Q: It is not easy to space buttonholes exactly the same distance apart, and it is very difficult to cut them precisely the right size . The tiniest slip of the scissors will make the hole too large, and even one thread uncut will leave *it* too small.
Are "the right size" and "it" the same?
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A: no

Q: The man lifted the boy onto *his* shoulders.
Are "The man" and "his" the same?
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A: yes

Q: The trophy doesn't fit into the brown suitcase because *it* is too small.
Are "The trophy" and "it" the same?
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A:
no