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Dealing With a Difficult Boss When Quitting Isn’t an Option


Whether it be your direct boss, or someone higher up the food chain, if you don’t have a great, or even tolerable, working relationship with someone you see often and directs your day-to-day tasks (plus determines your performance) there can be a lot of unneeded added daily stress, anxiety, and personal issues that will directly affect your ability to perform well, lessen your desire to be at your job, and that will trickle down outside of the office into your work life.

In fact, when it comes to bad or difficult bosses, over 75% of the workforce says that their difficult boss is the worst part of their job, and employees with bad managers are the least productive.

These types of relationships can cause you to want to throw your hands up and run away and give up, even if you love the work you are doing or are on your way down a path that will payoff later. Frustration can quickly increase when you know quitting isn’t an option, and you’re stuck with that boss for a while as you move forward in your career.


What Makes a Boss Difficult?

To clarify, when we talk about a bad or difficult boss, we are not talking about a toxic or abusive boss, we are referring to a boss that might:

  • Make assumptions about you and your dedication to the job
  • Assume the worst intentions
  • Nitpick your work and look for mistakes constantly
  • Seemingly doesn’t respect your time because they shoot off emails at odd hours of the week and request tight deadlines for your work
  • Sets seemingly unrealistic expecations and expects you to consistently meet them without complaint or failure
  • When asked for feedback, only provides the negative

In general, a boss who makes your job a bit more stressful and harder because they aren’t operating and leading in a way that works best for you and your preferences. But what if having a difficult to work with boss doesn’t have to create all that stress and anxiety? What if there was a way to handle it well?


Why Quitting Isn’t the Answer

Even if quitting was an option for you, it isn’t the answer in most cases. If you leave your current position to pursue another path to get away from a difficult relationship with your boss, you’re not solving the true issue, instead, you’re carrying the mental stress with you into your next position and risking repeating the cycle again and again. Instead, you have to work through what is going on with you mentally and understand and modify how you react to problems and difficult relationships. If the reason your relationship with your current boss is so difficult is because you feel like they don’t think you’re good at your job because they provide negative feedback to you on your work, you will carry that anxiety with you to your next boss who will eventually have to provide you negative feedback, and those negative and stressful thoughts that were created in your prior position will pop back up again.


Understanding Where They’re Coming From

In corporate America, everyone has someone else to report to- employees report to their managers, their managers report to their bosses, and everyone reports to the CEO, who reports to the Board, who reports to the consumer- and because of that, the actions and mindset of your leader may be a reflection of what is being served from above and demanded from above their heads. If your manager is consistently setting high expectations and short deadlines, or often times doesn’t take no for an answer, it truly may not be their fault, but from direction above them that they have to abide by. Additionally, no manager enjoys setting tight deadlines, creating difficult situations, and generally inflicting stress upon an employees (most managers don’t) and in some environments, their hands may be tied so tightly that they unknowingly end up taking their own stress and anxiety out on you with these actions.

As your difficult boss rose in the ranks in their career, there were times where they were held to seemingly impossible standards, critiqued heavily by certain leaders, and faced the same difficultness that they are “inflicting” on you now. In their mind, because they are successful in their career, they may believe that leading in the way they were lead (no matter how difficult it made their job) is the correct path to take, because it eventually lead them to a position of power. When managers seemingly “haze” employees with stressful timelines, tasks, and to-dos like those that they experienced during their ladder climb, they are continuing a vicious cycle all on the premise of “if I had to suffer for success, so do they”. By playing into this old school rulebook, managers are creating a toxic and non-innovative environment for all involved, oftentimes, unknowingly. To take the wise words of Dr. Bertice Berry:

“Don’t haze these young women the way we were hazed.”

Lastly, there is the possibility that your boss is being difficult with you simply because they lack the skillset and knowledge to know what they are doing, and they don’t have the soft skills and people management training to help them properly handle their position and the needs. Companies, especially under duress, oftentimes skip the proper training that their leaders need for success, leading to poor people management skills and no prime examples of great leadership for their new managers to work from.

