Political Questions to Ask Someone
Twenty questions that get at how someone reasons about politics rather than which side they land on: where their views came from, what would change their mind, where they draw the line on government, how they decide who to believe, and what their own side gets wrong.
The questions
Open any question for the note
Which issue do you actually follow closely, and which do you mostly ignore?
Why ask it
A safer opener than asking what matters most, because admitting what you ignore is easy and honest. It also tells you where the conversation can go deep and where you would both be repeating headlines.
Where did your politics come from: family, work, something that happened to you?
Why ask it
People argue about conclusions and agree about experiences. A view traceable to a job loss, a hospital bill or a military posting is much easier to understand than the same view stated as a principle.
Have you ever changed your mind about a political issue, and what did it?
Why ask it
The mechanism is the useful part: a person, an event, or an argument. Anyone who has never changed their mind on anything is telling you that new information does not reach them, which is worth knowing early.
What does the side you lean toward get wrong?
Why ask it
This is the question that separates a thinking position from team membership. Most people have an answer and rarely get asked for it, and giving it usually makes them more candid for the rest of the conversation.
What is the strongest argument on the other side that you cannot easily answer?
Why ask it
Note whether they can state it in a form the other side would recognize. An opponent's argument described as obviously stupid means they have only encountered the version their own side repeats.
Where do you draw the line on what government should do, and what should it stay out of?
Why ask it
Asking for the line rather than the principle gets a specific answer. Most people are not consistent here, and hearing where they are inconsistent is more informative than any label they would accept.
When personal freedom and public safety collide, how do you decide?
Why ask it
Almost every contested issue reduces to this trade-off. Ask for a case they found genuinely hard, since the easy cases only tell you which side they start from.
Which worries you more: a government that does too much, or one that does too little?
Why ask it
A forced choice, which is why it works. The answer usually predicts their position on issues you have not discussed yet, and it puts a name to the fear underneath their politics.
What should be decided locally, and what nationally?
Why ask it
One of the few political questions that rarely maps onto party lines, so it produces real thought instead of a scripted answer. Watch for whether the answer changes depending on who is currently in power.
How do you decide who to believe when two sources disagree?
Why ask it
You are asking about method rather than conclusions. Answers that name a check, looking at the primary document, seeing who reported it first, are different from answers that name a trusted outlet and stop.
Where do you get your news, and is there anyone you read who you usually disagree with?
Why ask it
The second half is the real question. Someone who can name a writer they respect and disagree with is in a different conversation from someone who only encounters the other side through their own side's summary.
What would have to happen for you to vote against the party you usually support?
Why ask it
This finds out whether their vote is a judgment or an identity. A concrete condition, even a demanding one, is a different answer from never, and both are worth hearing plainly.
Do you think politicians are mostly corrupt, or mostly constrained?
Why ask it
It distinguishes cynicism about people from criticism of systems, and those lead to opposite conclusions about what reform would even mean. Ask what they think a well-intentioned politician actually cannot do.
What do you make of money in campaigns, and what would you actually change?
Why ask it
Almost everyone dislikes the current arrangement, so the interesting part is the proposed fix. Vague answers here are common and honest; a specific one tells you they have thought past the complaint.
What should courts do when they overturn something a majority voted for?
Why ask it
It gets at whether they think of democracy as majority rule or as rules that bind majorities. Many people answer differently depending on the ruling, and asking directly makes that tension visible.
Is there a political view you hold that you would not say out loud at work?
Why ask it
It surfaces the gap between what people believe and what is sayable in their circle, which is often the most interesting thing they will tell you. Do not push if the answer is that they would rather not say.
Have politics ever cost you a friendship, or strained things with family?
Why ask it
This moves from opinion to consequence, and it is where most people become noticeably more careful and more honest. The story usually explains why they hold certain conversations at arm's length.
How do you tell the difference between a compromise worth taking and a surrender?
Why ask it
Answers reveal whether they think in terms of outcomes or of positions. If the line is drawn only around their own side's concessions, that is worth noticing rather than pointing out.
What do you think this country genuinely does well?
Why ask it
Useful late in a conversation that has been mostly about problems, and people are often unprepared for it. Cooling the temperature before you finish tends to be what makes a second conversation possible.
What would you want to ask me before we stop?
Why ask it
Handing over the questions is the clearest signal that this was not an interrogation. What they choose to ask also tells you what they assumed about you for the previous hour.
Having the Conversation Without a Fight
Practical guidance for the conversation itself
Choosing the Moment
One to one, and not at a table with an audience
People defend positions in front of others and explore them in private. The same person who will not concede a point at a family dinner will think out loud in a car or on a walk, because nobody is keeping score.
Say what you are doing
Opening with something like I am not trying to change your mind, I want to understand how you got here changes what follows. Without that, most people reasonably assume the questions are the opening move in an argument.
Decide in advance what you will not raise
If there is one issue where you cannot stay curious, leave it out of this conversation. Trying it and losing your temper costs you the goodwill you would need to ever discuss it well.
While You Are Talking
- Ask for the story behind the position rather than the evidence for it. Evidence invites counter-evidence; a story invites elaboration.
- Repeat their view back before you respond to it. If they correct you, you had it wrong, and you have just avoided an argument about something they never said.
- Distinguish what they believe from what they think should be law. People often agree on the first and disagree entirely on the second, and conflating the two produces false conflict.
- When they cite a fact you doubt, ask where they saw it rather than telling them it is wrong. Sourcing a claim does more than contradicting it, and it keeps the exchange out of scorekeeping.
- Notice when you have stopped listening and started drafting. That is the point at which the conversation becomes a debate, and it is usually visible to the other person before it is to you.
- Let a bad argument go by. You do not have to answer everything, and picking one thread rather than five is what keeps a conversation going.
- Say when something they said landed. It is rare in political conversation and it changes how the next twenty minutes go.
When to Stop
- Wind it up when either of you starts repeating a point louder. Nothing after that is new information.
- Change the subject if it turns to the other person's character rather than their view. Once it is personal it will be remembered as personal, whatever gets said afterwards.
- Close it out before you are tired, or if either of you has been drinking. Most political fights between people who like each other happen at the end of long evenings.
- Leave a topic open rather than forcing a conclusion. I want to think about that is a better ending than a stalemate, and it makes the follow-up possible.
- If it is family, agree on the rule rather than the topic: no politics at the table, or fine one to one but not in front of the children. Rules hold better than resolutions.
- Accept that some views are not going to move. Understanding how someone reached one is a separate goal from changing it, and only the first is within your control.