Questions to Ask an Inmate

The questions

Open any question to see why it works.

1. 1

   How are you sleeping?

   A better opener than how are you, which gets a flat fine from almost everyone inside. Sleep is concrete, it is one of the first things to go, and answering it truthfully does not require anyone to admit to struggling. What you learn from the answer is usually the state of everything else.

2. 2

   What does your day look like from wake-up to lights out?

   Gives them something ordinary to talk about and gives you a real picture instead of an imagined one. It also tells you when they are likely to be free for a call, which matters because phone access is limited and timed and missing each other repeatedly wears people down.

3. 3

   What is the best way to reach you, and what does it cost you?

   Mail, phone, and tablet messaging all work differently by facility, and most of them charge, sometimes by the minute or by the message. Asking about the cost lets them tell you they are rationing contact for money reasons rather than avoiding you, which people rarely volunteer.

4. 4

   What can I send, and how does it have to be sent?

   Rules are specific and enforced literally: some facilities only accept mail from an approved vendor, some reject anything with staples, stickers, coloured paper or polaroids, and some scan mail and deliver only copies. Ask them or check the facility website first, because rejected mail is usually returned or destroyed without notice.

5. 5

   How does the commissary work, and what is actually worth having?

   Money on an account is the most useful thing most people can send, and what it buys varies: food, stamps, phone credit, thermal clothing, over-the-counter medicine. Asking what is worth having is more respectful than guessing, and the answer is often something small and unglamorous.

6. 6

   Am I on your visiting list, and what do I need to do to visit?

   Visits usually require approval in advance, photo identification, a dress code, and sometimes a booked slot, and being turned away at the door after a long drive is common. Ask what the rules are at their facility specifically rather than assuming the ones you read about somewhere else apply.

7. 7

   Do you have a job or a programme, and did you choose it?

   Work assignments, classes, and treatment programmes structure the day and sometimes affect release timing. Whether they chose it or were assigned tells you how much control they have, and programme waiting lists are a frequent source of frustration that people are glad to have someone ask about.

8. 8

   What are you reading?

   One of the few questions that is genuinely light and still substantial. Books are among the most requested items and often have to come directly from an approved retailer, so the answer doubles as a practical list. It also gives you something to talk about that is not the situation.

9. 9

   Is the food alright, and are you eating properly?

   Plainly practical, and one of the ways people first show that they are not coping. Weight loss, skipping meals, or living entirely off commissary items are all worth noticing, and asking directly is easier for them to answer than a general question about their health.

10. 10

    Are you able to see medical or dental staff when you need to?

    Access usually runs through a written request and a queue, and delays are common. Ask calmly and without alarm, and if there is an ongoing condition, ask what they have requested and when. These are questions for the facility's medical staff and, if it goes on, for their lawyer or an advocacy organisation, not for you to solve from outside.

11. 11

    Is there anyone in there you can talk to?

    Isolation is the thing outside visitors most often fail to ask about. One decent cellmate, a chaplain, a counsellor, someone on the same block, changes the experience entirely. If the answer is no, it is worth knowing, and it should change how often you write.

12. 12

    What is happening with your case, and who is representing you now?

    Ask the shape of it rather than the detail: who the lawyer is, when the next date is, whether they are able to reach them. Calls and messages from a facility are generally recorded and monitored, and anything specific about a pending case belongs in a conversation with their attorney rather than on a monitored line.

13. 13

    What can I do to help you stay in contact with your lawyer?

    Reaching an attorney from inside is genuinely difficult, and unanswered calls are one of the most common complaints people have. Passing on a message, confirming an address, or sending a phone number are small things you can do without involving yourself in the case itself.

14. 14

    What is your expected release date, and is there anything that could move it?

    Ask so that you are working from the same date they are, because family often carry a number that is out of date. Good conduct credits, programme completion, parole hearings and detainers can all move it in either direction, and hearing which of those apply tells you what the next year looks like.

15. 15

    What do you want me to tell people, and what would you rather I kept to myself?

    You are their connection to a lot of people who will ask about them, and they have very little control over what gets said. Getting this settled early prevents an awkward call later, and it hands back a decision that is theirs to make.

16. 16

    What do you want to hear about from out here, and what makes it harder?

    News from outside can be the best part of a letter or the worst part of it, and the line is personal. Some people want everything, including the difficult things; others find photographs of a family holiday unbearable. Asking once saves months of guessing.

17. 17

    What do you miss that I would not think of?

    The answers are rarely the obvious ones. Silence, choosing when to turn a light off, cold water, being able to walk somewhere with no one watching. It is a question that treats them as a person with an inner life rather than a situation to be managed, and people remember being asked it.

18. 18

    What worries you about getting out?

    Release is anticipated and dreaded at the same time, and the worries are usually concrete: no identification, nowhere to live, a supervision condition that conflicts with work, people expecting them to be who they were. Naming them early is what makes them solvable later.

19. 19

    What needs to be in place before you come home, and what part of it can I start on?

    Identity documents, a mailing address, a phone, a bank account, transport, and a first appointment with a supervising officer are the standard list, and several of them take weeks and are far easier to arrange from outside. This is the most useful question on the list if you have any capacity to act on the answer.

20. 20

    How do you want me to be with you: distraction, or straight talk?

    People inside get a lot of relentless cheerfulness and a lot of pity, and most want neither. Asking directly lets them set the register of your letters and calls, and it can be revisited, since what someone needs in the first month is rarely what they need in the third year.