How to get better at conversation

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Being better at conversations would seem to be a pretty powerful thing personally and professionally. Since most people are essentially horrific at maintaining or developing conversations beyond small talk or what they immediately need from you (former is normative in personal discourse; latter is normative in professional), being good at conversation could probably make you stand out and get you a bunch of stuff. Isn’t that the goal of most white-collar existence? Stand out and get a bunch of stuff? Isn’t that why teens join social media? Right.

I got this from Jordan Peterson and Carl Rogers

So I just started reading that Jordan Peterson 12 Rules book, and by “just started” I mean my bookmark is somewhere around Page 260, but that’s seemingly taken me six weeks to achieve. It’s a good book but it can drag. I digress.

In the current section I’m in, he talks about this rule from Carl Rogers that he subsequently has adopted in clinical therapy sessions:

Each person can speak up for himself only after he has first restated the ideas and feelings of the previous speaker accurately, and to that speaker’s satisfaction.

Seems pretty money, right?

The fraught thing about listening and communications

Back in my way olden days of writing this blog — May 2014, before I even lived in Texas — I wrote a post called “How to get people to listen to you.” The timing of that specific post is amazing because in May 2014, I was finishing graduate school and couldn’t get a job (or a job interview) to save my fucking life so at the time, no one was listening to me, despite me writing posts about it. Ha. Comedy is tragedy plus time, you know?

But the big problem with listening is really about confirmation bias. People enter conversations with agendas, and it’s really hard for them to move off what they know or what they already believe. This is also called “latitude of acceptance.” This is part of the reason why so many meetings are soul-draining disappointments. Silo A believes something beyond all measure (“Marketing rocks!”) and Silo B believes something different (“Marketing sucks and is actually impeding us!”) and everyone just speaks at their point, instead of trying to listen to the other side and make shifts. It also explains a ton of bad relationships, one-sided friendships, deals gone awry, etc.

In short: listening is important. But it’s often done wrong. I hope you knew both of those things.

My Chicago White Sox story to blow smoke up my own ass

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I live across the street from a bar. I live in Texas. By way of understanding the context/background of this story, I spend too much time and money at this bar, but over time that’s gotten slightly better. I probably could have had a down payment on a house without this joint in my life, but ya know, you live and learn.

Because said bar is in Texas, you wouldn’t expect a lot of conversations about the Chicago White Sox, but one random weeknight, I found myself there, eating/drinking, and I got in exactly such a conversation.

Now, look, I worked for ESPN for six-seven years, so I understand sports and can generally discuss it. But partially because I worked at ESPN that long, I no longer have the passion for sports I once did. It wanes when you see how “the sausage gets made.”

So I’m buzzed, this business traveler is buzzed, and we’re discussing the White Sox. The whole convo on my side was 80–20. I just asked questions, listened, and repeat the answers.

“Oh, so who are your pitchers?”


“Oh OK, these guys (name them) are your pitchers?”

Very basic. Went like that for 20–30 minutes. I maybe said one or two things about baseball teams I liked or knew or anything. It was all listen, restate, look for new thread, ask, listen, restate, etc.

At the end of the half-hour, the dude is tabbing out and gives me his business card and says he wants to do some stuff with me in the future. I don’t even think he knew what I did professionally.

This other guy then comes over. He asks me:

“Hey, you in sales?”

“No sir.”

“Well, you should be, because you just worked that sale better than most of my guys.”

Now, can I truly compare talking to some buzzed road warrior about his baseball team to selling B2B widgets? Of course I can’t. I’d probably be awful at sales in many respects. But you can get stuff by just listening, restating, getting their trust in the process, and then pulling on a new thread and repeating that. It’s actually not super challenging.

Begin with thinking of communication differently

It’s not about one person getting the upper hand or getting the “deal” or “the win.” It’s about two people exchanging information, but beyond that, it’s information in context. Why should the other person care?

Like, to me this is why social media is often so gag-inducing. When people just post and there’s no real context to the posting, what is my reason for caring? What is the context of what I am seeing or supposed to experience? Now, a lot of people do this just to show their life as curated baller, or they want only their real friends to see it but are too lazy to use a private channel or DM. I get it. But communication isn’t just about blasting your message, and most brands — and, honestly, individuals — miss that. Communication is about understanding both sides of what’s being conveyed and why it matters. You only get there through purposed listening, which admittedly now that I’ve typed it sounds like thought leader buzzword bullshit drivel 101.

But if you take nothing from this, take this: simply listening to understand and showing you did that through restating their last points can be incredibly powerful — and lucrative! — for you.

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