What the worst leaders can teach us about career perspective

Everyone wants to work for the best leaders, but working for the worst leaders can often teach you so much more.  

Perspective is such an undervalued tool. I’m so thankful that I have it in my career to be able to guide my decision making process and understand how and why decisions are often made. Perspective allows us to know when things feel right or wrong in the workplace. Perspective allows us to understand what the big rocks and the small rocks are and when and what to get frustrated with. Perspective and experience allows us to look at the situation and realize it may be circumstance, or it just may be terrible leadership. Perspective is a thing that you can’t learn any other way than through time.  

My second job out of college I was essentially working for a startup. This company had been in business for several years focused mostly on selling hardware for the retail advertising space (I think, in fact, still to this day I have no clue what they were doing before I started). Back in the early 2000’s the retail space became obsessed with displays that were visual to showcase a product. For example, if you were at a makeup counter at Nordstrom, a brand would want to feature a mirror with their logo and perhaps a TV embedded in the back of it. This company was selling products that fit a need but eventually moved into a space they had no knowledge of.  

I went to work here due to the advice of my mentor and while the story ends badly, I’m so incredibly thankful still to this day that I accepted the job. Before I delve much deeper into this story, I also want to note the absolutely incredible people I met at this company who I still have admiration for today.  Many of whom taught me principles that I will never forget and in addition, gave me the opportunity to start my career.

In late 2005, the company had just acquired some new technology. They purchased a product and a group of people with it, including me, who was hired with the new team. I started in January 2006. The product was basically a 42” iPhone, (the iPhone wasn’t released until mid 2007) which made us ahead of our time. The concept was simple. You walk into an airport where there is a large audience and you place several kiosks for someone to interact with. The touch TV screen would feature weather, news, traffic, sports updates, and even the opportunity to book a hotel room in the city you’re flying to. You could purchase tickets to an event and maybe even secure a restaurant reservation. Back in 2006, this was well ahead of the time and we thought we had the chance to make something big. The concept was so exciting that we had plans to go to big box retail companies and place the kiosks in the aisles to help you navigate to the items you were looking to purchase. There was a time when finding something at Home Depot was like a scavenger hunt.  

If all this sounds familiar, it was essentially the iPhone. At the time, we were running fast on a product that we felt like we could make some big waves with. I was hired as an Advertising Sales Manager. Funny I was given that title considering I had never sold anything and or managed any people but let’s go with it. My job was to sell advertising on the screens that we had featured in the Sea-Tac airport. It was my first foray into sales and one of the hardest sales jobs I ever had. I made 60-70 dials a day with no CRM and no training. In fact, I kept all my notes on a running word document. I was trying to sell a visual product over the phone to ad agencies who were spending money on television instead of the unproven product I had. I had no way to quantify viewers or those who were interacting with it. It was a concept sale at it’s best. The bulk of the deals I sold were to direct response advertisers with “ As Seen on TV” products. Remember “Focus Factor” pills? Yeah I sold pay per lead advertising to them!

To say it was a challenging sale was selling it short. Along the way we iterated on the product with subtle UX improvements. We also expanded to the Detroit Metropolitan Airport and we eventually purchased the 270 TV screens in the Port Authority Trans Hudson (PATH) subway system in New York and New Jersey. I was traveling quite a bit and by June I was promoted to Business Development Manager. This was another title I had no understanding of but again, let’s move forward.  

It became clear as the months passed that we were a lost company. We were short on funding, people, process and most importantly, leadership brains. There were some really intelligent people that the company had hired along the way and people who today are still mentors of mine, but at the very top of the pyramid featured some of the most incompetent leaders I have ever worked for. The lack of vision, the lack of organization, ability to motivate and inspire, and just run a day to day operation was amazing to witness. Every day I came into the office I felt like I was earning a PHD in how not to lead a team of people one day. Keep in mind this was so early in my career that I had zero perspective. The nine months that I spent at this company was without a doubt all the fuel that I would one day need to help shape and drive my leadership principles for the future. I kept thinking, there had to be better leaders out there than these folks.  

By early July the company was floundering further. We had acquired an ad agency for god knows what reason out of New York. I recall our first meeting with the agency and thinking, “you are all really smart people, why did you agree to merge with these folks?” They were blindsided by the lack of leadership at the company, but for them it was an exit strategy. That exit strategy later came back to bite them as the parent company ran them ragged for months before they had to take over again. Every week it was more obvious that I would need to find another job. It became clear that we would fail and this was for sure not the company or product we once thought it could be. Still to this day I believe we could have made a lasting mark on the out of home digital advertising space. The thing that stopped us wasn't the product, it was the leadership team. 

