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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.
Explanation: