Managing Up: Dealing with Difficult Bosses

Working For A Difficult Boss? It Might Be Hard To See What You Can Do To Survive, Let Alone Thrive In This Type Of Environment. Having Been There Myself, I Know What Works And What Doesn’t. Here Are My Best Tips For You On How To Deal With This Situation.

So, you’re working for a boss who is difficult. Seriously, who has time for this, but nevertheless it happens. The worst boss I ever worked for was beyond difficult. She was never pleased, she had unrealistic expectations that could never be met. She was not inclusive of my thoughts if they differed from hers. She severely micromanaged everything. She made it clearly known she didn’t like me. She withheld important information for me to do my job, she belittled me, she bullied me.

I spent a tremendous amount of time and effort wondering why she was so difficult. I considered perhaps that she was getting pressure from above, maybe she had low self-esteem, maybe she didn’t know me well enough, maybe she grew up in her career learning from other leaders that this was the way to be, maybe she was bullied as a kid, the list went on and on. But no matter what, I considered the ‘why’ behind her being so difficult. It didn’t matter because she was also not an open person, never letting a vulnerability be seen, farthest from what I would consider being an authentic person. Regardless of what I thought I could figure out about her to fix this situation, it just wasn’t going to work. So, I had to learn to deal with it and manage up. These tips below have come from experience, my own trial, and error, and have risen to the top that I’d recommend you try if you are in this situation yourself.

  1. Contribute, be helpful, but do not suck up: Never let your work ethic or personal standards suffer. So, continue to make excellent contributions with your work and continue to offer additional assistance when you can or see an opportunity arise. Do not, however, suck up to your boss. It won’t be authentically who you are to be so overtly accommodating, so you won’t be able to sustain it or stomach it for too long. Your boss also likely has a sense that perhaps you don’t have the best relationship, so they will see right through the attempts to win them over. They either won’t care much or will take significant advantage of you – neither are good options.
  2. Try to understand what is behind their motivations: Please do what you can to listen closely to what they say and observe them in interactions with others. You might pick up on the sense that they are on high alert whenever a request comes from a key partner in the business. Knowing this, you can find ways to think critically about mitigating their concerns or worries without ever letting on that you are doing this. You can offer well-thought-out suggestions, with the first next steps that can ease their worry or stress and put you in a good light with them, or at least keep them off your back.
  3. Document everything: Ask as many questions as you need to to ensure you are clear with what your boss is telling you or asking of you. And then document it, particularly the key decisions and rationale. I also like the tactic of sending recap emails after important conversations, which summarize the key information and outlines the agreed-upon next steps, timelines, ownership, etc. This keeps everything clear. When your difficult boss inevitably changes their mind without telling you or is unsatisfied with what you have delivered, you can keep the conversation professional versus emotional, referring back to the facts that you documented in summary.
  4. Kill ‘em with kindness: Channel your inner Michelle Obama, remembering her quote, “When they go low, we go high.” As much as you want to unleash on them, call them out on their BS, put them in their place, ignore them, disregard them, do what they do to you, do not do it. Just don’t. Say hello when they don’t, hold the door when they would let it slam in your face, keep the upper hand, excuse yourself to gain composure if needed. But keep showing up with integrity; you ARE better than what they make you out to be. It’s a form of abuse to see you squirm and get upset; then they know they have got you. Never let them see you sweat.  
  5. Get emotional support: Some bosses are just bad; some are abusive. Know the difference. And get support for your emotional and mental needs. You need to vent about these situations and work through them. It doesn’t matter if it’s a spouse or partner, best friend, coach, therapist, just don’t go it alone. Please don’t hold it in; it will eat you up and change you. And if it does, then create an exit plan and get the hell out. Leaving is NOT a signal they have their own. You are always the winner when you put yourself first and treat yourself with grace and kindness.
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