2Tim. 4:2 Preach the Word; be prepared in season and out of season; correct, rebuke and encourage — with great patience and careful instruction.
The word encourage or encouragement is used around 100 times in the NT. In this particular verse, the verb used is parakaleo. It is a combination of the two Greek words para and kaleo. Para means "to the side of" and kaleo means "to call, aid, or help." In our English language, the word is a combination of en + courage. You are walking along on a path and beginning to tire. Wondering if you can make it to your goal, someone comes along side and begins to say, "you can make it, you are strong enough, do not quit, I am right here for you." Encouraging is pouring in courage to another person to make the mark.
In any accountable relationship, both the positive and the negative must be included. However, it must be done with great patience and carefulness. May we fill people with courage and strength of purpose.