The Board of Directors decided it was time to appoint a new President as the previous one was simply not cut out to lead the type of endeavor that we were running. The new President was even more incompetent than the previous one. We will call him John Doe for the sake of this drill to protect the incompetent. John Doe had been with the company for quite some time and was immune to the level of incompetence that the company had come to know. I always felt his perspective was skewed as he had spent quite some time within the walls of the company. When you don’t have any other perspective you simply do not understand the level of failure that you may imply in your actions and routine.  

John Doe sent an email out one day in mid July that will forever stick with me. His email was about future growth plans. We were a small enough company (>40) that we would often solicit replies to the plans ahead for either buy in or to double stamp the bad idea that someone had, I’m still not sure. No matter the case, I hit reply all to Doe’s email and gave my response or direction that I felt suited based on my conversations with advertisers and time on the road. I had been with the company for six months at this time, and I was recruited by some important folks and felt I had a good grasp on the direction. After all, they kept sending me on the road on important projects and while I was still shy of my 24th birthday I felt my perspective was important to showcase. I wanted to act as an owner. 

What happened next is what has stuck with me for years. John Doe replied back to my email directly with the following: (the following is a re-creation, cue the music)

In sports, they refer to comments in the media as “bulletin board material” and for me this email will forever be my bulletin board material.  

I can still recall standing on the deck of my condo on the west side of Queen Anne in Seattle reading this on my first T-Mobile BlackBerry. I was so taken aback I went inside and grabbed my laptop to make sure the BlackBerry didn’t transcribe something wrong. Perhaps he meant to send this to someone else as how could he send a reply like this to a valued member of the team. The funniest part was I remember thinking, “2009, maybe 2010, there isn’t a chance we have that many years left with our run rate!” I sat on my deck for the rest of the night in shock that a leader in the company would shut an employee down so badly.

Imagine writing an email like this to an employee on your staff today. Imagine shutting out someone's opinion or thought and then telling them that they aren’t even good enough to give you that opinion. 

In late September upon returning from a trip with my co-worker and mentor from New York to meet with NBC Universal, CNN, and other media outlets to talk about a content partnership on the PATH TV screens, I was laid off. I was given a two-week severance package along with seven other folks in the company. They decided that the business line that I was working so diligently on would no longer be their vision and they decided to shut it down. They attempted to sell the product off but were unsuccessful. Less than one year later they shut down the company and it was all done. The entire company disbanded, the fancy titles for the leaders at the top meant nothing at this point and our stock was relegated to the OTC (penny stocks). 

The email that I received from John Doe will forever give me the perspective of a company, a leader, vision, a plan, and the process in which we lead people. John Doe is the worst leader I have ever worked for and the unnamed company is the most poorly led company I have ever been involved with. Sadly there were some really talented people there who got caught up in the middle of it all but this perspective to witness such poor leadership will always stick with me. Working for a bad leader sucks. It is life draining and growth killing. When we work for bad leaders we are relegated to their poor tactics of leadership that drown out all the resources.

Perspective from poor leadership is key to understanding your career navigation. Poor leaders give us the insight to understand just how bad things can get and it fuels us to perform better for our future teams than past leaders have performed for us. It also allows you to understand the concept of the grass being greener on the other side as you may think you have challenges with your leader until you really taste what poor leadership looks and feels like.  

Everyone I meet wants to be a leader no matter the tenure in their career. Whether someone has two months or two years of experience in their respective field, people tend to think they are ready to lead a team. The question I always ask is geared around readiness. Is this candidate ready to lead or have they been through enough experiences to understand how to lead. It’s the one thing that is so incredibly hard to explain to candidates. Time equals experience and good leaders tend to have been through the battlefield a time or two to understand the perspective on issues, challenges, and growth obstacles.  

Working under John Doe shaped me. It taught me that no matter how bad of a leader that I will work for in my career, it could always be worse. John Doe taught me that there are big rock obstacles and small rock obstacles and he put into perspective the problems that arise at work. People tend to think that the situation they are going through is a giant rock, but in reality you don’t understand giant rock issues until you’ve worked for someone who crushes your career path and soul. Poor leadership puts into perspective how amazing a really good leader can be as I was fortunate to go to work for some really talented people after being let go of this company.  

The next time you consider changes in your career, consider if you’re making a change over a giant rock or a small rock issue. Do you have enough perspective to understand what the future may look like or should you spend more time developing?  

There is a chance you leave a good leader, and you leave the company to go to work for a terrible one based on the concept that you don’t have enough perspective. There is also a chance that you take for granted what a really good leader looks like based on your own lack of career perspective. 

by Scott Bond