Wendy Williams needs some time off.

The host of “The Wendy Williams Show” announced Wednesday that she’ll be immediately taking three weeks off from work — though, she says she’ll try to make it two, because she has to “pay [her] bills” — per doctor’s orders.

Williams is suffering from thyroid issues related to her Graves’ disease, an immune system disorder that leads to the overproduction of thyroid hormones, Mayo Clinic says; symptoms can include anxiety, bulging eyes, chest pain, fatigue, and sensitivity to heat. Williams admitted she hasn’t feel her best lately, describing experiencing some of these symptoms firsthand in a video posted to Twitter, and having even fainted from “overheating” on her own Halloween broadcast in October.

Williams is finding herself in a situation that many other workers have, too — the dilemma of when to take a leave of absence from work to address medical issues, and how to broach that delicate conversation with bosses and HR.

Sometimes, companies are understanding, like in the case of Nancy Gretzinger, 66, a former teacher in Phoenix, who told Moneyish that she’s taken four leaves of absence from 1996 to 2014, to treat medical issues including a spinal tumor.

“Believe it or not, [managers] are very empathetic, at least in education,” Gretzinger said, adding that the public school system she worked for offered her a stipend to buy more comfortable home furnishings to ease the recovery process. “I even got a card from the superintendent,” she added.

Of course, not all companies are so generous — so experts say the situation must be handled delicately. Indeed, there are multiple legal and HR-related considerations you need to make if you’re facing a medical leave of absence. Here are a few factors to consider.

  1. Understand the laws: The Family and Medical Leave Act (FMLA) is a federal law that applies to organizations of 50 or more employees, granting workers 12 weeks of unpaid leave to address health- or family-related issues. For organizations of fewer than 50 employees, there is no federal statute governing paid or unpaid leave, so you should research your state laws for further information. In the case of small companies such as mom-and-pop retail stores with few support staff, it’s feasible that employees could legally be let go for needing time off — but it’s unlikely, experts say.
  2. Consult your employment handbook: “See how leaves of absences are handled,” at your organization, said Amy Polefrone, CEO of HR Strategy Group in Baltimore. “Talk to the person in your organization who’s responsible for HR-related issues,” to understand what your short- or long-term leave options may be; many organizations have benefits in place to ensure that employees still bring in income while they’re off work.
  3. Offer solutions: Ask your manager for a face-to-face meeting as soon as you know you’ll need time off, and follow up afterward with a confirmatory email to outline what you’ve agreed upon. Polefrone added that you should offer solutions for how your manager can handle the extra workload in your absence: “You have to do your part in completing forms and keeping your company apprised of the situation and when you will return to work. It’s not fair to keep the company dangling.”
  4. Supply helpful documents: If your diagnosis requires surgery or other medical procedures, your primary care provider should give you appointment itineraries and detailed breakdowns of what you’ll deal with. While your doctor is only obligated to you, if you ask him or her to provide a letter or supplementary materials to show your manager what you’re going through, “the manager is likelier to give that support,” said Dr. Sandhya Pruthi, chief medical editor for Mayo Clinic.
  5. Train someone to do your job while you’re out: Make sure another person can take care of many of the tasks you do at work while you’re out, said executive coach Dr. Marc Dorio. And share what you feel comfortable sharing with your colleagues — such as by sending an email a few weeks before your absence to explain that you’ll be out, seeking medical attention — so they can pitch in too. Plus, you should relay all of those efforts to your manager, he said. “In the interim, they can cover the things that need to be covered. That makes it a lot easier for most companies.”