By Rebecca Knight

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.

Be Empathetic 

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 the 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.”

Be Patient

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 

Do:

• Determine whether your employee’s organizational challenges are impacting performance.
• Explain how improved organization is in your employee’s best professional interest.
• Summon compassion. You might not know the struggles this person is going through to be productive.

Don’t:

• Coddle. Help your employee grasp the impact of their disorganization and the consequences it has on the team.
• Keep your own organizing strategies to yourself. Share how you stay on top of things with your employees.
• Be impatient. Progress takes time so acknowledge your employee’s efforts and celebrate their achievements

Case Study #1: Help Your Employee Understand the Impact of Their Disorganization and Offer Professional Advice

Amy Brachio, a partner at EY Global who specializes in risk management, has supervised several disorganized people over the course of her career.

One individual — we’ll call him Zack — stands out. “Zack’s disorganization showed up through a lack of discipline in managing his calendar,” says Amy. “As a result, he disappointed team members and clients by cancelling at the last minute or unexpectedly missing meetings and deadlines.”

Zack was smart and capable, but his inability to show up when needed left Amy and other colleagues feeling disappointed and frustrated. “While I believed strongly in his talent, intellect, and creative problem-solving, he became known more for unreliability and irregular follow-through,” she says.

After reflecting on the problem, Amy knew she needed to speak directly with Zack. She made sure that Zack understood the impact his behavior had on the company. She told him that “his unreliability was getting in the way of client relationships and team productivity,” she says. She also “let him know that his disorganization was damaging his personal brand.”

Then, she moved into problem-solving mode. They discussed ways to fix the problem. “We focused on leading practices within the organization, including how to best utilize his executive assistant and how he could better engage the support of the rest of his team during meetings,” she says. “I believe he appreciated the candid feedback.”

The conversation went well, and Zack began to “implement some of the practices” he and Amy discussed.

Not long after their talk, however, Amy and Zack determined that he was not in the right role. His strengths aligned elsewhere within the organization, she says.

“In his new role, Zack adapted how he works to include more support from others and was able to maintain a positive reputation with his peers and clients,” she says.

Case Study #2: Be Empathetic and Willing to Coach Your Employee

Rosie Perez, lead financial officer of global consumer business planning and analytics at American Express, recalls a time early in her career when she managed a disorganized employee.

Rosie had hired this person — we’ll call him Aaron — from outside the company. “A few weeks in, I noticed he began missing deadlines, losing information, and generally looked flustered,” she says.

At first, Rosie thought it was just the challenge of learning a new job and navigating a new company. “But, several months later, when his disorganization began impacting our team’s ability to complete projects efficiently, I realized he needed guidance.”

Rosie remembers feeling uneasy about the situation. “I wasn’t sure when or if I would receive the deliverables we agreed on. This also made me feel guilty about the toll it was taking on the rest of our team,” she says.

When she addressed the issue with Aaron, she was empathetic and made it clear that she was his ally. “I told him that being organized does not come naturally to everyone — including me,” she says. “I let him know it took me time to discover what systems would work best for me. But, once I did, it was a huge benefit.”

She also appealed to Aaron’s sense of teamwork to help him understand how important it was to be more organized. “I told him that while I was thrilled with his enthusiasm to take on new projects and more work, he could benefit from adding structure to his project timelines and building in the time he needed to review and reflect after each step.”

Together Rosie and Aaron discussed how he could create detailed timelines and project plans with milestones along the way; add buffer time into the schedule for reviewing, reflecting, and planning; and schedule regular check-ins with Rosie so she could help address any obstacles before it was too late.

It was not easy and there were some setbacks along the way, but Aaron did eventually get better. “I am proud to say that he made improvements that enhanced the quality of his work and his overall processes,” she says.

“It takes a lot of time to change ingrained behavior, but it can be addressed,” adds Rosie. “Most importantly, as leaders, it is our job to help coach our colleagues [with] constructive and pointed feedback.”

Rebecca Knight is a freelance journalist in Boston and a lecturer at Wesleyan University.  Her work has been published in The New York Times, USA Today, and The Financial Times.