I’m training my replacement and worried she’s not right for the job

A reader writes:

I was recently promoted to a mid-level job in my department after 2.5 years as an administrative assistant. It’s a great change, but it’s also a very stressful transition: on top of learning the ropes, clearing my predecessor’s backlog and taking on brand new duties, I also have to train my replacement. We happened to have a temp in the office when I was offered the promotion, and my boss liked her enough to offer her the assistant position. Because of company rules regarding hiring temps full-time, she is my “temporary” replacement and her continued employment here will be re-evaluated later this month, which is an unusual occurrence.

When her evaluation time rolls around, I’m sure I’ll be asked my opinion, and I’m not really sure what to consider. I’ve been training her on and off since she finished her original temp assignment, which was about two months ago. I should add that this is my first time training someone in a job like this (a previous college job provided a clear structure for training newbies). In the beginning, I spent good chunks of time training her on everyday tasks of varying difficulty, most of which are repeated often, and I’ve done my best to accommodate her learning style even though it’s different from mine. Most of the job is learned by doing, anyway, so I started watching over her less and less. I’ve found that she still makes some mistakes and has a hard time remembering things we’ve gone over, even things she’s taken notes on. Her desk is a mess and I don’t know how she keeps anything organized.

I’m frustrated by a number of things: is she just thinking about the work differently than I would? Will she eventually know it all, and is that moment after she’s hired full-time? Will she reflect badly on me in my boss’s eyes, especially since I want to impress him with my new work? Am I even training her well or just overwhelming her with information?

Another thing that’s happened while training her is that my own skills are being highlighted, especially those in logic and writing — great for my self-esteem, not so great for my frustration levels (or my conscience) because I can’t help but feel like I’m smarter than her. It doesn’t help that I find her a bit annoying. She comes off as friendly but aloof, and her tendency to be vain and insensitive reminds me of overly-snarky ex-friends. Her crass reaction to Robin Williams’ suicide really put me off.

I want her to make the job her own, and I definitely don’t want to micromanage, but I also have trouble feeling confident in her skills. More than anything, I want to let her be and get back to my new work, which sorely needs my attention. Do I need to get over myself? I know I should wait until her evaluation time to have an opinion, but should I be worried?

It’s hard to say for sure from the outside, without knowing a lot more. In many jobs, it’s not uncommon or alarming that a new hire wouldn’t have everything down perfectly two months in — small mistakes and even forgetting things that you’d gone over previously could be normal. But so much comes down to the nature of those mistakes, and you’re better positioned than I am to know if the ones she’s making — and her work habits in general — are alarming. You’ve done the job yourself, and you probably have at least a decent sense of what the learning curve could be. If I had to bet money, I’d sat your alarm is probably well-founded.

Here’s the good news though: You don’t need to know for sure. You just need to relay what you’re observing to the person who manages her.

And even if you’re not asked, you should do that — because as the person who’s training her, you’re well-positioned to see how she’s doing, and part of that responsibility is speaking up when you have concerns. Nor do you have to wait until an official evaluation period to speak up; if you’re seeing things that concern you, you should get your/her manager in the loop now.

I’d just lay it out all to her boss, similarly to how you have here: “I’m not sure if my expectations are unrealistic for two months in, but I’m concerned that she’s still making mistakes like X and Y and that’s she not retaining key things we’ve gone over, like A and B. She’s the first person I’ve trained in a role like this so I don’t really have a framework to assess her relative to other people — but I do know that’s she’s struggling more than I was myself at that point, and it concerns me. Right now, I don’t have total confidence in her ability to do the job without my help, but I also know that I can’t train her forever.”

And a bit about that last piece — your letter sounds a bit like you’re thinking that you’re supposed to just keep training her until she’s perfect, and it’s unlikely that that’s the case. Or at least, if that is your manager’s plan, it’s a bad one. That’s not how this should work; you should give her a reasonable amount of training, and then leave her to the work (staying available as a resource occasionally if she has questions for you — but even that shouldn’t be forever). So at some point soon, it would also make sense to say to your boss, “I’ve been working with her closely for two months now, and I think it’s time to see how she does on her own.”

