Perfect SoftwareThere is no perfect software in the world. The big question is, "Will it work for us and do what we want it to do?" That question will only be answered through time.
2 Moment You Know That Software Will Not Work
Usually, you will stick with software until one of two moments occur.
First, the moment when the software doesn't do what you want/need it to do. Eventually, you will get to a point where you need it to do something. Either is can or it can't. When it can't, is the break point moment at which you start looking for something else. For example, you need it to track technicians. If it doesn't, then it doesn't work for you. It's as simple as that.
Secondly, when something better comes along. Something new, something hip, something that does tricks will catch your attention through either a friend, colleague or competitor and you will salivate because your software doesn't do it that good. This is simply the grass is greener on the other side.
Tradeoff
There is no perfect software and I know all too well that software is simply a tradeoff. Having it do certain items really well and having it not do certain items well is in every software. The look and feel, the interaction, the interface, the upgrades, sooner or later you will see that all software is simply trading one aspect for another. My wife will usually choose the one that looks pretty and works reliably. Hence her iPhone 6. I choose works reliably as a top priority and usually stay away from the bleeding edge technology. It's nothing more than a tradeoff.
4 Sofware Principles to Focus On
In light of this, and with a handful of experience from a tech perspective, I have four unconventional areas that I typically focus on. They are:
1-automating best practices:
Too often software is concerned with customization (you can eventually get there) rather than focusing on what needs to be done (here is the shortest path). The answer to this is simple. If software is automating best practices, then this is a good signal the software company is a good fit and focusing on customer needs.
2-simplicity:
I shouldn't need a masters degree to run/setup/maintain the software. Easily adapting from my current knowledge base is key. A simple interface and hiding the complexity behind the curtain is the second signal.
3-extensibility:
This means the software should have the option to extend beyond. Beyond what? You might ask. Beyond it's current state. This issue is the future. The unknown. There needs to be an outlet for the unknown items that the future holds. Having a way to tap into that is vital to the survivability of software.
4-reliability:
This means that the software should work the first time, every time. Anything less is unacceptable. If anything is shown to be insecure, it needs to be replaced with the best available option.
I didn't come up with these items sitting under a tree. They came from reading the works of Gordon Rowell. I was lucky enough to meet with Rowell a few years back and it's amazing how true these principles still hold true today.