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My First (Worst) Boss (110/365)

Yesterday, I wrote and published a piece about my memories of my first (best) boss. Of course, this has led me to think about the opposite: my first (worst) boss. This has been slightly more challenging, for a number of reasons.


  1. I am generally a positive person, who doesn't think or speak poorly of others.

  2. I believe that dwelling on the negative or the past isn't productive.

  3. If I'm being honest, I have had far too many bosses with many of the same characteristics, making them "a bad boss".

There's been much researched and written about people complaining about their bosses. That's not my intent here. In fact, I'm quite fortunate to work in my current setting, working with the people with whom I work, daily. I'm reflecting more about my most formative years. It's been a good 25 years for me


As "a kid", I worked in food service, retail, for "Mom and Pop" businesses and in large corporations. Camps, for coaches, and with teachers. So many memories, so many stories.


I've had many jobs and many bosses.


Most have been, forgettable. And some, memorable, but for all the wrong reasons.


The 3 Characteristics of My First (Worst) Bosses:

  • A lack of clear expectations and inconsistent communication.

It's said and written often, of top performing organizations, how employees can playfully and respectfully impersonate the boss's mannerisms and catch phrases. These are generally the company mission or vision, the top leadership priorities of the person who oversees day-to-day operations. This is only possible, with a clear communication style and ability to articulate what's most important in the organization. I aspire to be this kind of a "boss".

  • A "mistakes are fatal" mindset and attitude towards others.

It's one thing if we are performing a high-risk, life-threatening surgery. Or engaging in a task requiring extreme concentration, one in which people's lives are in our hands. Or the case of our military professionals, or those in police, fire, ambulance, or hospital settings where the detailed sense of interwoven teamwork is mission-critical, essential to the safety of others. The people serving in these industries are unique and amazing. The rest of the world is not doing this sort of work. So, in cases where a small detail is missed, if words are said with good intent, that are misinterpreted by one person, if a mistake is made, it's generally fixable. Organizations that learn create a sense of psychological safety. It's members can reflect together, and improve and support the growth of others. Engaging in daily in-person dialogue (or even banter) makes engaging in a process such as after-action review routine, and even welcomed. The reason? Learning is always the top priority.

  • A "do as I say" mentality of command and control.

Without realizing it in the moment, this is one area that I have made improvements on, in the last two or so years. Sure, I know how school works, how to teach, and how to create an environment in which students learn best. But I have not done this work "on the front lines" and I have never done this before, during, and (hopefully soon) coming out of a global pandemic. I am not a command and control kind of leader/manager. Never have been, never will be. But I did find myself giving some people, in some cases, "the bottom line" on certain things. Maybe it was my own mismanaged stress in the moment. Or my lack of awareness of exactly how complex my "small request" was in the larger context. That's why, heading into this year, I have evaluated and prioritized my new approach.





Build relationships. Seek first to understand. Learn to lead. One day at a time, this appears to be working. It's also allowing me to practice my communication, to embrace and celebrate learning moments together, and to never be a boss who says (even without saying it), that people should fear me or not know what to expect from me on any given day.



My worst bosses, like my best bosses, have taught me a great deal. Probably more than they know, and many, unintended lessons.


With learning in mind, communication, collaboration in an organization can thrive.

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