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I am networking to change jobs. I want to train a replacement at my current job. I have identified the person. I need to have more one-on-one time with that coworker, but it is challenging to arrange.

My bosses cannot know that I am considering leaving, because they will make my worklife miserable.

I want my coworker to be well established to fill my role and be in line for promotion and a good opportunity after my departure. We are not close, but I know that they are in such a situation as to benefit greatly personally and professionally. So I also do not want to let them in on my plan. Especially as it may cause bad repercussions for them if they are found to knowingly go along with my plan.

Having them well trained will also minimize any stress to my employer, though they may not appreciate it, if they knew my plan now. How can I give my coworker the training in the time I have left?

I'm concerned if I propose training someone, the company would never select the individual I have in mind. They like to create paths for their 'favorites'. I want to disrupt that unfair practice by creating a formidable replacement that cannot be argued against and is not going to perpetuate partiality. But perhaps I'm becoming the thing I hate, but being partial myself? I just realized my folly.

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    Comments are not for extended discussion; this conversation has been moved to chat.
    – Neo
    Aug 18, 2019 at 19:02
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    Any reason why you can't propose them as a replacement when you hand in your resignation and use your notice period to train them (if your employer agrees to that)?
    – Leon
    Aug 19, 2019 at 9:38
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    “perhaps I'm becoming the thing I hate” — I'm not sure about that, but your question could be summed up as “How can I get several other people to do their jobs in exactly the way I want, without them realising?” At best, that's a really, really ambitious goal. At worst, it's manipulation of people's livelihoods to satisfy your own preferences.
    – Paul D. Waite
    Aug 19, 2019 at 10:34
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    "My bosses cannot know that I am considering leaving, because they will make my worklife miserable." If they are that petty, then why do you care? Get another job, give them the notice you are obligated to give, and let them deal with the consequences.
    – Davidmh
    Aug 19, 2019 at 12:28
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    I care about some of my colleagues.
    – user107558
    Aug 19, 2019 at 13:12

12 Answers 12

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Start working with the person where you can

Several answers suggest dishonesty. I would however stay away from that if you can, especially since it may not even be needed.

If you have absolutely no opportunity to work with the person, or have no reason to ask them to pick up work, then you are pretty much out of options. However, otherwise look out for the following situations:

  1. When you have collaboration moments, try to use these for things that are important to transfer.
  2. If you have the chance to ask the colleague to pick up any work for you, just ask them to pick up the stuff that will help them build knowledge.
  3. If you are in a position to help/do work for the other person, make sure to do this in a way that helps them understand what you are doing as well.
  4. When you are together, talk about work. It is no real substitute for doing, but it can help build understanding and knowledge allowing them to pick things up quickly later. On top of this, it also helps the other person know what they would be getting into.

Especially if the person is eager/junior to you, these kinds of things should simply be seen as nice opportunities from their perspective. And assuming they are not doing things that are really outside their responsibilities, the manager will likely not be bothered by it as well.

If all goes well, and the person is growing to be more capable you can ultimately recommend them as a replacement to management based on what you have seen them do. However, keep in mind there is a fair chance the management will still overrule your suggestion, in which case you should show your professional side and train that person to the best of your abilities.

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    Absolutely. There is another answer which is short, to the point, and correct, which is the answer that anyone in a similar situation should choose. And OP obviously as well.
    – gnasher729
    Aug 19, 2019 at 9:14
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    It's not just that the management can overrule your choice. You may be setting up your chosen successor for a world of hurt. If the management has someone else in mind for the position, that means that there now are two people with a "claim to the throne", and the easiest way to resolve such a situation may be to let one of them go. Your favourite coworker can get fired as a direct consequence of your undercover training.
    – TooTea
    Aug 19, 2019 at 9:36
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    @TooTea really? Easiest way is to fire them? That then leaves management with another position that they've got to hire/train for. Regardless, if two people go for the same position, and management does decide to hire one and fire the other, I think the co-worker is best off not being at that company in the first place!
    – crazyloonybin
    Aug 19, 2019 at 10:12
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How can I give my coworker the training in the time I have left?

You don't, this is your boss's job to assign not yours. When you resign from the company, your boss will decide who ( if anyone ) will be trained to fill your role. They will also decide if you will be the one doing the training or not.

