The Best Boss and the Worst Boss You Ever Worked For?

Every manager, good or bad, has influenced you. Make a list of their traits.

Posted Apr 22, 2014

One way to think about how to be a better leader is to think about who was a good leader for you.  A useful exercise in improving your leadership skills, especially in the area of being firm, fair, and consistent with discipline, is to take a pen and make a list of the traits, behaviors, characteristics, and even the eccentricities of the best bosses you ever worked for. 

And don’t just consider your previous law enforcement bosses for this list; go back through every job you ever held and consider how you were treated, led, taught, praised, disciplined, and communicated to by your direct supervisors.  Some current bosses say that their best boss was their first sergeant, or their best experience was in a fast-food job, or while working for a family-owned business, or that their best boss was when they were in the military.

Of course, this list is not complete until you consider the dark side.  If one side of your page contains what was so good about certain bosses, the other side must describe the truly horrible bosses you worked for, and how you survived their alleged leadership skills.

When I use this Best Boss-Worst Boss exercise in the police supervision classes that I teach, I get quite a range of interesting replies.  On the Best Boss list, the participants write traits like, “great listener, mentored me, treated everyone fairly, used lots of praise, kept the group informed about issues, went to bat for us with senior management, gave out assignments fairly, taught me how to do my job better, gave me the freedom to learn and make mistakes, caught me doing things right, and was always available but didn’t micromanage me.”

On the Worst Boss list, I often see comments like, “alcoholic, liar, screamer, slept at his desk, stole money from me, timed my bathroom breaks, took credit for my ideas, couldn’t or didn’t want to communicate, was never satisfied with my work, never praised me or anyone else, never taught me anything, seemed bothered when I asked questions, didn’t make eye contact with me, threw us down and blamed us in front of senior management, gone all the time, micromanaged me.”

If you look at your list side by side, you can say that many of the Best Boss characteristics are the opposite of the worst boss characteristics, and vice-versa. 

The context of these work situations is a part of the comparison as well.  You may have been exposed to a lot of yelling in the military, since that is a big part of the basic training environment.  Some people thrive under that kind of treatment; other people not so much.  What some employees think of as a micromanager might simply be a boss that sets the performance and behavior bars high and demands results.  What some employees label past bosses as missing managers, might simply mean that they gave every employee the freedom to do their jobs without too much unnecessary over-the-shoulder scrutiny, thereby expressing confidence in their people. 

As you consider the items on your Best Boss – Worst Boss list, ask yourself these questions: “Do my employees ever make their own lists?  Do they compare me to the best boss or the worst boss they ever had in their careers?  Do they talk with each other about my leadership style?”  The answers are: yes, yes, and only on days that end in the letter “y.” 

This list-making process can be eye-opening.  What are the traits and behaviors you need to do more of and which ones should you stop doing?  What are the things that the best bosses in your career did that you want to emulate and which ones from the worst bosses do you want to avoid?  When it comes to supervising, leading, and disciplining your people, which list do you want to end up on?

Dr. Steve Albrecht, PHR, CPP, BCC, is a San Diego-based speaker, author, and trainer.  He is board certified in HR, security, and coaching.  He focuses on high-risk employee issues, threat assessments, and school and workplace violence prevention.  In 1994, he co-wrote Ticking Bombs, one of the first business books on workplace violence.  He holds a doctorate in Business Administration (DBA); an M.A. in Security Management; a B.S. in Psychology; and a B.A. in English.  He worked for the San Diego Police Department for 15 years and has written 15 books on business, HR, and police subjects.  He can be reached at or on Twitter @DrSteveAlbrecht