Questions to Ask Criminals
Questions for a journalist, researcher, student, or volunteer talking with someone who has committed crimes or served time, covering how it started, how they read the risk, what custody and release were actually like, and what they want people on the outside to understand.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
How do you describe yourself when you meet someone new?
It hands the framing to them before you impose one, and the answer tells you a great deal. Some people lead with the conviction, some never mention it, and some have a rehearsed line. Whichever it is, use their vocabulary for the rest of the conversation rather than yours.
- 2
What do people always ask you that you are tired of answering?
Ask this early and you find out which questions will produce a worn out script. It also signals that you would rather hear something true than something familiar, which is often the moment the tone of the conversation changes.
- 3
What was going on in your life just before any of this started?
Starting with the context rather than the offence gets you a person rather than a case file. Listen for the practical details, a job lost, a house move, someone who left, since those are usually more explanatory than anything about character.
- 4
How did the first thing actually happen?
Most people expect to be asked about the worst thing and are surprised to be asked about the first. The first is usually smaller, more accidental, and much better remembered, and it is where the reasoning that led to everything else is visible.
- 5
At the time, what did you think the chances of getting caught were?
Almost nobody says they thought they would be caught, and the reasoning behind that belief is the most useful thing in the conversation. It is also where deterrence arguments meet reality, so press gently on why the odds seemed acceptable.
- 6
Who else knew, and what did they think you were doing?
The circle around an offence is usually part of the story: people who helped, people who suspected, people who were told nothing. Be careful here, because you are asking about others who did not consent to being discussed, so let them decide how much to name.
- 7
What happened to the money, or to whatever you got out of it?
Answers are rarely what people expect. Debt, rent, someone else's medical bill, or nothing memorable at all are far more common than anything dramatic, and the plainness of it is often the most honest part of the account.
- 8
Was there a point where you could have stopped?
This invites them to locate their own agency rather than having you assign it. Some people identify a specific moment and some say there was never one, and the difference between those two answers is worth following rather than correcting.
- 9
How did it end?
An open question that lets them choose between being caught, being informed on, or stopping on their own. How it ended shapes everything afterwards, particularly whether they feel they were unlucky or whether they feel they were finished with it anyway.
- 10
What do you remember about the arrest itself?
This is usually recalled in unusual sensory detail, down to the time of day and who was in the room. It is also a moment where accounts of what was said and done can be checked against records, which matters if you are reporting rather than only listening.
- 11
What did your lawyer tell you, and how much of it did you understand at the time?
A great deal turns on the plea conversation, often conducted quickly and under pressure. Asking what they understood, rather than what they were told, gets at how the process actually works for someone inside it.
- 12
Who were you thinking about when you were sentenced?
It moves the account away from procedure and toward the people attached to it, usually a parent or a child. Ask it quietly and let the silence sit, since this is often the first question in an interview that is genuinely difficult to answer.
- 13
What did the first week inside teach you?
Early custody is where the rules are learned, and the lessons are specific: what to say, who to avoid, what to do with your property. Concrete answers here do more to convey the reality of prison than any general description of conditions.
- 14
What did you do all day?
The ordinary shape of a day is the part outsiders never picture and the part people inside remember most exactly. Ask about the schedule, the work assignment, and the boredom, which is usually named before anything else.
- 15
What did you have to become in there that you were not outside?
Most people describe adopting a posture, a silence, or a readiness they did not have before. The follow up matters more than the answer: ask how much of it came home with them, because that is where the effects of a sentence show up years later.
- 16
Who stayed in touch, and who did not?
Contact is expensive, restricted, and a real measure of what survived. Whether they hold anything against the people who fell away tells you a lot about how they think about their own responsibility.
- 17
What was the first day out like?
Release is often described as more disorienting than arrival, with small tasks such as a phone, a card, or a crowded shop becoming difficult. The details are specific and rarely reported, so this question usually earns something new.
- 18
What is closed to you now that you did not expect?
Beyond the obvious employment barriers there are usually surprises: housing applications, a licence, travel, a volunteering role at a child's school. This is the part of a sentence that continues long after it has formally ended.
- 19
What do you say when an employer or a landlord asks?
Everyone develops a script and most people can quote it. Ask how it has changed over the years and what happens when it does not work, since the practical answer is more instructive than any policy discussion about disclosure.
- 20
What would you say to someone who is about to do what you did?
A closing question that most people have thought about carefully. Be alert to whether the answer is about consequences or about the person they hurt, since the difference between avoiding a sentence and regretting the harm is the whole of it.
Interviewing someone about a criminal past
Practical guidance for the conversation itself.
Before you start
Before you start
Be clear about what this is
Say who you are, where the conversation might appear, and what you will do with their name. People who have been through the legal system are used to their words being used against them, and vagueness here will cost you the whole interview.
Do not ask about uncharged offences
Questions that invite an admission to something they have not been convicted of can create real legal exposure for them, and in some situations for you. If they raise something themselves, stop and check that they understand it is on the record.
Check the practical constraints
If the person is in custody, calls are usually recorded, monitored, time limited, and paid for by them. If they are on probation or parole, there may be conditions on speaking to media or on discussing the offence at all.
Read what is public first
Charging documents, sentencing remarks, and contemporaneous reporting. Turning up without that wastes their time on the parts you could have looked up, and it makes it harder to notice when an account is inconsistent.
How to ask
How to ask
Tone does more work here than any particular question:
- Ask plainly. Softened language reads as squeamishness and invites a softened answer in return.
- Do not perform sympathy or shock. Both produce a version of the story shaped to your reaction rather than to the truth.
- Follow one answer at a time. The second question about the same thing is where the account stops being rehearsed.
- Let silences run. This is the single most productive technique in a difficult interview.
- Ask about victims directly rather than skirting it, and accept that the answer may be evasive. How someone avoids the question is itself information.
- Say when you are moving to a harder subject. A short warning gets better answers than an ambush.
Handling what you are told
Handling what you are told
- Assume the account is partly shaped for you, as any account would be, and check what can be checked against records.
- Do not agree to conditions you cannot keep, particularly around anonymity or letting them approve the finished piece.
- Be careful with names of family members, co-defendants, and victims, none of whom agreed to this conversation.
- If the person becomes distressed, offer to stop rather than pushing to finish the list.
- If you are a student or a volunteer rather than a reporter, check the rules of the organisation you are with before recording anything or publishing any of it.