Good Job is Slate’s advice column on work. Have a workplace problem big or small? Send it to Laura Helmuth and Doree Shafrir here. (It’s anonymous!)

Dear Good Job,

I manage a small satellite office with four employees. The relationship between two of these employees has devolved to the point that the office is barely functioning, and they cannot be in the same room together. “Stella” is a very good employee. She’s in her 40s, single, and childless. “Jill” is replacement-level. Her work is OK, but absent the headache in actually onboarding, I could get someone else to produce the same easily. Jill is about 10 years younger and has three children under 10. I’ve had to speak to Jill in the past for making snide remarks about Stella, things like, “Her life is so easy without kids, no wonder she can live near the beach.”

Recently, Jill and her kids popped into Stella’s house “just to say hi,” which is weird because they are not friendly. After a few minutes of awkward small talk, Jill asked to take the youngest to the bathroom. While she was in there, the oldest child broke something expensive. Jill hurried the kids out and left without offering to pay for the broken item.

Stella is, justifiably, incensed. She’s certain (and I agree) that Jill only popped in to use the bathroom because the nearest public restroom was a half mile down the beach. Regardless, Jill’s child broke something, and she should pay for it. Jill refuses, saying, “Stella can afford it; I have to support my family.” Stella has come to me with an ultimatum: Jill goes, or she does. Jill is, when push comes to shove, a jerk. And her work isn’t great. I began the paperwork to fire Jill. Our home office, whose sign-off I need, has refused to do so and stated that we can’t fire Jill for an incident that happened outside of work.

I am tap dancing as fast as I can to keep Stella from quitting, and I have laid out the performance issues and attitude problems with Jill in the office to try to get the home office to agree. I’ve highlighted the great work Stella does and the very real threat we will lose her. They won’t budge. In the meantime, we are getting no work done and are going to miss our numbers for the month badly. Besides walking into the ocean and letting myself get swept out to sea, I am out of ideas. My nightmare is ending up in an office with Jill for the rest of my life. People get fired for things they do outside of the office all the time! It’s not unreasonable to have repercussions for mistreating a fellow employee, is it?

—Beached

Dear Beached,

Before we get to Jill’s future with the company, let’s talk about yours. Missing your office’s numbers for the month is ultimately your responsibility, even if drama from Jill—and Stella, frankly—is the proximate cause. You’ve clashed with the home office twice now, and whoever rejected your requests to fire Jill may doubt your judgment. They may have the impression that the office you manage is dysfunctional and dramatic, and blame you. You need to manage down (with Stella, Jill, and your other direct reports), sideways (with human resources), and you need to manage up (to your boss and the home office). I’m laying this out not to be harsh—please don’t walk into the sea!—but to help you think about your own role. Managing difficult people is one of the hardest parts of the job.

If you haven’t been talking to your direct manager, who I assume is part of the home office, do so now. Warn them that you are unlikely to meet your goals for this month, so they’re not surprised when the numbers come in. Tell your boss about any steps you’re taking to improve monthly performance. Ask for their feedback and advice. Acknowledge that the team has been disrupted by interpersonal conflicts. Brief them, succinctly and calmly, about the challenges with Jill and Stella, and say you’re determined to fix the problems. Ask them if they would support you meeting with human resources to discuss your options regarding Jill.

After getting approval from your manager, speak with your human resources representative about Jill. Your home office is right that you typically can’t fire someone for something they do outside of work, aside from extreme circumstances. They might not have said so explicitly, but it’s also wrong to fire someone because another employee gives you an ultimatum. But Jill may provide enough reasons herself to be “managed out.” Explain to your HR rep, calmly and with an air of reluctance, that Jill has been rude to co-workers, inappropriate with you, and disruptive to the point that your team is missing deadlines and not meeting your targets. Review the employee handbook ahead of this meeting so you can flag every violation you’ve observed so far. Keep the focus on Jill’s harm to the company, not to Stella. Ask for HR’s help with next steps. This might include a “difficult conversation,” with an HR rep in the room, laying out Jill’s violations of company expectations and giving her a final warning before termination. You might put Jill on a “performance improvement plan,” or whatever system your employer uses for documenting problems. Depending on the employee protection rules for your country, state, and company—and your legal team’s assessment of the risk of a lawsuit—you’ll probably need to build a detailed, documented case for termination. (I recommend you start adopting corporate-ese euphemisms, like “termination” and “manage out,” because the flat language might improve communications with HR and the home office.)

While you’re starting that process, use your best leadership skills to set expectations in your satellite office. Your conversation with Jill will likely be a three-way with someone from HR, where you lay out the rules for appropriate behavior in the office and give formal notice that further disruptions could lead to termination. If you put Jill on a performance improvement plan, there will probably be an agreement for her to sign. Ask HR to provide a script so you know exactly what you should and shouldn’t say.

