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Six Lessons from Fifteen Bosses

Updated: Feb 5, 2021

I've Never had a Bad Boss, I've learned from each Experience


Photo Courtesy of RossHelen


A prior post grew out of an idea I planned to explore stating I had never had a bad boss. Instead, I focused on simple advice and examples I gleaned from one boss I reported to in a flickering moment relative to other experiences. His name was Don.


The purpose of highlighting the subject grew out of my realization that while I may not have enjoyed chemistry with each boss, I learned from every interaction, even the bosses I may not have appreciated in the moment.


Of course, the relationship works in both directions. I hope I taught some of my bosses as well. I can say emphatically how much I have learned from those that have reported to me over the years. In fact, I got the better end of the deal in my career. I have been extraordinarily fortunate to have worked with an array of talented individuals far more talented than me.


When I evaluate my experiences from a distance, I realize that each experience taught me something powerful. I have had bosses that were charismatic, focused, experienced and extraordinarily knowledgeable. Some were filled with wisdom and others clearly valued hard data and relentlessness in pursuit of their ambition. Some were extremely well connected inside of the organization and others suffered from the lack.


Few bosses were tone deaf. Nearly every person I have worked with exhibited high emotional intelligence in addition to their domain expertise. I acknowledge that I learned a ton from working with someone who did not exhibit as much EQ as others but had attained their lofty position based on sheer tenacity, smarts and drive. Still, he broke a lot of glass along the way. Here are six things I learned from fifteen bosses that might surprise you.


1. Strategy, Strategy, Strategy. I can still hear this phrase intoned in a heavy Boston accent. My boss Eleanor was big on execution, but it all started, she would echo repeatedly, with a strong strategy. She focused obsessively on how to get things done effectively. Of course, she taught me about more than strategy. She knew how to organize people, create a culture, transform an operation, look deeply at segmentation (although, I have to say one time an exercise in it nearly killed me and my administrative assistant.) She went to great lengths to instill a coaching culture. She also preached testing in a way that I co-opted later in a different time and place. Her belief in using the Caliper Profile (testing tool) was dead on. She would often say that you could never cheat on a Caliper nor could you hire against it and win. She was right.


2. Network, Network, Network. I was extremely fortunate to report to the same person for nearly a decade. Ordinarily, you might think that amount of time would be a detriment, and all good things need to come to an end. You need to worry about complacency. I get it. But we worked in an environment where we faced constant challenges, new systems and operations, new products, new strategies. Paul was excellent at navigating strategy, but his bigger and lesser acknowledged gifts included his knack for dealing with and leveraging people. He had “gravitas.” And he knew everybody. If you needed to get something done through an informal channel, he knew where to go. If you were stuck because of a bottleneck, he knew who to call and how to deal with it. That level of connectedness serves as pure gold in a company with over 30,000 associates, even if you represent only a tiny fraction of that number.


There were several times he would point me in a direction and let me work out the issue. He would not necessarily solve the problem, that was my job, but he knew where to go and if needed to get involved, he would tell me: call me and I’ll work on it. Big companies thrive on process and connections. Once again, I know this is not new, but it is an important lesson for any leader — or for that matter anyone — early in their career. Aside from treating people well, cultivate relationships that will help the entire organization face challenges with more strength and connection. Ultimately, the broad array of connections meant he represented a one-man silo buster! We all know how detrimental entrenched silos can be organizationally.


3. Patience. Farsightedness. Queue the movie music, “In a world…. where everything needs to be done yesterday, patience and far sightedness still have a place.” Pretty dramatic, I know. The aforementioned Paul once allowed me to spend two years on a project because as he told me at the time, “We don’t need this to fail because we did not prepare. This whole effort is intended to support our sales efforts for the next decade. Get it done right.” And we did.


4. Work Less. Better Results. One boss, Kelly, was as smart and polished as anyone I have worked for. She also possessed an incredible knack for leading as though she was conducting an orchestra. I remember she once said, “I’m most effective when I’m working less.” That statement did not imply she did not work hard, she did. She meant she did a combination of things well that relied on the people who worked for her and could be trusted. Kelly was a master delegator who trusted you to do the job but had excellent follow up disciplines in place to make certain all the various priorities were accomplished. It also meant she reserved more time for strategy and longer range planning.


Early in my career, she taught me the value of hiring people smarter and more talented than myself — because when you do, you can trust them to do their jobs and make the entire organization better. One seeming byproduct of her leadership style: she rarely if ever appeared rattled, no matter the emergency facing her. She knew she could trust her team to face any challenge.


5. Diversity, Opportunity and Humor. I get this combination will not make a ton of sense. Let me explain. Along the way, an exceptionally good friend of mine became my boss. We climbed the ladder together over a decade. We were close, had similar backgrounds, rose at the same pace, moved from different locations along the way. Jim possessed a wicked sense of humor and incisive intellect. His sense of humor meant that he could disarm any tense situation by seeing its silliness. His demeanor meant people gravitated to and trusted him. Equally important, he had a knack for seeing opportunities where others did not.


One of those skills involved constructing teams. He knew how to put together people with different skill sets to get a truly diverse set of inputs, knowing that the output would be that much better. I worked on a project team he ran, where he put three people with much different backgrounds together and watched as the product grew better as a result. Plus, he saw potential in people that others either ignored or simply could not see.


6. Discretion and Balance. I learned this lesson from someone who failed to display it. It’s often hard for young leaders to understand that they are the only way their boss will get to know one of their direct reports. That dynamic places a lot of pressure on you to be balanced and discrete in your feedback. I once had a boss that did not fully grasp this truth and was not shy about sharing his negative feedback with anyone who would listen! He spoke openly and freely about his opinions to his peers and his direct staff.


The result? No matter the discerning ear of those hearing the feedback, it's hard to overcome mud. He felt the HR people moved too slowly (not uncommon) and lambasted one of the leaders openly to others (not cool.) He had a challenging relationship with one of his direct reports early in their time together while they were getting to know each other and shared his observations broadly, so much so that there was a rumor circulating that the person, a long time well respected employee, was on the precipice of termination.


Toxic words carry a certain energy with them that once in the air act as lethally as a virus. Moreover, when you do not weigh your opinions of others, if for whatever reason the opinion changes based on new interactions or examples, the cake might just be baked.


Interestingly, this boss exhibited other phenomenal strengths. The same attitude that enabled him to recklessly share his opinions of others meant he was willing to break glass and taboos all over the place. No working model or standard operating procedure existed beyond questioning and potential change. And he worked extremely hard. He expected much from his team and gave it back in terms of his time and focus. I think he simply faced a learning curve on discretion that he would eventually master. Ultimately however, when you speak ill of others publicly, it reflects poorly on you. I still admire the tried and true adage: praise in public, criticize in private.

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