “because that’s how I was taught.” Good analogy Really and thank you for that! :D

  18. Mishsmom*

    i bet when she interviewed they thought she was a “go-getter” and didn’t realize that it was just arrogance with nothing behind it… i also am willing to bet that this woman has had issues in previous jobs and never made the connection that she might be the issue, it’s got to be everyone else who is wrong/a whackjob/whatever (i’ve worked with a woman like this. it was never her – it was always other people that she had worked with that didn’t understand/treated her badly/etc.)… just a thought

  19. Liz*

    IT Company Administrator v. longtime Legal Assistant in a showdown over “Who knows this job better?”

    I somehow suspect that couldn’t have been a fun day for anyone. Although I do agree the new hire should have been a lot more tactful.

  20. Elizabeth West*

    A written manual is GOLD. I took a job once where the person I replaced moved away before I got there. She had left an entire file full of detailed SOPs and I was so grateful. The job wasn’t hard, but it was very detailed. Without that help, it would taken much longer to get up to speed. She came back for a visit about a year later, and I was like “OMG THANK YOU!!!”

    Since then, I have found that writing things down as I’m being trained is a huge help. And I plan to make a manual if I can for each position I have. In case I’m sick or on vacation and they have to bring in a temp, or someone who doesn’t normally do the work has to cover me, it’s all right there. I produced a complete indexed manual for my (now obsolete) ex-job, but it contains procedures the rest of my former colleagues can use since they are now doing some of what were once my duties.

  21. Liz T*

    If my first week on the job were learning how to scan documents and use spreadsheets, and ignored when I made clear I knew how to do those things already, I would be pretty miserable.

    1. Ask a Manager* Post author

      Except that it turned out that the woman didn’t actually know how to use their scanning system (see the OP’s update in the comments about coming back from lunch and finding the woman lost at the scanner).

  22. Cassie*

    I would be frustrated if I was trying to train someone new and they kept telling me how things *should* be done. My job isn’t to find a new/better solution to some problem, my job is to train you to replace me. If you want to implement a new system, you’ll have to wait until next week. I wonder if this is just a part of the trainee’s personality. Some people are very prone to making comments like this, sometimes without even noticing.

    I can see why the trainee might be bored learning stuff that she already knows (or feels she already knows), but I guess it’s not clear to her that the sooner she picks up these menial tasks, the sooner they can move on to more substantial work.

    1. Jamie*

      This. I am all for opportunities for improvement, and a new employee should bring fresh ideas to the table.

      But not day one.

      I love to hear about better, more efficient ways to do things…God knows this week I could have used someone full of these ideas. But I will give ideas a lot more weight if they are based on an analysis of how things are done now vs a proposed improvement rather than a competition between how we’ve always done things vs how you’ve always done things.

  23. Ivy*

    OP I’m loving the updates! It’s great to be kept up to date in an unfolding situation! I’m not really saying anything new, but I like to hear the sound of my own typing so here it goes… :P

    I think the main thing here is remembering that you only have 1 week left. You don’t have to work with this person, and if she is truly as incompetent as she is appearing to be, then that will become apparent to your boss eventually. If your boss is at all reasonable, he will not blame her incompetence on you.

    The best you can do is train this person to the best of your abilities and then say arrivederci when the time comes. If you care for your boss then it makes sense to bring up these grievances, but I wouldn’t push it too hard. If you tell your boss, “I’m worried about new hires ability to do x, because of situation y” and he says “oh I’m sure she’ll get the hang of it,” then your job is done. You have no obligation to ensure your boss has hired a competent person. The onus is on him to do that. Your job is to do your best in training her. Keeping your boss in the loop at the end isn’t even necessary, but it is nice of you (and also covering your own butt in case new hire pulls a “oh I wasn’t taught that” move).

    Keep the updates coming OP!

  24. Dogwoman*

    I am a supervisor at a retail store. About a month ago, they hired a rather elderly person to work nights. She has not had any retail experience. She last used a cash register decades ago at a grocer. Three of us have been trying to train her but she seems to ignore or disregard anything we show or tell her. After 30 days, she is still having lots of issues. She takes 20 to 30 minutes to count onto her till. If she makes errors doing this, she remarks that the till is wrong which it isn’t. So she’s told to keep doing it till it’s correct. It worries me that she may not be counting back change corrcctly to customers. Three of us have typed up or handwritten notes to try to help her. She recently told me that she already knows what to do. But she does not. We have had three different people in one shift show her how to do something very simple like stack items in size order. Then the next day, she forgets how to do it. She even has problems turning of the store lights at night even though they are clearly marked on the fuse box in a bright color. She’s come in to work 30 or more minutes late. Then she has argued with me that I am wrong. I pointed out that the schedule in the break area is correct and it has not been changed since it was posted. She never apologized or even said that she may have made a mistake writing down her schedule. I have to constantly micromanage her. I also have to constantly tell her what to do as she is not self motivated. Other coworkers remark that they never hear her greet customers or ask them if they need assistance. She seems not to take any responsiblity for any errors she makes. She has said that either a customer or coworker confused her when she makes errors using the cash registers. The store manager tells me to be more patient. But the store manager has never worked with her. I even mentioned that she was due for her first month review. And the store manager told me that she would not get a review till 90 days. But I got monthly reviews the first few months I was employed via a different manager. Am I suppose to keep doing her job and mine in hopes that she will catch on to her responsibilities????

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