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Keeping a conversation going: great questions

If you are focused on learning about the conversation partner, you will naturally ask good follow-up questions and thereby create engaging conversations. For example:

Here are some types of follow-up questions that are particularly good at keeping a conversation going.

Questions that prompt stories

We've already covered those questions. They make great first questions but are equally handy at other points in the conversation.

Questions that prompt reflection

Questions that invite your conversation partner to reflect on past experiences will make a conversation more meaningful. If you ask such questions, your conversation partner is likely to remember the conversation with you as deep rather than superficial.

To prompt reflection, you can ask "What was it like to _ (insert something your conversation partner did)?". But there are other ways of prompting reflection, as the exercise below illustrates.

Suppose your conversation partner has just mentioned that their most recent project at work did not go well. Which of these questions invites them to reflect on their experience?

How did this experience change your views on good project management?

In hindsight, why do you think things went wrong?

Was the project stressful for your colleagues as well?

What did you take away from this experience?

"Tell me more."

This simple prompt can be used to dig deeper on anything your conversation partner says. Of course, don't overuse it.