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    And employees make management harder when they take it upon themselves to try to do it instead.
    – Lightness Races in Orbit
    Aug 17, 2019 at 19:39
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    Exactly this. If OP wants to be a "good citizen", they can start documenting the systems and knowledge that they have. Start writing lots of documentation on the wiki... when you leave, refer the boss to the wiki
    – vikingsteve
    Aug 19, 2019 at 7:32
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    Everyone wants to assume they are irreplaceable. I'd say the company did a good job fooling you if you feel like that. They'll continue on with or without you there.
    – Dan
    Aug 19, 2019 at 14:34
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    @vikingsteve +1, this could be its own answer. OP said in a comment on the question that they "care about some of [their] colleagues." This will help ALL of them, not just the chosen replacement (who likely won't be up to speed by the time OP leaves, even with the added training time they're hoping to orchestrate).
    – zr00
    Aug 19, 2019 at 18:45
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Present the training activity to both the trainee and your managers as improving the bus factor. It is prudent to have at least two people capable of doing any job.

Talk to your manager first, so that you are certain who they want you to train.

Training the wrong person could create an extremely difficult situation when you resign. Training person X would make them expect to be your successor, and leave them feeling resentful if your manager prefers person Y. Your X training effort would have been wasted, and you would have to do hurry-up training of Y during your notice period.

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    They would select a different person for the training. I have a particular person in mind.
    – user107558
    Aug 16, 2019 at 16:40
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    @RR2 I have expanded my answer in response to your comment. Training anyone other than your manger's choice would be inappropriate. You can recommend, but ultimately selecting your successor is your manager's responsibility, and not something you should try to preempt.
    – Patricia Shanahan
    Aug 16, 2019 at 16:50
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    Looping the relevant managers in on any training/skill sharing/etc schemes is also important as they may have more knowledge about your coworkers and the business's long-term plans and goals than you. - You also don't want to get caught in the awkward spot of having independently focused on skills development of a junior coworker who then jumps ship with their 'new and improved skills' before you get around to leaving...
    – TheLuckless
    Aug 16, 2019 at 21:55
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    @RR2 Yes this, and if simply saying it will improve the bus factor doesn't convince them, try saying there's a rising trend that you're getting more work than you're confident in accomplishing, that one of these days you will have to start choosing what to do instead of what to do first. You would like a junior to delegate some low hanging fruit to so you can focus on the larger issues with less interruptions, and person X seems capable enough.
    – Kevin
    Aug 17, 2019 at 12:24
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    Perhaps in your next job you will have the privilege of making these decisions, @RR2!
    – Lightness Races in Orbit
    Aug 17, 2019 at 19:42
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Don't make plans for other people or assume you know what's best for them.

This includes the colleague you want to train to be your replacement, and your employer.

You've got good intentions here and that's commendable. But the fact is, your version of what people will want to do once they learn you're leaving is likely wrong.

For instance, it's very possible that your colleague simply isn't interested at all in doing your job. Or perhaps they're planning to leave themselves. Or even if they'd be interested, the employer would have no intention of promoting them into the position anyway. Or, maybe with you leaving they'd restructure the team(s) and your position would cease to exist. The list goes on.. you just don't know what will happen. What you see as an obvious opportunity, worth twisting yourself in knots to give to your colleague, may just turn out to be nothing.

If you want to leave, and want to give your colleague the option of the opportunity to replace you, then secure another position first and then do the following:

  • Give your contractually agreed notice to your employer. Mention nothing about your colleague at first, but ask them if they're OK with you telling people straight away.
  • If yes, then go to your colleague and ask them privately if they'd be interested in your job.
  • If yes, suggest a handover training plan to best prepare them for this. Make sure they know this is you suggesting this, not the employer, and you'll suggest it to the employer if they agree.
  • Only if they are OK with it, then go back to your employer, sell your colleague as a good potential replacement, and suggest the handover plan.
  • If your employer agrees it's a good idea, implement it.

Assume nothing. Do everything in the open. Make suggestions, sure, but let everyone involved take their own decisions about what will happen at every stage before you proceed.

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"Getting hit by a bus"

You're training someone to do what you do so that if you're out sick one day, get hit by a bus, or have some other emergency your company has someone ready and trained to fill in your role until you come back (or don't).

Its just a level of insurance that your company's management should see as a "good thing" not something to fear that you're intending to leave. It just so happens to let you extricate yourself without leaving the company in the lurch when you do hand in your resignation.

