Letters from Esther

The Art of Conversation

Letters from Esther is my monthly newsletter to stay in touch and inspire reflection and action in areas that are important for your relational intelligence. This month's theme is: The Art of Conversation.

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Shall We Begin?

All too often, I see the tension between speaking and listening. We expect to hear people drone on about themselves in professional settings, hoping to stand out, get a promotion or  investment, or make a life-changing connection. But lately that mentality of pitching oneself is showing up in smaller circles. How many dinner parties have you attended where one person seems to be talking AT everyone, at length, about their business or their back problems? 

From the very beginning, Western parents tell children “use your words.” The current norm emphasizes direct communication and the ability to clearly articulate one’s needs as an essential step to building confidence and self-esteem. It’s interesting, isn’t it? We make of point of encouraging one another to be assertive—speak up! Communicate! Advocate for yourself! Yell it from the mountain tops!—but we don’t quite prioritize listening in the same way. 

The art of conversation is about healthy amounts of both: thoughtful speaking and hardcore listening, asking questions and navigating commonalities and differences. Consider Erich Fromm’s six rules of listening. Or David Bohm’s writings on the paradox of communication in which he says “if we are to live in harmony with ourselves and with nature, we need to be able to communicate freely in a creative movement in which no one permanently holds to or otherwise defends his own ideas.”

In an age of self-surveillance, of measuring oneself’s likeability based on “likes” and one’s network based on how many “connections” they have on LinkedIn, the collapse of simple but depthful conversation was almost bound to happen. Now, at least in cities, we’re more likely to meet a friend at a co-working space—those of the “venture-backed belonging” variety—than in our homes.

The gap between work and life is narrowing. So many of us are putting our whole selves into our work, investing everything we’ve got by betting on ourselves. In this state, transforming dialogues into monologues feels like a survival tactic. We know we need the support of our friends and communities, but we feel as if we must advocate for it. Rather than deep exchanges that are rooted in curiosity, or even superficial conversations floated by fun, our conversations become performances. How many opportunities do we miss because we didn’t ask someone about themselves? 

There are ways of shaking it up. I love to throw dinner parties and unify guests around one question. A new question can make you hear people that you know well in totally new ways. Recently I asked, “what is a relationship question that you have at this moment?” Fifteen people around the table all said completely different things: about sex after having kids, aging, monogomy, and more.  One of the more shy guests immediately spoke up: “how long do you continue to try to have a relationship with your adult child?” A simple question allows people to share at the level of intimacy and disclosure they are comfortable with.

When we stop being so focused on having to shine, we can see the shimmering lights of others and engage in a real give and take. Long, deep listening around a dinner table opens up a whole new world of connection. And get this: you won’t need four drinks to get through the night. 

Let’s Turn the Lens on You

Invite friends to come together (dinner or not), and try out some of the below questions.

  • What would you tell your 20 year old self?

  • What is one of the lessons learned from a heartbreak? 

  • What is a conversation that you know that you need to have with yourself? 

  • When did you know that you were no longer a child?

  • What’s the best piece of advice you’ve ever received? 

  • What is the relationship legacy from your own family of origin that you want to keep?

  • What is an aspect from your relationship culture that you're set on changing?

  • What’s a challenge that you have successfully faced and how you have handled it?

  • What would you say makes you not the easiest person to live with?

  • Describe a time when you changed your mind.

  • What would you do if you had a different career?

  • Were you raised for autonomy or raised for loyalty?

  • What is something that you wished you had known or been told as a child?

Watch and Listen

Unsent Love Letters / A Six Part Blog Series

Unsent Love Letters is a six-part series of real unsent love letters from people who wrote to a loved one, but in the end kept their words to themselves. Each article includes the original letter, a playful video discussion, and an exercise for those who resonate.

Letter from Esther / On Connection

A meditation on the importance of building your village and advice about how to maintain it.

“How’s Work?” Podcast / Season 1

Season one of my new podcast about relational dynamics in the workplace is  available soon on all podcast apps, including iTunes. Episodes will be released weekly starting February 4, or listen to the full season on Spotify.


A compendium of highly recommended sources of inspiration and information       

I’m Reading: 

I’m Listening To: 

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