In a one-on-one conversation with Stella, tell her you can’t discuss specifics (any HR actions regarding Jill should be confidential), but you are working to improve the workplace. Then shift the conversation to Stella herself. Have you praised her work recently? If not, express your appreciation for her accomplishments. Tell her you’re confident she will hit her numbers next month and you want to help her achieve those goals. Are there perks you could offer to recognize her good performance? This would be a good time to review her responsibilities and ask if there are new projects she would like to take on or old ones she’d like to sunset. Show her that she has options for keeping this job interesting and fulfilling despite any annoyance from Jill.

Schedule appointments to meet individually with your other two employees. The tension between Jill and Stella must make the workplace unpleasant for them. Acknowledge that it’s been a stressful time, tell them you’re working on reducing tensions, and say you appreciate their collegiality. Invite them to provide feedback on how to make the office more efficient—you just missed your monthly targets, after all—and thank them for their work. Keep these conversations professional, encouraging, respectful of their perspective, and focused on your team’s performance.

This conflict is probably keeping you up at night, but you can get through this. Keep thinking about managing down, sideways, and up. Meet regularly with your direct reports and encourage collegial, productive behavior. Thank HR for their help and bring them in earlier in the process next time there’s a problem. Update your boss on your office’s successes as well as problems, and ask if there are other people in the home office you should meet with to build better relationships. It’s easy for people at headquarters to ignore satellites. Look for ways to participate in cross-office projects so people don’t think of you as just that manager with the problematic office.

Dear Good Job,

My job pays OK, but it has terrible insurance. It’s so bad that most of us elect not to carry it. How can I find a job that offers decent insurance without wasting my time going through five interviews?

—Healthy Unhealthy

Dear Healthy Unhealthy,

You’ve probably seen that most job descriptions say whether their benefits include health insurance, but don’t provide additional details. You can search for information about a company’s benefits on websites that rate employers (like Glassdoor or Indeed). You may want to look for jobs in unionized or larger workforces. If the employees are unionized, there’s a good chance they’ve negotiated for decent benefits. Larger employers typically offer several choices for health insurance plans, so you’re more likely to find the right combination of coverage and cost you need.

It’s perfectly acceptable to ask about benefits in an initial (or “screening”) interview. Don’t make it your first question about the company or put too much emphasis on it, for two (of many) reasons: You want the interview to focus on your qualifications for the job, and you don’t want to give the impression that you urgently need expensive care. (Employers are legally prohibited from discriminating on the basis of disability, but it’s hard to prove a violation at the early interview stage.) Simply ask the screener to clarify what health insurance benefits are included with this position.

In the meantime, have you advocated for better health insurance at your current job? If you and others are not participating in the employer plan, that potentially raises the costs for everyone who does enroll. Talk to the benefits representative in your human resources department. Ask if your health insurance is standard for your industry, and if there’s a way to improve it for next year. Tell them you (and presumably other employees) would join if the insurance offered more coverage or were less expensive. I assume your workplace doesn’t have a union, or else they’d negotiate for better benefits. Could you and other employees who are dissatisfied with your benefits start one?

Before you jump from your current job to a new one with better health coverage, run the numbers. If you would lose out on salary, time off, retirement contributions, or other perks, it might make sense economically to continue to buy your own insurance while you keep looking.

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Dear Good Job,

I’ve been a registered nurse at my current hospital for four years, and I am beyond ready to change to a different unit. I was planning on applying for a job in the emergency department. The application opens April 1, but the job doesn’t actually start until mid-August. There is a six-month training period. I am also actively trying to conceive right now. I won’t know if I am pregnant (or will get pregnant in the next couple of months) by the time the application is due, but if I do get pregnant, I will need to take leave right in the middle of the training period, which is not ideal. If I pass this opportunity up and stay in my current job, I’m not sure when this opportunity will present itself again. And I’m just tired of where I am. I’m not sure what to do or what’s fair to the employer.

—(Hopefully) Knocked Up Nurse

Dear (Hopefully) Knocked Up Nurse,

Apply for the job. Apply for any job that appeals to you. You’re ready for a change, you’re tired of your current position, and you should prioritize your own career and job satisfaction.

It’s considerate of you to think about how a potential pregnancy could interfere with the training for this new position, but it’s not your job to sort that out. It’s your future managers’ job. The people in charge of training for, staffing, and running the emergency department (or any department) regularly have to shift responsibilities around to cover for any type of leave, predictable or not. If it helps ease your worries about fairness, please know that it is in the hospital’s best interest to keep you—a highly trained employee with four years of experience—fulfilled in your work and eager to advance in your career. Good luck.

—Laura

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Last year a close friend sought my advice on something, and inadvertently revealed they’d basically stopped paying income taxes a few years ago. What had once been their cash-based “side hustle”—coaching individuals in a high-cost sport—on top of their full-time job had turned into their full-time job since the pandemic. They’re basically being paid cash by clients and not reporting any of it to the government. I urged them to report it and pay income and Social Security tax, but they demurred.

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