A good reference is Douglas Hubbard's
How to Measure Anything. The idea is that most people can calibrate their sense of probability to be fairly accurate, by intentionally adjusting for some common biases. (In particular, if you prevent anchoring and availability bias, and actively engage system 2 and your loss aversion, you get a long way. There are specific techniques to do that in the book.)
This is really easy to practise and test too, since all you need are a bunch of questions where the answer is known, but you are uncertain of it. Then you can guess a range in which you are 90 % certain the true answer lies, and after 10 such questions, you should be correct roughly 9 times.
Points are a way to do this, but I prefer engineers who are calibrated. It's very powerful to ask someone for a calendar day when something will be done (or really just about any other question about anything), and be able to be reasonably confident in the span they respond with.