Say I believe that Melbourne are a 20% chance to win a hypothetical game of football - and some years it seems that this is the only type of game they have any chance of winning - yet you claim they're a 40% chance. How, and when, can we determine whose probability is closer to the truth?
In situations like this one where a subjective probability assessment is required people make their probability assessments using any information they have that they believe is relevant, weighting each piece of that knowledge according to the relative importance they place on it. So the difference between your and my estimates for our hypothetical Melbourne game could stem from differences in the information we each hold about the game, from differences in the relative weights we apply to each piece of information, or from both of these things.