Managing a disorganized employee is often a maddening experience. How can you help your scattered direct report develop better systems? How can you drive home the importance of staying on top of meetings, calendars, and emails? And is it even possible to help a person overcome a natural inclination toward disorder?

Reflect on the size of the problem: First, “be clear about the cause and effect” of your employee’s disorganization, says Hill. Start by looking at how it manifests itself. “Are there piles of paper everywhere? Do they miss deadlines? Are they always late to meetings?” Then think about how your employee’s behavior “interferes with the team’s performance.” Ask yourself: “Is this person’s approach creating negative outcomes, or is it just a style difference?” If your report is “disorganized but otherwise reliable, you may have to back off,” she says. Saunders agrees: “Figure out which issues are negotiable, and which are nonnegotiable.” For example, how messy your employee keeps their desk — no matter how much it grates on you — is, in most cases, probably not that big of a deal.

Be empathetic: Consider the root cause that’s driving this behavior. Has your employee always been this way? Or is this behavior new? Be empathetic and understanding. You might not know the struggles that this person is going through to be productive. It’s possible that your direct report struggles with Attention Deficit Hyperactivity Disorder (ADHD) or another issue that makes staying organized even more challenging. Summoning compassion will help you approach your employee without judgment and without blame. At the very least, recognize that neatness is not everyone’s forte. It may be easy for you, but it’s very hard for some people. A little humility goes a long way. Keep in mind that you’re not perfect either.

Talk to your employee: If your employee’s tendencies are damaging the team’s productivity, you need to say something, Help your employee grasp the impact and consequences of their disorganization. Perhaps because they miss deadlines, the company ends up going over-budget on a project; or maybe it creates a crunch for other team members down the road; or perhaps it looks bad to clients. Talk to them about ways to remedy the situation. Say, for instance, that you prefer things to be done in advance, while your direct report tends to procrastinate until last minute.

Share best practices: You can help your direct report through modeling. You might talk through your systems and explain to your employee how you keep track of things. This could include things like your project to-do list and your filing, labeling, and review system. There may be simple things that you do that the other person hadn’t thought of. One thing to bear in mind: people with messy desks tend to be more visual and therefore they tend to do better with a paper planner or whiteboard, rather than an Excel spreadsheet. You can make sharing best practices a team effort, but don’t go overboard

Offer career advice: Rather than reprimanding, appealing to the self-interest of your disorganized employee could be of great help. Helping them understand how improving in this area will benefit them will make it more likely they’ll want to make changes. Typically, disorganized people end up compensating by working extra hours. Tell this person you don’t want them killing themselves by doing that. You might also point out the impact their disorganization has on how they are perceived by others. Ask them to think about how they are perceived. Even if your employee is able to get their work done in a haphazard fashion, other colleagues may not appreciate the chaos. Let them appreciate the fact that clients and other colleagues may be of the impression that they are overwhelmed and it is not the best for people to think of them in that manner.

Break down assignments: One of the most common characteristics of disorganized workers is an inability to properly allocate their time to particular tasks. They can’t prioritize because they don’t even know where to start. If this is the case with your employee, help them learn how to break down their assignments into smaller chunks. At the beginning of each project, design a checklist and populate every action point or deliverable. Monitor and evaluate when necessary.

Be patient: Finally, understand that there is no quick fix for this problem. I have seen many people get better at this, but it’s hard and it takes a lot of time. Don’t get short with your disorganized employee, particularly if they are trying to get better. Instead, acknowledge their efforts and celebrate their achievements. You need to appreciate it when they do show up on time or hit a deadline.

Disorganized people can get better with time, we are made who we are based on nature and nurture, environmental impact on people can be of a disadvantage to them. Coaching and mentoring can help them turn things around. It may require time but it will be worth a try.

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