Three Questions To Become A Better Listener and A More Effective Leader

It’s easy to be a bad listener, especially as a CEO. When I open up my calendar for the day it’s packed full of conversation after conversation. I often plan my next meeting while I’m in the current one. Recently, a mentor of mine caught me half-listening and told me that “bad listeners are bad leaders.” The feedback stuck. I spent months researching how to be a better listener. As I quickly learned, the key to being a better listener is asking the right questions, and getting truly curious about the answers. After meticulously testing every methodology and framework on listening I could find, I found these three questions to be the key to unlocking deeper conversations.

It’s surprising how rarely we ask open-ended questions. In both personal and professional settings, we ask close-ended questions like “how was your weekend?” or “do you think this is a good idea?” These close-ended questions elicit surface level responses such as “it was good” or “yes.” I started shifting my language, asking open-ended questions such as “tell me about your day” or “tell me about the challenges you’re seeing.” Bigger, open-ended questions can often require more thought, and it’s important to give the person you’re conversing with adequate time to think and respond. As Alexandra Carter puts it in her book Ask For More, you have to “land the plane.” In this context, “landing the plane” means that you ask a big, open-ended question and then keep your lips closed, letting the question “land” without jumping in with your own commentary. As a chatterbox, I had to stop myself from asking questions like “Tell me about the challenges you’re seeing” and then quickly filling the silence with “I’m seeing…” which would impede my employees ability to give me their unbiased feedback on the situation.

Anyone who has thought about effective listening skills has likely heard of paraphrasing. By summarizing and expressing in our own words the meaning we received from what someone else said we can show that the other person’s thoughts were understood, and their ideas are respected. But there is one key trick to this that experienced conversationalists know. As Sam Kamer points out in the Facilitator’s Guide to Participatory Decision-Making, the key is to begin the paraphrase with a comment like “It sounds like you’re saying” and end it with “did I get that right?” Giving the speaker a chance to clarify or confirm their thoughts can help avoid misunderstandings and build a shared foundation of trust upon which to continue the conversation. This is particularly important in complex or emotional conversations.

  1. What did you hear me say?

Even people who’ve spent their entire careers focusing on meaningful, connected conversations will inevitably trigger an emotional outburst in a conversation partner. Carol Robin of Stanford’s legendary Interpersonal Dynamics class and author of the book Connect, tells the story of how she once stepped into the kitchen and asked her husband what he was cooking, only for him to defensively respond, “I don’t need any help!” Instead of matching his anger, and shouting back “I didn’t offer any help!”, she calmly asked him “what did you hear me say?” As it turned out, in Carole’s offer to help, her husband had heard an implication that he didn’t know what he was doing in the kitchen. I recently had a conversation with my co-founder where he was acting uncharacteristically defensive over what I thought was a totally normal line of questioning about our current search for a new head of operations. Asking “what did you hear me say?” uncovered that he felt my questioning was implying that he wasn’t leading the search properly.

With so many people now working permanently or partially remote, effective listening has become even more important. Without the full body cues of in-person meetings, leaders have to lean even more strongly into asking the right questions, and listening for misunderstandings or trigger points. Deep listening builds trust, and teams who trust their leaders and each other are much more likely to be successful.

Ask for More: Learning Summary

  • A negotiation is any conversation in which you are steering the relationship
  • The key to negotiation is transparency: getting and sharing the right information
  • Creating is not a result of genius. It is the result of thinking: a series of mental steps consisting of problem, solution, repeat
  • We often don’t recognize our needs, and instead focus on our demands

    • Needs are the reasons why we make demands
    • Love and belonging needs come up often in negotiations
    • Esteem needs, self-esteem (pride, accomplishment) or esteem of others (respect, reputation)
    • Self-direction needs, including freedom or autonomy

  • Mine your past for ways in which you have successfully handled similar challenges. This helps you access your inner wisdom and gives you confidence for future negotiations.

    • It’s a powerful positive anchor
    • Summarize their past success

  • Land the plane! Ask an open question, like “tell me about your kids” and then stop talking
  • “Tell me about yourself”
  • Tell me more
  • Summarize and ask for feedback -> ____,that’s everything I have in my notes, what did I miss? Can you tell me more about X?
  • Asking about needs is a gamechanger in a conversation —> what do you need?

    • Okay, so you’re not sure what you need, so maybe tell me more about what’s running through your head right now

  • Once they say, I need X, you say, “okay, what would that look like?”
  • Did I get that right? It looks like I missed something, please tell me so I can understand better
  • Focus people on what they can gain, rather than what they can lose. People are loss avoidant

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