How to Have a Deeper Conversation With Ximena Vengoechea

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

Simena has honed her listening skills through user research at companies like LinkedIn, Twitter and Pinterest, and she is now sharing it in her new book, Listen What You Mean: Reclaiming the Lost Art of True Connectivity . Hear Ximena give some brilliant tips on how to ask the right questions to foster a more interesting conversation, how to be a more open and compassionate listener, and how to gracefully exit the conversation when you need to.

Listen to The Upgrade above, or find us in all the usual podcast locations including Apple Podcasts , Google Play , Spotify , iHeartRadio, and Stitcher .

Highlights from this week’s series

From an interview with Ximena Vengoechea

On what a good listening attitude actually looks like:

What I’m saying is that listening has three main components. So it brings in qualities like humility, curiosity, and empathy. And humility really comes with an open mind and a willingness to listen to what someone has to say, to be willing to learn from them, which is different from coming … with assumptions or preconceived notions or opinions that we want to convey. … So it’s actually flipping a switch and saying, “I’m here to learn from you,” not, “I’m here to teach you something.” And curiosity is what allows you to go a little deeper, because it is what allows you to truly get to know and understand the other person. What is their point of view? Why do they think so? … And then it’s almost like a funnel. You start with humility and start with openness, gradually sinking into curiosity. And in the end, you gain empathy, which I think is the third quality about listening that really allows you to really get to know someone because they are talking about emotions and their emotional experience. And this does not mean that we should talk about a specific situation in which someone is going through in order to sympathize with him. If someone is going through a divorce, you’ve never experienced it, that’s okay. But you can relate to the feeling, oh wow, they are grieving at the end of their lives.

How to ask questions correctly in a conversation:

[Many times] in conversation, we ignore the types of questions we ask. And so we can inadvertently ask questions that actually get nowhere. Questions that may end in “yes” or “no” lead to a “yes” or “no” answer or a one-word answer. And they tend to start with “do,” “eat,” and “eat,” as opposed to more open-ended questions that start with “how” or “what.” So even ask someone, “Are you mad at me?” Will get a very different answer than “Hey, how are you feeling now?” One of them kind of leads someone on a certain path, and the other just leaves him very open. All in all, we really want to try to get to more open-ended questions, at least at the beginning of the conversation, so that we can let the other person lead, you know, wherever they want to go.

When remembering the other person’s need for a conversation:

Thus, we may have a goal to get to know someone better or to know something about a person. And these questions can be used to achieve this goal. But we also have to keep track of what happens to the other person. Are they starting to offer fewer and fewer answers? They catch their breath due to the fact that we ask them questions all the time, and they kind of give us the answers in paragraphs? I think that attention to these signals may be familiar to us, maybe we will lean back a little or start proposing something from our own point of view. I think this is important in the conversation. There are two sides. There is a listening side. There is a speaking side. You want mutual concessions. And then I’ll say one more thing that I think can help with this instinct, in particular, is to find out what the other person needs in this conversation. Because when we ask all the questions, it probably stems from our own need … We want them to feel comfortable. We want to get to know them to a certain extent. But the other person also has a need. So, you really want to make room for both of these conversation needs. And that takes some balance.

For more advice from Ximena on the art of deeper conversation, we recommend listening to the entire episode.

Episode transcript

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