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Close to 30 per cent of millennials have texted a manager outside of work about stuff that’s unrelated to their job, compared with just 10 per cent of baby boomers – according to a 2014 survey by Linkedin. As a result, many have developed friendships. The millennial boss is chill and wants to be your friend. That’s cool. But how do you deal when she just doesn’t get that she’s overstepping her boundaries?


1. The no-filter boss


It’s a problem when your boss turns to you to blow off steam. “My direct supervisor casually brought up her dissatisfaction with one of my peers, and implied he should get another job because he was ill-suited for his current role,” says 26-year-old accountant Jennifer*. “I smiled politely, but remained silent. I guess she took that as a sign to continue, because she then dissed another colleague.”

Draw the Line: It’s easy to get drawn into the discussion. Don’t. She’s still your superior. If she doesn’t remember that, you have to. Don’t feed her rant, says Terence Chiew, author and career coach with, adding that you should shut her down by changing the topic. If it persists, Rachel Lee, APAC head of talent acquisition at bicycle sharing company Ofo suggests focusing on the other person’s motivation instead of your boss’s opinion.  For instance say something like, “let’s not jump to conclusions but find out his reasons?”


2. The can’t-take-no-for-an-answer boss


Marketing executive Ivy*, 26, remained on good terms with her boss even after leaving the company. “I saw her as a mentor, and she would confide in me. Then she bugged me to go on this weekend trip with her,” says Ivy. When she refused, her ex-boss guilt-tripped her, and implied that Ivy wasn’t keen to go on vacation with her. Eventually, Ivy caved so as not to risk offending her.

Draw the Line: “When you go from colleagues to friends, you might have new expectations of each other, which could jeopardise the relationship,” says Terence. Recognise that as friends, you can say no, he adds. Or make a graceful exit by saying no, then suggest an alternative date to meet up for brunch or drinks.


ALSO READ: How to impress your boss without being a suck-up


3. The needy boss

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You’re the work bestie your boss never had. “My boss and I became close friends, and that’s where the boundaries blurred. She would tell me about her family troubles and
boyfriend problems, and texted me whenever she was feeling down, even on weekends,” says creative professional Gwen*, 28. She felt compelled to respond, which drained her.

Draw the Line: Put the brakes on your boss’ needy behaviour early on. “As soon as she starts to overshare, joke that you’ll charge her if she continues to use you as an outlet,” says Tricia Tan, HR director at professional recruitment firm Robert Walters. That should give her a hint. But if things get worse, Tricia says you need to tell her you’re not up to helping her work through her issues, and that she needs a stronger support network, or even professional help. Watch your tone – be kind, not brusque.


4. The zero-boundaries boss


She just wants to be the cool boss. But it can get too much. “My supervisor would talk about her sexual exploits and share too much about who she found attractive,” says commercial executive Nicole*, 25.

Draw the Line: Call your boss out on what makes you uncomfortable. Try saying “Yikes, too much info, boss!” or “I really didn’t need to know that, boss!”, says Tricia. Using the word “boss” reminds her she’s in charge. Too awkward? Ignore her, and turn the discussion to work.

*Names have been changed. 


ALSO READ: True story: “Help! My boss from hell is giving me nightmares”


This story was originally published in the February 2018 issue of Her World magazine.