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    yes but that would be another bus :)
    – brett
    Aug 17, 2019 at 13:40
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    @Abigail You training one replacement might not change the bus factor after you leave, but that's not your problem. To your superiors you're changing the bus factor from 1 to 2 (you leaving is the bus from their perspective).
    – Draco18s no longer trusts SE
    Aug 17, 2019 at 15:36
  • "you're out sick one day, get hit by a bus, or have some other emergency" Or get promoted, or get another job within the company.
    – Acccumulation
    Aug 17, 2019 at 21:41
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Before all of that surreptitious training the easiest and best way to do this is to write a whole bunch of great documentation and comment your code. That way no matter who gets picked after you're gone will have a good starting position. Even the person that comes after them will benefit (especially if it is kept up to date.) You also won't need to worry so much about training them up yourself, they can learn after you leave.

But if you really want to try to secretly train this specific person you'll need to get them to start working on the system. You could try claiming illness or just being overworked and ask if they could cover just this one "little task" for you. Start getting them to work on little bits of the system. Let them ask you a bunch of questions about it.

This isn't really a morally okay thing to do. Your co-worker isn't going to appreciate it while you're doing it. You may get in trouble for not doing your own work. The only way (except for good doco) that they will learn about the system is to work on it. So you'll need to find some way to get them to do that. (Alternatively just tell your co-worker what is going on and let them study the system and ask you questions. As long as they won't tell your boss.)

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  • Not sure how to vote as I like the documentation part, but think that feigning illnes etc. is not an appropriate recommendation. Have tried to provide an alternative to the second part of this answer here: workplace.stackexchange.com/a/142373/19191
    – Dennis Jaheruddin
    Aug 18, 2019 at 11:19
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    Who anything about code / software development?
    – Peter Mortensen
    Aug 18, 2019 at 17:05
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    This job might have nothing to do with coding.
    – ruohola
    Aug 19, 2019 at 14:45
  • Documenting what you do has nothing to do with code per se. Just write stuff down, don't worry about the specifics
    – user90842
    Aug 19, 2019 at 19:04
  • I could've sworn they said something about code in the question but on rereading it I was mistaken. Regardless, documentation is a good thing. Though maybe my answer is less directly helpful than I thought. (Probably just my own biases bleeding in since I'm a software developer...)
    – Mike D.
    Aug 21, 2019 at 21:54
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Document, Document, Document.

This is something you should be doing anyway, but if you don't, write down the things that you do as part of your job. Write down all the details, all the things that you hit your head against, how to overcome them, basically anything that you'd give to anyone you would consider training. It is not a replacement for training but it will make the training process that much easier when you do leave. It's also easy enough to use as a cover as 99% of the time, documentation needs no explanation as to why it might be a good idea.

You have no control on who replaces you

When you leave, the documentation will likely be picked up by the person the company chooses to replace you. This may align with your pick, it may not. You don't have any hope of changing this, especially post-departure.

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My bosses cannot know that I am considering leaving, because they will make my worklife miserable.

I want my coworker to be well established to fill my role and be in line for promotion and a good opportunity after my departure. We are not close, but I know that they are in such a situation as to benefit greatly personally and professionally. So I also do not want to let them in on my plan. Especially as it may cause bad repercussions for them if they are found to knowingly go along with my plan.

So your plan is to sneak around and be deceptive, both to your bosses and your colleague?

That doesn't sound like a good plan.

I can understand your not wanting to tip your hand to your bosses, but involving your colleague in your plan without their knowledge is deceptive, dishonest, and could potentially put their job in jeopardy.

I'd caution you to rethink your approach to this issue.

