Everything here is my opinion. I do not speak for your employer.
Books that explain (parts of) how the world really works
I spend a lot of time answering various people's tech-business questions. Occasionally, I will say something that sounds brilliant, and an unlucky listener will exclaim, "Avery, how do you know so much stuff?"
Answer: I read it in a book. Now, I don't actually read very many books. But I've been lucky enough to receive some great recommendations. Here are mine. Now you, too, can sound like a genius.
To make it more interesting, I'll start with the questions, then tell you the book that answers them.
Q: Why is your multi-year epic project still not profitable?
Because you don't understand how the "technology adoption life cycle" (the one with visionaries, early adopters, mainstream, laggards, etc) really works. The ultimate book on this topic is Crossing the Chasm, by Geoffrey Moore in 1991.
(You're going to notice a pattern to my book suggestions: they're old. It turns out really good advice stays relevant.)
Crossing the Chasm is very dear to my heart: it was recommended to me by one of the VCs that invested in my first startup - unfortunately a bit late. Chapter by chapter, it was like reading the post-mortem for my startup, except it was all written before we ever started.
Don't do this, because that will happen. Oh, crap, that's what we did, and that's what happened. Whatever you do, avoid this common mistake, because it always results in xyz. Yup, xyz everywhere. And so on. When we finally turned things around, I gave all the credit directly to this book. It is that good.
My favourite part is their definition of a "market segment." Most people don't know what they're talking about when they talk about a market segment. You think you do, but you don't. I thought I did, but I didn't. You can't run a startup without understanding what a market segment is. You will fail. Read the book instead.
One of their bits of advice: don't try to capture 10% of a big market. Capture 100% of a small market. Anyone who says "if we can just get 1% of this 10 billion dollar market..." is admitting defeat. Nobody will buy your product if it resolves only 90% of their obstacles, and for every market segment, it's a different 90%. You need to find a market segment, even a small one, for which you can solve 100%.
Q: Why are all these Cloud service providers losing money and offering terrible products?
Because the "Cloud" market has already Crossed the Chasm and has moved into the mainstream ("hypergrowth") phase, where the rules are nothing like what you're used to.
After the chasm has been crossed and you've made a product that serves several adjacent market niches, it gets easier to win even more market segments, partly because your company is actually making money and growing. Each new segment makes you more profitable, so you grow more and expand more, in a positive feedback loop.
The only problem is that, once you start taking off, you attract competition. Crossing the Chasm is largely about staying orthogonal to your competitors, but as you enter the mainstream, that stops working.
That's Cloud services right now. And ride sharing.
Inside the Tornado, also by Geoffrey Moore, a few years later in 1995, talks about this situation and how to deal with it.