How Can I Manage a ‘Challenging’ Employee?

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Disrupting the Workplace

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.

That said, this is indeed a complicated situation and you clearly need help handling it. When I ran your question by the human resources executive Lisa Failla, with whom I’ve worked in the past, she wondered whether you had educated yourself with the guidelines in the Americans With Disabilities Act about making accommodations for employees who were facing illness.

“Your description of her chronic health condition becoming worse may also indicate that she could be eligible to go out on short- or long-term disability,” she said. “Your H.R. partner should handle any such conversation. As an effective and compassionate manager, it is best to provide your employee with the outside support mentioned above in order to accommodate her illness within the guidelines provided.”