OT, this concept was explored by British author Robert Westall in his 1983 SF dystopia Futuretrack 5 :

"Was it just coincidence that computerspeak, which we'd learned with such throat wrenching difficulty, was also a complaining, niggling, nit picking noise that gave any normal human being a pain in the arse?"

Now me, I used Graffiti a ton as well as the not quite so single stroke and therefore not so patent encumbered version that MS used on their late PDAs. I even implemented my own version on an early windows touchscreen netbook (angular delta and Levenshtein distance, match) so much so that it still pollutes my hand writing to this very day. I find it elegant and immediately understandable. Every one else thinks I'm writing in pig pen cipher.

Or the way we google. It would mean acknowledging that the listener (the computer) is severely limited. Actually it happens when speaking with foreigners with low proficiency in our language.

Acknowledging that the computer is severely limited seems like a good first step. Some people hate thinking of it that way though, and I have no idea why. It's annoying.

https://en.wikipedia.org/wiki/Lojban ?

Communicating with computers was one specific goal of Loglan!

Here's an example, at least for code. "Using Python to Code by Voice" https://www.youtube.com/watch?v=8SkdfdXWYaI

While we're at it, maybe all my coworkers could speak in an American accent, too. That would just be so much easier.

Like Totally!

I wonder if we will get there gradually, as "power users" of Siri/OkGoogle/Cortana/etc, and features targeted to them, start to emerge. Initially it won't be couched as a new dialect but more like "shortcuts" which will become more sophisticated over time.

This is an interesting question. I wonder if the limitations are due to particularities of English and other common languages in general, or to particularities of human speech in general.

This poster[1] might be interesting. English spelling-pronunciation mapping is really complex compared to Italian for example. I wonder if Italian would be a better language for speech recognition. Most of speech recognition research is targeted at English, but with similar effort, maybe Italian would enable lower error rates.

[1]: http://web.psych.ualberta.ca/~chrisw/ML3/84.pdf