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WILLY: Don’t be so modest. You always started too low. Walk in with a big laugh. Don’t look worried. Start off with a couple of good stories to lighten things up. It’s not what you say, it’s how you say it—because personality always wins the day. (Act 1)
Willy, who ironically considers himself an expert on being well liked, believes that personality is what matters most. Once again it's not like this is totally untrue. A good personality is probably a really valuable thing for a salesman to have.
BIFF: He’s off salary. My God, working on commission!
HAPPY: Well, let’s face it: he’s no hot-shot selling man. Except that sometimes, you have to admit, he’s a sweet personality. (Act 1)
Yep, it looks like Willy's "sweet personality" hasn't really served him that well. He's been demoted at work and is even soon to be fired. Happy's comments may suggest that he is no longer convinced that personality is as central to success as he previously thought. But we wonder, if Willy was actually as popular as he says he is, would it have made a difference?
LINDA: His blue suit. He’s so handsome in that suit. He could be a—anything in that suit! (Act 2)
Linda's fixation on Biff's physical appearance as the source of his success denies the importance of other qualities and virtues. The play seems to suggest that, if Biff's parents had spent more time grooming his character, then he might actually have the respect and reputation needed to make it in the world.