Listening is a skill that many workers stuck at home over the past year have had to refine. We lost a lot of the physical and visual cues we were used to when interacting with people in person. And we lost feelings of connection that provided the foundation for conversations to go deeper and be more meaningful.

Ximena Vengoechea is a professional listener. She was a user interaction and market research manager at Twitter, LinkedIn, and Pinterest. In those roles, she would ask strangers questions related to tech products, with the aim of generating insights the companies could use to improve them.

Now, in Listen Like You Mean It, due out at the end of this month, Vengoechea details tactics that the rest of us can deploy in our own professional and personal relationships. “We need to feel connected more than ever,” she writes. “Listening provides a way forward.”

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Research suggests we often get it hopelessly wrong. I wrote recently, for example, about new findings that we are strikingly bad at intuiting when another person wants to end a conversation with us. As Vengoechea notes, a lot of our everyday go-to conversational techniques—such as projecting our own feelings onto what someone is telling us—get in the way of understanding how they’re feeling. 

“This explains why some teams never seem to gel no matter how many team-building activities they try, why some siblings struggle to grow close despite their blood ties, and why even lifelong neighbors can still find themselves with little to say to one another years later,” Vengoechea writes. She contends that we need to move from superficial listening to empathetic listening. 

Vengoechea’s technique includes what she calls “connecting” questions.

  • Exploratory questions like ”How do you feel about that?” and “What does ‘ideal’ look like?” can lead to rich conversations. Open-ended is better.
  • Encouraging phrases such as “Tell me more” provide an extra nudge. “Sometimes all they need is to be asked to keep talking, so they can continue processing and working on things aloud,” Vengoechea writes. (p. 126)
  • Reflection questions often use comparisons to help people think and share through how they feel. “Is it more wanting a raise or wanting to be recognized?” is an example. (p. 133)

Other helpful advice:

  • Follow up on broad statements like “it’s good,” “I like it,” and “sure” with questions such as “Help me understand what you mean by…”
  • Let go of stray thoughts—like items for your to-do list—that occur to you when you’re speaking with someone. They’ll come back later if they’re important. 
  • You can ask the person you’re speaking with how to best respond. Asking “Would hearing [a different perspective, some advice, a similar experience] help?” is one option.
  • When people stall in answering a question, it’s often because their answer is not positive. We’re usually more quick when we’re confident in our response.
  • Prefaces such as “to be honest,” can signal that you’re not getting the truth.
  • Phrases like “You always” and “You never” generally signal a deeper emotion. You can respond with “I can see talking about this is important to you; help me understand your reaction.”
  • Recognize when it’s not the right time for a conversation, such as if you’re too tired, and explain that.
  • “How,” “What,” and “Tell me…” questions are preferable to “Why?” because that can feel judgmental.

To be sure…

  • The book is valuable for describing patterns of conversations, and recommending phrases to use for more productively navigating them. But most of the examples center around conversations Vengoechea had as a researcher and manager, which aren’t always compelling to the reader. 
  • It doesn’t help that she anonymized them and removed many of the original details because she didn’t want to identify people or product features. Examples from other fields, and research—which would have helped—are relatively sparse and superficial. 
  • Just by the nature of the topic, some of the advice feels obvious, like listening for changes in a speaker’s tone or observing whether their body language is closed.

Choice quotes:

  • “Too often, we ‘solve’ for miscommunication by focusing only on what we say and how we’re saying it: if we could only get our message across, things would be much easier. As a result, we may decide to adjust our messaging or dial up the volume. But when we focus solely on our capabilities as speakers, we risk turning our conversation partners into an audience rather than equal collaborators. It will be hard for others to relate to us, much less put their trust in us, if that happens. Instead, if we want to unpack others’ behaviors, motivations, and the way they think about the world, listening can help us get there.” (p. xiv)
  • “There is no quicker way to end a conversation—or a relationship—than to appear distracted.” (p. 32)
  • “Attempting to finish other people’s sentences may be our way of bidding for attention, but it rarely gets us there.” (p. 57)
  • “If you can train yourself to stay silent for a hair longer than is comfortable, it’s likely your conversation partner will jump in to fill the void. When they do jump in, it’ll be worth the wait.” (p. 149)

The bottom line is that we’re in a moment in history where listening mode is how we spend much of our time. Podcasts are booming, live audio platforms such as Clubhouse are emerging quickly, and Zoom is how many of us do our work. Then there are the individual conversations of the sort that Vengoechea focuses on, which ultimately provide the depth and connection behind any productive relationship, professional or personal. Her book is a reminder that there’s a skill to them and we can make them better.

You can pre-order Listen Like You Mean It at or Amazon. (We may make a commission on any purchase.) All page numbers referenced above are for the hardcover edition.

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