Deep Questions to Ask a Prisoner
For volunteers, chaplains, journalists and family members. Twenty questions about daily routine, how time feels inside, keeping relationships going, making amends, and what release looks like, with notes on what not to ask and how to stay within visiting rules.
The questions
Open any question for the note
How do you spend a normal day?
Why ask it
A practical opener that is easy to answer and tells you a great deal: whether they have work, education, association time, or long stretches locked in. It also gives you the vocabulary of their particular institution, which every later question depends on.
What is something you look forward to each week?
Why ask it
The answer is usually small and fixed: a class, a library trip, a phone slot, a particular meal. Knowing it means you can ask about it next time, which is what turns a series of visits into an actual relationship.
What has surprised you most about being in here?
Why ask it
Invites observation rather than confession. Answers often concern noise, boredom, paperwork or unexpected kindness rather than danger, and they correct the picture most visitors arrive with.
What do people outside get wrong about this place?
Why ask it
Distinguishes the institution from the person, so they can speak about the system without having to speak about themselves. Listen for whether the correction is about violence, about idleness, or about how much of the day is spent waiting.
How has your sense of time changed?
Why ask it
Most people inside have a considered answer to this and are rarely asked. Some describe time collapsing, some describe counting in units other than days. It is a way into a serious subject that does not require them to be upset.
What keeps you steady when a day goes badly?
Why ask it
Ask about method rather than hope, since method is answerable: a routine, a letter reread, exercise, a particular person. If the honest answer is nothing, that is worth hearing quietly rather than filling in with encouragement.
Who do you stay in touch with, and how does that work practically?
Why ask it
Contact runs on credit, timetables and postage, and the practical detail explains a lot about who has faded. Asking how rather than only who tends to surface obstacles that a visitor or volunteer can sometimes help with.
What is hardest about phone calls and visits?
Why ask it
Common answers are the queueing, the lack of privacy, and having to reassure everyone that you are fine. Hearing this changes how you conduct your own visits, and it is often the first thing nobody has thought to ask.
What have you learned about reading people?
Why ask it
Treats them as someone with expertise rather than only experience. The answers are usually precise and unsentimental, about noticing shifts in mood, and about who to stay away from without making it obvious.
What have you been able to study, work at, or make while you have been here?
Why ask it
Courses, jobs, drawings, letters written for other people. This is often the part of their time they are most willing to talk about, and it also reveals what they have applied for and been refused, which matters for release planning.
What do you miss that you did not expect to miss?
Why ask it
The unexpected qualifier moves this past the obvious answers. People name silence, choosing what to eat, darkness at night, being touched casually, walking somewhere without being counted. Concrete answers rather than sad ones.
Who has stuck by you, and who has not?
Why ask it
Sentences reorganise a person's relationships, usually within the first year. Asking both halves lets them talk about loss without having to introduce it themselves, and it tells you who they can still count on at release.
What do you carry from before that you are still working through?
Why ask it
Deliberately open, so they choose whether that means childhood, addiction, grief or the offence itself. Do not narrow it for them. What they select, and what they leave out, is their decision about how far this conversation goes.
How do you think about the harm that was done?
Why ask it
This asks about their thinking rather than the facts of the case, which they may be legally unable to discuss. Answers range from full acknowledgement to distance and deflection, and it is not your role to grade the response.
What does making amends look like from in here?
Why ask it
A practical question about a subject usually kept abstract: letters that cannot be sent, money that cannot be earned, a family that will not take a call. It also shows whether anyone has ever discussed reparation with them in concrete terms.
What would you say to someone arriving here today?
Why ask it
Lets them speak from the position of someone who knows, which is a different footing from being asked about themselves. Advice tends to be specific: who to talk to, what to keep to yourself, how to get through the first fortnight.
What do you want people to understand about the sentence itself, separate from you?
Why ask it
Separating the policy from the person makes it possible to talk about the system without asking them to justify their own case. Useful with journalists, who often need this distinction made explicitly before anything can be printed.
What are you afraid of about release?
Why ask it
Fear of getting out is common, real and rarely voiced, because everyone expects excitement. Answers cover housing, work, technology that has moved on, and people who have changed. Only ask if release is actually on the horizon.
What is the first ordinary thing you want to do when you get out?
Why ask it
Almost always small: a specific meal, a bath, a walk with no one watching. It is a lighter question that follows well after a heavy one, and it gives the conversation somewhere to land before a visit ends.
What do you want your life to look like five years after you leave?
Why ask it
Five years out is far enough to be honest and near enough to be real. Listen for whether the picture includes work, housing and people, since a plan with only intentions in it usually means nobody has helped them make one.
Visiting and corresponding well
Practical guidance for the conversation itself
Before you visit or write
Learn the rules of that institution first
What you may bring, what may be discussed, whether calls are recorded, and what ends a visit varies between facilities. Volunteers and journalists usually receive this in writing. Family members often do not, and find out by having something refused at the gate.
Do not ask about the case
Appeals, charges and details of the offence can affect legal proceedings and are frequently prohibited under the terms of a visit. If they raise it themselves, listen, but do not lead them there or ask follow-up questions about the facts.
Bring news, not only questions
An hour of being asked about yourself is tiring and one-sided. Ordinary news from outside, what is happening with people they know, a match result, a change on their street, is often the part of a visit that is valued most.
Be exact about what you will do
Say when you will next visit or write, and then keep to it. Vague promises to come back soon cost the person more than saying you cannot come until March, because they will count on it either way.
Choose the questions in advance
Visits are short and interruptible. Pick three questions, and know which one you would drop. Working down a list uses up time that would be better spent on whatever the first answer opens up.
What to avoid
Treating the conversation as research
Questions asked to satisfy curiosity about prison life, rather than to know the person, read as exactly that. If you are a journalist, say so plainly and agree at the start what may be published.
Assuming a release date
The last three questions do not apply to everyone. For someone serving a very long or indeterminate sentence, asking what they will do when they get out is careless. Ask about the next year instead.
Offering to help before you know you can
Money, calls to lawyers, contacting family members: agree to nothing on the spot. Say you will look into it, then follow up. Undelivered help does more damage inside than a straightforward no.
Pressing for feelings
Someone who has to return to a wing in twenty minutes may not want to be opened up and then left. Follow their lead on depth, and let a short answer be the answer.
Framing them as either a victim or a lesson
Responses that describe them as inspiring, or that reach for what the experience has taught them, close the subject. Plain acknowledgement is better than either sympathy or admiration.
Notes by relationship
- Family: expect to be told everything is fine, and ask about the practical things instead, since those are easier to answer truthfully
- Volunteers and chaplains: keep the same questions across visits, because consistency is what makes trust possible in short sessions
- Journalists: agree on the record and off the record before you start, and put the boundary in writing
- Long correspondence: letters allow slower and harder questions than visits, since there is time to think and no queue outside
- First visit: stay with the questions about routine, the week and what they miss, and leave the rest for later