Either Way
THINKING NOTE

Conversation Starters That Do Not Feel Like Interviews

A practical look at why simple choice questions can be more interesting than they first appear.

Avoid a résumé rhythm

A chain of factual questions—where do you work, where did you grow up, what do you do—can feel like an intake form. Choice questions interrupt that rhythm.

A chain of factual questions—where do you work, where did you grow up, what do you do—can feel like an intake form. Choice questions interrupt that rhythm. In practice, the simplest way to test this is to say the question out loud and notice whether it produces an immediate, effortless answer or a short pause. That pause is useful: it means both options have enough weight to deserve consideration.

Give both people the same task

A two-choice prompt is symmetrical. The person asking can answer too, so the exchange does not place one person under a spotlight.

A two-choice prompt is symmetrical. The person asking can answer too, so the exchange does not place one person under a spotlight. In practice, the simplest way to test this is to say the question out loud and notice whether it produces an immediate, effortless answer or a short pause. That pause is useful: it means both options have enough weight to deserve consideration.

Choose ordinary subjects first

Food, travel, routines, weather, books, and small conveniences are easy starting points. More personal subjects can wait until the conversation naturally moves there.

Food, travel, routines, weather, books, and small conveniences are easy starting points. More personal subjects can wait until the conversation naturally moves there. In practice, the simplest way to test this is to say the question out loud and notice whether it produces an immediate, effortless answer or a short pause. That pause is useful: it means both options have enough weight to deserve consideration.

Let answers wander

The best use of a prompt is often to abandon it. If the answer leads to a story about a trip or a strange meal, follow the story rather than racing to the next question.

The best use of a prompt is often to abandon it. If the answer leads to a story about a trip or a strange meal, follow the story rather than racing to the next question. In practice, the simplest way to test this is to say the question out loud and notice whether it produces an immediate, effortless answer or a short pause. That pause is useful: it means both options have enough weight to deserve consideration.

Do not force a clever answer

Conversation works better when people can answer plainly. A prompt should make room for humor, but it should not require someone to perform.

Conversation works better when people can answer plainly. A prompt should make room for humor, but it should not require someone to perform. In practice, the simplest way to test this is to say the question out loud and notice whether it produces an immediate, effortless answer or a short pause. That pause is useful: it means both options have enough weight to deserve consideration.

Keep it simple

The format does not need a scoring system or a complicated rulebook. A clear pair of choices, a reason, and a follow-up question are enough. The question has done its job when people stop thinking about the format and start talking to each other.

← Back to all articles