Understanding and Working with Difficult Bosses

By dedicating themselves to their job and becoming indispensable, employees can build a better working relationship with their boss.

By dedicating themselves to their job and becoming indispensable, employees can build a better working relationship with their boss.

In Understanding and Working with Difficult Bosses, Reverend Geary Reid discusses a reality that many employees face: working for a demanding boss. While some bosses are, unfortunately, uninterested in their employees’ well-being, many bosses do care about their employees and award those who prove themselves to be hard workers. Thus, Reid offers tips on how employees can endear themselves to their boss. Oftentimes, employees can be their own worst enemy by not taking their work seriously enough or treating their job as a stepping stone to something better. By being punctual, meeting deadlines, effectively communicating, and being a team player, employees can improve not only their relationship with their boss but also their overall experience at work. To boost office morale, all employees—including the boss—must do their jobs accurately and efficiently. 

Because most people have a boss, it is crucial for them to understand how to work with—and for—their boss. With the knowledge contained in this book, employees can develop their skills and become more competent workers. By doing so, employees may find that their boss is not as difficult to work for as they had once thought; additionally, they may find work not only bearable but also enjoyable.



No employee likes to work with difficult bosses, but difficult bosses can be found in most organizations. Some of these bosses are unaware of the problems they cause for the employees. Many employees resign from organizations because they cannot manage to work with difficult bosses. When employees change organizations, they sometimes find that they have to work with another difficult boss at their new job.

The problems that some employees go through at work are not always caused by their bosses’ behavior towards them. Some employees contribute to their bosses being upset with them. For example, if employees arrive at work after the required time or produce inaccurate output, then it will make their bosses upset. However, employees can win the hearts of some difficult bosses by attending work punctually and regularly. Having a pleasant personality is another important thing for employees to practice. Employees must continue to be respectful to their bosses, and they will see positive responses, even from difficult bosses.

Effective communication is something that employees need to practice. Before they approach their bosses, they must plan what it is that they want to discuss, then write down that information in a sequential manner, in order of priority. In meetings with their difficult bosses, employees must listen carefully, take notes, and choose which types of non-verbal communication will be most appropriate to use during their meetings. If employees go the extra mile, they may win the hearts of difficult bosses.

Employees need to invest in their knowledge and skills. These investments may give them opportunities to move from one department to another, and they may have the chance to be promoted. 

Each employee must try to understand their bosses. Some bosses do not like to delegate, while others like to micromanage. Still other bosses do not like to deal with conflicts and meetings. Some bosses got the job only because it is a family organization. When employees understand their bosses better, they will find ways of working around their bosses’ shortcomings and beginning to work as a team, rather than enemies. Not all bosses like to be corrected, even when they know that they are wrong, so employees need to be aware of such traits in their bosses. 

If employees recognize that even their best efforts will not cause their bosses to change, then it may be good for them to switch to a different department. On other occasions, employees may have to take a job with a new organization. The bad behavior of some bosses may be a good indicator for employees to leave the organization and become an entrepreneur. Some persons started their own businesses because their bosses’ behavior pushed them out of the organization, and they have no regrets about starting their own businesses.


Many people dread going to work because of their boss. Perhaps their boss has unreasonable expectations for his employees, or maybe he is ambivalent about his employees’ well-being. Rather than leaving an otherwise good job and risking the possibility of working for someone even more difficult, however, employees should first learn how to work with and understand their boss. What are some habits that will endear employees to their boss? How should employees act in meetings? How can employees learn more about their boss’s delegation style? In this book, Reverend Geary Reid offers answers to these questions—and many more. Ideally, a work environment should be collaborative, and employees should feel as though their boss hears and respects them. While some bosses will, unfortunately, always treat their employees poorly, many bosses will appreciate their employees more if they are diligent, punctual, and responsible. By dedicating themselves to their job and becoming indispensable, employees can build a better working relationship with their boss. 

Author Bio

Over the years, Reverend Geary Reid has worked for many organizations; thus, he has seen his fair share of both good and bad bosses. To Reid, it is incredibly important to build a healthy, communicative relationship with one’s boss. Oftentimes, employees may, in fact, be at least partially responsible for their poor relationship with their boss. Maybe they show up to work late, or maybe they have trouble meeting deadlines. However, by improving their skills and becoming more competent at their job, employees can improve their working relationship with their boss. By sharing his valuable insights and firsthand experience, Reid hopes to help employees reach their full potential and thrive in their workplace.

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