There are many stories about bad bosses, which makes one about a positive experience seem like an endangered species. But sometimes an IT pro is lucky enough to stumble into such a situation.
Several years ago, I started working for a boss, "Zack," who owns the company and, as I soon discovered, has good business sense as well as technical skills. Zack used to be a programmer/analyst, but hired me to do that part. He determines the general direction and the use cases of our work, but often leaves many of the technical decisions up to me and gives me the freedom to implement a fair number of changes without checking with him.
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For the most part, Zack is reasonable about expectations. But as in any company, one has to think about the business sense when communicating with the owner. On one project, I ran into a potential problem when I was developing an in-house billing application he had requested. At first, I hadn't seen any problems with the project and figured I'd have it done fairly soon.
Then I got started. I worked out how to handle data entry into the various tables and discovered that Zack wanted the data entry for the transactions table to be different than the others in the project. I experimented and determined that his request was reasonable, but its complexity would make it time-consuming because I had to proceed in a rather different style.
I didn't want to be in the situation of taking a long time to work something out, then getting criticized after the fact -- and hit with questions from the boss: "Why did you take so long? Why didn't you say anything?" Based on my experience with other superiors, I dreaded going to him and explaining that the project would take more time than at first expected.
I gathered my courage and explained the situation to Zack. To my relief, he told me something that I valued very much. He said that he did not care how long it took, just to do it. With that level of commitment from him, I completed the project in the timeframe the project required, and not on some seemingly random date that didn't make sense.