Work can be a marathon of mishaps. While every employer has blushed their way through office awkwardness, not everyone knows how to emerge unscathed.

So we phoned a friend for advice.

HR expert Katie Evans-Reber shared the top issues employees come to her with, along with tactical tips on how employers can resolve them without breaking a sweat.

Repeat after me: Deep breaths, in and out. Okay, let’s go.

How to handle 5 embarrassing work situations

1. “My deskmate smells bad. Like, really bad.”

We’ve all met people who are a little too cool with the idea of BO. Or perhaps their perfume is suffocating, they haven’t found a shower they liked, or they just love topping off every meal with onions. Whatever the scenario, we’ve got some tips for dealing with an odor-challenged colleague.

First, be sure it’s a legitimate issue.

See if you can smell it for yourself. Watch out for employees who are just trying to stir the pot with their coworkers.

Be tactful.

Be sure to start the conversation with “I’ve observed…” so it’s not obvious you received complaints from others on the team. That just makes it unnecessarily awkward.

Make sure you know them.

The first time you meet shouldn’t be when you’re telling them they stink.

Talk to them in private.

No one needs to overhear this conversation.

Be friendly and understanding.

There’s no getting around the stickiness of this situation. Try saying this: “Our chat is going to be awkward, but that’s okay. It’s just that the perfume you’re wearing/smell around you/food you’re eating is bothering the people around you. Do you think you could take care of it while you’re in the office?”

Move the person.

Reshuffling desks can be an easy fix if the offender is only offending one person.

2. “My teammates are hooking up with each other. Is that allowed?”

When sparks fly, it’s hard not to notice. Over one in three employees have dated someone at work, found a CareerBuilder survey, and 33 percent of those relationships have resulted in wedding bells.

We spend so much time at work, which has made office romances inevitable. At the same time, people have varying definitions of what is and isn’t acceptable. Therefore it’s no surprise that 6,758 sexual harassment claims were filed with the Equal Employment Opportunity Commission (EEOC) in 2016. But there are things you can do if you’re ever stuck in this awkward love triangle:

Make sure it’s not a supervisor-supervisee relationship.

Sexual harassment laws warn against this type of romance, but don’t really have any hard-and-fast rules on this matter. If the relationship isn’t between a supervisor and supervisee, you may be able to end your involvement.

The Society for Human Resource Management (SHRM) found that out of the companies it surveyed, 99 percent of those with workplace romance policies shun dating between supervisors and subordinates. However, nearly half go one step further and forbid dating between employees of very different levels.

Rejigger the team.

If the romance does involve a supervisor and supervisee or members of the same team, see if you can change the team structure. While there’s not an explicit law that says two people can’t date at work, most companies try to prevent it because it could lead to sexual harassment, favoritism, and/or retaliation. Eesh. Basically, too much can go haywire.

Address it in your employee handbook.

Want to set things straight right from the start? There’s no better place to do that than in your handbook. In fact, according to a survey conducted by SHRM, over two out of five companies have a workplace romance policy in place.

You may also want to add a blurb that says if an employee does know of an inappropriate relationship, they have to report it to HR, just so you can help prevent any icky harassment situations. This sample policy from Workable will give you a jumping-off point.

3. “So last night was fun. Minus the fact that my manager was dancing on a table.”

During the holidays, it seems like every work event is soaked with alcohol. If one of your employees is turning work into their own Mad Men episode, they may have taken things way too far. And when that happens, it can be hard for everyone involved. Here’s how to deal.

Don’t accuse anyone.

It’s possible that a person you think is drunk could be on medication that makes them act a bit odd. Instead of saying outright, “I think you’re drunk,” focus on the reasons why you’re concerned. For example, you could sit them down and say, “Your slurred speech is worrying to me. Are you okay?” Then give the person a chance to respond.

If you do know someone is drinking too much, give them a heads up before a work event.

Send a reminder when there will be alcohol at an event so they can adequately prepare themselves. If the person in question is in fact grappling with alcoholism, they may want to avoid the event altogether, or you may want to reconsider having alcohol there.

Give them treatment options.

Was it just a wild night with the team, or does that teammate have an alcohol problem? Is alcoholism treatment covered by your health insurance plan? Many policies offer at least partial coverage. Find out the story from your plan administrator, and then send them resources where they can get help.

As a last resort, use a breathalyzer (but check with your state first).

Has the drinking caused too much trouble on your team? If the person’s employment is contingent on passing a drug or alcohol test, then you may have grounds to fire them if they don’t pass the test or refuse to take it. This area gets muddy, so check with an employment lawyer before you ask them to take the test.

4. “Uh, my direct report just expensed a solo trip to Hawaii.”

Expense fraud is for real. Overcharging the company card, double billing, expensing things that shouldn’t be expensed—there are tons of loopholes people poke through if they’re trying to steal.

In 2012, the Association of Certified Fraud Examiners found that the median amount of loss companies face from expense fraud is $26,000, and most companies take at least two years before discovering it. If you suspect someone is going overboard on their expense reports, don’t look away. Here’s how to address it.


Before accusing an employee, see if their receipts are valid and in line with your expense policy. Don’t have one? Now’s the perfect time to set one up.

Address it head on.

If it’s likely your employee did fudge some numbers, sit them down and ask them about the discrepancy. Don’t accuse them. Simply ask if they misplaced a receipt, expensed the wrong item, or need access to your expense policy. You never know, it could be a simple mistake.

Use expense-tracking software.

Gone are the days of having employees forward crinkled receipt after receipt. Consider using a program like Expensify to make the process easier and hold more people accountable.

5. “It’s been my lifelong dream to be on The Bachelor. Mind if I take time off to pursue it?”

Random time-off requests happen at every company. Whether it’s auditioning for reality TV or zipping across the world, many folks need to halt work to chase a dream. When an employee asks to take time off for a unique reason, you can show them a few different paths to take.

See what your PTO or vacation policy says

Depending on how many days are available to them, you might want to ask them to exhaust their PTO or available vacation days first. No policy to speak of? Use this guide to set one up.

Check if their time off qualifies for FMLA leave.

The Family and Medical Leave Act (FMLA) applies to certain employers and allows people to take time off for a few reasons. If your employee’s situation falls into one of the following spheres and your company is subject to the FMLA, they may be entitled to take this flavor of leave:

  • To take care of their health if they can’t work because of a serious health condition
  • To spend time with and care for their babies or newly adopted kids
  • To care for immediate family members who are sick or injured
  • To handle military-related demands

Keep in mind that the FMLA requires you to offer unpaid leave and you need to continue your employee’s health insurance while they’re out. Make sure these two things are clear before they choose this option.

Go the leave of absence route.

If your employee doesn’t qualify for FMLA leave, but still wants to take time off, they can request something called a personal leave of absence. Remember that it’s up to you whether you grant it since it’s not controlled by the FMLA.

Check the ADA. 

Another thing to watch out for is whether their leave is covered as a reasonable accommodation under the Americans with Disabilities Act, or ADA.

This law protects people with disabilities from being discriminated against. If their leave is covered by the ADA, then under most circumstances, your employee’s role and wages are protected. If it’s not, you may not be required to give them job protection or benefits, but check your state and local laws before making the call.

Work is bound to make you feel funny at times. But the best thing you can do for your team is to recognize the awkwardness, seize it by its oddly-shaped horns, and then try to deflate it before it spreads.

Fortunately, all you need is a little empathy and an acknowledgment that yes, these things happen to everyone—and that’s okay. And with a script on hand for each scene, nothing will faze you now.

Kira Deutch Kira Deutch is a former Gusto editor. She has a background in publishing and content marketing for startups.
Back to top