Five Ways to Deepen a Conversation

Five Ways to Deepen a Conversation May 4, 2015

direction sessionSpiritual directors have five conversational tools we use to help the person we are talking with share more deeply. These aren’t secrets and you don’t have to be a spiritual director to use them. They are especially helpful if the person you are talking with feels safe with you and wants to talk about important aspects of their life. They are “hospitality-in-action.”

  1. Silence. Listen in order to understand what the person is saying and not to develop your own witty quip or response. Allow pauses in the conversation. Sit with the person when they become quiet.
  2. Gentle prompts.  It sounds a bit corny to suggest but simply keeping eye contact and offering a few “hmmms” along the way can be helpful to the person who is sharing. One-word or short phrase responses such as “how so?” or “can you say more about that?” are much better than launching into an analysis or fix-it mode. (By the way, if you want to help someone who is sharing their story, never ever launch into analysis or fix-it mode. That is not what they need.) A favorite gentle prompt among spiritual directors is to notice when one word is used several times and repeat that word back as a question. For example, if the person says “ever since that day I’ve felt terrified,” you respond with “terrified?” It’s a simple way of asking them to say more about their feelings.
  3. Summarize by paraphrasing. After someone has finished telling you their story, it can be very helpful and nurturing for the listener to paraphrase what was said. A short summary using different words—so you aren’t parroting—tells them you heard them. And even if you get it wrong, they know you were trying to understand. Do keep it short. No one needs to hear their whole 20-minute story told back to them in intimate detail.
  4. Make simple observations or reflections. In the spiritual direction field we call this contemplative listening. Refer to a part of the story and share only what you noticed or felt within yourself as you heard it. You are observing something about the story or the person telling it and reflecting it back to them. For example you might say “when you told me about your experience of feeling terrified, I noticed you put your hand to your heart.” Or, “when you spoke about your disagreement with your sister, I got an image of a blocked roadway.” So the basic template is:  “When you said ____________, I felt/noticed/saw/heard/received an image of _______________.” Resist temptation to go any further than one sentence. The beauty of contemplative listening is its brevity.
  5. Brief honest open-ended questions.  Questions are the most invasive of all conversation techniques but they can also be among the most helpful. When you are listening to someone share their story and you want to ask a question first ask yourself—is this question brief and to-the-point? If you have to give a big speech before the question to set the stage then it is not brief. You want the question to be simple, succinct and understandable. Also ask yourself, is this question really a question—or am I trying to get them to see things my way? If you have no idea how the person might answer the question, then it probably is an honest question. If you really want to make a statement of judgment or opinion but are couching it as a question then you are being dishonest because it’s not really a question. Attorneys call these “leading questions” and judges make them re-state such questions. So be your own judge and make yourself adhere to the discipline of asking only honest questions. Finally, make sure the question is open-ended. We want our questions to be invitations to greater conversation, not show-stoppers. An example of a classic open-ended question in a serious conversation would be “what is your desire in this situation?” Questions that begin with the word “how” are frequently open-ended questions.

Try these communication techniques out the next time you and a friend have a deep conversation and see how well they work. You may even want to schedule times with a friend for spiritual conversations where both of you use these listening techniques as guidelines.

For more about spiritual direction as I practice it, please check out my website.


Photo by Teresa Blythe


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