Employee trains her replacement for 3 months, replacement constantly asks her questions 6 months into the job: 'My old boss has also told me multiple times that he wishes I was still there.'

Author image for Emmy Pratt
Emmy Pratt • Writer and Editor
Feb 5, 2026 11:00 AM EST

She needs to ignore her emails and let her sink or swim.

It shouldn't take you months and months to get the basic hang of your job. It takes around a year to fully figure out your role in the company, and it's okay if you're not literally an expert on all of the happenings of the company six months into your position. Heck, it might even take a few years to feel like you've completely gotten a grasp on what you're doing in your job. That's why it's not great to job-hop every year. If you can grow into your role instead of speedrunning it and leaving at the first sign of strife, you're going to learn a lot more about yourself as a professional. Unless you're really good at every job you get right off the bat, you shouldn't leave a job you don't even have a full grasp of to begin with.

You shouldn't feel like you have to be the perfect employee immediately, but if you can't master the basic everyday tasks that go along with your position within a month of getting hired, it just might not be the job for you. It's common for trainers to tell their trainees, "You can ask me anything; there are no stupid questions." While that might be true in the early stages of training, there comes a point when the trainee needs to stop asking questions and start using their noodle to solve problems. 

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  • Two women sitting at a table looking at a book
    via Pablo Merchán Montes (Unsplash+)

    Image is representative only and does not depict the actual subjects of the story.

  • The employee in this story was tasked with training her replacement. She was being moved to her company's sister organization after her company was acquired, so it isn't like she was fired and had to train her replacement. Unfortunately, her replacement has been a real lemon and won't stop asking her questions about the job months after she left.

  • Am I wrong for refusing to help the person who was hired to replace me?

    A few months ago my company got acquired and I was moved over to a sister company.
    via u/Supmeg_
  • We knew it was happening ahead of time, so I spent about 3 months training my replacement before I left.
    via u/Supmeg_
  • I didn't just show her things once and leave. I made step-by-step how- to guides with screenshots for the harder tasks, walked her through processes multiple times, and told her she could reach out if she had questions after I moved on.
    via u/Supmeg_
  • A group of people sitting around a wooden table
    via Pablo Merchán Montes (Unsplash+)

    Image is representative only and does not depict the actual subjects of the story.

  • It's now been almost 6 months. She is still emailing me constantly with questions. And I mean constantly.
    via u/Supmeg_
  • A lot of the time it's things that are in the guides or things we went over more than once.
    via u/Supmeg_
  • Stuff that, honestly, feels like she could figure out if she tried. The part that really gets me is that if I don't answer right away, I often get another email from her saying "never mind, I figured it out." So she clearly can figure it out.
    via u/Supmeg_
  • She just seems to ask me first instead of trying. My old boss has also told me multiple times that he wishes I was still there because she hasn't really gotten the hang of the role, which makes this feel even more awkward.
    via u/Supmeg_
  • What's messing with my head is that when I started in that job, I replaced someone who had been fired.
    via u/Supmeg_
  • An upset and sad young Asian unemployed businessman is sitting on the stairs in front of the corporate office with a box of his personal stuff after losing his job
    via Getty Images (Unsplash+)

    Image is representative only and does not depict the actual subjects of the story.

  • There was no one to train me. I had to learn everything myself, including things I had never done before in my career.
    via u/Supmeg_
  • I figured it out by reading, trial and error, and just using my brain. So part of me feels like she's leaning on me in a way I never had the option to.
    via u/Supmeg_
  • I offered to help after I left because I wanted to be kind and professional during the transition, but now I feel like I accidentally became her ongoing support person.
    via u/Supmeg_
  • I don't work there anymore. I'm not being paid to train her. And every time another email comes in, I feel more and more annoyed.
    via u/Supmeg_
  • But at the same time, I did say she could reach out with questions, so I feel guilty suddenly wanting to stop answering.
    via u/Supmeg_
  • AITA if I set a boundary and stop responding because I feel like at this point she needs to start thinking things through herself instead of defaulting to asking me?
    via u/Supmeg_
  • analogascension Dont message her, message her boss saying that she's still asking the most basic of questions six months later. Clearly the hire was a mistake. NTA.
    via u/analogascension
  • justanother1014 NTA. You could begin forwarding every email to the old boss with the note, "I'm available for $/hr for consulting. In lieu of an agreement, I think you should be aware of how much your employee reaches out for help on simple tasks." ETA: op says "I don't work there anymore" which I presume means the company, not just the department. If you still work for the company, go see your former manager to discuss in person because, at the very least, constant emails over 6 months distract
    via u/justanother1014
  • AntiquePop1417 6 months? 6 months? Are you for real?
    via u/AntiquePop1417
  • HotSalt3 NTA. Just reply to her with a professionally worded email that you are no longer able to provide her support for her position as it has been 6 months since you left. Wish her the best moving forward and then forget about it. You've already been more than accommodating. As a sidenote, make it a goal for yourself to get better at setting professional boundaries. Right now you're letting her abuse your kindness to your detriment.
    via u/HotSalt3
  • monyxara You created a comprehensive training guide, not a 24/7 support hotline. She's treating your inbox like it's Siri for her job and you're not getting paid for the subscription
    via u/monyxara
  • 1039198468 NTA: Is this taking time away from your current responsibilities? have you spoken to your current manager? What is their opinion?
    via u/1039198468
  • standardissuegreen NTA. OP, you need to learn to let emails go unread.
    via u/standardissuegreen
  • jdo5000 I mean YTA to yourself for letting it go on this long. Just tell her straight you have your own job to take care of and if has issues she needs to talk to her boss, not you.
    via u/jdo5000
  • BelliAmie I would not respond for at least 3- 4 days. Most of the time she will figure it out. The more you do this, it will teach her to be self reliant. Eventually, she will stop emailing you because she will realize it would be faster to look it up rather than ask you. When you do finally respond, direct her to the manual where the question is answered. Don't actually answer the question. Again reinforcing the notion that she is already in possession of the answer. Nta
    via u/BelliAmie
  • CMeNaught Ask A Manager's standard advice for situations like this is that you should stop responding to each request right away. Leave a deliberate pause, long enough that your reply will no longer be helpful, then reply saying that you were too busy to get to her issue and you hope she figured it out. By making yourself a less convenient, immediately available resource, you train her to stop relying on you for answers and start doing the legwork herself. Also, if this is taking time from your
    via u/CMeNaught

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