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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?
What the Experts Say
Even if you’re not the type of person with a tidy desk and an ordered to-do list, it can be frustrating — not to mention stress inducing — to manage someone who’s disorganized. “You’re not sure if the other person has dropped the ball or even if they are going to hit the deadline, and so you may feel anxious,” says Elizabeth Grace Saunders, author of How to Invest Your Time Like Money. It may be hard for you to fathom that other people operate this way. “One of the biggest reasons you’re frustrated and upset is that it’s different,” she says. Addressing the issue may be a challenge, but it’s often necessary. Your goal, says Linda Hill, a professor at Harvard Business School and the coauthor of Being the Boss: The 3 Imperatives for Becoming a Great Leader, is to express, “what your team needs” and “what you need as a boss to be as productive and effective as possible.” Here are some strategies.
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.
Next, consider “the root cause that’s driving this behavior,” says Hill. 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 ADHD or another issue that makes staying organized even more challenging. Summoning compassion will help you approach your employee “without judgment and without blame,” adds Saunders. 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, says Saunders. 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. Saunders recommends saying something like: “When the deadline is Friday, and you don’t get me your part of the project until 11 PM, I feel anxious because I can’t give you feedback. So, from now on, I’d like you to send me your piece by Thursday morning so that I can look at it and make adjustments if needed.” Remember, as the boss, there “are things you can ask for.”
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,” says Saunders. 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,” she says. 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 could make sharing best practices a team effort, but don’t go overboard. “Sharing is good, but it shouldn’t be a directive. People’s brains are wired differently, and there needs to be room for flexibility.”
Offer career advice
Rather than reprimanding, Saunders recommends appealing to the self-interest of your disorganized employee. 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,” she says. “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, says Hill. “Ask them to think about how they are perceived,” she says. Even if your employee is able to get their work done in a haphazard fashion, other colleagues may not appreciate the chaos. She suggests using the cluttered desk as a metaphor. Say something like: “When people — colleagues and clients — look at your messy desk, they might think you are overwhelmed. It’s not in your best interest” to have them see you this way.
Break down assignments
One of the most common characteristics of disorganized workers is an inability to properly allocate their time to particular tasks, says Hill. “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,” says Saunders. At the beginning of a project, she suggests you and your report sit down together and, using a white board, lay out “project management milestones, goals, and deliverables.”
Finally, understand that there is no quick fix for this problem. “I’ve seen many people get better at this, but it’s hard and it takes a lot of time,” says Saunders. 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,” she says.
Principles to Remember