When is your next question born? In the moment before.

Going into a difficult conversation with a little forethought is wise indeed. Being curious and figuring out in advance what you want to understand better is also wise. But don’t become so wedded to your list of questions that they get in your way. There is a better way to ask good questions.

The problem with prepared lists of questions

Here are common mistakes I see people making when they bring their prepared list of good questions into difficult conversations with them:

• They become so focused on the questions they want to ask that they don’t fully listen to the answers.
• They don’t allow themselves the freedom to go where the answers to their questions might take the conversation, instead using the list as a script of sorts.
• They miss opportunities to ask other valuable questions because they’re too focused on the original list.
• They work through the list like it’s an interrogation or an interview instead of fully connecting with the person in the conversation with them.
• They allow the prepared questions to substitute for good curiosity in the moment and miss opportunities for better understanding.

Here’s the thing about prepared lists of questions and topics: The desire to use them comes too often from a place of fear…fear that if you don’t have questions prepared, you won’t know what to do, what to ask, what to say. I hear this fear particularly from new and unseasoned mediators helping other people in difficult conversations — the list becomes their safety net and they just never stop using it.

An alternative approach

I invite you to try something different, something that takes a tiny bit more courage at first, but which I believe you will find more satisfying and which will help you avoid the traps listed above.

This is how to ask good questions: Allow each question you asked to be born from the thing that was said in the moment before.

Here’s how to do it if you’re afraid to let go of your prepared questions crutch/safety net. Do some advance thinking about what you need to understand better — about the other person, about the situation, about the past, about the future. Draft your usual list of questions. But tuck your list away when you sit down. Don’t look at it. Don’t let it become a crutch that distracts you. Instead:

1. Listen deeply to the thing just said.
2. Breathe and wonder.
3. Allow a question to be born that very moment.
4. Ask it.
5. Rinse and repeat.

If you must, before wrapping up the conversation, look at your list to make sure you didn’t miss something critical. I suspect you’ll will find that the questions on the list you tucked away are less compelling than you thought they’d be when you wrote them.

Challenge yourself to let go of the fears that keep you clinging to your prepared list. Afraid you’ll miss an important question? You have your list in your wallet if you need to double check that. Afraid you won’t know what to say? When you listen deeply, your response will be there. Afraid you won’t ask something in the perfect way? You won’t ask it in the perfect way even with a list in front of you…there is no perfect way. Afraid you won’t ask the right question? The right question is the thing you really want to know and understand, born in the moment. You cannot help but ask the right question if you stay present and open. Afraid strong emotions will block your ability to do that? If you’re so hijacked by strong emotions, no question list in the world will help you because you won’t be able to fully hear the answers anyway.

Listen. Breathe. Wonder. Ask.

What do you think about this?