I see the following conversational mistake a lot. While it doesn’t necessarily kill a conversation, if you want to have great conversations, it helps to know what you’re doing. If you’re reading this blog, with the phrase “If you want extraordinary performance, know extraordinary performers” on the top left of the home page, you probably want to perform extraordinarily.

It came up when I was coaching a friend on Meaningful Connection exercise so I’ll write about it in that context, but the principle applies to many conversations.

That exercise starts by asking someone for one of their passions or something they like to do. After they answer, you connect their activity to your life, then ask them to elaborate.

My friend skipped the step of connecting their passion to his life. After I told him my passion, public speaking, he just asked “Why do you like public speaking?”

That question was the mistake, even if not necessarily a conversation killer. Here’s why.

Asking too many difficult or personal questions without sharing information about yourself asks them to do the work of the conversation. It feels to many people like you’re interviewing them. You risk leading them to disengage.

By contrast, connecting their activity to your life shows you listened and thought about their activity, then offered information without distracting from the important thing you just asked them about. You contribute. Skipping that step means you don’t contribute except to ask them to work. Two probing questions in a row may not feel like too many to you, but if the other person feels like they’re personal and make them think a lot, they’ll lose enthusiasm. You may think you’re giving them a chance to talk or showing interest, leading you to conclude you’re helping them, but your feelings don’t motivate them, theirs do.

In the best case, the person wants to share about their passion with enthusiasm already. Then they’ll probably share about it anyway, so asking doesn’t help.

If the person doesn’t already have that enthusiasm to share, asking them to share asks them to dig around their motivations and past to find the relevant answer for you. That takes work on their part, while you just ask a few short questions. Who wants to be your dancing monkey?

The exercise’s middle step of connecting and sharing from your life shows you’re in the conversation with them. It makes it a dialog, not a monologue or interview.

A general principle I find helpful in conversations is

If I’ve asked too many difficult or personal questions in a row, I should contribute something or they’ll withdraw.

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