An Example of Leadership

A story about one of my early bosses

I’ve been studying leadership all my life, initially without me being aware, but it’s one of those things you take notice of. Having an excellent boss is night and day compared to a horrible boss. When I became a consultant, each client became a new boss. So I’ve worked with quite a few different types.

I’ve been thinking about examples from my past that may show some leadership concepts I’d like to put a fine point on.

One of my first bosses that I felt was a real leader was this guy, let’s call him Sam. I worked at a local Internet Service Provider in the customer service department. I had already been working there for maybe a year when he joined the sales team as most new employees did but he was already friends with the owners. So even though it may have been unsaid, it was clear he wielded seniority outside the normal process.

He owned a convenience store which he had bought from one of the owners. It was very strange almost like he was working two jobs but primarily the time was spent with us. The convenience may have had high priority, it especially did when there were emergencies like employees walking off the job or robberies. The store also connected him to the local business community, so he had a good existing network when Internet services were needed. These events would lead to great stories he’d tell us the next day.

He and I had a connection, he would specifically ask me questions because I was able to break down answers into easier understand concepts. I helped train him on some of the technical aspects, he needed to know for the job. He was a quick learner and the Internet was new to the public. There were high demands and no one knew much. He didn’t have to know everything just the common questions that were frequently asked. We, technical support staff, would back him up on anything out of the ordinary.

He was quite adept at talking to customers and even cracked dumb and silly jokes to the staff to see if he could get a reaction out of us. The jokes may have been his defining characteristic. I don’t know if he had natural charisma or if he gain it from all the practicing and experimenting he was doing. He would do voices and characters. Maybe it was to better integrate with the younger technical staff that was mostly teenagers, some barely of age to work, myself included.

He also used jokes to play with delivering stern uncomfortable messages, he would say a truth and then say “just joking”. It was an interesting technique because it he was done in a way to give you just enough time to reflect on your fault and then allow you to move on with your day. Initially I took them as jokes but I figured out the technique after many years of watching him.

He quickly moved from doing just sales to helping out with the book keeping and data entry. He had several ideas, sometimes wacky, but he’d write up this binders with his vision. The binders were mainly for himself. They’d only come out if he had to show us his competitor research he did.

He picked up all the slack of each employee that would leave and new employees were put under him. So he quickly rose to the top of this small company.

At one point, we were moving off one accounting system to another. It took Sam and our part-time book keeping couple months work to transfer the data. I was responsible for migrating the new system to a hardware and I did not backup and a transfer bug ate all our data. I was punished, I lost some employee perks but was not fired. Sam had to rekey everything again into the new accounting system. It only took him a couple weeks this round, as he was more familiar with the new layout and had solved all the previous conversation tasks.

When we moved into the age of the dot-com startup, there was a notion we were an Internet company, so we should be doing similar things to other seemingly rapidly growing companies.

Sam tried to grow our company but it was vastly different than other dot-com start ups. We expanded our local coverage to serve the entire state. We tried to sell wireless service as there were gaps where the telecommunication companies would not serve. We tried to sell phone service as technology replaced large clunky internal phone exchange system for small business. We grew big in customers and services.

Sam entertained various suitors interested in purchasing us. We had several of these events where we would have a meeting, we’d have to get several things done including a lot of cleaning. We would prepare for a week. We would ask our friends to come in and look busy, so we seemed like a larger company. An investor would come in take a look around for a few minutes and that’s all we’d see. They would go out somewhere, probably to drink and eat and finish the pitch. Most of these investors we never saw or heard from again. Most didn’t understand the Internet or what we were doing.

Failing to sell the company, Sam looked into several mergers. One I can remember was an actual local dot-com start up that was selling digital music online. Way under funded but a group of guys on a mission, it was very inspirational, the vision they had. Their interests and a local Internet service provider were very different and ultimately the music sales vision needs more flexibility. And so that merger didn’t happen.

Sam had mini-mergers where we would take on a small-one person company and they would work with us for a while. Most seemed to part ways over a long enough time line. These became unique and interest assets that helped us deliver a great personal/personalized service.

Ultimately Sam lead us to merge with our rival. I don’t know a lot of details of this period because I had left the company and ended up selling my company to him. for this merger He explained my company would help their revenue numbers on paper and would make them look larger. Image and numbers were important to Sam.

Sam got demoted to 2nd-in-command and was given the more profitable services to focus on. Times changed and the Internet growth wave begun to stabilize. The original CEO left and Sam found himself in charge again. He stayed with the company for just about a decade until he had fight with the board and decided to try his hand at something else. A decade in Internet years with everything that was happening and changing around us, I don’t blame him, I would be curious too, what I could I still keep in touch with him and see him every once in a while.

What I respected the most about Sam was that he wasn’t above any job even though he had the clout and power to do so. He would get his hands dirty with the rest of us. He cared about his coworkers and constantly would find opportunities to check in with us. He constantly thought of new ways to grow the organization and new ways to achieve.