Red Flags: Caution in Mentoring Ex-Prisoners

Taking the step to mentor an ex-prisoner could be one of the most rewarding things you ever do. It’s also an area where many confident volunteers find themselves in uncharted waters.

Ex-prisoners must navigate a myriad of new choices, and they need a strong friend to help them along the journey—and that’s you. Therefore you need to be equipped with particular wisdom to help your mentee make positive decisions, as well as the instinct to notice if he or she is falling into negative patterns.

To equip you to recognize areas where your mentee might struggle, Frontlines took a few minutes to chat with Minnesota InnerChange Freedom Initiative® reentry manager and 22-year prison ministry veteran Rocky DeYoung.

Here are the three significant pitfalls that Rocky advises mentors to be aware of when coaching their mentees.

1.  Girlfriends

Most guys are not ready to manage a romantic relationship in a positive way if they’ve never been in a healthy relationship before. If they try to find a girlfriend too fast, they’ll likely end up in a lot of chaos—the kind of chaos most guys were in before they went to prison. Something a lot of guys don’t think about is that most women with good judgment would not choose to date a man in prison or a man who just got out of prison. I like to tell guys that in any normal household, a mother doesn’t encourage her daughter to hang out with a prisoner.

If a guy was in a significant relationship before he went to prison, that’s a bit different. Still, I would advise the couple to meet with a pastor, and perhaps the pastor’s wife, who can give them advice on how a healthy relationship should work.

2.  Isolation

If an ex-prisoner isolates himself, that automatically means there’s trouble. In prison he’s never alone. Never. So he highly values solitude. But when he gets out and he’s finally alone, he might not know how to manage his newfound freedom.

This freedom can be like a trigger, kicking a guy back into his old patterns and habits if he’s not careful. For example, instead of choosing to find new friends at church or work, he might gather the same people he used to hang out with and head back into his old activities. Ex-prisoners should be encouraged to find community within local churches, addiction recovery groups, and healthy family relationships. These bonds will steer them away from isolation and toward healing and accountability.

3.  Missed Appointments

Most guys with missed appointments will have lots of excuses. And none of those excuses are valid. Ever. Missed appointments are rarely due to forgetfulness. They are indications that other things are taking his time. In prison you are always on time for everything or you will pay the consequences. On the outside you are always on time for whatever is your priority.

When an ex-inmate misses an appointment with his mentor, it means he just blew him off for something else—and that “something else” is usually not part of the mentee’s plan for making a good transition back into society. If an ex-prisoner misses a mentor meeting, it’s unusual that he will call to apologize. That leaves the mentor wondering what happened, and perhaps feeling stood up.

Dealing with a mentee who regularly misses his appointments requires a mentor to draw very clear emotional boundaries. Most ex-prisoners will respect smart compassion, but they’ll recognize compassion that has no boundaries and they can abuse that.

By watching for and recognizing these three red flags of mentoring ex-prisoners, you can better assist your mentees in successfully transitioning into society. Be on the lookout! If a red flag pops up, deal with it immediately. Because when it comes to prisoner reentry, mentor involvement makes all the difference.

-30-