Question:
Jack is an optimist, and Adam is a pessimist, then he looks at the cup half empty.

he
Answer:
Adam
Question:
Seth is smarter than Sai, and consequently he got a better job.

he
Answer:
Seth
Question:
John wanted to vote for Doe, but he did not seem like the right candidate.

he
Answer:
Doe
Question:
The product fair showed Office 365, and it showed off with a game.

it
Answer:
Office 365