Leadership Lessons I Learned from a Horrible Boss


Let's talk about compassion in business. Here's a trait I've always thought I performed well at. Therefore, when I meet those who lack it, I'm taken by surprise. "What did I ever do to this person to deserve this?" I internally ponder. You may tell yourself: "Well, duh. Leaders should always exercise compassion!” But what happens when they don't? Here's a tale of lost compassion (aka: leadership lessons I learned from a horrible boss)...

It began my first day on the job. This was my first real job straight out of high school, working in the world of fashion retail. I had made a small error due to a lack of training, inquired about what I should do to fix it, was told to ignore it, then a week later was confronted about it and virtually blamed as though it were my fault that a consequence occurred from her decision. A good leader accepts responsibility for their impact on situations.

Then it turned ugly. More passive-aggressive, nagging behavior ensued: she would yell at me (and my coworkers) from across the store whenever she desired, condescendingly speaking to us as though we were not competent enough to ask our customers the required questions. A good leader has faith in their employees to get the job done and well, and releases the reigns to facilitate confidence-building.

She would stand there with all the resources in the world to help customers, and demand that we do it with the universal, loudly-stated claim: "You have ladies waiting for you!" Customers would remark: "Can she not help me?" We shook our heads and simply said, "Nope, she can," with a smile. A good leader would've jumped in and motivated the team to work collaboratively.

While "driving, directive and coercive styles of leadership may move people and get results in the short-term, the dissonance it creates is associated with toxic relationships and emotions such as anger, anxiety and fear." (Psychology Today

The best day was when we had to dress six mannequins for our window displays given just 15 minutes (of course, without any previous training). She put check-marks next to the shoes I needed to grab from the back, and when I returned with the correct number of shoes, she pointed to one in the catalog and said: "Where are these shoes?" When I calmly but firmly explained to her that she told me to "only grab the ones with the check-marks next to them," and that the pair of shoes she was pointing to did not, she breezily replied: "Well, we'll have to figure out something for her, then, but let's just work with this for now," yet again denying that she had any personal responsibility for the outcome. A good leader would have apologized, exercised restraint and encouraged their employee.

On the same occasion, she arranged the mannequins' outfits in a particular order, sending me off to dress them. When I failed to place an outfit on the correct mannequin, she snarkily remarked: "Oh, Kathryn--you're killin' me!" She then pitted us against each other, "jokingly" commenting about how so-and-so "won the contest", when teamwork was supposedly our company's motto. A good leader never insults or makes their followers the butt of a joke. My favorite moments were when she would laugh at past conversations she thought were amusing because of the employee's presumed stupidity, proclaiming: "You know, some of the things people ask me... I dunno!" with a smirk. A good leader would've provided proper training ahead of time to avoid follow-up "annoyances". You should assume your employees are going to have follow-up questions if you don't give them detailed explanation to start with--but not her, of course.

She also crossed boundaries, referring to my appearance on multiple occasions, telling me: "You look like you've lost weight! Whatever you're doing - it's workin' for ya!" There's a rumor that she told someone else they needed to get their eyebrows done. There isn't even an option for a good leader here, because it would never happen.

Above a plethora of other experiences, these are the ones that have left the biggest imprint. For four years, I watched her emotionally ruin my closest friends and observed the dominos fall, as girl after girl left our establishment with the highest turnover rate you could imagine. She failed to recognize the real reason people were leaving the store (her behavior), and vocally stood by her anti-compassion policy, claiming that if they're not doing their job correctly (through no fault of her own), compassion isn't exactly necessary!

To top it off, when I went to higher leadership to discuss my experiences, I was dismissed and told that it was "just a personality difference," and that I should talk to her about how it made me feel. Not only did I discover that the company's HR structure was corrupt, but that there was a serious lack of compassion in my workplace.

Should I have called her out when she behaved in certain fashions? Sure. Should I have taken more initiative to train myself when I wasn't receiving the proper training necessary to do my job? Probably. But was it my job at age 18 to tell my 40-some-year-old boss to get her shit together and act more compassionate? No.

All it takes is one leader who chooses to "create a ripple effect" of compassion, setting a strong example for their followers. To foster loyalty and trust between you and your followers, you must lead with compassion and an open heart. With a 60% higher risk of suffering a heart attack or other life-threatening cardiac condition for employees under these abusive conditions, we must end the trend of inconsiderate bosses once and for all.

So, while I never did anything to this woman to deserve her mistreatment, I surely developed the prototype for the leader I hoped to one day be. It might be a while before I can come to terms with this in a positive light, but I'm working at it. As I launch my new business, I keep this in mind:

“Companies who want to survive are smart enough to know that caring and cooperation are key." -Richard Branson (CEO, Virgin Group)

Have you experienced something similar? Who has shaped your concept of good leadership?