We ALL like to pay as little as possible but we're happy to pay $4 for a latte from Starbucks because a, caffeinated beverage is worth more than that at that time and to that person.

Prove the value. Prove that your software is worth (either saving them money or making them money) 2X or 5X or 10X what it costs. If the value is clear, you change the discussion on price.

If you're doing mostly online sales and have enough traffic, then A-B testing could be useful. A-B test different pricing along with different value propositions.

You tell by just trying!

You tell by just stating the price and see what they do.

There's lots of ways to experiment. For example, raise prices but then use "if you buy before Friday it's only $X." Then you can play with the offer week after week without actually having "raised prices."

The best sales people can very quickly identify the biggest pain point for a customer; if you do this it's easier for the prospect to associate money with that pain e.g. "how much it's worth to alleviate that pain".

If something is a nice to have it's not worth that much to them, if something is a must have, it's worth more... try to put your product in the must have, or at least in the "what a pain it would be without your thing" category.