Free Character Writing Prompts #17:

Don't show up late to these 10 character writing prompts about bosses. Many stories, especially those that spend time in an office or a police station are prone to showing overbearing and angry bosses. The recent movie Horrible Bosses portrayed these division heads as sharks, jerks and even nymphomaniacs. While many bosses are not well-versed in the ways of effectively running a team of employees, not all of them are mean and a few of them are even revered by their employees. In addition, unless a boss has the letters CEO on the front door of the office, he or she has one or multiple bosses to report to. While it may not be easy being an employee, it can be even more stressful to have both employees and bosses to deal with. 

Free Character Writing Prompts #17: Bosses

1. He was one of the most laid back people you've ever met and as a result, your office never got anything productive done. He'd come around to everybody's desk and chat with them for what seemed like hours. Any goals he set he'd change if anybody complained for even a second. You loved not getting yelled at, but in a way, you missed the authority. Why is he so laid back and how will he keep his job if he fails to reach all quotas possible?

2. Everyone at the office knew that he was corrupt, but they were too afraid to do anything about it. People talked about him as if he had connections to the mafia, and with the tough-guy clothes he seemed to wear, almost everyone was willing to buy it. He openly talked about stories of his old days on the streets of Brooklyn. You weren't sure if they were true but they were intimidating. Is he actually corrupt or is he simply blowing smoke to appear dangerous?

3. There were those at the office who believed she only earned the position because of who her father was, but when she settled in, she may have been effective enough to write a book on the subject. While her dad was known as a ball-buster who ordered everybody around, she trusted people and seemed like more of a mentor than an employer. What in her life caused her to be such a respectful boss?

4. You were hired at the same time, but here you were still languishing at the same position while she had become your boss after several successive promotions. It didn't seem like she did anything that much more special than you. As far as you were concerned, you were equals. Then again, she did have one of the best attitudes you'd ever experienced. Will she continue to move up the business ladder?

5. He was only a year or two away from the Baseball Hall of Fame and now he was going to be your manager. Your previous coaches had always said you weren't living up to your true potential, but your new boss wouldn't say anything of the sort. He watched you swing a few times, motioned you over and had you watch him a few times. He didn't say anything, he just hoped you'd pick it up. You weren't completely surprised to end up with the best year of your career. How well does this new coach do for your team as a whole?

6. It was impossible not to smell your boss coming from a mile away as he reeked of alcohol. He would rarely attend meetings, even the ones he called and he could usually be found sitting in his office wearing a pair of sunglasses. He seemed nice enough when you chatted, but you never knew if you were talking to the real him. When did he become such a drinker and will he ever be able to overcome it?

7. She fancied herself extremely creative and full of new, strong ideas. One of the reasons she rose to the top was because she was always coming up with new plans that management seemed to love. When she finally became your boss, however, she drove you crazy with her flip-flopping and always changing one more detail in a project to make it perfect. She even rearranged your desk once without asking for your permission. How will she do as your boss and is she creative or simply scatterbrained?

8. She was an extremely diligent employee and when she was promoted to manager, nobody blinked an eye because she had certainly put in her dues. She always showed up early and stayed late. She was perpetually punctual and kind. Her only issue is that she had no idea how to manage and frequently got frustrated and confused as to what to do with her new responsibility. How will she cope with these changes to her job description?

9. As you moved up the ranks in the White House, you never expected you would have gone as high as one of the personal assistants to the President himself. He was extremely intelligent and always busy trying to solve all the conflicts in the world. He knew everyone on the staff by name and as the man who picked out his wardrobe and took his food orders, you were privy to a very inside look into who he was. What was one situation in which you saw the true him come to the surface?

10. Motivated, energetic and powerful were words you'd use to describe her personality, but absolutely nobody in the office could figure out exactly what she did. You all knew that she had an office and that she never seemed to be in it. She rarely responded to e-mails, her assistant tended to do that for her. Some days she didn't show up at all and her assistant said she was away "on business." What are a few things, if there are any, that she actually does as your boss? 

Did you enjoy these character writing prompts? Keep an eye out for the book 1,000 Character Writing Prompts in late 2011. 

Done with Character Writing Prompts about Bosses? Go back to Creative Writing Prompts.

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Written by Bryan Cohen

Bryan Cohen is the author of more than 30 books, many of which focus on creative writing and blasting through that pesky writer's block. His books have sold more than 20,000 copies. You can find him on and Facebook.
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