Are you an Asker or a Guesser? summarises a metaprogram which explains that some people “ask”, fully expecting the answer could be no, others “guess” and hint around things but never ask unless they know the answer will be yes.
In corporate culture askers could be perceived as having an “entitlement mentality”, when in fact it’s just that they’re testing the waters and hoping for a yes.
They do say “if you don’t ask you don’t get”, but it’s worth looking at your own programming and deciding whether guessing or asking works in your organisation.