#1 skill taught by executive coaches

How to have better conversations everywhere all the time

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Trying to depict a deep conversation

Here’s a conundrum most people on Earth face:

• We communicate for one major reason: to feel better. 

• The way we communicate does not reliably achieve this.

Here are the strategies I instinctually employ, as many dudes do, in any conversation when emotions are involved:

• Give advice (“Have you thoughts of X?”)

• Share about our own experience (“That happened to me last week”.)

• Emotionally rescue (“Don’t worry you’re a great guy”)

• Ask why (“Why do you think that?”)

In a cruel twist of fate, these are dogshit strategies for emotionally resonant conversations. Neither I nor the people I talk to walk away feeling significantly better. Or if we do, it does not last for long. 

And there’s a reason for this. People like feeling emotions, and these strategies are designed to soften or change emotions. 

• I give advice to people who are frustrated because I either don’t want to deal with their frustration. 

• I share my own experience or say stuff like “I’m so sorry to hear that” because I can feel someone’s sadness and hope that softens the vibe.

• While I might not realize it, when I ask “why” to someone, they stop feeling and start getting cerebral. 

Counterintuitively, if we want to feel better, we often have to fully feel “negative” emotions like anger and sadness before feeling “positive” ones. If I’m freshly pissed off, and someone is trying to cheer me up, I’m going to resist cheering up. I want to feel angry. And in fact the resistance to me being pissed off will likely keep me pissed off even longer. 

If someone invites me to fully explore how pissed off I am, I either do that for a short while and it gets out of my system, or all of a sudden I don’t feel pissed off anymore. Last week I gave a rock to a pissed off dude and invited him to slam it into the ground. His whole body softened and he simply dropped the rock. 

What do we do instead?

Every top executive coach that I’m aware of shares a similar strategy for solving for this. Tony Robbins, Matt Mochary (coach to Sam Altman and the CEO of Reddit, the founder of Instacart) and Joe Hudson (founder of Art of Accomplishment) all teach a version of something called active listening. 

Why?

Because they don’t have a choice. 

To date, active listening is the western world’s top answer to a number of similar issues:

• How do you get to the bottom of the thoughts and feelings another person is experiencing?

• How do you replace small chat with deep conversations?

• How do you hold space for someone?

It was originally devised in the 1950s by psychologist Carl Rogers, whom psychologists rate as the second most influential clinical psychologist ever (behind Sigmund Freud). The basic concept is that if you listen to the totality of what someone is communicating, good things happen. And by giving a name to that phenomenon, active listening became a skill people started playing with.

The first to fuck around with active listening were parents. A book and workshop called Parental Effectiveness Training popularized active listening in the 1970s, as parents were seeking non-combative ways to deal with their bratty kids.

Today, doctors use it to learn about patients. Sales men use it to engage new prospects. Business leaders use it to understand how their employees are dealing with issues. It’s friggin everywhere. 

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What does it look like?

Carl’s original book on it is vague as hell. As a result, there’s a lot of different iterations on what it looks like. The simplest version I’ve found of active listening consists entirely of doing just three things: 

1) being silent 

2) echoing back their words 

3) asking clarifying questions (except the aforementioned “why”)

I like this because it is dead simple and yet effective everywhere. The guy who taught this to me, Bill Wich, teaches this to CEOs and prisoners at Folsom. The only skill required for this is staying curious and the ability to not talk about myself.

But there’s plenty of other riffs on active listening that are useful for different needs:

• Tony Robbins teaches folks to read people’s physiology (posture, breathing, tone of voice, movement), focus (the subject of what someone is talking about), and language (what words are they choosing to describe the situation). This helps you listen to the read the full state of what someone is experiencing and attend to it. 

• Chris Barber wrote wonderful document on a version of active listening he calls “resonance.” It focuses on how to make people feel understood.

• Matt Mochary wrote a document for managers dealing with emotions in the workplace.

• Joe Hudson teaches a whole course on active listening called “Connection” where he teaches students to view life with a sense of vulnerability, impartiality, empathy, and wonder. The key to this in conversation is to focus on asking “how” and “what” questions.

Compassion with a masculine flair

While I’ve seen men and women benefit from training in active listening, dudes get especially jazzed by the practice. I think that’s so for two reasons:

1. Women ask questions about emotional stuff all the time. I don’t even think it would occur to most women to give that practice a name.

2. Active listening is a portal into what empathy looks like with a masculine flair. I got interested in active listening after watching former Folsom Prison inmates do it in a men’s group. It looked like compassion without comfort. They sought emotional truth without wanting to share in those emotions. It resonated.

Listening is one of those skills that feels silly to practice. But it’s a skill, and we do a ton of it, and doing it better transforms the fabric of life. Some day, I hope one of these executive coaches figures out how to market the shit out of it.

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