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Tools for Mentoring #1



“Questions you should be asking”


One question I get a lot from the mentors I work with is, "What sort of questions should I be asking my mentee that will help us get started?" This is a common question and it’s an important one, where do you start? Here's some necessary information you might want to start with that I think will lay a foundation for continued progress as you attempt to help individuals leaving prison adjust to the legit world. Hope it helps!

Let’s call these Foundational Pieces (FP), and we'll number them. No order of importance, just important stuff that should be covered.


FP #1: “What’s going to be different this time?”


Here's an example of an open ended question that should lead to a variety of other questions, or at the very least, give you a clue as to how much thought your mentee has put into this next phase of life. If you get crickets, then you don't have a lot to work with in terms of self-motivation and direction. Most of the time, you'll get generic answers like "I don't plan to go back" or "I'm going to stay away from certain people." These answers are way too basic but will serve as an entry point for you if you learn to build on them. Let’s look at response #1.


I don’t plan to go back: This is the most common response I get when I ask this question in prison or at the halfway house. It indicates a desire but is only a fantasy. A wish without a plan means nothing. Your approach should be to communicate your understanding that this is a desire, but that you want to help make it a reality. The word plan is not a word most individuals embrace but it can be your entry point. Suggest the possibility of putting together a solid plan for making this a reality. Now we’re creating hope and hope will fuel this thing. Now let’s look at response #2


I’m going to stay away from certain people: This response at least identifies some action that is intended to yield some results. Here's where I try to introduce the idea that anything you leave or run from, must include something you're going or running towards or it will fail. Without identifying something positive to run to, you will eventually get bored with the empty space. Familiarity will win out, and soon you'll be touching base with that old crowd. Start identifying people, places, and things that are new and build a strategy to connect with them. One thing at a time, slowly, but very intentional.


FP#2: Tell me what it looks like just before the wheels come off.


I know this is going to get some push back from the “sensitive” crowd but hey – we are in a serious situation here that can have serious consequences if we don’t get down to some serious Stuff! Your mentee will respect this question, and that's all you need to worry about. Everybody else who's not in the game can have their opinions, but at the end of the day, you’re the one doing the work and time is valuable. You might have the internet, PSR reports, BCA, and all kinds of other resources, but you are asking your mentee to give you a picture of what’s happened in the past so that you can recognize patterns moving forward. I stress that I don't care about the past, but I need the information so I can help with decision making in the future.


FP#3: What’s the plan moving forward for where you’re going to live?


This question will give you several great topics to discuss. Housing is tough for anyone with a felony, but you can still have a plan, or a dream, to have your own place. If the plan is to live with mom for the foreseeable future then once again, you will need to start building some hope, by discussing a pathway to responsible, independent housing. The worst scenario is hearing about how your mentee met someone on the bus, and now they're going live together. This is just more of the same, in terms of life patterns from the past, and it will lead to all kinds of drama and complexities. Many guys I've worked with do not want the responsibility of their own spot, so this is a tough sell. Stick to it! And if it happens – do all you can to encourage your mentee to keep it. This means they need to show up at work – every day. Keep the negative people far away and do not let cousin jimmy move in for a month. Set this as a top priority.


Hopefully, this helps to get you started. Remember to ask open-ended questions and then most importantly – listen.

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