Career challenge: Should you socialize with your boss

You spend a lot of time around your colleagues on the job, so it may seem natural to continue that connection outside the work setting. 

But while socializing with your workplace peers outside the office is one thing — that’s a bit easier to navigate than socializing with a manager or boss — is it a good idea to plan social outings with your workplace superiors? 

FOX Business asked several experts for insights — who explained the pros and cons of this type of activity. 

WANT JOB SUCCESS? QUIT GOSSIPING AT WORK — AND HELP OTHERS GET OFF THE GOSSIP WHEEL AT WORK, TOO

Grabbing a quick lunch or an after-work dinner with a boss can offer some benefits, with a few important caveats.

Make sure it’s about ‘building a relationship’

“The benefits of socializing with a boss are about building a relationship” with that person, Ramona Shaw, a leadership coach based in San Francisco, told FOX Business. 

People need to “demonstrate a mutual appreciation for each other’s differences,” said a leadership coach.

“When we spend time with another person,” she said, “when we experience them in different social settings and have conversations about a range of topics that aren’t limited to work-related issues — we naturally get to know that person better.” 

If the one-on-one time goes well, both parties will develop a greater sense of trust, understanding and respect, said Shaw. 

PAID TIME OFF: 3 REASONS YOU SHOULD USE ALL YOUR PTO

“These factors are foundational to good work relationships in which both people demonstrate a mutual appreciation for each other’s differences, assume best intent and navigate opposition or conflict in a constructive way,” she said.

There’s a good chance you see your boss more than you see your friends or family members, so being friendly toward each other makes sense, Amy Morin, a psychotherapist in the Florida Keys, told FOX Business. 

two females having a drink

Two parties can develop a greater sense of trust, understanding and respect outside the job setting.

Morin also hosts “The Verywell Mind Podcast” and is the author of “13 Things Mentally Strong People Don’t Do.”

“Despite how much you tell people outside the office what you do for a living, your boss is the one who truly understand what you go through each day,” she explained.

Know the caveats about socializing with the boss

Yet there are some downsides to socializing with your boss and those must be acknowledged. 

For starters, any personal information you share might be used against you, said Morin. “If you say you’re thinking of having kids, your boss might worry about how that could affect your job,” she cautioned. 

Coworkers “might assume you’re just trying to get ahead at work, which won’t earn you any favors among them.”

“Or, if you mention you are a little stressed about your parent’s illness, the [boss] may take that to mean you’re not concentrating on work right now.”

Additionally, “sharing details about your life might affect how likely they are to assign you upcoming projects or promote you,” Morin noted.

manager and worker

While a boss may be interested in learning more about you, that information may also affect future employment decisions. (iStock / iStock)

Co-workers may have a strong reaction to your friendship with the boss, too. 

“They might assume you’re just trying to get ahead at work, which won’t earn you any favors among them,” Morin added.

Take these tips to heart about socializing outside of work with a manager

If you do choose to see your boss socially outside the workplace — which isn’t advisable for everyone but may be inevitable at some point, depending on the position, the industry and other factors — take these insights to heart.

1. Make sure happy hour doesn’t get out of control.

“Even if the boss drinks a lot, don’t join in,” warned Morin. “Nothing good will come from getting drunk together.”

CAREER CHALLENGE IN 2022: HOW SHOULD YOU HANDLE A LAZY CO-WORKER?

2. Don’t overshare your personal business; be conscious of the information you share. 

“Remind yourself that while your boss might be interested in learning more about your life outside the office, that information might affect future employment decisions,” Morin said. 

Discuss subjects that are light and keep the conversation friendly. 

She also suggested making a conscious decision about why you’re going to hang out outside the office. 

TAKING A VACATION? WHY 1 IN 2 EMPLOYEES CAN’T UNPLUG

“It’s important to stop and think about what sort of boundaries you want to set beforehand,” she added.

3. Don’t badmouth your co-workers to the boss.

“Don’t gossip and don’t speak ill of other people’s performance,” Morin advised. Instead, keep your conversations focused on your own performance, discuss subjects that are light and keep the conversation friendly. 

Two work colleagues are having a happy discussion in an office setting

Invite colleagues to join you in a social setting — but be “conscious that not all social settings are appealing to all people,” said a leadership coach. (iStock / iStock)

Consider chatting instead about neutral topics — what shows you’re streaming or what hobbies you enjoy.

OHIO MCDONALD’S FRANCHISE OWNER, A VETERAN, PAID WORKERS AMID CLOSURE: ‘I’VE BEEN IN THEIR SHOES’

4. Realize that a social riff may carry over to work.

Keep in mind that if you have a disagreement outside the office, it may carry over into work, Morin said. “It’s unlikely your boss is going to compartmentalize their frustration with you, so remember that your relationship outside the office is going to affect your relationship at work, too.”

5. Try to be inclusive.

When you socialize with your boss outside of work, be as inclusive as possible, suggested Shaw. “This means invite colleagues as well — and be conscious that not all social settings are appealing to all people.”

CLICK HERE TO READ MORE ON FOX BUSINESS

If a group is going for happy hour after work, this may exclude parents of young kids who must go home to take care of them, for example.

“Engage socially in a range of settings and solicit ideas from all team members to make the socializing with colleagues and bosses as inclusive and fair as possible,” said Shaw.