Thought Questions

Thought Questions, day 84: How do you deal with someone in a position of power who wants you to fail?

I got these questions from Danielle’s blog Underland to Wonderland, where I came across a post in which she talked about the website Thought Questions and their 365 thought-provoking questions to ask yourself. My friends Katrin, Celeste and Jasmine have also been answering these questions, so be sure to go check out their blogs too!

Day 84: How do you deal with someone in a position of power who wants you to fail? I’m thinking this is a career-related prompt, and I honestly have some very long and complex thoughts on this. You could alternately title this post “Career advice: how to deal with a bad boss” (and trust me, I’ve got loads of it!).

Thought #1, because I’ve been there, done that:

Be sure of your relationship with this person and whether or not you’re reading them correctly. Also, ask yourself: am I, perhaps, just possibly, also being a bit of a pill? (Prickly in response to constructive criticism, etc.)

Case in point: for several months I had a boss who could be a bit of a jerk and also seemed kind of stupid at times. I felt like this person didn’t like me and was kind of running me into the ground with extra tasks just because they didn’t feel like completing them.

When I took a promotion and realized I’d be training side by side with this person for two months,  I decided that while I couldn’t change their personality, I could change my attitude and try not to view them as an enemy. Once I did, I realized that, dragon-ish exterior aside, they really did know a lot about the job I would be doing and could teach me a ton if I was open to learning. I started to realize that all of the extra tasks they threw at me were simply their way of pushing me to learn and perform above my pay grade–they were just kind of crappy in their execution–and I’m now immensely grateful for that two month push, because it’s saved my butt countless nights. I also had to admit that I was going into work each night with a poor attitude in anticipation of their bad attitude, and was therefore simply feeding a negative cycle.

Today, I honestly think that a lot of their training is why I have such a good relationship with our head manager (the big big boss!); they taught me a ton of things that my other managers were not able (or willing) to teach me. I still think their personality could have used some tweaking, but in hindsight I realize that I created an “enemy” where there was none just because of a personality clash. Thank goodness I changed my tune.

Thought #2, for when #1 is not applicable:

You really have to assess the situation and be honest, not emotional, about what’s going on. It’s tempting to run to a higher boss and complain, but slow down and put it together like a court case. Ask yourself: is what this person is doing illegal? Unethical? Interfering with my ability to do my job? If so, what examples do I have, and how can I frame them with concrete language? Am I sure that s/he isn’t just annoying me?

  • Good example: “I feel that my boss overloads me with projects on a very short time frame, and I’m not able to turn in my best work. When s/he does _____, it makes it very difficult to do my job to the best of my abilities. I’d like to discuss a solution that will let me maximize my quantity without compromising my quality.” Follow with a specific project example from a recent workweek.
  • Bad example: “My boss gives me too much to do, and it’s not fair!”

Basically, make sure you don’t sound like you’re whining, and don’t accuse anyone else of not doing enough. This just makes you look bad. Also: be concise. My head manager wants concise explanations of problems, zero fluff, dithering, or drama. If there’s an issue, he wants a very straightforward explanation with firm facts: “My boss asked me to do ____, and I feel it’s unethical because _____.” Be prepared for feedback that you may not want to hear (going back to point #1, “are you also a pill?”).

Most of all, stay calm. Don’t raise your voice or, heaven forbid, do something like roll your eyes or swear. Professionalism should be paramount in your mind, even if you feel the other person isn’t being professional in return.

Thought #3, for when all other options have failed:

If your boss is honestly trying to make you fail, and you don’t think HR can/will help (or you’ve tried and gotten nowhere), you need to decide whether to seek new employment. It’s wonderful to say “quitters never win, and winners never quit” but I think you can set yourself up for a lot of grief by following that advice, so I would tell you to consider these bullet points:

  • Will this person’s actions damage my reputation or my future career, or are they possibly illegal? (Versus merely being annoying.)
  • How long have I worked here? Less or more than a year? (In other words, do I have an invested relationship with this job/company?)
  • What benefits do I stand to lose? (Hours that let you go to school, a killer vacation package, etc.)
  • Is this job just paying the bills, or is it a stepping stone to my dream career?
  • Could I afford to be unemployed for a while (do I have six+ months’ living expenses saved in the bank)?
  • What’s the worst possible thing that could happen if I leave this job?

