Conversing: Two roles in a conversation

I assist in an online podcasting workshop where a student recently asked:

Could knowing all these [interviewing] techniques be making us more aware of the style, and […] getting us further away from the natural, inherent style we all have […] ?

I’ve mentioned before that I distinguish between “interview” and “conversation” in what I’m currently recording for podcast publication, (for Movers Mindset and other shows.) Today, I’m just going to gloss over that distinction and riff off this student’s excellent observation. Whether we label it “interview” or “conversation,” there’s a key milestone people go through when they realize that practicing something intentionally, is going to—at least partially—paper over their own innate style. This is a normal step in any journey involving mastery practice. After sufficient practice, you will find you still have an innate style; It’s simply different than the one you started with.

I believe that my role as a conversation partner, (being who my guest needs me to be for us to have a great conversation,) and my role in serving my listeners, (being who the listeners need me to be for them to enjoy and/or learn from a great conversation,) are antagonistic. The better I perform at one of those roles, the worse I perform at the other. That’s the balance I’m trying to work out each time I press record. Techniques which serve well for one role, can be detrimental to the other role.

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Conversing: Generating great questions in real-time

What more could you ask for?

Pick any two ideas, presume they are connected, and present that connection as a question.

I’ll wager you’re thinking, “that’s easier read than done.” But, it is easy. Simply ask:

Is there a connection between X and Y?

Exercise: Pause here and think of a few random pairs of ideas. The faster you pull the ideas out, the better. Take two ideas and say the question in your mind. Are they not surprising, the trains of thought which spring up? If you manage to stump yourself in finding a connection, would it have been an interesting exchange if another person had been involved?

Where’s the trick?

The trick is right there in the very first line I wrote, in the first phrase:

Pick two ideas.

The two ideas are connected; that’s how your mind was able to pick them. The trick uses your mind’s built-in super-powers of observation and curiosity. To ask a great question, people focus on finding a question. It’s far easier to make a question out of something great.

Clearly the degree of greatness of your question depends on what ideas you pick. Fortunately, the more you pick-two and ask about the connection, the better you’ll get at picking better ideas. You’re refining your mental observation skills and refining your taste in which ideas will combine into a great question.

Complications

In mechanical watches, a “complication” is some additional function. Indicating the day of the week, the date, or the phase of the moon, are in reality not that different in terms of complexity; They are each simply a complication. It’s the total number of complications that impresses the watch aficionados.

I’m going to throw a bunch of complications on top of this idea. By analogy with the watches, I’m suggesting that no one of these is any better or more complex. Each complication is simply a possibility you could add. One of your goals, in any conversation I care to think about, is to have your tools and skills disappear in service of the conversation. Only through experience can you learn how complicated to make things. It varies based on every conversational parameter you can imagine. Sometimes, the barest simplicity is the best choice—“is there a connection between X and Y?”—and sometimes…

It’s not you, it’s me. If the question you’re posing might be too personal, taboo, etc. you can couch it in a dash of self-deprecation. “I know this sounds weird, but is there a connection between X and Y?” Your conversation partner can easily parry—in fact, people will automatically and subconsciously parry this way if they are uncomfortable—with, “Yes that’s weird. What sort of wacko would ask that?” Being a great conversationalist, you can then proceed in another direction. (Or press on!)

The joy of wonder. Rare, (and possibly psychotic,) is the person who isn’t sucked in when you express honest wonder. If you really are wondering—that is probably how you picked those two ideas in the first place—then it’s going to be obvious that you’re enjoying asking about the connection. “Oh, wow! Now I’m wondering if there’s a connection between X and Y.”

Grammar ain’t all that. Did you catch that? That last example wasn’t a question. Turns out, it’s not necessary to speak a grammatical question. All you ever need to do is convey that you have a question. In the Movers Mindset podcast I get endless mileage out of saying, “And of course, the final question: Three words to describe your practice.” Which is a statement stapled to a sentence fragment, and I don’t even pitch-up at the end to make it sound like a question. Statements using “wondering” are the obvious way to do statement-questions. But there are more: “I’m astounded I never realized there’s a connection between X and Y.” That one has a quiet little question—“is there actually a connection here?”—tucked in under the loud astonishment. There’s also, “I can’t believe I never noticed the connection between X and Y.” Even snarky, “…next you’re going to tell me X and Y are connected.” Complications sure, but filigree has its place.

There can’t possible be more

I’ve described this entire thing as if it were something you do once, (and then use the question.) Eventually, you can generate two, sometimes three or more, two-ideas-and-a-connection questions before the pause gets pregnant. With practice, you can regularly generate 2, and then choose the one you like better.

