The biggest question in my mind, when starting to write this blog, is how to actually approach the material. I could simply rehash all my experiences at each company, in chronological order, analyzing what went right, and what went wrong, in each chapter. I could pick out each lesson learned, and make a chapter out of it, and simply use my experiences for examples.
I then realized that the way I needed to resolve this question was actually analogous to one of the most important lessons I've learned: One must have a vision of the future, from which they can make strategic, and ultimately, tactical, decisions.
All too often, I find people confuse the idea of a corporate vision with a corporate strategy. In fact, these are very often completely different concepts, and you need both of them, as well as your shoter-term tactical plans, to succeed.
What's the difference? It's actually quite simple. Your corporate vision tells you where you want to be. Your corporate strategy outlines how you'll get there. Your product development plan is more tactical, determining each move you're going to make to follow through on your strategy.
Consider the life of your business as analogous to driving around a strange city. Your corporate vision might very well be fairly generic, such as, "Let's check out the east side." From this, you work out a strategy; perhaps you simply mount a compass on your car's dashboard, and plan to try to keep driving east. When you get to an intersection, and you have a choice of directions to go, you can make an educated guess based on the compass. Sure, you might take a wrong turn; maybe you end up at a dead end and have to turn around, or perhaps you end up getting funneled onto a one-way street that isn't going in the direction you want to go.
Just as you don't usually drive around a city aimlessly (at least, not unless that's your intention!) why would you attempt to run your company the same way? And yet, all too often, I see companies being run either without a real vision, or without the adequate communication of the vision from the executive level, down to the lowliest peon. What usually happens, I find, is that people tend to be too near-sighted in how they approach things. Rather than work out a far-reaching vision, they focus on "what can we accomplish in the next 3-6 months" (if I had a nickel for every time I heard that one...) They actually confuse strategy and tactics with vision.
The unfortunate reality is that you cannot intelligently determine if your product plan is a good plan, if you have no clear idea of what the end goal is. The tendency to focus on the near term, though, seems to have gained in popularity due to the efficient development strategies that have become popular lately, such as "agile development", "rapid prototyping", and the like. These strategies, touted as being the best way to get a startup moving, tend to fool people into being very lax in their strategic planning.
It makes some sense, that if you can churn out a functioning website application in two months, by focusing on production, rather than planning, why wouldn't you? Even if you needed to completely rework the product when you're done, you've only invested two months of development. If you spend three months on "version 2.0", you're much closer to where you need to be, because you were able to learn so much from "version 1.0", and it's still only taken you five months, right?
Sometimes, this works, but often, it's a trap. Because this rapid development cycle allows companies to be nimble, companies ignore the larger picture in favor of "trying different things". At best, you can actually learn quite a bit from your mistakes, but at worst, you're fooling yourself into thinking you're making progress, when you've actually lost all focus on your vision, and your product becomes a disjointed combination of poorly integrated features.