In my job, the managers rotate every six to twelve months. By comparison, I’ve put in seven years at this job and now enjoy three-day weekends, decent health insurance, and three weeks’ paid vacation per year. That’s pretty swanky by almost any standard and I’ve worked way too hard for it to toss it out because a boss is making my life hard, especially when I know they’ll be gone within the calendar year. This job is also a good stepping stone to future management opportunities, within and outside of the company I work for, and it provides me with a pretty comfortable paycheck that I would be hard pressed to find elsewhere in my current situation. So overall, while I have had moments of feeling that my current boss tries to use me as a scapegoat, their actions aren’t enough to merit an official complaint and they certainly aren’t worth jumping ship.

By contrast, I’ll use a brief story about my husband. He had a boss who took a personal dislike to him and was actively looking to make him fail. He didn’t have a lot invested in the job, he had a good idea of his other employment options, and we knew we could afford to live on one income even if he didn’t find another job right away…so he quit. It was abrupt and a little odd but in the end it worked out for the best in ways we couldn’t have foreseen at the time.

Moral of the story: be honest, be objective, and consider your options carefully. It’s not easy to come to a conclusion when you’re in the heat of the moment and you’re angry. As I love to say, sleep on it!


  • Arielle Thibodeaux

    I think my boss is like this to everyone in our office. She rotates who she picks on each month. I don’t complain to anyone because it would go absolutely nowhere. I have just learned to accept it and only have contact when necessary. I’m looking to move on from there, though.

    • Martha Woods

      It sucks to work under someone like that. It sounds like you manage to cope with it though. It’s a shame that some people feel the need to use their power to make other people feel like crap!

  • Pang Ly

    I agree with pretty much everything you mentioned. I can’t speak for others because every managers or workplace deal with employees in their own way. From my personal experience, I have some managers that were more sophisticated than others, depending on the type of work, educational background, and type of training they’ve had.

    Yes, there is some bad management out there but I believe most managers don’t enjoy having to address employees when there is performance, attendance, and behavior issues. Being a supervisor myself, I don’t pick on them because I just don’t “like” them but I do have to talk to them when they are not compliant with policies and procedures or don’t understand the goals and expectations because that’s part of my job. Most of them are very defensive when you have to bring up something they’re not doing right and sometimes are either in denials or too ashamed to admit their fault and put the blame on others. There may be ego issues going on with that too. I’ve dealt with employees who are incompetent and when I have to bring up the performance talk, they either blame the nature of the work or that they weren’t properly trained. When I ask what kind of training they need they have no answer.

    I like it when you say be honest and be objective. I find this is the thing people struggle with because they often react on their emotions. Learn to take constructive criticism positively and with dignity. You really need to be able to look at the facts and be able to admit what role you played before you jump the gun on your boss. Believe me, I’d much rather praise employees (it’s easier) than having to confront them with issues. I have bigger fish to fry and stirring drama is not on my laundry list. I say in most cases, it’s miscommunication or misinterpretation. Coming from an all female office, it amazes me how sensitive people get about the smallest things so I’m very careful with the words and tone that I use.

    • Martha Woods

      I totally feel that. I hate having a confrontation with an employee but sometimes issues arise and there’s no way around it, they have to be addressed with the person responsible. I’ve heard the “training” excuse countless times!

    • Pang Ly

      One employee told my director that she wasn’t properly trained and that she was just “thrown” into it, her exact word, when he asked her about why she was making so many mistakes and I was in disbelief she had the nerve to throw me under the bus because I taught her everything I knew. Other co-workers were in the room too and heard it and they told me it was so wrong. I emailed her later that I wasn’t aware that she felt that way about the training and that I would be happy to go over it again or go over the things that confuses her but she did not reply. I mentioned to my manager and director that I was very disappointed that she waited until confronted to explain that her mistakes were due to poor training and they told me that they don’t believe her either because she has worked too long to pull that kind of excuse. Months later, my manager mentioned about her unethical behavior to her during her review and she eventually came to apologize to me. I don’t think she would have if they didn’t have the conversation and she probably felt sorry to know that it bothered me. She even admitted that she knew she had said something wrong but didn’t think it affected me. It was another palm face moment all over again, lol.

  • Katrin

    Sleeping on it is definitely a good advice. Sometimes you make bad decisions when you are in a rush. But dealing with stupid bosses can definitely be a pain in the ***.

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