One other thing: Make sure that you’re giving your replacement direct feedback too. Part of training someone is making sure that they understand when there are problems, and giving them direct feedback in general. So if you haven’t told her directly that by this point she should be handling X without your help or remembering Y without needing it covered again, you should. She may not realize that these things are problems, and it’s possible that she’ll pick up her pace of learning if you tell her directly that she needs to. (And if she doesn’t, she’ll at least have the benefit of understanding that there’s a problem. You don’t want her to be blindsided by that.)

{ 37 comments… read them below }

  1. AdAgencyChick

    Great advice from Allison. Your boss has probably had multiple assistants work for him over the years, so if he’s been paying attention, he’s likely to have a better perspective than you on whether you yourself were unusually good at the assistant job. If that’s the case, the new person’s not picking up things as fast as you did may not actually indicate that she’s not good at the job, just that she’s not as good at it as you were, and depending on your boss’s standards and the difficulty of finding another superstar, that may be okay.

    The conversation Allison is suggesting will bring this kind of thing out. Give your honest assessment of what you think she’s struggling with, what she’s doing well with, and where you were yourself at this point in your own trajectory. I think then you and your boss together can figure out where the bar is that she has to clear, and what to do about it if she doesn’t. I would also ask, since both of you report to him, how he would like you to phase out the training period so that you can best help him with (insert tasks that are part of your new job here).

  2. Adam

    I think when we’re training our replacements part of us feels we need to get them up to our standard of where we were doing the job when we left it. Thing is though this can cloud realistic expectations. I’ve been in my current position for four years and can pretty much do my job standing on my head at this point. But it wasn’t until I tried writing an employee handbook specifically for my position that I realized all the ridiculous little minutia that goes along with my job had added up over the years.

    Note: my position is sort of a dumping ground for all those little tasks that don’t require special handling that no one else really wants to do. If job titles were accurate to reality mine would include Jack-of-all-trades in their somewhere. If this were Final Fantasy I’d straight up be a Red Mage.

    Anyways the best instructor in the world can’t account for time on the job and experience that slowly builds as you do the job every working day. I think in training your replacement your role is to get her up to speed with the necessary tasks and leave her in a good position to build on everything else as necessary, as most people don’t usually have a job down 100% pat after just a few months but they can still get by. As handy as flat out cloning ourselves would be it’s not a requirement that you leave a duplicate in your place. Good luck!

    1. KarenT

      I think when we’re training our replacements part of us feels we need to get them up to our standard of where we were doing the job when we left it. Thing is though this can cloud realistic expectations.

      So much this. It’s hard to see a job you worked so hard at turned over to someone who is still learning, but it’s a natural part of moving on. Last time I trained my replacement I really had to force myself not to compare how she was doing to how I would do something (as it’s really not fair to compare someone who has had the job for three years to someone who has had the job for one week). Instead I focused on making sure she had all the information she needed and knew where to get answers if she didn’t.

    2. Amber

      Agreed. In my current job I wasn’t doing so well for awhile. When the person training me moved to a different department, it wasn’t until then that I felt comfortable enough to really own my part of the work. I really didn’t like her judging me and her comparing me to herself. Once she moved, I could then learn how I wanted and felt free enough to change the incomplete and outdated handbooks that she had written. Since she had a lot of say in my success I never told her but she was a terrible trainer. I’m not saying that’s the case with the OP but I’d say at least have a direct 1 on 1 conversation with her. Not just about any issues you have but make her feel comfortable enough to talk to you about any concerns she has.

    3. LBK

      If this were Final Fantasy I’d straight up be a Red Mage.

      Love this. I’m totally going to petition to have my title changed to Red Mage.

