His name was Jerry, and he was the best boss I've ever had.

I was working at a small startup in Minneapolis in the 90s. Being young and hungry to show the masses I was ready to conquer the work world, I had somehow fallen into a role as a middle manager reporting to a director who had the ear of the CEO.

My daily routine was to saunter over to the corner office looking for anyone who had some authority and engage that person in witty banter. Most days, I found Jerry doing roughly the same thing. This was long before the age of cellphones being permanently affixed to our hands and ears, so making an in-person drive-by in an office setting made more sense than trying to find someone using a clunky desk phone.

The one thing I remember about every conversation I had with my boss at the time, especially during these impromptu chats when I was trying to impress the bigwigs, was that he was an exceptional listener. In fact, his number one skill as a leader was that he would always listen to me first and then speak. He was obviously skilled at this technique. By listening first, he was gathering information. He was surveying. He was analyzing.

I hate to use a sports analogy, because some of you just tuned out. (It's the same group of people who watched the Super Bowl earlier this month because of the commercials.) Yet, it's perfectly appropriate in this case. In sports, it's always best to listen first. It's like a coach who first watches his team play and then determines where they need to make changes. How can any leader start by talking first and directing people, making demands and relaying company information, or trying to steer workers in a new direction if he or she hasn't done some homework? It's critical to look and listen first.

Jerry usually asked me about my team. He was genuine about it. He wasn't just using the technique because he was waiting to speak and waiting to tell me what to do. He listened carefully because he wanted to provide the best guidance possible. He'd start with a basic question about how things were going and if I had any issues.

It's an interesting communication strategy. We all like to be heard. No one likes to feel as though they are just being told something, that this is all a one-way street, and you don't have a voice. I immediately liked my boss from the moment he hired me (in fact, he mostly listened to me during the interview as well). And, I kept liking him in every discussion we had for the five years after my hire date. (Sadly, knowing his age at the time in the 90s, I am sure he is either well advanced in years or dearly departed.)

That's what made him such a good leader. That was the hook. By listening first, you let people share information about their work issues and their personal life. They like you because you are good at listening. At the same time, you are gathering information. I'm convinced all wisdom comes from the ability to listen first, because you can't direct people effectively until you know more of the information. We say a fool will rush in, and we mean that a fool starts speaking and acting without discernment.

Jerry was a great boss because he knew how to listen. And, when Jerry spoke, it was always after accumulating enough information and asking enough questions.

What's your approach to leadership? Too often, I see the leaders of small companies who talk first, act second, and then listen as a last resort. They don't seem to realize why that doesn't work. By speaking and acting first, they assume they are leading a team because they are the first to share and direct employees. There's a mistaken belief that leadership is being the first one to come up with the solution. In my experience, the best leader in a company is often the last person to come up with a solution, because the best decisions come after getting all of the facts straight. This is the classic "quiet leader" who sits in the back of the room and waits to reveal the real course of action, the one people will actually follow.

In many ways, I miss Jerry because he was so full of good advice. I've striven to model that example of listening intently and being slow to share my advice.

Who is your favorite boss? If you have some good examples of what made that boss so exceptional, share them in comments or on my Twitter feed.

Published on: Feb 18, 2015
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