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 ...
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.
If I said something very direct like "Sending multiple one word emails in succession clutters everyone's inbox. Instead, let's use Slack for communications of that kind from now on. (Insert link to company's guide for installing Slack app and logging in)." Would that be too harsh or unprofessional?
Not at all.
It reads as polite as possible (in fact, it ...
"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 ...
Throughout your working life, there are going to be a lot of situations where people above you who are not your direct supervisor are going to ask you to do things.
This is something that you will have to get used to.
Yes, the proper procedure would have been for the "upper boss" to contact your supervisor and clear it with them. However, you have to be ...
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 ...
It's a good sign - you have useful skills that have come to the attention of someone in a position of authority! Just make sure your own boss is aware of any requests that come in, it's up to him to take it up with the other boss if he has an issue with it.
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 ...
I plan to resign. I simply feel terrible from not being able to keep up,
First of all, it seems like you are under a lot of stress and you already made your decisions to leave. You decided to put your own mental health first, which is the right thing to do, as your well-being is absolute priority.
so it is also what I deserve. No one is asking me to ...
it wasn't a problem until recently, as he used to sit a fair distance
away from me.
What's the best option in this situation?
Ask management if you can move your desk a fair distance away, so you are back to the situation where it wasn't a problem for you.
That's the simplest solution to your problem.
First Question: Do I ask for a raise for myself and my "integral employee"?
When you feel underpaid, you should seek a raise. There is nothing wrong with informing your boss that you believe you're worth significantly more and are unhappy with how your paid. You can inform the owner that you will look elsewhere if you don't get an adequate raise as long as ...
IMHO, best way to accomplish this task is to get your / his manger involved in the issue
It can be done directly or indirectly,
You and few colleagues can mention it to manager on several occasions or as group letter
If manager frequently will be exposed to his way of communicating and will be bothered by it, he on his own will request style / medium ...
The problem of Sales and Marketing over-promising is not something you can control. A career strategy that depends on preventing over-promising may not be realistic. You could encounter similar problems in your next job, and turn into a job-hopper as you resign each time.
Instead, I suggest working out strategies for coping. Concentrate on the things you do ...
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 ...
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., hen you are pretty much out of options. However, otherwise look out for the ...
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.
Do this once ...