This is particularly important if you’re trying to lead the conversation—“lead” as in “let’s go for a stroll and I secretly want to show you my favorite bakery along the way,” not “I want to lead you to a mugging”. Being able to ask great questions is one thing, but being able to ask a series of great questions that lead to a through-line, however tenuous, is pure wizardry.

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Conversing: Be the hornet?

Is it better to be the fly on the wall, or the hornet in the room?

I variously categorize conversations on a spectrum from formal to casual. (I can think of other ways that I categorize them, but I’ll leave that for another day.) At the formal end would be police interrogations and then—perhaps—live, antagonistic interviews of politicians. At the casual end would be pillow-talk and long-term friends around a campfire with their preferred beverages. I’m generally not interested in the formal end of the spectrum; I plead the Fifth. While I’m deeply, personally interested in the casual end, today I want to talk about conversations that fall in the middle.

So what’s in the middle? Conversations built on a shared intention: Two people who want to resolve a difference, who want to co-create something new from their individual experiences, or who are simply excited about taking a leap into the unknown experience that is a good conversation. It’s that third one which really calls to me these days.

The leap

I’ve now done enough recorded conversations to say two things:

I used to think I was doing interviews. In fact, I began using a process and format intentionally meant to create interviews; I showed up with things I was interested in and I wanted to learn more about from my partner. I soon discovered that when we veered away from the formal-end of the conversation spectrum, (away from the “interview” I had intended to create,) into the more middle-area of simply good conversation, that was when I most enjoyed the experience. My conversation partners clearly enjoyed it more, and the listeners did too. (“hmmmmm… maybe I am onto something here?” #seecraiglearn )

The first thing I have to say is that the form of the created artifact follows from the process.

If I use a process intended to create formal conversations, that’s what I’ll get, (more or less.) If I use a process intended to create more casual conversations, then I get that, (more or less.) The insight is that the process for creating casual conversation is not itself casual. The process is specific, rigorous, and frankly exhausting. It’s exhausting because I want to execute the process in order to create the best possible conversation, and I want to experience that conversation. That’s in contrast to my conversation partner who is only attempting to do the latter because they’re only aware of their desire to experience the conversation. They’re not aware of the process, and they probably shouldn’t be aware.

Each conversation—each performance, since I’m today talking about when we are recording—is better if we’re comfortable going just a bit farther than we might normally. This is where the process pays off. Everything I’ve done in preparation, and everything I do during the conversation, from the obvious to the subtle to the outright manipulative, is in service of creating the best space for that conversation.

The second thing I have to say is that to create good, casual conversations I have to help my partner leap.

Be the hornet?

I recently listened to Jesse Thorn’s interview of Werner Herzog for The Turnaround. If you’ve read this far, I can’t imagine you wouldn’t enjoy listening to that ~35 minutes of Thorn and Herzog.

In the conversations that I’m currently interested in creating and recording I simply cannot be the fly on the wall. I have to literally sit down with my conversation partner. But there’s an enormous range of engagement that I can vary. (More realistically I can only try to control this, as I’m always balancing the observer-process and the participant-creation experiences.) In my first recorded conversations there quickly became far too much of me performing, (and I’ll leave it at that for today.) Then followed me reigning myself in too far, then some relaxing back towards more of me, and currently I find that I like the amount of me that appears in the conversations.

After listening to Herzog’s thoughts on documentary film-making, (but he talks about a lot more than that in the podcast,) I now see that I need to work on being the active hornet in the room. This is the dimension where I actively lead the conversation—not upstage my partner, but actively lead in the way that two intimate dance partners have a leader, (and, yes, who is leading can change at any moment.)

I need to more often be the hornet. I need to more often suggest simply by my presence that a sting might be imminent. Then if they decline to leap, maybe, sting just a little.

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Conversing: Listening

As opposed to listening to refute, or listening to respond.

Sometimes I simply have a conversation. I find they spring up through a crack in the concrete: A random encounter begins with some words exchanged per social norm, and quickly expands as both sides shift their focus to the person before them. More often they push up through fertile ground; a social gathering where, “get together and socialize,” is literally on the agenda. My journey exploring conversation began with these found conversations; I simply found myself having cool conversations.

I soon learned that I love creating conversation. I began trying to create conversation, (between myself and one or more others,) initially simply for fun and later in the context of recording podcast episodes. I was surprised to find that having recording gear, an agenda (“I’d like to interview you about…”), and simply acting like I knew what I was doing, was sufficient to get things going!

If I truly do want to engage in a good conversations, it turns out that my actions follow automatically. I share things about myself and doing so invites the other person to share. I take things seriously which conveys that I value the interaction and what I’m hearing. I express my interest directly by asking questions about what—in the moment, not the day before—is interesting; questions which show the other person I’m generally curious. Overall, I demonstrate that I’m listening because I’m interested, rather than because I want to immediately do something with what I’m about to hear.

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