Making The Most Of Working For A Difficult Boss

Josh Didawick

Making The Most Of Working For A Difficult Boss

Throughout an entire career, it is likely that everyone will have to work with a difficult or bad boss at some point. It can be a trying experience and some of the effects can be long-lasting and detrimental to one’s career and career path. For those early in a new job or industry, a difficult boss at the wrong time can drive someone out of what could have been a promising experience. For mid-to-late-career types, working with a difficult boss can feel like it puts the brakes on growth and feels like the next step or position will never come.

First, we should probably clarify what is meant by the term “bad boss.” Horrible bosses, like the ones depicted in the movies, do exist but are rare. Those characters are like caricatures of bad bosses and horrible human beings.

This article will not necessarily address what to do if a supervisor is harassing, threatening, or creating a hostile or downright miserable working environment. Those types of people are evil bosses, and while they do exist, they are different than a bad boss. It is important to know how to document an evil boss and who to speak with about concerns and violations of company policy or civil rights.

The assumption herein is that many difficult bosses are well-intentioned. They may be unprepared or they just do not necessarily jive with everyone. In other words, one person’s difficult boss can be another person’s dream boss. Among other factors, personal preference can be a major part of the equation.

In fact, this has been my experience working with employees and managers throughout my career. Someone will come to me looking for guidance on how to work better with their boss, and in a lot of cases both sides are not doing anything wrong; they simply do not understand each other or mesh well together. This is not a reason to give up or not try to improve the relationship, but let’s take a look at navigating some of these difficult waters.

Change Agent

Defining a bad boss is difficult and is going to depend on the boss, the employee and each of their personal preferences. Let’s not forget that the business environment can also have an effect on relationships. In thinking about the environment that the organization is operating, one has to develop a situational awareness. Some bosses are hired as change agents and change can be difficult for many people involved. In these instances, a supervisor may have directives to carry out or marching orders from upper management about changes to make within a unit or team.

As an employee, sometimes you have to take a step back and recognize the environment the organization is operating. Is the company or industry under pressure? Are there changes being made in the business that we are behind in adapting? As hard as it may be, sometimes it is best to embrace the change, even if that means embracing uncertainty. It may mean the difference between a company evolving and thriving versus dying. An aversion to change is, in some ways, a fear of the unknown, something different and/or not being in control.

Consider playing a more active role in the change by offering your advice and suggestions about how to make change successful. Adopt a strategic mindset and open yourself up to the possibilities. By embracing something new that a manager is doing or rolling out, three things can be accomplished. First, you may find yourself as an early-adopter of the future of the organization. Second, the change agent boss will likely recognize and appreciate the trust and support. Lastly, you will likely feel less anxiety about change and your boss because you have taken back some control by becoming an active participant.


Another type of boss that gives some employees difficulties is the micro-manager. This is a type of supervision and can take many forms. Sometimes the supervisor tells the employee what to do, then how to do every step in specific detail. Other people are bothered when a supervisor checks in with them too often on a project or assignment. Micro-managing early in a relationship is often helpful for the supervisor to understand the work and his or her colleagues. Long-term micromanagers may simply like to be in absolute control or, worse yet, may be insecure. People sometimes micro-manage when they are uncertain about an outcome or have been burned in the past.

In dealing with this type of supervisor, try to understand from where they are coming. If the boss is perceived to not be confident in your abilities, you will want to interact with that person in a way, and deliver results, that builds his or her confidence in you. If you are still being micromanaged after successfully showing what you are capable of, use the capital you have built up. Talk to the manager about your perception of their management style and ask if there are things you can do to help allay some of the supervisor’s concerns. Not only is this a less-threatening way to approach the topic, but it conveys that you want to help the manager be successful as well.

Learning On The Job

One of the most common complaints I have fielded from employees about their supervisor is, “I have to train my new boss!” In some sense, this is often true. When someone is hired from the outside, they usually need to get up to speed on the new team, company, industry, etc. It is natural to be frustrated by this dynamic when you clearly know more of the technical side of your job and role. What is often missed is what the supervisor is bringing to the table. He or she may have experience and skills that are meant to be complementary to the team already in place.

I recommend giving this situation your best. Embrace their success as your own. There is really no reason not to. The new boss, like it or not, will have some influence over your career and in a lot of ways your success is now tied together. On the other hand, if the new boss flames out (not that you would wish that on anyone), you have hopefully gotten some good exposure by providing some guidance to your new supervisor.

These are only a few examples of difficult or bad bosses, and as mentioned earlier, these are well-meaning supervisors, not psychopaths. Dealing with a mean or selfish supervisor is a different dynamic altogether. Working with someone who has good intentions that you do not necessarily mesh with can be difficult, but it is not insurmountable. Try to understand their perspective and motivations. Meet them halfway where you can. You may not only improve your working relationship with the person, but you could give your career and personal brand a boost.

About The Author

Josh Didawick

Josh Didawick is a seasoned HR professional and consultant with extensive experience creating and guiding organizations’ HR strategies, as well as coaching individuals committed to successful careers. He specializes in taking on complex organizational issues to affect positive change and high performance. For individuals, Josh helps them put their best foot forward when seeking that next career, promotion or milestone in the workplace. Josh has had several articles published and presented at conferences on HR-related topics.

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