How to Coach a Disorganized Staff Member

Last updated: 6/21/21
Estimated reading time: 5 min


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!”

Some roles require strong organization and attention to detail. For other roles, it’s not a dealbreaker on its own even though it causes problems and frustration. As a manager, your first step is to distinguish the must-have skills and habits from the nice-to-have ones.

  • In a case where being organized and detail-oriented is a core part of your staff member’s role, you’d want to approach the situation as a performance issue—being honest and clear that you need to see significant and sustained improvement. You would start off the same way (with check-ins, feedback, and coaching), but you’d want to be clear from the outset about your expectations and the arc of the performance improvement process. This arc could proceed to a performance improvement plan and letting go if they don’t meet core functions of the job.
  • In this case, your staff member is doing great at must-haves (core responsibilities), so what you need is a plan for coaching on team norms, and dialogue to identify some strategies to either build this skill or mitigate its impacts. Coaching—the ability to support and empower someone to achieve a goal or develop a skill—is a key part of being a manager.

For this disorganized department head, you’ll want to give feedback, seek perspective, and make a plan that leads to the best results. 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 and a fellow team head that they haven’t received responses when they emailed you. They didn’t raise this as a huge concern and when I probed more, they shared that they generally feel good about your work and communication with them. But, I’m concerned that if this persists, it may make us look unresponsive and could lead to some downstream communication issues for our team. I want to be clear that, right now, I don’t consider this a performance problem. You’re doing a great job meeting job expectations. I consider this a valuable growth opportunity and I want to keep an eye on it. How are you feeling about your organization systems and the impacts I just described?”

Acknowledge any context that might be posing a special challenge, as well. 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. Use our feedback worksheet and our “CSAW” model (Connect, Share, Ask, Wrap-up) for help structuring the conversation.

Seeking perspective is always important. You might learn things that surprise you—for example, that your staff member incorrectly thought another department member was owning a particular task or that the two of you aren’t aligned on how quickly activists should be getting responses and what rises to the level of “important.” Seize these moments to clarify team norms and add specificity to each level of your MOCHA.

3. Develop a plan.

You can invest in your staff member’s success by rolling up your sleeves and building their skills, or you can make adaptations to mitigate the impact of their work style.

  • Roll up your sleeves and build their skills. An otherwise stellar employee can often turn a short-term investment of your time spent coaching into real changes. Ask your staff member to walk you through their existing organizational systems (if any!), and delve into what’s breaking down when emails or tasks go unhandled. Some people who are disorganized struggle to spot the inefficiencies in their systems or to envision how they might set up a stronger system, so invest some time in coaching and problem-solving, just as you would with any other skill you wanted to build in someone. By spending time digging into their work habits, you might spot relatively easy ways to build better systems and habits. For example, if you learn that they keep email sitting in the inbox whether or not it’s been dealt with, you could suggest they start using folders to organize messages and tags to highlight messages that require a response. You could also suggest adding a one-hour workblock to the calendar Tuesday and Thursday to answer emails or get to those languishing expense reports. The goal is to help them develop new habits and new systems.
  • Look for ways to mitigate the impact. Because your staff member is outstanding at the core work of their job, consider whether there are creative ways to mitigate the impact of the disorganization. This means adding new team norms and looking for win-wins. For example, your team might benefit from a regular 15-minute check-in to flag things that need immediate attention—and verbally reinforce certain emails before they get lost in the inbox ocean. You could also leverage the strengths of your admin team to find a tech solution to automate reminders, help create a folder structure, or provide other support. You may even find this is something other staff would appreciate.

Given your concern about the downstream impacts, we’d suggest rolling up your sleeves with this staff member. Set up some time to review their systems, ask staff who have great systems to share examples your disorganized staff member might want to see in action, and offer them the training, tools, or habit-forming time they need.

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