What Our Worst Bosses Teach Us About Leadership

Midway through my military career, I was asked to coordinate a strategic plan that would define the U.S. Navy’s approach for the next five years of defense spending. It was a massive task that required consulting with senior officers throughout the Pentagon and Navy and consolidating their viewpoints, which didn’t always align neatly. After months of work, I was scheduled to brief my senior admiral boss and then the admiral in charge of the entire Navy. It was also a busy time in my personal life – my wife and I had just purchased a house and our three daughters were still quite young and transitioning into a new school system.

On the day that my boss was to meet with the senior leadership of the Navy, he took a close look at the report and realized he didn’t like one phase of the strategy. In fact, he hated one of the recommendations.

And though I was really just a messenger representing the views of the entire Navy, he didn’t waste time assigning blame.

“You’re responsible for this, Commander?” he yelled, jabbing his finger toward my chest. “You’re fired!”

He wasn’t exactly the most level-headed guy. Neither the other admirals that had approved the document nor I had anticipated this reaction. Even as he raged, I was already worrying about how to cover a new mortgage without a job. I went back to my office and started gathering my personal items in a box.

Suddenly, my immediate two-star admiral appeared in the door. He said he had no one else knowledgeable enough to brief the head of the Navy on a strategy this complicated.

So 15 minutes later I stood in the briefing room and presented the report, minus the small objectionable recommendation, to the highest leaders of the Navy. Then I returned to my office and resumed packing. The two-star admiral came back and said he had convinced our mutual boss to give me my job back, effective immediately. Not only that, the Navy’s senior leadership had received my report very positively! In the years to come, the two-star admiral who saved my job became a great mentor who took a strong interest in my career. I learned a lot from him.

But I learned even more from the boss who fired me, specifically this: You cannot lead effectively without empathy. And I didn’t want to be the kind of boss who lacked it.

Empathy, of course, is the ability to see from someone else’s perspective and understand their feelings and motives, even if you don’t necessarily agree with them. It demands more intellectual and emotional engagement than mere sympathy.

My boss didn’t value empathy. If he had, he would have considered a few things before firing me. The report didn’t promote my personal views on the Navy’s strategy; it was a reflection of what the majority of our senior leaders thought and was, in fact, a solid plan. It’s impossible to produce a report that canvasses an entire organization and creates 100 percent agreement on every point from everyone. Also, my young family would be severely affected by his gratuitous decision to let me go. Looking back, it’s also true that I could have had more empathy for my boss. The recommendation that he didn’t like would have put him in an awkward position with some of his peers, and I should have recognized that in advance.

So empathy is a two-way street, and research conducted by the Center for Creative Leadership and other institutions shows it is also one of the greatest predictors of executive success. The absence of it almost always undermines careers, especially in senior roles. Throughout my 45-year working career, I’ve had a handful of truly bad bosses. None of them had empathy and all of them, including the one who fired me, ultimately saw their careers either plateau or derail. Lack of empathy is one of the major reasons why 50 percent of managers are seen as poor performers or failures in their jobs.

Empathy, then, is not only critical for our own career success. It’s also crucial for unleashing the full potential of our women and men. If we are able to put ourselves in their shoes and truly grasp the nature of their motivations, behaviors and challenges, we can almost always earn their trust and coach them to greater success – and elevate our organization’s overall performance.

Empathy also makes us more responsive to our clients. We are better able to understand opportunities and problems from their vantage point and then move more rapidly to develop solutions that address their unique circumstances.

Best of all, empathy is not a fixed trait; it can be learned. The earlier we start the better because, as with most leadership skills, we can’t develop it overnight. Here are a few steps, identified by a team that includes CCL researcher William Gentry, that we can take to cultivate it in our workplaces.

First, as leaders, we need to talk about the importance of empathy – and we need to model it. Of course, bottom-line numbers always matter. But, in the end, those results come when a workforce is fully engaged. The more our employees feel they are heard, the more motivated they will be to perform.

Second, emphasize good listening skills. Empathy starts with really hearing what others are saying. As with empathy, listening can be learned. It requires setting aside our smart phones and paying full attention, reserving judgment, asking clarifying questions and summarizing what we’ve heard in a conversation before it ends.

Finally, make a habit of putting ourselves in other people’s shoes. In meetings at the office, try to imagine you are the person on the other side of the table. What is their background? What pressures are they facing? What unique skills do they bring? We can practice this skill all day long – with our spouse, children, friends, neighbors and people we pass on the street.

Over time, our horizons will expand. So will our insights and effectiveness as leaders. And for the improvements they have inadvertently inspired us to make, we might just ironically owe our worst bosses some thanks.