two women at work
Careers

Friendships at work: can you ever truly be friends with your boss? And is it ever a good idea?

What’s the secret for establishing a friendship with your boss that means you can confide in them without repercussions and without overstepping boundaries?

It sounds ideal, doesn’t it? Having a boss who’s also your friend – they can vouch for you, care for your wellbeing and happiness, be a shoulder to cry on when you need one and maybe even take it easy on you during those shifts where you’re very clearly hanging. 

You may also like

Friends with the boss: how much personal stuff should we be sharing at work?

But is it all that a good idea? After all, they are pretty much in charge of how far you progress in the company, maybe even what you get paid, the hours you work and so on. And ultimately our managers represent the company we work for and are judged by their loyalty to the brand, not individuals. So, how can we expect them to prioritise our interests? 

You may also like

Job burnout: an expert explains what it is and how to manage it

In the Great Resignation, which has spurred millions of Americans and Brits to leave the workforce - an estimated 6.5million Britons will quit their jobs in the upcoming months – many workers are disgruntled with their jobs, feeling the brunt of increased work loads, burnout and navigating a pandemic that rages on. Having a supportive boss can make all the difference. They may be able to have open and honest conversations about the needs of an individual and how conditions can be ameliorated and leave employees feeling valued.

You may also like

Mental health at work: how to ask for support if you’re struggling

Let’s also not forget that our bosses are also people with needs and feelings: it’s totally natural for them to find friendship and camaraderie in their staff. They may even be able to find a balance in being able to represent the company while advocating for their employees’ needs, and showing compassion and understanding towards them too.

So you might find yourself getting friendly with your boss, sharing details of your personal life and seeing them outside of work beyond Friday night drinks and leaving dos. But, unfortunately, for some, it doesn’t always work out.  

You may also like

Friendship psychology: the 5 signs of a people pleaser and how to overcome it for your wellbeing

“I’ve told my manager personal things, gone for lunches, cocktails, shared activities with her,” explains Afia*, 26, who works for a charity.

“We’ve both shared personal details regarding mental health, struggles, our ambitions, relationship woes. But every once in a while, I’m reminded she’s my superior. I know part of it comes from what she’s expected to do and achieve as a manager, and she has her own people to answer to, but there are times when you can’t avoid being employer/employee.

“For example, when an opportunity came up, she knew I had the relevant qualifications and was really interested in it, but didn’t endorse and support my application for whatever reason. While that is obviously totally fine – I don’t expect any special favours for me just because we were friends – I was surprised at the lack of heads up or conversation about it.

“And I get it from her perspective, she can’t really confide in me about these things as they’re confidential and legally protected, but she knew how excited I was for the opportunity and was holding out for it. In an ordinary friendship, it would be easy to support each other through this disappointment, but because of the boss-employee dynamic, she can’t even console me as I knew her input affected the decision, so it felt like there’s a bit of resentment there. And how can a friendship then prosper?

“It kind of went sour since then and we didn’t know how to recover from it, so we are now keeping each other at arm’s length.”

Though Afia didn’t have the most positive experience, for others, making a friend out of a boss made all the difference at work. 

two women chatting in a cafe

Vidya*, a writer based in the U.S., says the latter is true for her.

She tells Stylist: “I have a really wonderful manager. We have very limited paid time off with my company so it’s often hard to just take time off. But my boss has been extremely understanding, encouraging mental health days off and being willing to take on mine or any other coworkers’ tasks, and not notify any higher authority to count the day against us.”

Vidya appreciates that their professional dynamic means they aren’t the best of friends, but are still more close than an average colleague.

“We are definitely friends in that we personally support each other outside of work on a personal level. He is an extremely private person in general so he is quiet about many things. But us being friends has fostered a really healthy and efficient work space, it has definitely made for a much less hostile environment.”

How to be friends with your boss

So, what’s the secret for establishing that smooth balance between a boss you can confide in without repercussion, without overstepping boundaries?

It might depend on your definition of friendship, says career coach and leadership expert Phoebe Gavin.

She tells Stylist: “If your interest is being friends with your boss, it’s going to be very important for you to be clear about what that friendship actually will look like for you. Do you want it to be just sort of a warm, cordial relationship where you take small peeks into each other’s personal lives where you have some shared interests that you talk about? That might be more of a friendly acquaintance, and that’s a great idea as it allows you to be yourself in a professional setting.”

You may also like

Women share the single best piece of advice they’ve ever been given about their career

But there’s the bit that gets tricky, says Gavin, and that’s because with friendships come personal feelings.

“Friends are people that we are our true authentic, unvarnished selves with,” says Gavin. “Close friends are people who we are very vulnerable with, and are people we receive vulnerability from. And it isn’t in your interest to be that with your boss, nor your boss’s interest to be that with you.”

It might not be good for either of your careers, adds Gavin.

“You want your boss to be able to be honest with you about areas where you’re coming up short. You want them to be honest with you about what they need to see from you at work to give you opportunities. You want them to give you opportunities because you’re truly ready for them not because they feel obligated to do so.

You may also like

The Great Resignation: the best (and worst) ways to quit your job, according to experts

“You want them to be fair to everyone at work. You don’t want them to give you or other people better opportunities or advantages because you’re friends.

“And so trying to become friends with your boss is usually going to create more problems for you than advantages.”

They might also be seen to be too easy on you (or hard, as they overcompensate for the friendship). If you’re not receiving a proper, unbiased assessment of your performance, it might be holding you back too.

So ultimately, sure, share parts of your real self at work – but remember, it’s still a professional environment. After work drinks on a Friday might be appropriate, but maybe not brunch the following day.

*Names have been changed. 

Sign up for the latest news and must-read features from Stylist, so you don't miss out on the conversation.

By entering my email I agree to Stylist’s Privacy Policy

Images: NoSystem images and Westend61 via Getty.