How to Start a Difficult Conversation with Dialogue

The way you open a crucial conversation makes a huge difference on the outcome. If you want better results, you need to do these three things in the first 30 seconds.

1. State the facts.
2. Share why those facts are a concern.
3. End with a question that invites the other person into dialogue.

The goal is to speak up in a way that encourages someone to share their perspective. What’s the best way to get their perspective? Ask them.

Recently, I had a confronted a family member about money. They weren’t spending it wisely, and I was afraid for what their future held. I had tried talking to him. I had tried convincing him to change. But it was never effective — until I asked the question that changed our conversations.

See, before he’d been resistant to my advice. But when I stated the facts, shared my concerns, and then asked him “the question” (all in less than a minute), things changed. We moved from an atmosphere of confrontation to conversation.

So, what’s the magic question? “What’s your perspective?”

This question invites someone else into the dialogue. After all, we’re just talking about the beginning of a conversation. You want the question to lead the other person to respond.

When you ask it well, you show both confidence and humility — confidence in your reason for opening the conversation and humility by admitting you don’t know the whole story.

As you seek to start a crucial conversation right, here are three tips for asking “the question” as effectively as possible.

1. Don’t think of this question as a problem-solving question.

Sometimes, we mistakenly try to use this question to solve the perceived problem. Don’t follow asking “What’s your perspective?” with an attempt to fix the problem.

Avoid asking questions like:

“How are you going to fix this?”

“What are we going to do to solve this problem?” or

“How will you make sure this never happens again?”

When you ask questions like these, you communicate that you don’t care about the other person’s perspective. You’ve already judged the situation from your limited point of view and only care about solving the problem.

If you want to be effective, make sure you see the problem accurately. You don’t want to solve the wrong problem. Maybe there’s not a problem — but you won’t know until you talk to the other person.

Invite the other person to pour their meaning into the pool.

2. Ask open-ended questions.

It’s natural to ask close-ended questions like, “You agree with that, right?” or “You’re not going to do that again, right?” But, these questions don’t ask for real input into the conversation. They invite simple responses and limit what’s contributed to the shared pool of meaning.

Instead, ask questions that invite people to tell their story.

3. Make sure the question is non-judgemental.

We want to ask questions without judgement. But sometimes, we make questions judgemental without even meaning to.

See, we can become so comfortable with the way we phrase our questions that we don’t realise the judgement they contain. Some nurses I trained gave a prime example of the kinds of judgemental questions overlooked in their environment.

At the point in our training when we start talking about keeping our questions non-judgmental, they said, “Wait! Our doctors think they’re using these skills, but they’re not! They do just the opposite!”

They said that doctors take them aside and say, “I noticed you did this. That affects patient care. Why’d you do that?” When faced with this confrontation, they felt defensive, judged, disrespected, and fearful of speaking up. Why? The question itself seemed to blame them.

So, be humble as you ask your questions. Instead, of asking, “Why’d you do that?” say something like, “I don’t want to come to an unfair conclusion. So, I wanted to come and talk to you in person first. Can you help me understand your perspective?”

With this approach, you show both confidence and humility.