  3. BRR

    I agree it’s tough to know without being there. I feel like training an admin assistant is difficult because they do such a wide variety of tasks that most of the time I imagine it’s impossible to cover everything in training. When she makes a mistake, I would ask her if she knows why it happened. If they’re the same mistakes, let her know she’s making the same mistake and it needs to not keep occurring. It also should be communicated to her that if she can’t improve the quality of her work, her job could be on the line.

    Other things:
    -Where were you two months into the position? Are there other people to measure her against?
    -It most likely won’t reflect poorly on you. You have obviously done your job well enough to be promoted, this reflects on her quality of work.
    -You mentioned a couple things on how she’s different than you (learning style, work space, difference in skill levels, different personality), I’m not sure what the deal is with this and I don’t want to read too much into the letter or speculate but it’s something for OP to think about why so many of these things seem to be an issue.

    1. Melly

      Yeah, the stuff about style (messy desk, personality) didn’t seem relevant to evaluating job performance. And sure, it’s hard for the OP to give up old responsibilities but there has to be a cut-point where OP gets to do her new job and the new admin can do hers, managed by her manager.

      1. Polaris

        Style could be very relevant to the admin’s job performance if the admin is in a public or client facing role. That said, I was under the impression that the OP brought up the personality comments to show her bias. She’s concerned that she is not a fair judge of the admin’s performance because she dislikes her personality.

  4. AndersonDarling

    This post could have been about me 10 years ago when I was training to be an admin in my first role. I only took notes on some things, I was messy, and my trainer didn’t think I was learning anything. I was really waiting for the training to be over so I could really get into the job and make changes without the trainer looking over my shoulder questioning what I was doing.
    I wouldn’t panic. If you have been working this closely for this long, it is easy to get judgmental (not in a negative way), and annoyed by little things. Let the new person try out the position on their own. After a month you will really be able to see if they sink or swim.

    1. C Average

      You bring up an interesting possibility: perhaps the new person isn’t performing as well under close observation. Some people get really, really anxious when they know they’re being watched closely, and that can impact performance. I’ve seen this with people I’ve trained: I’ve turned someone loose after training pretty much expecting them to fail, and then been pleasantly surprised to see them work much more effectively without me hovering over them.

      1. AdminAnon

        Absolutely. I’ve been that way my whole life. If someone is watching me closely or micromanaging me in any way, I freeze up. Even when I was a kid and my mom would stay in the room while I dusted or did the dishes or whatever, I would always make stupid mistakes or turn into a total klutz (despite the fact that I was perfectly capable of doing those things without an audience). To this day, I can’t clean properly when my roommate is around and I can’t work with people looking over my shoulder or micromanaging–I make stupid mistakes and everything takes six times as long. Luckily for me, my manager travels constantly and gives me room to breathe and manage my own work.

        1. Not So NewReader

          Many, many people have this problem. I had to train people to run various machines/tools. Every.single.person had shaky hands. (The only one who did not, never learned the jobs.) So I would tell them point blank- I am only here watching to make sure you know how to keep yourself safe. Once I see that you understand and are keeping yourself safe, I will walk away and that is when you will really start to figure this out. Very few people learn or do well with someone standing over them.

          1. Windchime

            I have some kind of typing anxiety. I normally type very, very fast and accurately–unless someone is watching me. Then I’m fumbling, can’t find the right keys, can’t find items from the drop-down-list: I’m a real mess. And I’m not even in training, so I can see how it would be much, much worse if someone was watching my every move like sometimes happens in training.

  5. Mister Pickle

    AAM’s advice is spot-on.

    Reading OP’s letter, it sounds like OP is sincerely trying to be fair about giving the replacement a chance to learn and settle into the role. But if she’s been training her for 2 months and is still wondering “is she just thinking about the work differently than I would?” – long story short, OP needs to trust herself. Which may mean coming to sadly accept the fact that this person just isn’t measuring up.

