can I teach a very disorganized employee to be more independent? — Ask a Manager

A reader writes:

I have a question about helping my employee get organized. She has two pivotal job duties which are closely tied but not directly linked — I could technically have two people doing each piece separately, but the volume as a small business doesn’t warrant that number of employees. Think the relationship between taking orders and billing/collecting for orders, but not producing the product.

Lenore is great at taking the orders — we almost never have an issue with making sure we got the order and it’s complete. There’s still some handholding she needs after three years, but overall, like I said, no issues here. The billing and collecting for the orders, however, is a bit of a problem. Continuing this overly simplified example, if a person pays their bill on time without question, then Lenore has no issues. She can take the payment, enter it into the system properly, done. But there are three problems:
• keeping track of the orders that have not yet been paid and chasing them down;
• remembering what she has previously done regarding trying to get paid on that account; and
• remembering how to do the stuff that is more complicated — I often have to sit with her and guide her step-by-step, mouse-click-by-mouse-click repeatedly.

I love her, and as far as work ethic and loyalty to the company goes, I wouldn’t fire her for the world. But this is DRAINING me. I am picking up the slack AND losing the time to do my own job. I think it’s important to note that I was promoted from the role that she is doing and while there were times where it was a lot of work, I usually found that with good organization and task management, I didn’t have any major issues.

I see two major problems that no matter how I try to deal with them, I can’t find the right solution. First, time management. I have worked with Lenore to come up with a monthly schedule to work around (since tasks tend to have a monthly routine), then working on other things at down times, but she can’t stick to it — she can’t even remember it. We’ve put it on a literal calendar, but she misplaces it. We hung it on her wall and she just forgets it’s there.

Secondly, organization as a whole. Lenore’s desk is littered with papers. She just puts things in piles. When I ask for something, she has no idea where it is. She’s digging through piles opening drawers, going through folders, flipping through several notebooks. She has no idea where anything is and no memory of what she has done with the tasks. I have sat with her and asked her what would be helpful, and she always says, “I have no idea.” I helped her organize into neatly labeled folders; she has a file drawer and a file tower sorter. I have tried using the task management system that is built in our software, and I have tried Asana. I have tried an online Kanban board (my personal favorite). I have tried a tabbed notebook. She doesn’t use ANY of the tools. She likes the idea of using them but then just … doesn’t. It’s like she puts it down after using it once and forgets it exists. When I ask her about using them, she just says something like, “Oh, I forgot about that. Where did I put it?”

I know she has a lot going on in her personal life and I want to be sympathetic, but that can only go so far.

What are other organizational tools I can give her so that she can be more independent? Especially those that are not electronic/computer based. Can you teach organizational skills and time management skills, and if so, how?

Sometimes you can teach organizational skills and time management. Other times you can’t — at least not in the amount of time that’s reasonably available to a manager.

You’ve tried all the things you should try with Lenore, but you can’t be more invested in getting her organized than she is … and right now, she doesn’t sound that invested in it.

Is there any chance that’s because she doesn’t realize that the level of support you’ve been providing — all the coaching and training and suggestions — isn’t something you want to be providing? Is it possible she doesn’t realize she’s performing way below the job’s requirements? I’m curious how clear you’ve been with her about that, because there’s a lot in your letter about all the coaching you’ve tried but nothing about any serious conversations where you’ve told her that she’s not meeting your expectations in key areas … and that the amount of support you’ve been providing is an effort to help her keep her job, not something that you can sustain long-term.

At this point, you’ve got to be very clear with her about those things. Rather than investing more and more time in trying to figure out the magical system that will finally work for her, focus less on the “how” and more on the “what” — the outcomes you need — and let her know that she needs to figure out how to get there. You’ve made lots of suggestions, and she can try those or she can develop her own systems. But the message needs to be: “Right now you’re not meeting the basic requirements of the job, and I can’t keep you in the job if we can’t solve this.”

Then, be specific: “I need you to come up with systems to follow up on orders that haven’t been paid yet, to track what’s previously been done on each account, and to remember what needs to be done throughout the month — as well as systems for knowing where papers are, so that when I ask for something, you’re able to quickly find it. I’ve suggested a lot of methods and you could try any of those, or you could find your own — it doesn’t matter what system you use, but I do need you to be on top of all of this. I also need you to figure out how you’ll remember the steps for doing things like X and Y since I can’t sit with you each time and walk you through it.. I can walk you through it one more time while you take notes, but after that you will need to manage it on your own.”

I do think you need to be prepared for the (strong?) possibility that Lenore simply isn’t a good fit for this job. Work ethic and loyalty are great, but they aren’t enough on their own. If she doesn’t have the skills to do the job, even after the extensive coaching you’ve provided, you’re better off figuring that out and bringing things to a relatively swift conclusion than continuing to invest more and more time, while you get more and more drained and don’t have enough time for your own work. At a minimum right now, you should be looking into what your company’s processes are for handling it when someone isn’t able to perform at the level needed, and start laying some of that groundwork. (For example, if you’re required to do a written performance improvement plan, start working on that now so that you’re not starting from scratch in two months.)

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