YOU SAID:

I should have asked him to take the test earlier.

INTO JAPANESE

私は以前テストを取るために彼を求めている必要があります。

BACK INTO ENGLISH

You should have asked him to take the test before I.

INTO JAPANESE

あなたは私の前にテストを取るために彼を求めているはず。

BACK INTO ENGLISH

To take the test in front of me you should have asked him.

INTO JAPANESE

私の前に試験を受けることには、彼の求めている必要があります。

BACK INTO ENGLISH

You need to undergo a test in front of me asking him.

INTO JAPANESE

彼を求めて私の前にテストを受ける必要があります。

BACK INTO ENGLISH

You must undergo a test in front of me asking him.

INTO JAPANESE

彼を求めて私の前にテストを受ける必要があります。

BACK INTO ENGLISH

You must undergo a test in front of me asking him.