    I also think her comments about “aloof”, “vain”, “insensitive”, and “crass” are worth paying attention to. If the thinking is to bring a person into the company for the long term, then it’s definitely worthwhile to find someone who is a good “personality fit”.

    Finallly: I noticed that OP was wondering if she was smarter than the person she’s training, and I sensed that she almost felt guilty about it. My comment is: that may very well be the case. Don’t feel bad about it, just accept it as a gift, and realize that there will always be people smarter than you and less smart than you. And use your powers for Good, and not Evil :)

    1. Koko

      Yes, I appreciate OP’s high level of self-awareness here, that she’s willing to consider that she might be letting her personal dislike of the replacement’s personality influence her evaluation and she’s trying to guard against that. Whereas for so many people that’s just an unconscious bias they carry and let influence them unknowingly.

  6. Cajun2core

    Has she tried using checklists and/or waiting a day before proofing her work? I found both very helpful in my current job. My job mainly involves filling out travel reimbursement forms for others. I created a check list (is this on it, do the totals match, do I have all of the receipts, etc.) which has helped a great amount. Further, after I initially fill it out, I wait a day and review it the next day (so I can see it with “fresh eyes”) before forwarding it to our accounts payable department.

    For many people, having to remember 100 details on one form isn’t that easy because like me they can focus on one item (the most recent they got wrong) but miss others (ones they usually or always get right). However, like me, the check-list and looking at it with “fresh eyes” can prove very helpful. This person may turn out to be a great employee if the right tools are in place.

    1. Angora

      Sometimes you have to let go of the reins to let your employees either fail or improve. I was in the situation years ago where I was the messy desk being trained by the individual that had been in the job that had OCD. We drove each other crazy. She worked 7:30 – 4 and I worked 9 – 5:30; I would come in the morning to find my desk organized and put back the way she liked it. I more or less blew up one day after repeatedly telling her to leave my desk alone. My prior co-worker kept watching everything I did, and would complain constantly because I wasn’t doing it the way she wanted months after the training period was over. It got bad enough I asked for mediation. I’m not neat, my desk looks like it blew up; but I am one of the best admin’s out there. But that’s because I tracked what I did and needed to do with the task manager on outlook. What was interesting was months later I found out from others that my personality was easier to work with and was told that I was the best admin they ever had in the job.

      I recommend that you stop back and let the individual work without supervision, but set up a 1/2 to an hour per day for them to come to you with questions. That way it’s a scheduled meeting versus constant interruptions that will interfere with you learning your new responsibilities. I agree with the others, someone watching someone can cause anxiety … which effects memory and can cause one to make mistakes.

  7. Student

    Two months of training is a lot of training. You’re the only person in a position to know what’s needed and what’s too much, but, I have to confess that when I read this letter my first reaction was, “Two months of training to be an admin?!”

    I’m in a technical field. I got about 1 week of online training courses (dozens of power-points, basically) to tell me all the things the corporate office doesn’t want me to do, about half of which are relevant to me. Then I got less than a day of training on the actual day-to-day work. I was expected to try to figure things out on my own, for the most part, and ask questions if I couldn’t find an answer or was about to do something dangerous for the first time. Sure, it would’ve been nice to get training on a lot of things that I do. Some things would’ve gone smoother, more efficiently. It wasn’t necessary, though.

    What tasks does this new admin do that really require in-depth training? What are the stakes if the new admin messes something up? Prioritize training on high-stakes work and let little things go. Admin work is widely considered to be low-level tasks that other people don’t want to do, especially time-consuming tasks or repetitive tasks. It’s usually entry level work, with no substantive education requirements. I genuinely can’t imagine a task list that would take two months of training in my own job, so I’m really struggling to understand what you’re training her on for a classic entry-level job for so long.

