Your Worst Manager Could Have Been Your Best

by | Blog, Leadership Development

If you ask yourself who was the best leader you ever worked for, it quite possibly was someone who was direct, gave you bad news, and honest with you when no one else was. They also cared enough. We often can misjudge people who on the surface seem “tough”, when they can also be a powerful window into our own development. I entered the field of organizational development because of my objection to the types of workplace environments employers tolerated. The organizational landscape is littered with bad leaders. Bosses who display bad behavior, are passive-aggressive, or who are just plain mean. Despite my objections to these environments, some of my worst examples of bad behavior represent many of the best work experiences I’ve had. They provided me with examples of what bad management looked, sounded, and acted like. Some of the people involved in these examples of bad behavior still accomplished great things and brought the best out of me.

Different Experiences

My first official management role started with a stern statement from my boss, Kenny, who said, “I’m promoting you to manager, and you’ll work your ass off. I will be tough and direct and will expect a lot. Do you want the job or not?” This sounded ominous, but Kenny was a good manager in my eyes because he was respectful. He worked me to the bone, but he also rewarded me in his passive-aggressive way. On the other hand, I also worked for, let’s call him, Joseph, who seemed nice enough in the office. However, he made me feel anxious, unaccomplished, and worthless. He never really expected much from me other than to make him look good. He refused to engage me as a valuable contributor. He questioned everything I did. I went to work feeling bad most days. That is until I found the courage to take him on.

Bullying Impact

Bullying can be defined as “repeated health-harming mistreatment of others, including verbal abuse, offensive conduct, humiliation, intimidation, and other threatening behaviors.” We’ve all been in situations where someone has approached this definition without crossing the line. What I’m talking about here is the authoritative approach to leading and managing that can be passive in nature, subtle, but powerful in keeping people in their place for the sake of “managing.”

A survey of workplace bullying completed by Zogby Analytics found that nearly 75% of employees have had exposure to bullying at work. Worse yet, 25% of employees surveyed said that the pandemic only exacerbated bullying at work. Of the respondents, 50% said they experienced or witnessed virtual bullying. According to the Zogby survey, 65% of workplace bullies are individuals with a higher rank than the target of the bullying.

Oppressive Management

For our purposes here, let’s not use the word bullying, but let’s call it oppressive management. The difference is that bullying is purposeful while oppressive management is more of a lack of skills and competencies in managing people and processes. When you have a hammer, everything looks like a nail, and for some managers, the only tool they have is oppression. So, if we open the bullying statistics to include oppressive management, the impact to our bottom line is staggering. So, when we are victims or witnesses to oppressive management, it can affect job stress, retention, and team well-being. It can sap productivity, destabilize our organization, and destroy profits.

Signs of Oppressive Management

Oppressive management isn’t as visible as you would expect. Rather, it is a damaged connection between people that is felt and used for control. Signs include good people leaving an organization, drama between the team, insecurity of the staff, and a sapping of confidence. Good talent will eventually realize they have choices and will surely find them. Another sign is a boss using oppressive skills in private, never in public, because they intuitively know that this would cause reputation damage. Oppressive leaders are charming with new relationships or in groups. When you sense oppressive management, you rarely see eye contact unless to emphasize a point, interruption of dialogue to assert themselves and a sense that you aren’t there, unless they need to demand something.

Skill Gaps

Joseph didn’t mean to make me feel badly, he just didn’t have the skills to deal with talent. He was likely an insecure person who learned his style from an oppressive authority figure. Kenny, on the other hand, made me feel respected, counted on and valued. After working me hard, he would take me aside and tell me that he appreciated me, give me time off and invite me out for a beer. The point here is that good managers make us feel valued. Kenny’s intentions were to get the job done through me as an extension of himself, and that felt empowering and important. In Joseph’s case, I was somehow the enemy, someone to boss around. We must be careful to identify and notice the intentions of the people who lead us. Kenny was tough on me, but his intentions were good. When I realized that I could be his soldier, I learned and thrived. I did not have to adopt his tough behavior but recognize it for what it was. Joseph was seemingly polite, and “gentle”, but his intentions were selfish. We must open the cover of the book before making judgement.


Oppressive leaders will be successful for a time. However, when they finally slip, they won’t get the support they seek. People will work for them for a while, but when events start to unfold, there will be an uprising. Modern workers have choices, and this old style of authoritative management is a deal breaker for most. We know who these people are, and they know who they are, too. There are ways to help and deal with oppressive managers. Consider the following interventions:

  • First, look deeper for intentions. It is my experience that most people are not so bad, they just need you to accept them for who they are. Try not to be thin skinned around them and push back a little. Most good people actually respect strength, or they behave better when faced with it. Bullies are unacceptable and will back down when they realize they can’t shake you.
  • Demonstrate personal courage – don’t hand over your power. You relinquish your power only when you allow their behavior to have an impact on your reaction. Authority only exists when you give in to it.
  • Bullies are really wimps. Test their courage with transparency. Confront them and call them out. Once you do, they will avoid you, so make sure you are ready for that.
  • If someone comes off just tough it could be a form of care. Judge the book by what is inside. You can do that by telling them how you feel and let them know where the line is, they will respect that.
  • Talk with someone about your concerns. Don’t keep secrets about how you feel, and this includes with the oppressors themselves. Sometimes awareness is a powerful tool to healing relationships.


As a society, we are transforming toward more civility and good corporate citizenship. Despite our best efforts, we all behave badly sometimes. We all may run into others who are having a bad day. The best thing we can do for each other is respectfully call each other out, forgive and move on. Kenny tested my limits and drove me toward being a very hard worker. Regardless, my memory of him is that of a liberator of my abilities. Direct is good when it is combined with respect. Oppression is bad if left unchallenged.




About Sojourn

Sojourn Partners is a results-driven executive leadership coaching firm that empowers the professional workforce to think differently in order to realize the full return on investment in themselves and their companies. Professional leadership thinking and intervention, based on years of research and experience, place Sojourn Partners at the forefront in executive leadership coaching, organizational development, strategic planning and culture and climate change.


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