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How Can I Manage a ‘Challenging’ Employee?

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I’ve been a manager of a small group in a large organization for several years. In general, my direct reports have been easy to manage; they are conscientious, competent, seasoned professionals. Among them, but not as easily managed, is a longtime employee with chronic health conditions that have gotten worse and impacted her dependability. She has personal circumstances that have added to her unreliability.

We’re an office responsible for producing analytic reports large and small. Some have hard deadlines. I prefer to assign people projects they can invest in and own. Unfortunately, we often need to change focus to respond to changing deadlines and priorities from higher-ups. I try to assign my challenging team member projects with long lead times. Even so, her unreliability means that I have needed to reassign her projects frequently in order to meet deadlines. I spend a lot more time managing work assignments as a result (or just doing the project myself). Sometimes, after I’ve reassigned one of her projects because she says she is not able to work, she shows up. I can either return a project to her, taking it back from another staff member whom I’ve had to redirect from one of their projects, or give her a new, lower-priority project.

I’m trying to figure out whether I should be changing my approach to managing people or to managing the work. Any perspective you can offer would be most welcome. I value this employee and her contributions, but she is taxing me.

— Anonymous

You ask some interesting questions — and some really complicated ones. There’s so much going on here, and I’m not sure I can address all your points in a helpful way. But here goes.

One missing piece of information is whether or not you’ve already had a conversation with this employee. Is she aware of the impact she’s been having? Even if it has come up before, I think you need to have a conversation with her about your concerns. But I would urge you to make that conversation about what you describe as her “inconsistency” — not her illness. It doesn’t sound like she’s making mistakes so much as being unable to make time for the job; in other words, when she’s actually doing her job, she’s doing it well. And you value her for it.

But before initiating that conversation, I think you need to acknowledge the somewhat loaded terms you are using to describe this worker, among them “challenging” and “unreliable.” As you point out, this employee has health problems that affect her ability to work. But the way you describe her makes it sound almost like you resent her — or perhaps don’t fully believe her. (Your reference to her showing up to work after she says she is unable to do so suggests you may not trust her.) So your own feelings toward her may be something you need to explore on your own.

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https://static01.nyt.com/images/2024/11/10/multimedia/10Workfriend-fwbq/10Workfriend-fwbq-superJumbo.jpg?quality=75&auto=webpPhoto illustration by Margeaux Walter for The New York Times

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