Should I stay or should I go? Tips for dealing with a difficult boss

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A relationship with your boss can be tricky to navigate at the best of times. But what happens when the person you signed up to work for transforms from Jeckyll to Hyde once you’ve settled into your new office? You ask yourself, did he seem so unnerving, impatient and apt to micromanage during those long-form interviews? How could you have missed her difficult communication style, you wonder. Those questions quickly turn to: what now? What are the best strategies to deal with my difficult boss? Do I stay? Do I go?

Don't ignore your gut feeling

We asked a few career specialists to offer their tips on how to manage challenging managers and when to know it’s time to move on. Among their advice, one thing they all shared is the importance of starting the conversation early. The best time to work on your relationship with your boss — or even determine if it’s one you can tolerate – is before you’re sitting at your new desk. Don’t ignore that all-knowing voice that shakes its head vigorously as you sign your name to the offer on the table. It recognizes the signs and knows the difficulties that lie ahead should you venture forth.

Of course, not all scenarios are black and white. But the interview process allows prospective employees to ask questions, to suss out their future boss and determine whether or not there’s a good fit. Interviews allow you to inquire into an employer’s management style and to share with them what it is about past managers that helped you succeed, says Gayle Hadfield who runs a Vancouver-based human resource consulting service. It’s also the perfect time to ask a potential manager about their performance measures, HR practices, philosophy and their ideal employee-manager working relationship. Hadfield suggests, “Ask your boss, ‘What’s important to you?’ It’s a question people don’t feel they can ask but the minute they’re in the job, it’s everything.” Should you find it hard to broach these questions, you’re not alone. But try to do it anyway, experts say. To make it easier, frame your questions around what’s in it for the employer, making it clear that a having harmonious working styles is a win-win. “You can say, ‘a lot of my success has been good organizational support with managers that were clear on expectations, so tell me a bit about your style,’” says Hadfield.

You could also leverage LinkedIn, where you can view current or past employees of the company you’re applying to in order to get a sense of how long they’ve been there, says Christine Cristiano, certified career strategist, job search specialist and professional resume writer. “If there are no longer-term employees, it’s an indication the company can’t retain employees, which often says a lot about their managers.”

Still, no matter how many questions you ask during the interview or how much research you undertake, you can’t always anticipate the issues that arise once you’re in the job. Much like dating, we’re on our best behaviour during interviews, masking the sides we’re less proud of. What’s more, even if those preliminary conversations cause concern about a prospective manager, sometimes reality is a stronger motivator. With bills and expenses piling up, the average prospect can’t always wait for a dream job to appear - or a dream boss for that matter. “Part of it depends on how desperate someone is,” says Karin Lewis, employment counsellor at JVS Toronto.

Communication is key

So if you’re already in the job, what now? The first thing to do is get a sense of your boss’ working style so you can do your best to work within it. Do they prefer weekly in-person check-ins or is email their preference? It’s also a good idea to discuss expectations and goals early on in the relationship. Schedule an informal meeting to talk about your role, current projects and what your boss expects of you, along with his or her preferred communication style, says Kate Parkinson, employment counsellor at Times Change.

“Get a sense of what they prefer and go with it,” adds Lewis, who explains that taking initiative can prove worthwhile. Ask your boss very early on to help you figure out what’s priority and what’s not. Communication may be key but the mistake people often make is assuming that managers know what they want and how to communicate it, says Lewis. “Remember your boss is human too. Maybe they’re shy, or having a tough time themselves.”

Though it can be difficult, all the experts we spoke to also caution employees to manage their own emotions. “If you’re anxious, don’t let it prevent you from sitting down with the boss. But you also have to manage your anger,” says Lewis, adding that depending on your boss’ preferred style, sometimes email communication is better than face to face. Watch what other people are doing and follow their lead.

Email can also allow for clearer responses and give you a paper trail to refer to. Along those lines, Lewis suggests employees keep a journal, a record of issues and questions that come up. That way you can amass a list of concerns that you can then share with your boss at a later date without bothering him or her too often. And, like that email trail, a journal gives you validation should things go sour.

Make sure to keep reaching out to people in the company. Establish a rapport with colleagues because they can also help. Figure out how those who are coping are doing it. And if you trust them, ask for an honest opinion in order to see the situation clearly. “Others can, at times, see things that aren’t obvious to us,” says Parkinson.

And before you make any rash decisions, look inward, she adds, explaining that if you experience the same problem repeatedly in different workplaces, it’s possible you’re the cause. “If this is the case make any adjustments needed to not repeat destructive behaviours.” Similarly, ask your boss for feedback concerning your performance. It might be painful but if your performance needs some adjustments you can learn from your mistakes and strive to do better going forward.

If you can’t make a change on your own, consider seeking professional advice or counselling, adds Parkinson. But even if you’re not the primary cause of the challenges, seek outside help, says Hadfield. Most organizations have employee assistance programs that are confidential – so take advantage of them. “Get someone else’s perspective. Is it that you just want things a certain way or have you really done your best?”

Making the decision to move on

But how do you know when it’s time to move on? “What I say to young people especially is you have to do a lot of things you don’t like before you figure out what you like,” says Cristiano. That doesn’t mean you’re stuck forever, and you can still look for work as you explore your options if you don’t have the freedom to leave just yet. And if that’s the case, she adds, make sure to find passion or joy outside the office, to give yourself something to look forward to.

To be sure, having a bad boss can be far more than just an annoyance — it can have a negative effect on your self-esteem and health. “If you find that you’re miserable and dreading going into work every day, and you have done everything possible to make the situation better, and it hasn’t changed, it could be time to consider leaving,” says Parkinson.

So if you’ve tried for open communication, stuck it out and conferred with trusted colleagues but your boss is not supporting your development, doesn’t seem to care about you and you’re feeling increasingly unrecognized, it’s possible your boss is not the best fit for you. More importantly, if you’re suffering as a result, change may be the only option. As Lewis explains, while some people can’t afford to leave, “for others, emotionally, they can’t afford to stay.”

Elisa Birnbaum is a freelance journalist, producer and communications consultant living in Toronto. She is president of Elle Communications and Publisher & Editor-in-Chief of SEE Change Magazine and can be reached at:

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