Asking Questions That Open Things Up

Conversations that stall are often full of questions. The problem is usually not a shortage of them but the shape those questions take.

Questions specify the size of the answer

A question that can be answered with a single word will be. Asking whether someone had a good weekend invites confirmation, not description.

Asking what they ended up doing requests a narrative instead, and most people supply one without needing any further prompting.

Neither form is wrong, but the first has to be followed by another question immediately, while the second buys several minutes.

Specific beats broad

Very open questions can be paralysing. Asking someone to describe their job is a large request with no obvious starting point.

Narrower questions are easier to answer and often produce more. Asking what the first hour of their working day looks like gives the speaker a handle.

Specificity also signals genuine interest. Broad questions could be asked of anybody, and people can tell.

Following up beats moving on

The most common failure is treating an answer as complete and asking something new. The conversation becomes an interview with no thread through it.

Almost every answer contains a detail worth pursuing, and pursuing it demonstrates that the previous answer was actually heard.

Two or three follow-ups on one topic will usually go somewhere more interesting than six unrelated questions would.

Some questions are requests in disguise

Questions carrying an implied correct answer are not really open. Asking whether someone did not find a film overlong invites agreement rather than opinion.

Leading questions do this quietly, and people generally take the offered answer to avoid friction. The result is a conversation that confirms what the asker already thought.

The same applies to questions used only to introduce your own answer. Listeners recognise the pattern quickly and stop investing in their replies.

Timing decides what is answerable

A question that would be welcome after twenty minutes can be intrusive in the first two. Depth has to be built up to rather than requested.

Reading that is easier than it sounds: if the previous answer was shorter than the question, the conversation is not ready for more depth.

Pulling back to something lighter is not a retreat. It rebuilds the ground on which a bigger question can later stand, and the conversation usually returns of its own accord.

The reliable sequence runs from concrete to personal. What someone did leads to how they found it, which leads to what they made of it, and each step is small enough to take.