How to Have Deeper Conversations, With Ximena Vengoechea

How to Have Deeper Conversations, With Ximena Vengoechea

Photo: Micaela Heck/Angelica Alzona

Many of us have spent a lot of time during the pandemic in isolation, so this week we’re re-learning the art of deep conversation with help from user researcher and writer Ximena Vengoechea.

Ximena honed her listening skills while conducting user research for companies like LinkedIn, Twitter, and Pinterest, and now she’s sharing them in her new book, Listen Like You Mean It: Reclaiming the Lost Art of True Connection. Listen to hear Ximena give some brilliant tips on how to ask the right questions to promote a more interesting conversation, how to be a more open-minded and empathic listener, and how to gracefully exit a conversation when you need to.

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Highlights from this week’s episode

From the Ximena Vengoechea interview

On what a good listening mindset actually looks like:

I talk about a listening mindset as having three core components. So that’s bringing in qualities like humility, curiosity and empathy. And humility is really coming in with an open mind and being ready to hear what someone has to say, being ready to learn from them, which is different than coming in...with assumptions or preconceived notions or opinions that we want to get across. So it’s really flipping the switch and saying, ‘I’m here to learn from you,’ rather than, ‘I’m here to teach you something.’ And curiosity is what allows you to go a little bit deeper, because that’s what allows you to really get to know and understand another person. What is their perspective? Why do they think these things?...And then it’s almost like a funnel. You’re starting broad with humility and starting open and you’re progressively getting a little bit deeper using curiosity. And eventually you hit empathy, which I think is that third quality to the listening mindset that really makes it possible to truly get to know someone because they’re talking about emotions and their emotional experience. And it’s not to say that we have to share the exact situation that someone is going through in order to empathize with them. If someone is going through a divorce, you’ve never experienced that, that’s OK. But you can relate to the feeling of, oh, wow, they’re grieving over a phase of their life ending.

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On asking the right kinds of questions in a conversation:

[A] lot of times in conversation, we’re not really paying attention to the types of questions we ask. And so we might inadvertently ask questions that aren’t really going to take the conversation anywhere. Questions that might end in a yes or no results in a yes or no response or one word, single word answer. And those tend to start with ‘do,’ ‘is,’ and ‘are,’ as opposed to asking more open-ended questions that start with ‘how,’ or ‘what.’ So even asking someone, ‘are you mad at me?’ Is going to yield a very different response than, ‘Hey, how are you feeling right now?’ One of them is kind of leading someone into a particular path and then the other is just leaving it very open ended. So in general, we do want to try and shift towards more open ended questions, at least at the start of the conversation, so that we can let the other person lead, you know, wherever it is they may want to go.

On remembering the needs of the other person in the conversation:

So we might have a goal of getting to know someone or a goal of learning something about a person. And those questions can be used to meet that goal. But we also need to be tracking what’s happening for the other person. Are they starting to offer smaller and smaller responses? Are they running out of breath because we keep asking them questions and they’re kind of giving us paragraph responses? I think paying attention to those cues can be a sign for us to maybe lean back a little bit or start to offer something from our own perspective. I think it is important in a conversation. There are two sides. There’s the listening side. There’s a speaking side. You want there to be a give and take. And then the other thing I’ll say that I think can help with that instinct, in particular, is to figure out what is the other person’s need in this conversation. Because when we’re doing all of the question asking, that’s probably stemming from our own need...We want to make them feel comfortable. We want to get to know them to a certain degree. But the other person also has a need. So you really want to make space for both of those needs in conversation. And that takes a little bit of balance.

To hear more of Ximena’s advice on the art of deeper conversation, we recommend listening to the full episode.

Episode Transcript

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