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Answer:

Boss could be a negative connotation if they were described as "tyrannical"

Boss could be a positive connotation if you're the boss at something as in "that game is so boss"

Answer:

Similar to "determined," a driven individual is inspiring. In any case, the second somebody traverses into "pushy" is a catastrophe waiting to happen.

Positive: Our new boss is incredibly driven.

Negative: Our new boss is incredibly pushy.

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