To Listen Better, Ask Better Questions

How are your listening skills? Do you ever think about them? Improved listening skills would make almost all of us more successful, and yet this is something most of us have had no formal training in. One way to improve your listening skills is to learn some active listening techniques.

Now, when I talk about improving your listening skills, you might be thinking, “Meh. Big deal.” But what about increasing your influence? Does that sound more exciting? The way former FBI hostage negotiator Gary Noesner puts it, your influence depends on rapport. Rapport largely depends on empathy. Good active listening demonstrates empathy, builds rapport, and increases your influence.

This makes sense too—it’s hard to influence people when they don’t even feel heard, understood, and validated. In this post we’ll discuss three key active listening skills, based on Dan Oblinger’s excellent book, Life or Death Listening. They are reflecting, paraphrasing, and summarizing.


You’re in a conversation. Everything the other person says has a backstory. Her stories have backstories. The words and phrases she uses have backstories, reasons she said what she said and not something else. These words and phrases are like computer files. Sometimes you’ll want to “double-click” to see what’s in a file.

To practice reflecting, you listen for key words the other person uses and then repeat them back in the form of a question, curling up your intonation at the end. In the example below, the speaker says, “We finally got a new boss and then we had to change divisions. There are some issues there.” In just these two sentences there are a variety of things you might want to unpack. You might start by repeating, “There were some issues?” Notice how the intonation at the end and the pause following it are like saying, “Tell me more about that.”

If you wanted to focus on the first sentence you could say, “You got a new boss?” (asking about the boss), or, “You said you FINALLY got a new boss?” (inquiring about the significance of “finally”). Similarly, you could say, “You changed divisions?” (asking about the division change), or, “You HAD to change divisions?” (asking why it was required).  

As you start practicing reflecting, you can think of the language you are attending to as a user interface. By choosing what key words to repeat you are choosing what folders and files you want to open. You can’t open them all, so your inquiry will lead you on a unique path through the speaker’s experience and story.


There is often an “understanding gap” between the speaker and listener. What has been said can be interpreted in multiple ways. Crucial details have been left out. Important words remain undefined. You might think you know what the other person means, what she was thinking and feeling. To what extent should you let your assumptions fill in these gaps? When you do, that’s called “mindreading.”

If you are tapping the rhythm to a song, you assume others will be able to guess what song it is. But they can’t. You can hear the lyrics and the rest of the song in your mind. Others don’t have that information. It’s the same here. When the speaker is struggling to verbalize thoughts, he will often assume the listener is experiencing what he is, can somehow see his thinking, know his meanings, and already has the backstory. It’s like a teacher whose lectures assume more expertise of students than they actually have.

Misinterpretation is a natural result. And it gets worse. In his book, Deep Listening, Oscar Trimboli talks about what we’ll call the “125/400/900 Rule.” In a conversation, the speaker is probably speaking around 125 words per minute, whereas you can listen to around 400. This creates a great temptation to fill that gap of 275 words per minute with your own thoughts. When you do, you’re listening to yourself, not the speaker. Now, while the speaker is speaking 125 words per minute, she can THINK around 900.

The speaker can think a lot faster than she can speak. She may not have tried really verbalizing these thoughts before. She may not really know why she did certain things or made certain decisions. She may be rationalizing or speaking about things that involve tacit knowledge, things she knows how to do, but more on an unconscious level. In short, her first attempts to express what she means might be a little off the mark.

Pausing and paraphrasing helps with all of this. It’s an antidote to mindreading. Instead of using the speaker’s exact language, as with reflecting, here you reword what was said and allow the speaker to validate it, to confirm you’ve got the gist of it.


When someone wonders whether you’re really listening, whether you really “get it,” just paraphrasing isn’t going to cut it. For this purpose, Oblinger says, you need to combine your paraphrasing with emotional labels. Listen for emotion. When it sounds like someone must be feeling (or must have felt) a certain way, say so.

State the hypothesized feeling in a nonjudgmental way. Whatever someone feels, after all, is real for him. Offer the label for validation and elaboration. You can do this by saying something like, “I imagine that would be frustrating,” or, “It sounds like that was really frustrating.” Instead of just moving on to the next question, labeling and offering the label elicits more of the backstory.

You have hypotheses as the listener, and you need to check them. You use paraphrasing to check your interpretation of the other person’s meaning. You use labels to check your guesses about how he must be feeling (or must have felt). The listener’s story, Oblinger observes, always involves both, both what someone means as well as how he feels about it.

In business there is a temptation to ignore this, to “stick to the facts,” Oblinger notes. This ignores that our reasoning and emotions really aren’t all that separate. We often decide things based on underlying values and how we FEEL about the matter. We muster facts later to explain, defend, or “rationalize” what has already been decided. If you miss the feelings, you miss much of the context.

Oblinger likens this to an FBI poster he once saw, depicting the “story” as the doughnut hole that only exists as the space created by the doughnut of emotions.

It’s important to keep in mind that saying, “I understand,” does not DEMONSTRATE understanding. Saying, “I know how you feel,” is not a very emotionally intelligent thing to say. By checking both your interpretation of what someone means and your guesses of how she feels about it, you demonstrate understanding. When you offer a summary and the other person says, “That’s right,” you’ve not only validated your understanding, you’ve made the other person felt listened to and understood.

To Close

Three key skills. Reflecting helps you excavate the thinking behind the thinking, exposing assumptions and underlying values. As Oblinger notes, when combined with open-ended questions, this becomes a potent mix. Paraphrasing is how you pause and check your interpretations. Summarizing is how you do this while showing empathy, demonstrating that you “get it.” It’s useful for wrapping up a conversation, for switching gears, or instead of having the speaker repeat himself.

As you use these listening skills, be sure you are also “listening to your listening.” As hypnotist Rob McNeilly puts it, you are always listening FOR something, FROM somewhere. If you are listening for problems, you are going to find problems. If you are listening for the ways in which you are right, what are you going to hear? (If you work in a fish market, you are going to smell like fish!) In line with this, Oblinger stresses the importance of listening for underlying values, for motivations, fears, and unmet needs.  

And finally, here’s a little secret about active listening. I learned this in a training from Gary Noesner. When you use these techniques, you aren’t just improving your listening skills—you are using facilitation to improve the other person’s thinking!

Remember the “Miscommunication” image above? With active listening, you aren’t just listening better. You are also probing what the other person says to continually reconnect it to what he really means, thereby countering the effect of the 125/400/900 Rule and reducing the potential for miscommunication. In NLP this is akin to reconnecting the surface structure (what is said) to the deep structure (the underlying experiences the speaker is trying to summarize).

As Trimboli notes, reducing miscommunication alone would save most organizations a fortune. Active listening also helps though with surfacing assumptions and generating options, which means it helps you reduce opportunity cost. And as we saw above, improving your listening skills is also key to improving your influence. That’s all value-added.

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