#1 Listening without interrupting.
This is very hard for me. Over the years I have heard enough self-serving whines and excuses and obvious lies to make my ears swell up and explode. And, since I understand all too well that those whines and excuses are destructive to my loved one, I just don't want to hear it all anymore. Ugh-oh, there it is again...I've made it all about me!
Now, first let me say this: it IS about me. Those of us who are affected by the incarceration of a loved one are dealing with a disaster not of our own making. (No, none of us were perfect parents, but except for those who coerced a child into the family's illegal activities, we are not responsible for the choices our loved ones made -- but that is another journey for another time.) We must deal with our own issues, but that is not what I want to share right now.
Here is why I believe God told us in Proverbs 18:13 "Those who answer before they listen are foolish and disgraceful." And that means me too, even when dealing with my fear for my child. So does that mean we have to keep listening and participating in the same "poor me" monologue? Well, I think sometimes we do. Maybe as we grow we will hear something new in there that we can reflect to our loved one in a helpful manner. They may let a truth leak out that will prove helpful to all, but we can't hear that if we assume we know all they are going to say.
What if we determine they are truly stuck in a destructive "loop"? We can start with silence. That was very hard for me when I was both very emotional myself and stretched financially to pay "jail telephone rates" from another state. But firstly, anything you do differently will make things different...no guarantee it will be for the better, but at least a new behavior by you, especially a gentle one, will change the dialog. It can make your loved one angry because you have changed the script and it is disconcerting. But, my fellow traveler, if nothing changes....well, then nothing changes. So consider a NON-hostile silence to let your loved one run down. Then suggest a change in topics, "Yes, John, I have heard you feel that way. But I want to ask you (share with you, let you know, discuss with you.....)" And keep a list by the phone so you have some things to discuss that are positive, inclusive, or hopeful.
If the looping occurs in letters, you can just ignore it, after you have carefully listened for anything that might be helpful. Especially when writing, refer to something you read or heard in a prior conversation that you can lovingly recall to assure them that they are being heard. I would consider a struggle I was hearing about and look for a scripture passage that I thought spoke to two issues: (1) to reassure that our struggles are not a sign we are hopelessly broken and lost, but rather this: as broken and lost as we are, God already knows about it, yet (2) God is present and for us at all times and in ALL places.
If I could have written a letter to prison every day I don't think it would have been too much and there were no complaints as I explained why my faith was the bedrock of my journey. So if you can combine feeding back to the person what you are hearing (fear both for today and the future, hopelessness, unworthiness, anger, rage, revenge, concern for children left behind, shame, loneliness, frustration and despair to name a few) and combine a quote, it can make a powerful message. You could write the verse or saying or lyric on a 3x5 sheet of paper that could be used to help in memorizing the message. It might even start a new and healthier conversation.
But none of this works well, if we don't listen fully first.