Last time, I covered the deceptive relationship we have with loneliness and how we can build empathy with others by opening up gradually about our struggles. I also mentioned that any connection that builds over time requires a conversation that goes both ways. Today, I’d like to discuss the perspective of the person on the other side. How can we as listeners cultivate empathy for a more free-flowing, honest conversation?
Start gently
I’ll focus on a few tactics that have helped my conversations flow and provided safety for others to open up. In particular, the types of conversations where these tactics work best are usually intensely personal where we deal with our own demons or interpersonal difficulties.
I like to start these kinds of conversations with open-ended, innocuous questions. This doesn’t have to be the common choice of “how are you?” As we discussed last time, this question is usually employed as a pleasantry in small talk and is intended almost to be dismissed with the one-word answer “good.” Instead, I like to ask: “what’s on your mind?”1 as I feel that it allows the other person to take the conversation in any direction they like and show me their thought process, making the conversation a joint venture rather than a unidirectional inquiry. Sometimes the response is clearly a deflection that avoids the underlying mood they project, in which case I usually try to push back gently. This might be something like: “Are you sure? You look like something is troubling you.” I try to position this as a non-judgmental observation, and because my genuine concern comes through, most people are willing to open up.
Build
How the conversation proceeds from here now depends on how you, the listener, frame the environment. The goal is to provide a safe space for the other person to speak their mind and explore their emotions. Doing this requires performing a delicate balancing act. On the one hand, you could sit back and do nothing while the other person talks at you. The resultant venting allows them to release emotional buildup, it rarely provides a mechanism for dealing with the problem and improving their condition. On the other hand, you could drive the conversation so strongly that it becomes a one-sided interrogation. This squashes the other person’s vulnerability and puts them on the defensive, which also doesn’t allow for a productive, free-flowing conversation. Instead, we want to achieve a golden mean and create a framework within which the other person can develop their thought process while deferring any external evaluation. To repurpose a common metaphor, we want to construct the box that the other person can think inside (or outside).
To do this, I deliberately inject moments where I paraphrase what the other person has said so far and ask clarifying questions to let them know that I am trying to understand them fully. This is useful for both parties: I get a chance to fill in any missing context into the thoughts they are sharing, and they get feedback that I am paying close attention to the words they are streaming to you. Sometimes, people talk in a rhythm that results in pauses where these recaps can naturally be injected. Other times, people may be thinking and talking so quickly that it is difficult to maintain the world they are building for me coherently. In this case, I try to slow them down by injecting clarifications while they’re talking so that my mental construction of their problem is accurate and faithful. Importantly, when I ask clarifying questions, I’m not only looking for what something is, but why it is as they have described it. In this way, I aim to go just one level deeper than our mutual understanding to uncover any basic assumptions that may break down under further scrutiny.
Once I have acquired the full context from the other person, I synthesize a narrative that is understandable to both of us and try to offer a neutral perspective of the situation (e.g., “From what you told me, it seems like A is happening, resulting in B. This seems to mean that C. Does that seem right?”). Often, the thoughts that come at you are a jumbled mish-mash of personal observations and emotions. When you provide a narrative that encompasses the observations that you’ve seen, you give the speaker useful feedback by giving them a chance to step outside themselves and see how their own story is reflected by someone else. Though this instance of the tactic is tailored to exploring the thoughts and issues of a particular person, I’ve also used this tactic with intense two-way personal conversations as well to great effect. In this case, the goal is simply to agree on what is being discussed so that we can move forward and explore any changes in the future together.
Nudge
From here, I try to guide the conversation towards one of two resolutions: either we move toward a course of action by exploring the topic further or we acknowledge that unfurling the problems is a sufficient amount of emotional work for the scope of this conversation. It is important to reinforce that action need not always be the desired end state. It may be the case that by exploring the problem sufficiently, the emotional intensity has been de-escalated and can be put behind us. In other cases, it takes time, space, and patience to process the results of exploring these observations and narratives deeper, particularly when they are emotionally fraught. Pushing too hard to solve an entire problem in the scope of a single conversation can be overwhelming for the other person and cause them to withdraw again.
However, if we do decide to move toward a course of action, I usually ask follow-up questions from the narrative and perspective I’ve established. I try not to lean on the questioning too heavily and instead provide some personal context in the questions I ask so that it’s clear that I’m participating fully in the conversation. This hypothetical reaction gives the other person a jumping off point, reaffirming the “box” that we are creating for the other person to explore. Again, I try not to provide sweeping judgments and advice (e.g., “Oh, you should just do X”) but rather provide anecdotes and personal evaluations that the other person can weigh themselves (e.g., “I’ve found that in situations like this, doing Y seems to work well for me. Is that something you’ve considered?”).
Of course, all of this assumes that the other person is willing to respond to your small probes and explore a topic with you. You may find that even after repeated questioning from different angles and shared vulnerability from yourself, the other person remains stiff, providing curt responses. In this case, I find it best to back off gently and either shift the conversation to a neutral space about something unrelated to either of us.
By providing this framework where the other person can surface concerns, we construct a method to develop their thoughts gradually and hopefully move toward a path of action to address these problems. Having an empathetic but detached perspective allows us to remove the emotional haze from the topic at hand and provide a calm, clear analysis that can benefit the other person. Doing this repeatedly with many people has helped me cultivate empathy for others and deepened connections that I value. In turn, it allows me to be more vulnerable and express myself more fully, creating a virtuous cycle.
Thanks for reading!
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I’ve been using this question for the last ten years or so (since college). I was both thrilled and appalled when I discovered that Facebookâs placeholder text when you make a post asks this same question. ↩︎