How to Coach a Disorganized Staff Member

A reader sent us this question: “I manage a department head who’s fantastic at the core responsibilities of her work – she’s really talented at what she does and has helped us get great results in her area. She’s also pretty disorganized – doesn’t always answer emails, even when it’s important to get back to someone, and will sometimes let non-urgent tasks fall through the cracks. This is the one issue in an otherwise great performance. Help!”

Disorganization can be fatal in some roles – but in some ways it’s trickier to address in roles where it’s not a deal-breaker on its own but is still causing problems and frustrations. Here’s what we recommend.

1. Start by naming the issue and the impact it’s having. It might sound obvious, but simply articulating what you’re seeing and why it concerns you can be powerful – and that’s especially true with strong performers, as they’re typically highly conscientious. In this case, you might say, “I’d like to talk about your organizational systems. I’ve heard from several activists that they haven’t received responses when they emailed you, and there have been a couple of times recently where smaller projects fell through the cracks. I’m worried that it’s making us look unresponsive or disorganized to people who we really need to trust us.”

You can also acknowledge any context that might be posing a special challenge, while still holding firm on the bar you want the person to meet. For example: “I know that you’re juggling a high workload, which is all the more reason I want to make sure you have systems in place that will support you in tracking everything coming your way.”

2. Ask questions. Don’t assume that you already know what’s at the root of the problem. Instead ask, and listen with an open mind. For example, you might ask, “What’s your sense of what’s getting in the way?” or “Why do you think emails keep slipping through the cracks?” At a minimum, this will help you get a better understanding of your staff member’s perspective. But you also might learn things that surprise you – for example, that your staff member incorrectly thought another department member was responding to activists or that the two of you aren’t aligned on how quickly activists should be getting responses. (Use our feedback worksheet and our “SAW” model – Share, Ask, Wrap-up – for more help structuring the conversation.) Then, assuming you don’t learn anything that changes your assessment that there’s an issue with disorganization…

3. Roll up your sleeves and try to build the person’s skills. Because people who are disorganized often struggle to spot the weaknesses in their systems or to envision how they might set up a stronger system, invest some time in coaching and problem-solving, just as you would with any other skill you wanted to build in someone. Ask your staff member to walk you through her existing organizational systems (if any!), and delve into what’s breaking down when emails or tasks go unhandled. By spending some time digging into her work habits, you might spot relatively easy ways she could build better systems and habits. For example, if you learn that she keeps all of her email sitting in her inbox whether or not it’s been dealt with, you could suggest she start using folders to organize messages she needs to keep and flags to highlight messages that require a response. Or you might suggest that she block off an hour of time on her calendar every other day to devote to answering emails or other non-urgent tasks on her list, or that she immediately block off time on her calendar for any piece of work that comes her way so that she doesn’t lose track of it.

As with coaching on most skills, you shouldn’t spend hours a week on it for months to come, but an otherwise stellar employee can often turn a short-term investment of time into real changes.

4. Look for ways to mitigate the impact. Because your staff member is outstanding at the core work of her job, consider whether there are creative ways to mitigate the impact of her organizational habits. For example, you might realize that a junior coworker could handle some categories of emails that are currently languishing, or that an assistant could take over her always-late expense reports. Realistically, you also might decide that you’ll manage the person more closely on projects that you know are more likely to fall off her radar.

5. Be judicious in using the plan above. We want to be clear that these steps wouldn’t make sense if being organized and detail-oriented was a core part of your staff member’s role. In a case where those traits are fundamental to the job, someone without them isn’t the right person for the role, and you’d want to instead approach the situation as a serious performance issue (where you’d need to see significant and sustained improvement or transition the person out of the role). But in a case where someone is excellent at their core work and this is the one issue they’re struggling with, looking for ways to adapt may be what gets you the best results.