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    "Don't worry boss man, I trained Bob! He knows all about it!"
    – Dan
    Aug 16, 2019 at 16:28
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    I do not want to deceive anyone. I do not plan on lying. I do not think this information is something they have a right to. Why is that deception?
    – user107558
    Aug 16, 2019 at 16:38
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    I'll give you several types of dishonest behavior that I think apply here. Look them up: 1. Lying by vagueness or ambiguity. 2. Lying by omission. 3. Withholding. 4. Tacit dishonesty.
    – joeqwerty
    Aug 16, 2019 at 16:47
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    In order to be any of those things (lying by...), it needs to be deceptive. I have not seen any deceit on the part of @RR2. The only thing I've seen is a desire to help an underdog have a chance. You can call it whatever you want but the normal practice that OP is trying to disrupt, promoting the golden boy at the expense of everyone else, is the only unfair thing here.
    – Aaron
    Aug 17, 2019 at 4:21
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    This is a very strong reaction. Would you have the OP tell his employer that he is looking for another job? Almost everyone on this site would advise against that until OP is ready to give notice, but withholding that is deceptive, no?
    – Summer
    Aug 17, 2019 at 19:22
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Think a bit further. You are trying to train person X. Person X will interpret that as you wasting their time. X will go to their manager and say “this guy is wasting my time, please stop them”. Now your boss finds out, and you are in the worst possible position. Worst case X or someone else gets your job immediately. Because your boss will figure out you were leaving, and going behind his back by training someone he wouldn’t consider as your replacement.

PS. Reading your other posts where you say that you have so many projects that you cannot finish, I can't help wondering that this project trying to teach someone your job without being asked isn't just procrastination?

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  • If that person would actually complain about learning something, they would obviously be an unsuitable person for the job, and not worth training. Let's give the OP a bit more sense than to pick someone like that
    – user90842
    Aug 19, 2019 at 19:02
  • @GeorgeM The person wouldn't complain about learning how to do their job better. They would complain about having to learn some job that they have no intention to do and that they likely will never do. If my manager tells me "X is leaving, you'll have to learn his job", fine. If a coworker steals my time to learn things that have nothing to do with my job, I complain.
    – gnasher729
    Aug 19, 2019 at 21:44
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  • Would having someone review your documentation help you in you make them clearer?
  • Would having your code reviewed help reduce bugs?
  • Would having someone who could fix problem while your are on holiday help your employer?
  • Would having another developer try building the software their machine help check the company can recover from a problem with your machine?

Is there any think else that needs to be done to train a replacement?

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You don't because the only ethical way to do what you suggest is if you could train this person on your own time, on your own equipment, outside of business offices. Or if your employer has a loop-hole allowing you to spend hours training people however you like which it doesn't sound like.

But perhaps I'm becoming the thing I hate, but being partial myself?

Absolutely. The fact you have your job proves that your employer is not as bad as you paint them. Unless you're saying that you don't really deserve the title/role you have. So we know that they aren't always bad & that they (according to you) aren't always good. That describes like 99% of the employers people actually want to work for, you know.

At any rate it's your employer's prerogative to manage employee positions. Not yours. Sometimes employers ask employees for advice/opinions on promotions but that's not the case here. Maybe if you told your employer that you're leaving they would give you the opportunity to help them train/select someone. Obviously you'd also face the risk of being shown the door before you want.

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Tell your boss you are quitting. They really can't do much to make your life hell. Just work your fixed hours at a regular pace and go home. Make sure to use all your holiday before you leave. As you are the one leaving, you have a lot of power. Your boss will want you to train a replacement. If they treat you badly, you will just leave.

EDIT

Do this once you find a new job, not before.

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    They can do illegal violent stuff to you and/or your property without any realistic way for you to respond if the premises are solely monitored by the company and the person in question is a sole proprietor-- getting evidence of any foul play is next-to impossible and if the foul play creates only civil rather than criminal liability acting on any evidence even should you eventually win your case and somehow get more back from the lawsuit than the process cost will nonetheless seriously hinder you from getting a job in the future.
    – Please stop being evil
    Aug 17, 2019 at 20:37
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    They can also verbally abuse you, cut your pay, reassign you to dangerous or unpleasant work, or otherwise engage in constructive firing practices. Maybe they can't make your life hell legally (though that very much depends on jurisdiction) but, at least in the US, making your life hell once they know you are leaving is almost typifying of bad employers.
    – Please stop being evil
    Aug 17, 2019 at 20:39
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    They can't verbally abuse you. You just walk out. They can't doing anything violent without it becoming a criminal matter. If you are that afraid of your workplace, just don't go back.
    – David
    Aug 18, 2019 at 0:06
  • @David: Who has the burden of proof?
    – Peter Mortensen
    Aug 18, 2019 at 17:07
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    I like the first part of this answer and feel this is almost the correct answer. However, I do not recommend using leave as typical American company will give it to you so it's a nice bonus as you depart but most companies do not allow you to use leave during your notice period. So check before you use it.
    – Dan
    Aug 19, 2019 at 14:39

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