    1. fposte

      The OP did say on and off for two months, but I agree that this is way overlong. I think this isn’t uncommon in a situation where the predecessor is still around, and that it’s really important to put an end date on the former employee’s involvement with her old job to avoid this happening.

      1. the_scientist

        Agreed. I got three days of corporate on-boarding and then 0.5 days of “training” when I started my job. It was 100% trial-by-fire, learn as you go. I did fine- I’m well-suited to this kind of (busy, unpredictable, understaffed) environment, and in retrospect I really don’t know that I would have benefited from more training, because most of my job was things I needed to learn on my own. What I needed to be trained on was straight operational stuff- who to call for X, where to send Y, all things that can be covered in a transition binder, things that a former employee doesn’t need to be there for. I did a lot of admin stuff when I first started, so OP’s replacement probably needs the same type of training.

        On the other side of the spectrum, our former program manager negotiated an eight-week transition period when she left to accommodate hiring and training her replacement. It worked out to about 2 weeks of transition training, and she said in retrospect that 2 weeks was much, much too long and more overwhelming for the new manager than useful. She had put together a really thorough transition binder, and that plus one or two days probably would have been sufficient- not that the new manager would be 100% comfortable right away, but would be able to muddle through and learn.

    2. Angora

      I disagree. Admins do more than repetitive boring duties. We do budget, purchasing, presentations, travel, draft correspondence, etc. please give us some credit here. But I believe the training period should be more than 30 days in most jobs unless it’s something technical, or highly detailed.

      Could be a case of not letting go of the reins.

      1. AdminAnon

        I’m with you on that! Most of the boring, repetitive work in my office falls to the receptionist (thank goodness). My job is wonderful. I draft presentations, work closely with the Board/Advisory Board and the committees of both, coordinate our annual giving drive (non-profit), assist with grant research and writing, coordinate meetings and events, arrange travel, coordinate and attend conferences….and that’s just a Monday. I’m an executive admin to 3 C-level executives, though, so maybe that has something to do with it. But still, my job is far from low-level and anything but boring. It took me a solid six months to even begin to understand everything that was expected of me (of course, I’m the first person in my role, so that could be part of it). There has been some talk recently of a promotion (I’m approaching the 2 year mark) and I fully expect that part of the transition process will involve training my replacement, but I don’t think it will be a quick task.

      2. Student

        To be more specific, admins at my place of employment are very explicitly hired as entry-level staff to do boring, repetitive tasks. They’re essentially paperwork-janitors and workplace-mother-substitutes for us. I’m glad you enjoy your job and it has tasks with more depth, but that’s very atypical in my field. Perhaps my industry is odd. I’d never heard of an admin managing a budget, giving a presentation, or going on business travel, so I learned something new about your field from you.

  8. Fee

    OP – after two months I really think you need to be focusing way more on your new role rather than the new assistant. After all she probably wasn’t offered the job on the basis that you would be there to hold her hand. What if she was replacing you because you had left the organisation? She wouldn’t have the benefit of your skills, experience and advice, but would still be expected to get on and do the job. It’s an added bonus to your organisation that you are still there to offer those, and to give them an honest evaluation of her, but the responsibility for the actual job being done well is now with her and her manager, not you.

    Not sure if it helps to give you a bit of context but I moved through about 8 different admin roles of varying levels during 12 years at Oldjob and my handover periods (each way) were more like a couple of weeks than months!

  9. anon in tejas

    in my last transition, I was no where close to being able to do 100% of my job effectively and efficiently. In fact, it took closer to 6. I worked closely with my boss, and she gave me a lot of feedback. I think that it may be hard to master a job in 2 months. I also think that it may be unreasonable to expect that she’s developed the skills/familiarity with the work to be where you were when you transitioned to your new position.

