Four years ago, a myriad of forces collided in my life like meteorites crashing to Earth. My already stressful-yet-fun job became fraught with anxiety, and my line manager was the one to pick up the pieces. She was brilliant: full of sympathy, support and grounded awareness. But as we set out on our umpteenth walk-and-talk together, the thought leapt up at me: am I sharing too much?

Fast-forward to an age of Covid-19 and the question of where our boundaries lie at work is increasingly loaded. “I think it’s important to be approachable and be open to a chat – especially these days when the lines between life and work have become so blurred with working from home, and our work being so impacted by our personal lives,” says Amali de Alwis MBE, UK director of Microsoft for Startups. “However, it is definitely possible to overshare.”

The problem is, of course, that if you’re going through something – whether that’s a bad breakup or the onset of burnout – it’s very hard not to let that crisis seep through at work. And the best leaders out there will respond in the style of a friend: with empathy and zero judgement. 

Our understanding of what makes a good boss is evolving. A fresh awareness of mental health, coupled with the fallout of a global pandemic, means we are no longer apt to bottle up our problems, Don Draper style. Plus, we know that workplace friendship is a boon for happiness and wellbeing.

“I think it’s so important to be able to confide in someone at director level,” says freelance PR consultant Julia Portelly, whose former boss at a London Tech PR agency supported her through bouts of anxiety and depression during their two years’ working together. “Work is such a huge part of your life and just shutting off that personal, emotional, side and ‘cracking on’ if you’re struggling isn’t good for you.”

Julia’s friendship with her boss was present from the get-go, but it became invaluable when her mental health issues came to the fore. “We got on well immediately, and I think within the first six months we were happily chatting away over break time coffees and after-work drinks,” she says.

“I cried in front of her many times. I always felt incredibly unprofessional and I worried that people would think I was being pathetic. But the main thing she did was reassure me that there was no judgement, and that it was completely normal. I was so grateful to have someone looking out for me.”

Bekah Whitney, a marketing assistant at Abigail-Elise Design Studio, found a similar bedrock of support in her boss, Wendy Yates, soon after beginning her first full-time role.

“As much as we wish we could be robots we just aren’t. You can’t simply turn off your personal issues and go into work mode,” she says. “Wendy has proven to be someone I can share my depression with over and over. Every time my depression affects my work, she is kind and understanding.”

For Thom Wyte, the lifeline of a friendly boss helped with relationship issues after he took up a new position at Manchester-based digital marketing agency Embryo. The move meant Thom had to grapple with a long-distance relationship alongside the stress of starting a new job; but his manager, Cicely Ward, always had his back.

“Cicely has always been very encouraging when it comes to opening up about personal problems, even if just by inviting me to a one-to-one and giving me a chance to just chat about any issues I have,” he says. “These conversations are incredibly supportive and Cicely is always looking for ways in which she and the directors can help to ease pressure.”

Clearly the Miranda Priestly mode of boss is on her way out – and good riddance to her. But the caring, sharing approach isn’t always the salve we imagine it to be.

“My work wife and I were always down the pub together in my old job – and it was our ritual to sneak cigarettes throughout the day too,” says Molly Arnagh, who works for a non-profit organisation in London. “She knew everything about me; including the money issues I’d had floating around for a while.

“When she was promoted unexpectedly, that knowledge became a real problem for us both,” Molly says. “It was awkward every time conversations about my salary came up. Suddenly that ease we had vanished entirely.”

Jasmine Birtles, founder and financial expert at moneymagpie.com, says debt is one of those issues that you need to be wary about sharing with your boss, no matter how close you are. “It’s not fair on employers to keep having to bail you out – or listen to your financial worries – on a regular basis,” she says. “Ultimately it’s up to us to take responsibility for our own finances.”

Kelly Battelle, vice-president of people operations at contextual intelligence company GumGum, agrees. “I think there is such a thing as ‘TMI’ between manager and employee,” she says. “For example, my employees don’t need to know that I’m stressed about a fight I just had with my spouse, or about my own financial issues.

“In my opinion, it’s OK for the employee to share as much as they’d like but a manager may not have all of the resources to know how to help,” she adds. “It’s important for companies to have outside resources.”

This combination of empathy and third-party support rings true for Amali. “It’s important to know when you’re not the right person to help,” she says. “I previously had a team member who had ongoing mental health concerns. I’m not a trained counsellor or psychiatrist, so when they and I chatted, I realised that the best way for me to support them as a manager was to connect them to specialists.”

Hannah Storm, CEO of the Ethical Journalism Network, went public with her diagnosis of PTSD last year and is campaigning for greater emotional awareness in the journalism sector. She believes there is a balance to be struck. “I kept my silence for a long time, partly because the nature of some of my traumas meant I felt shame and I had been conditioned to stay silent,” she says. “I think sharing [with your boss and colleagues] is important, but boundaried sharing is equally important.”

Professional feedback is an issue, too. If you and your boss become firm friends, there’s a danger you won’t feel able to share how you really feel about one another’s performance.

Natasha Hanson bonded with her former boss, Debbie Francis OBE, when the pair went on a women’s empowerment programme in India together, as part of their work at Direct Rail Services.

“We hit it off right away,” Natasha explains. “My style is to ensure I deliver what is asked of me and my team, but I am always willing to push back when I don’t think a decision is right. Debbie is not one who is backwards in coming forwards, and there were a few times when I received feedback that things needed to improve. But it was always fair and balanced.

“That honesty between us means a filter isn’t required,” Natasha goes on. “I don’t always like what she says; she doesn’t always agree with me, but we work it though.”

Perhaps, above all, the line between being a good boss and a friend lies in the ability to listen rather than act. “It’s not about solving people’s problems for them, but more about making people feel relaxed enough to talk about personal issues when it suits them best,” says Thom. “Cicely has always been great at offering support without ever becoming intrusive.”

Hannah agrees. “The best managers I know are those who have empathy, and who listen and don’t try to fix,” she says. “It’s the people who take the time to understand that communication is a two-way street; listening, and listening some more.”

However friendly you feel with your boss, it’s worth respecting this invisible line as an employee, too. “I really do think there needs to be a limit on how many nuggets of information you share,” says Julia. “It’s how you get to know one another, but the last thing you want is for either person to be in a situation where they know something they shouldn’t. Is it their responsibility to flag that higher up? It becomes very complicated.”

“My advice is that it’s okay to be friendly with your manager and to share aspects of your whole self and to be authentic,” adds Kelly. “However, the friendship will not protect you from the fact that you’re both there to deliver well on your job. While I think it’s important to have friends at work, it’s probably best to share the more detailed aspects of your personal life with a friend who is a peer versus your manager.”

A work friendship is a rare and beautiful thing; but like all friendships, it comes with parameters. Respecting those and retaining a degree of separation in what you share will keep that relationship on an even keel – no matter what squalls come your way. 

Images: Getty, Unsplash, Rex

For support with mental health problems, contact Mind. Speak to Relate for relationship help or find support for debt issues with Step Change.