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National Rip On Your Boss Day!


As part of the leadership series that I started on my YouTube Channel and will be continuing with a new video today, I’d like to propose another one of those holidays that someone makes up like national bring your kid to work day. I’d like to call it Rip On Your Boss Day. This may sound mean-spirited -- especially if you’re a Boss. Here’s the thing, I write about organizational agility and agile journeys and good leadership is an essential part of it. To illustrate, I’m going to tell you a little story.


Many, many, many years ago (yes, I’m just that old), I was given my first role as a supervisor. I had exactly one employee and I had no clue what that meant (having been given the guidance, “here, he reports to you now”). We had worked together for a while and liked each other, so I figured not much would change. As you might expect, I learned the hard way that, indeed, things had changed. He didn’t like me much anymore.


I learned this through the grapevine. Even though we had been “friends,” he was not comfortable sharing his concerns with me. This was one of the most important lessons about leadership that I ever learned. Fast forward a few years and a few more roles as a supervisor and I found myself running a startup.


The great thing about starting your own company is that you have a clean slate -- a tableau rosa if you will -- on which to build your culture. Having learned my lesson the hard way, I knew that the most important thing would be for me to fully engage every member of my team. I was never under any illusion that I knew enough to be successful on my own. I worked hard to hire smart people, even if I had to sacrifice some valuable experience. I have learned that smart people close the experience gap pretty fast.


To maintain the two-way communication that I craved, I had little tolerance for anything that smacked of brown-nosing (sucking up, ego-boosting, etc.). On the other side of the coin, I was always appreciative of any kind of feedback or suggestion. We didn’t necessarily try every suggestion, but we certainly discussed each of them.


In time, something emerged organically, which I came to call Healthy Disrespect. The open dialog I encouraged, along with the chiding I doled out for brown-nosing caused a few people to start openly teasing me. I could have easily put a stop to this in order to protect my ego, but I knew that it was healthy as a leader to keep my ego in check and this was as good a way as any to practice doing so. I earned my respect from others by doing a good job for them and the rest of it just made for a fun working environment.


I eventually came to realize that some of the ribbing I took was legitimate and valuable feedback about how I was conducting myself. I learned things that few leaders ever get the opportunity to know about how their behavior affects those around them. When I tell you this is “pure gold” I’m not exaggerating. Leaders should dream of getting this kind of detailed, ongoing feedback from the very people they serve.


The culmination of my efforts came one day in a company meeting in our large conference room (we only had 13 employees at the time). One of our newest employees started sucking up to me and (almost) the entire rest of our team turned on this poor guy and tore him up for brown-nosing. I actually had to defend him, by calling them off and noting that “you probably won’t do that again.”


Not everyone is able to take a good ribbing with the humility and joy that friends often experience when they do this with each other. Somehow, there’s a sense that you need to protect your stature with subordinates. This is, of course, bull$hit. Whoever came up with that idea was an ego-driven, command-and-control, commander (not leader). Leaders inspire. Leaders motivate. Leaders give you the “why” for the work you do.


With regard to this last item, check out my YouTube channel at 2:00 PM EDT today, when I drop the second leadership video that will discuss this very topic.


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