  10. CaliCali

    Subconsciously, this could be a case of wanting to cling a bit to the job where you’re the expert as opposed to fully moving on to the new job where you’ll be the newbie again. Two months seems a bit long, and I think your efforts would be best expended in learning the ropes of your new position rather than being overly worried about the performance of someone in your old position. I’d follow Alison’s advice, and then let the cards fall where they may. If you’ve given her all the tools and information she needs, as well as constructive feedback, your job is done — and I’d also make that clear to your boss/bosses, since they likely value performance in your new job more highly than having a perfectly trained person in your old position.

  11. soitgoes

    I could go both ways on this one. On one hand, it’s only been two months, and the new hire might still be easing out of “temp” mode (or even scared to put in too much effort and get her hopes up, lest it end up not working out). Is the OP going to be her direct supervisor or be otherwise affected by the new hire’s quality of work? As long as she’s competent, it might be easiest to just say “not my problem” and move on.

    On the other hand, yeah, two months is long enough to know if someone isn’t getting it and/or doesn’t have the capacity to eventually improve. It might be irresponsible of the OP to act like everything’s fine while knowingly passing a problem on to someone else to manage. I guess it depends on how crucial the work is.

  12. Buried the Lead

    The most important advice came at the end of the post. At this point in the training/on-boarding process, the last thing to do is loop-in the manager. Let the new hire know there are issues and give them a chance to correct them. If it remains an issue, then let the manger know. But don’t blindside them with a trip to the boss’s office or a visit from the boss in the first couple weeks with an on-spot performance evaluation! That’s just asking for bitterness.

  13. LuvzALaugh

    You may want to look at what she does when she makes a mistake. Noone is perfect…even seasoned professionals make mistakes it’s how you react when you discover/it is pointed out to you that you made one that would make me comfortable/uncmfortable with someone I was training.

  14. Not So NewReader

    Just a thought: Can you tell her something like, “Pretty soon you will be on your own here. Is there anything you would like me to revisit? Is there anything that you feel we have not touched on and we should?”

    Then just see what she says.
    Reminding a person that they will be expected to do something under their own steam very soon some times provokes an insightful response.

  15. Callie30

    Hi OP – Good advice on here thus far from Allison and others. It is definitely hard without being there. However, I’m wondering if your annoyance with her on a personal level is making you increasingly critical of her? It may be something to evaluate internally as you look at your own management/training style. And it may be something that’s on a sub-conscience level.

    I also find it helps to have a manual with the important protocols of the position, as well, for the trainee to look at for reference (we do that for volunteers). It does take a certain amount of time to get acquainted with a new job and having the training done mostly or all verbally could be problematic – a few months seems a bit long though, but we don’t know the full nature of the position.

  16. Cheesecake

    I know it is hard to train someone to do *your* old job, when not only he is not fully coping (which is totally fine at the beginning), but is also somewhat annoying. I has a similar case, but on top person was supposed to do same job as i did at that moment, only supporting smaller countries. What helped me is realization that i am NOT going to get 2 salaries if after training she performs 100%. So i trained her on necessary things (instead of total hand-holding), told boss my findings, provided some support after and moved on. I think you should “red-alert” your boss only if the person is totally useless/behaves nasty or inappropriate. Otherwise let this go.

  17. OP

    Thank you Allison! Helpful as always. Sorry for the vagueness…I don’t want to reveal exactly what I do in case a colleague recognizes my situation. I did have a chat with our boss, and he was very happy that I came to him. We talked it over (without any nastiness) and while we agreed that the new hire isn’t making the progress he had hoped for, she still has potential and may just need a few more months to get up to 100%. Admittedly, the assistant job has changed since I started, and it’s much more complicated than a “normal” admin position, especially for someone new to our field. He reassured me that her errors aren’t reflecting badly on me and there’s only so much I can reasonably do. I’ve been able to devote most of my time to my new job and am available for any questions the new hire may have, though I’ve noticed few improvements in her memory retention or attitude. I really hope a few more months will be all she needs to succeed in the future, but I’m happy my boss is clear-headed enough to see if something isn’t working.

Comments are closed.