My First Job: What Unloading Beer Taught Me About Leadership

My first job is not included on my LinkedIn profile. The description would include, “joining the teamsters, driving a truck poorly, and drinking beer at 7 am.” However, the softer skills I gained - the ones that do go on the CV - greatly influenced the way I lead.

The summer after my senior year of high school, a friend’s dad asked me to work at his Schlitz beer distribution company. “You’ll make good money,” he said. I was in. It was a union job and the first requirement was that I join the International Brotherhood of Teamsters. The job started at 6:30 am in a Chicago warehouse far from my home. There were about 25 trucks, each with a driver and an assistant. My role was to substitute for the assistant whenever he was on vacation or otherwise unavailable.

My first assignment was with Harvey Outlaw, an intimidating guy with a monosyllabic speech pattern. I wasn’t sure what to expect; Harvey wasn’t either. “I don’t know why they gave me you!” he said upon meeting me. Harvey’s route was Cabrini-Green, the infamous public housing project and probably the worst in neighborhood in Chicago. This was an all-cash route and some of the stops weren’t safe. Harvey carried a gun in his sock and would leave me locked in the truck. (His regular assistant was in the hospital after someone had hit him over the head with stolen beer.)

So the job had potential risks, but it also had definite perks. One morning, Harvey noticed me sweating, went to the cooler and pulled out two beers. “Here,” he said. I was 18 years old, it was seven in the morning and I was thinking, ‘This is the greatest job ever.’ (18 was the legal drinking age at the time.) Another benefit: we could take home any broken cases for 10 cents a can. Needless to say there were a lot of cases “accidentally” dropped.

Every week the job brought a different route and driver. My favorite driver was Harry, who was a big jovial guy and let me do jobs no one else had, including allowing me to drive the truck into the warehouse at the end of the day. The trucks were big - the cab and container were on a different axel - and they were difficult to maneuver. In one unfortunate attempt, I didn’t get the angle right, and slammed the truck into the doorway of the warehouse. I dented both, amounting to thousands of dollars of damage. I was terrified. ‘There go seven years of wages,’ I thought.

I went to tell the chief warehouse guy and Harry. Surprisingly, Harry quickly said, “It’s my fault; I let him do it.” The warehouse chief got a stern look on his face, which slowly crept into a smirk and then a smile. Laughing, he said, “Don’t worry about it.”

In retrospect, that summer unloading beer taught me two great leadership lessons. First, I had to get along with many different types of people. And rather than wishing they were like me, I learned from their diversity, their approaches to their job and the different ways they interacted with me. Today, when I meet people, I routinely ask: “What is this person’s good qualities and what can I learn?” This is one of the most powerful tools I have available to me as a leader. People intuitively know when you are looking for the best in them—and that it is critically important in creating followership.

The second leadership lesson was the value of trust. Harry showed me something incredible in the moment he stood up for me. He communicated his belief in me. He took responsibility. I spent the rest of the summer incredibly motivated to do the best job possible. I was insanely loyal to Harry.

My summer distributing beer allowed me to earn more money than I ever expected at that age. But working with Harvey, Harry and others on those trucks also gave me experience and insight that has paid off many times over in my career.

For example, every day I try to practice an operating principle called “Presume Trust.” We used this when I was Bain, where I started as an associate consultant and eventually became CEO. I now practice this principle at eBay, and I encourage everyone in our company to embrace it. People think you have to earn trust, but that mindset reduces team effectiveness. Instead, why not presume trust until someone does something untrustworthy? In doing so, you approach colleagues with the understanding that we are all on the same team. Presuming trust communicates support, motivates everyone and ultimately makes everyone more successful. This practice can be scaled. It works one on one, with a team, and across an organization.

I believe this is how you build a strong team, and it’s a lesson I first learned from Harry that summer on the beer truck. My first job taught me that every interaction with people is an opportunity to learn and become a better leader. It was a great lesson for me at a very young age. Thanks, Harry.

Photo: John Donahoe

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