In your examples, and often at the beginning of a sentence, "well" isn't really a word at all. It doesn't have any meaning.
It's just a "filler." It's a kind of noise that means "I'm thinking about what to say next." It's like "Um" or "Ah" or "Hmmm."
Everybody uses fillers, everybody--but in public speaking courses they try to teach you NOT to use them. Fillers are a way of saying "I want to speak, even though I don't know what to say yet." It's not a good speech habit.
Notice how ahdictionary.com explains this use of the word. It simply says how it is used--it doesn't try to say what it means, because it doesn't mean anything.
"interj.
1. Used to introduce a remark, resume a narrative, or fill a pause during conversation.
2. Used to express surprise."