While none of these items excuses bad management’s behavior, it pays to know and understand their situation and demands asked of them before automatically dismissing them as a bad boss that you can no longer tolerate.


So How Do You Deal?

Work it Out

While an eventual intervention with HR or upper management may be needed in the near future, before escalating the situation (which can take a turn for the worst and lead to even more conflict) the most important next step is to work from a common ground of understanding with your manager. Some of the most common conflicts with manager and employee relationships stems from different personality types and preferences clashing in the office, and one another feeling a sense of animosity towards one another for not operating under their preferred “standard operating procedures”. Adaptive leadership and communication (from all parties) is a must in order to strive for more successful working relationships- if your preferred style of communication is detail-heavy, but your manager prefers a high-level approach at first, adapting the way you present yourself can help create a more positive interaction. On the flipside, if your manager is very detail oriented (hence them nitpicking at the fact that two graphics in your powerpoint were 1/8 of an inch offset from one another, or the colors weren’t an exact match to the company colors) thinking from that different perspective can save a lot of heart and headache in the end.

In order to get to that point, you must have the conversation first with your manager, at an upcoming one-on-one or performance meeting, bring up your concerns: “I’ve noticed a lot of my feedback and issues has been around the smaller details in my work being overlooked or missed, and I completely understand that and will work on that. With my personality type, I’m not as detail oriented as some others, and it is something I’m working on a lot.” Similarly, you can also add “I appreciate all of the constructive feedback you’ve been giving me, and I was wanting to also have a conversation around what I do well here and what you believe my talents are, so that I can hone those more and use that feedback as an additional motivator. I’m more of a feelings person and thrive of of both positive and constructive feedback.”


Just Accept it

While working to “work it out” and come to a common ground of adaptation is an important step to take, the best solution to the problem is not to attempt to get others to change how they interact with you and for them to operate by your SOPs, but to accept the fact that, in this world and in your job, you will have managers, colleagues, friends, and family, who all have different personality types, different communication methods, and different leadership styles, and your relationship with them can be as difficult or as easy as you choose to make it.

You must stop assuming that everyone has to adapt to your preferences in order to create a better relationship with you.

While, in your mind, consistent criticism and nitpickiness is negative and rude in others minds, it is the best way that they can help you push farther into your career and do more. To them, focusing on what you can fix and telling you to fix it, is the best way for them to manage and develop you. In their reality and in their experiences, sending a work email at all hours of the week (even Sunday at 6am) is normal and acceptable, because, to them, when you’re awake you can be working, but in your reality, any email after Friday at 4 or before Monday at 8am is unacceptable and inconsiderate to send. Their reality of what is good or bad is shaped in the same way you have shaped yours, through unique experiences and interactions. This does not actually mean all of the things you are making it mean- they probably don’t hate you, don’t think you’re bad at your job, don’t believe that your weekend should be spent in front of your laptop- but the more you believe that all of their difficultness means those things, the more it will feel true for you, and the worse your relationship with them will be.

The best way to move forward and create a working relationship with your difficult boss is to change your mindset around what their actions mean to you, the impact their actions have on you, and to stop making baseless, harmful assumptions about them and their feelings.

You can consciously choose to believe that their actions mean something negative about you, or you can choose to believe that they are doing the best that they can with the abilities and personality that they have.


It should be noted that there are times where you can adapt all that you can, do all of our own internal work around your thoughts and feelings on their actions, and still have a bad, and trending towards, or already invested in, toxic relationship, with that boss. If it gets to that point and you have had the hard conversations with them to try to work it out, done the work, and more, and nothing has been done, you have to do what is best for your sanity and satisfaction, and bring this to the attention of HR so that change can occur in how they treat their employees, because, in the end, maybe that little voice in your head was right, and they really are a difficult, and bad boss.

If can choose today to take back your power in the situation by working with your boss to adapt to one another as needed, and to accept the things you cannot change, you will come out of the situation stronger, more ready to lead, more mindful of others, and with less of an emotional burden- all of which align with the very definition of what a great CEO is.



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