When I was 13, I got my first job. I was a newspaper carrier. I learned a ton of formative personal leadership lessons from that experience and I wrote them all down here. With that job, I was my own boss. I worked alone.

When I turned 16, I got a second job, in addition to the paper route. My next-door neighbor, Bruce, ran his own candy vending machine business. These were the small pedestal machines with bulk candy in them. You put in a quarter, and get a handful of M&Ms. I believe he had nearly a hundred machines placed all over town. I was his first and only employee.

He offered me $8/hour, which was nearly double what my friends made at McDonalds. I remember feeling the burden of that. My wage was coming right out of his pocket. I was motivated to make sure the quality of my work was well worth it.

Training

This is the first job I had that required training. The paper route was self-explanatory. This, on the other hand, had very specific expectations. Bruce was a very particular boss. He wanted things done a certain way. This was his business, his machines, and his customers. He explained what I was to do very carefully.

The first day on the job, I walked across the lawn and met Bruce in his garage. He had a vending machine all set up and taught me how to clean it. He demonstrated it a few times and then asked me to do it while he inspected my work. He emphasized the importance of a clean machine. He said people won’t buy candy from a dirty machine. It just grosses them out.

After that, we went on the road in separate cars. He gave me the route of machines to clean. He told me that he would follow me, inspect my work, and then do the other tasks of refilling candy and taking the money out.

After a few days of this, he was satisfied with my cleaning, so he added the task of refilling candy, first showing me how in the garage, of course.

Finally, a week or so later, he gave me the financial responsibility of collecting the quarters from the machine. That required a special key, which he gave me.

Eventually, he stopped following me around and just trusted that I did the work.

Logistics

Bruce wasn’t just particular about his machines. He also gave me very explicit instructions on driving. He planned my service routes, very explicitly to minimize the number of left turns. After all, I was 16, a new driver. And I was driving his car, not mine. He explained that fewer left turns meant fewer accidents.

He also gave me a second set of keys for his car. He wanted me to keep it running so the A/C would prevent the candy from melting, but I could also lock it during my service stops.

Selling

Right at the onset, Bruce told me that he would pay me a $50 bonus if I ever sold a new vending machine location. In two years, I never sold a single one. I think I know the reason: He never showed me how, nor did I ever watch him do it. The financial incentive wasn’t enough to bridge the skill gap.

Trust

I worked for Bruce for two years before I left for college. Over those two years, I helped with many aspects of his small business including machine repairs and refurbishing. He did the selling and the bookkeeping. I did most of the physical work.

Few have a good boss experience right out of the gate. People who employ teenagers are not renowned for their leadership skills. I was quite fortunate.

The lessons

Nowadays, I lead a big team in a large corporation. What did I learn from Bruce that I carry on today?

1. Pay people well. It shows that you value them. It inspires them to work at a level worthy of their pay. Before people even prove themselves, show them that you believe they are capable. Most times, they prove that they are.
2. Teach. I don’t tell people what to do without teaching them how to do it. That’s one of the reasons I write this leadership blog. People aren’t born leaders. The need to learn how to lead. Even people with management experience don’t necessarily know how to lead, so I take the time each week and write these leadership lessons.
3. Inspect. After training, Bruce didn’t micromanage me. I was on my own, but I knew he was checking my work. As a leader of a large organization, I cannot possibly stick my nose in everyone’s business, but I need to pay attention to the signals and indicators of performance and outcomes.
4. Develop people incrementally. I try not to throw people into the deep end to sink or swim. I didn’t learn that way. I learned by mastering something, and then getting a little more. Then I mastered that. Then I got a little more. My whole career journey has been marked by incremental growth, and it started back with Bruce.
5. Start with why. While Bruce was meticulous, it wasn’t just because he had a peculiar personality. He explained the rationale for everything: the cleaning process, the A/C, the left turns, everything. I didn’t just know what to do, I knew why it was important. Similarly, I’m a big proponent of connecting the dots for everything we do to “why.” CHS creates connections to empower agriculture. Every IT product, project, and service we have needs a straight line connected to that purpose. It matters.

Time to reflect

It’s amazing what I learned from a teenager job servicing candy vending machines. My neighbor, Bruce, passed away quite a long time ago, but I’m pretty sure he’d be happy to read this if he could. Looking back, I am who I am because of the sum of all the leadership experiences I’ve had in my life. This was an important one. What lessons did you learn from your teenager jobs? I’d love to hear your stories in the comments.

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