Often the emphasis of the phrase is like so: the simplest thing that could possibly work. However, recently Ian Robinson was discussing the idea that the emphasis should be: the simplest thing that could possibly work. The difference is only emphasis, but it's a change worth considering.
I'd suggest that we go one further, and emphasize it as the simplest thing that could possibly work. When you think about it, what does it mean to work?
- To successfully compile?
- To run without crashing?
- To be well-designed?
- To be easily maintainable?
- To please users?
All these could be used as criteria for "working", given a particular context.
In my mind, ultimately the most important question to ask in applying this maxim is, "how do I define 'work'?"
