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Why Doesn’t My Boss Respect Sick Days?

January 10, 2026
in News
Why Doesn’t My Boss Respect Sick Days?

Send questions about the office, money, careers and work-life balance to [email protected]. Include your name and location, or a request to remain anonymous. Letters may be edited.

The Boss Who Needs to Be a Boss

I work a retail job. I have, on the surface, a good relationship with my manager: we work well together, and we talk to each other about our personal lives. But whenever I’ve come down with a cold or the flu — which happens a few times a year — he doesn’t show much understanding.

If I’m at work and say that I’m feeling sick, he doesn’t ask if I need to go home. Furthermore, the onus is on me to find someone to fill in the next day. I’ve worked while sick (and masked) before, because I felt pressure to.

I realize that I should speak up for myself and enforce a clearer boundary, but I’m hesitant to do so. When I get sick and need a day off, he sometimes says things that imply that I’m letting him down. And he has complained to me that workers take too much time off, leaving him to fill in. On the other hand, he often arrives to work late or leaves early, at times without explanation.

What’s the best thing to do to avoid this situation in the future? Am I wrong to think that it’s the manager’s responsibility, not mine, to find coverage when I’m sick?

— Anonymous

You’re not wrong. In fact, in New York and California it’s illegal for your employer to require you to find a replacement as a condition for taking paid sick leave you’re owed, even as a part-time or seasonal worker. Elsewhere, workplaces may differ. But even in states with less empowering sick-leave laws (or those with none at all), staffing is usually a managerial responsibility for the obvious reason that, when you’re sick, you should be resting and recovering rather than scrambling to find shift coverage — or, worse, working in public with an infectious disease.

Is this annoying for managers? No doubt. But, well, that’s why they’re paid more than you. Like a lot of bad managers, yours wants to have it both ways: to get paid more money without extra responsibility, and to be your buddy while still wielding power over you. He wants to use your ambiguous but pleasant interpersonal relationship to set the terms of what is, in fact, a clear professional relationship. This is exactly backward. A real friendship in the workplace can be cultivated only in the context of a settled professional relationship.

He may not be consciously aware of what he’s doing. In a sense, you’re training him to act like this by hesitating to enforce a clearer boundary. When you give in to his pressure, you’re showing him that a small amount of friendliness and a heavy dose of guilt are all he needs to offload his annoying duties on to you.

But I don’t think you need to have a one-on-one meeting or workplace summit to address this problem. If anything, I think you need to communicate with your manager less. Don’t give him emotional leverage or opportunities for negotiation like excessive description or apology: “I’m sick and I can’t make it to work tomorrow” is more than sufficient.

Ignore any implication that you’re “letting him down.” Working is not a favor you’re doing for him. And if he explicitly asks you to find coverage, simply tell him: “I’m not in a position to do that. I’ll leave it to you.”

This might make him angry or frustrated. But setting boundaries is always uncomfortable, especially when one party has benefited from their absence. The good news is that his laziness works to your advantage, too. Is a guy so allergic to doing his job really going to go out of his way to fire you, given how much extra work that will create for him?


The Plight of the Middle Manager

I am a middle-level manager for a business that has locations across the country. My employees here seem reasonably satisfied with the local situation, but often directives from the corporate offices are annoying at best and obstructive at worst.

The corporate office puts a great deal of stock in our annual worker satisfaction survey, which does not distinguish between what the employee likes about the corporate office and the local office. They have come down on our local leadership because our latest survey showed a lower satisfaction rate than the rest of the company. The negative comments on the survey were directed toward corporate policies, and our retention rate is one of the highest in the company. Yet because the overall score was low, we have to come up with a remediation plan.

I feel caught: If we emphasize that our local office is doing well and it is a corporate problem, we are accused of fostering an “us against corporate” culture. Yet it seems like our worker complaints are something we can’t solve. Help!

— Anonymous

I suspect that many readers breathed a heavy sigh of recognition at this letter, which describes a familiar dynamic for middle managers: being caught between the frustrations of their employees and the idiocy of their bosses. You deserve credit for reaching a state of “reasonable satisfaction” — the most any manager can really hope for — at your satellite office. It’s exceedingly frustrating for that accomplishment to somehow become a liability.

Unfortunately, such is the lot of middle managers, whose duty it is to absorb dissatisfaction from below and insanity from above and never, ever complain. For better or worse, ensuring that your employees and your bosses are never in close enough contact to begin strangling each other is the actual substance of your job. I can understand why this situation is stressful.

One option, of course, is to take your bosses literally: If they don’t care about employee retention but do care about employee satisfaction based on surveys, one straightforward solution would be to find new, presumably more satisfied employees.

Letting go of people simply to satisfy your corporate overlords’ need for positive survey results would likely be bad for the company and worse for your soul. On the other hand, what’s bad for the soul is often quite good for the career. Many middle managers have succeeded simply by acting as henchmen for upper management.

But I can’t recommend that course of action. (Among other things, it would be an enormous amount of extra work for you.)

Instead, perhaps you can turn the remediation plan in your favor. Rather than see it as a punishment, think of it as a means of advocating for yourself. An important tool in any middle manager’s kit is bureaucracy, and making your case in the context of this bureaucratic process will go a long way to easing the pressure you feel.

Whatever kind of documentation is produced for this remediation plan should lead with your retention rates and include specific complaints about corporate policies from your employees. Even better, you can try to organize the remediation plan around innocuously positive ideas, like “improving communication between employees and corporate leadership” or “ensuring employee feedback reaches decision makers.”

Make it pointedly constructive and slather it in enough bland corporatespeak, and perhaps you can avoid the accusation of an “us against corporate” culture.

If nothing else, it might buy you time until the next idiotic corporate intervention.

The post Why Doesn’t My Boss Respect Sick Days? appeared first on New York Times.

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