Problem: Sentence1: He used pliers to work the wire into shape.
Sentence2: The salesman works the Midwest.
Q: Does the term work mean the same thing in both these sentences?

Answer: different meanings

Problem: Sentence1: He checked the point on his compass.
Sentence2: A row of points.
Q: Does the term point mean the same thing in both these sentences?

Answer: different meanings

Problem: Sentence1: The club has a busy calendar this year.
Sentence2: I have you on my calendar for next Monday.
Q: Does the term calendar mean the same thing in both these sentences?

Answer: the same meaning

Problem: Sentence1: He could not work the math problem.
Sentence2: Work one's way through the crowd.
Q: Does the term work mean the same thing in both these sentences?

Answer:
different meanings