I used to work with someone like that, the way his brain was wired he just didn’t understand what the hell he was doing and had to learn steps by rote.
Once he had the steps down, he could repeat that process perfectly forever, but ask him to change or skip a step and you’d see his brain fry.
He also had a lack of self confidence that seemed to come from being belted for making mistakes before so he was overly thorough.
My suggestion is to reconsider your written instructions to him and really dumb them down like you were were writing to someone with no background or assumed knowledge. The first time you do that, follow up straight away with contact asking if he finds that way of writing more useful on the off chance he thinks you’re being condescending.
IME these “my colleague really sucks” threads always present a very black-and-white picture, both because people generally have difficulty seeing things from other people’s POV, but also because it makes for a more interesting, shorter OP.
Also when someone estimates how much time they waste doing something, they tend to overstate a lot.
I’m not suggesting the OP is doing either of these things.
I’m just saying they should pause before going in to see the boss all guns blazing. Is the situation really as simple as described in the SD thread (or what you tell your friends)?
OTOH, an informal chat about a colleague should be risk free.
So you’re not really working together, you’re just handholding during this never-ending transition?
I think, after two years of this, it would be appropriate for you to tell your own boss that this transition isn’t working out because coworker can’t seem to fly on his own. Mention that this is impacting your own work because you’re still spending time on your old task. You might even ask to have the task reassigned to you, since it’s faster than having to coach Ron (let’s call him Ron) through it every week. And speaking of informal chats - maybe your boss can have a little chat with Ron’s boss about what is even Ron’s deal?
He could be lazy. He could have an actual learning disability, he could do this as some petty power/dominance display, he could be illiterate or nearly so, and so on. There’s no way to be sure what the actual issue is with just the information and behavior that you have.
I think it’s best to approach the issue in good faith (like you have been), so I’d recommend he try some text-to-speech software/apps (there are a lot of free ones) first. If that really helps him, awesome! If not, or if he doesn’t even want to try it, then I’d say it’s appropriate to go to your manager to discuss the issue. Trying to find a solution first (the software) would demonstrate good-faith effort and attempts to resolve the issue before going to him/her.
You’re not his supervisor, manager, mentor, or assistant, right? It’s not your responsibility to do what you’re doing.
I would have given him about two weeks and then told him if he couldn’t make progress on taking over this project, he would need to talk to his manager about it. And that I didn’t have time to both give him directions and then go over the directions, over and over and over and over.
It’s not your responsibility to find other ways to make this understandable for him either - not after two years. If he can’t process the written word, he needs to either change jobs, or take reading comprehension lessons, or otherwise make arrangements to learn how to do so. I.e., if he can’t understand email directions, HE or his manager should be the one figuring out a way to only get directions orally.
If he’s doing this to you, he’s probably doing it to everyone. How many hours are wasted holding this guy’s hand? Some people just aren’t cut out for a certain job. Maybe he’s one.
Two years you’ve been transitioning this project?? I can’t even.
A few have suggested the OP’s memos may be need to be clearer. That is contradicted by this information.
Instead, you bend to the will of others. And the others know it.
This. Seriously, this is not your problem at all. Inform your supervisor.
The problem guy’s alleged “lack of confidence” may be from the very fact that (apparently) he isn’t good at getting information from written communication. Obviously his productivity is limited by that.
I think sending him some voice message is a poor idea. It’s just giving in to the problem. But if you must, don’t use voicemail. The usual voicemail doesn’t allow you to keep a copy of your message, so that’s a bad idea, because sure as shooting, he will say, “You didn’t say that” and you will need something to cover your ass. Send some kind of voice message you can keep a copy of.