John 16:4-16 (15.26)

15.26 The word parakletos for the HS is a tough one to crack! The noun literally means "one called along side of." Originally it meant a "legal assistant." Hence the affinity for the term advocate. Yet, the whole field of words related to parakletos pushes against a cold, judicial term. So, have fun and look over the job description John gives for the parakletos and you tell me what this sounds like!
14.16 The parakletos is a gift from God
14.17 The parakletos will be with us, even abide in us forever
14.26 The parakletos will teach you and cause you to remember the words of Jesus
15.26 The parakletos will witness about Jesus
16.8 The parakletos will prove the world concerning sin, righteousness and judgment.
16.13 The parakletos will guide you on the way
16.13 The parakletos will listen to the Father and Son
16.14 The parakletos will glorify Jesus
16.14 The parakletos will make Jesus known

Interestingly, the Vulgate does not even use the term advocate to translate parakletos, instead transliterating the word "paracletus." In fact, the Latin does translate the word "parakletos" from the Greek into the Latin "advocatum" once, and this is from 1 John 2.1, where the sense is different. Indeed, here the idea is Jesus interceding for us against the judge of the Father concerning our sins; in John the idea of the parakletos has nothing to do with a legal metaphor before God the Father, but the enabler of Christian before the world of unbelievers.

16.6 John here uses the word "plehro-oo"; Jesus says sorrow has filled their hearts. This will be the same word that Luke will use to the desribe the Holy Spirit, that the Holy Spirit filled them.

16.9 "Concerning sin, because they do not..." The because here is a "hoti" clause; it could also be translated, "concerning sin, that they do not believe in me." This applies for 16.10 and 11 too, ie, concerning righteousness that...concerning judgement that...

16.12 The word hear for "bear" is "bastaz-oo" This word Paul will use in Galatians, to bear one another's burdens.

16.13 The verb here for "guide" is "hodege-oo" which means "hodos+ag-oo"=lead on the way; the verb we say two weeks back with Philipp and the Eunuch.