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How do I know if I am being encouraging and helping someone with accountability or if I am being judgemental,  Grumbling, or gossiping?

Encouragement – building each other up
REF: https://www.blueletterbible.org/lang/lexicon/lexicon.cfm?Strongs=G3870&t=KJV

1 Thessalonians 5:11 ESV
Therefore encourage one another and build one another up, just as you are doing

.

Accountability – Equipping one another for spiritual warfare
REF: https://www.blueletterbible.org/lang/lexicon/lexicon.cfm?Strongs=G2008&t=KJV
REF: https://www.blueletterbible.org/lang/lexicon/lexicon.cfm?Strongs=G2675&t=KJV

Luke 17:3 ESV
Pay attention to yourselves! If your brother sins, rebuke him, and if he repents, forgive him,

James 5:16 ESV
Therefore, confess your sins to one another and pray for one another, that you may be healed. The prayer of a righteous person has great power as it is working.

Brothers, if anyone is caught in any transgression, you who are spiritual should restore him in a spirit of gentleness. Keep watch on yourself, lest you too be tempted. Bear one another’s burdens, and so fulfill the law of Christ. For if anyone thinks he is something, when he is nothing, he deceives himself.
Galatians 6:1-3 ESV
http://bible.com/59/gal.6.1-3.ESV

Judgmental – Spiritual pride of measuring another’s imperfections
REF: https://www.blueletterbible.org/lang/lexicon/lexicon.cfm?Strongs=G2919&t=KJV

So speak and so act as those who are to be judged under the law of liberty. For judgment is without mercy to one who has shown no mercy. Mercy triumphs over judgment.
James 2:12-13 ESV
http://bible.com/59/jas.2.12-13.ESV

Judge not, and you will not be judged; condemn not, and you will not be condemned;  forgive, and you will be forgiven;  give, and it will be given to you. Good measure, pressed down, shaken together, running over, will be put into your lap. For with the measure you use it will be measured back to you.” 
Why do you see the speck that is in your brother’s eye, but do not notice the log that is in your own eye?  How can you say to your brother, ‘Brother, let me take out the speck that is in your eye,’ when you yourself do not see the log that is in your own eye? You hypocrite, first take the log out of your own eye, and then you will see clearly to take out the speck that is in your brother’s eye.
Luke 6:37-38, 41-42 ESV
http://bible.com/59/luk.6.37-42.ESV

Grumbling – Complaining about the circumstance that God has you in
REF: https://www.blueletterbible.org/lang/lexicon/lexicon.cfm?Strongs=G4727&t=KJV
REF: https://www.blueletterbible.org/lang/lexicon/lexicon.cfm?Strongs=G1112&t=KJV

Be patient, therefore, brothers, until the coming of the Lord. See how the farmer waits for the precious fruit of the earth, being patient about it, until it receives the early and the late rains. You also, be patient. Establish your hearts, for the coming of the Lord is at hand. Do not grumble against one another, brothers, so that you may not be judged; behold, the Judge is standing at the door.
James 5:7-9 ESV
http://bible.com/59/jas.5.7-9.ESV

Do all things without grumbling or disputing, that you may be blameless and innocent, children of God without blemish in the midst of a crooked and twisted generation, among whom you shine as lights in the world, holding fast to the word of life, so that in the day of Christ I may be proud that I did not run in vain or labor in vain.
Philippians 2:14-16 ESV
http://bible.com/59/php.2.14-16.ESV

Gossip – Corrupting talk about others
REF: https://www.blueletterbible.org/lang/lexicon/lexicon.cfm?Strongs=G988&t=KJV
REF: https://www.blueletterbible.org/lang/lexicon/lexicon.cfm?Strongs=G4550&t=KJV

Let no corrupting talk come out of your mouths, but only such as is good for building up, as fits the occasion, that it may give grace to those who hear. And do not grieve the Holy Spirit of God, by whom you were sealed for the day of redemption. Let all bitterness and wrath and anger and clamor and slander be put away from you, along with all malice. Be kind to one another, tenderhearted, forgiving one another, as God in Christ forgave you.
Ephesians 4:29-32 ESV
http://bible.com/59/eph.4.29-32.ESV

There are six things that the Lord hates, seven that are an abomination to him:  haughty eyes, a lying tongue, and hands that shed innocent blood,  a heart that devises wicked plans, feet that make haste to run to evil,  a false witness who breathes out lies, and one who sows discord among brothers.
Proverbs 6:16-19 ESV
http://bible.com/59/pro.6.16-19.ESV

Here is the pearl – it matters which way we are looking. We are to be looking forward, not looking back. Focused on hope and commitment for now and the future, nor dwelling on the past.

I don’t mean to say that I have already achieved these things or that I have already reached perfection. But I press on to possess that perfection for which Christ Jesus first possessed me. No, dear brothers and sisters, I have not achieved it, but I focus on this one thing: Forgetting the past and looking forward to what lies ahead, I press on to reach the end of the race and receive the heavenly prize for which God, through Christ Jesus, is calling us.
Philippians 3:12-14 NLT
http://bible.com/116/php.3.12-14.NLT

He said to another person, “Come, follow me.” The man agreed, but he said, “Lord, first let me return home and bury my father.” But Jesus told him, “Let the spiritually dead bury their own dead! Your duty is to go and preach about the Kingdom of God.” Another said, “Yes, Lord, I will follow you, but first let me say good-bye to my family.” But Jesus told him, “Anyone who puts a hand to the plow and then looks back is not fit for the Kingdom of God.”
Luke 9:59-62 NLT
http://bible.com/116/luk.9.59-62.NLT

But Lot’s wife looked back as she was following behind him, and she turned into a pillar of salt.
Genesis 19:26 NLT
http://bible.com/116/gen.19.26.NLT

We have to stop looking back. Forgive for the past – and encourage and hold accountable going forward. If we slip up, we confess to our accountability partner(s) and pray together for forgiveness and that we will repent and build each other up in that area of weakness – that we will see His strength come to bear and overcome those chains.

If we are harping on something a person has done in the past – we need to forgive and make it right between ourselves and that brother or sister – looking for a fully restored relationship encouraging one another starting now. We are to be peacemakers.

If we are complaining about something,  we are allowing the Spirit of offense to build up bitterness in our hearts over the past,  instead of focusing on what can’t be changed,  we should focus on what we can do now and for the future to improve the situation.  We are to be overcomes – challenge minded,  not problem minded.

If we are talking about what someone did in the past, instead of about the hope we have for their future – we are both participating in gossip and we are not holding out hope and faith that the Lord will answer our prayers for them to be alive and growing in Christ.

Words have power,  and they are important.

“Either make the tree good and its fruit good, or make the tree bad and its fruit bad,  for the tree is known by its fruit.  You brood of vipers! How can you speak good, when you are evil? For out of the abundance of the heart the mouth speaks.  The good person out of his good treasure brings forth good, and the evil person out of his evil treasure brings forth evil.  I tell you, on the day of judgment people will give account for every careless word they speak,  for by your words you will be justified, and by your words you will be condemned.”
Matthew 12:33-37 ESV
http://bible.com/59/mat.12.33-37.ESV