We need to talk about your cat because your cat is pissing me off.

Your cat is eating my socks. No. Really. Your cat has eaten four pairs of my socks.

Yes, I know cats can’t digest cloth. Your cat does not have super-feline sock-eating and digestion skills. Your cat nibbles the toes off my socks and then throws up these toe parts all over my closet floor as little gooey sockballs.

Your cat is pissing me off and we need to have a conversation about it.

The Topic of Conversation

In How to Run a Meeting, I describe a conversation as “verbal ping pong… you bat the little white verbal ball back and forth until someone wins”. This describes a simple conversation, but conversations are rarely simple. They have a variety of structures that are carefully negotiated and molded by the participants.

To understand the different type of structures, we need to define a base unit of conversation and the actions that potentially surround it. Let’s call this base unit of conversation a topic.

A topic is the headline you’d give to the current content and state of the conversation. Examples:

• The problem with our bug queue.
• I can’t stand Stan.
• You are bugging me in indescribable ways that I will now attempt to describe.

In my head, a topic looks like this:

The key parts of this model are:

1. Stop button. For any number of reasons, a conversation can stop or be interrupted. When this occurs, all conversation participants are effectively agreeing: “This topic is done and there will be no further discussion during this conversation”.
2. The agreed upon Topic of the conversation.
3. Progress Bar. This is a totally subjective measure that indicates how close a conversation is to being resolved. If the bar is moving, this topic is currently in play.
4. Pause button. A healthy conversation is rarely only focused on a single topic. Conversations meander from one topic to the next. When paused, a topic is no longer being discussed, but it remains open and unresolved in the minds of the participants.

This is a lot of preamble to describe an act we do automatically. If this model strikes you as overly complex, know this — you are going to spend half of your goddamned life suffering through the alignment of differing perspectives in any given conversation. It’s the single biggest waste of your time in dealing with other people and the better you understand, the less time you’ll waste. So, let’s circle back to…

Your Goddamned Cat

As we sit down to have our conversation regarding the sockballs littering my closet floor, I’m thinking about how I’m going to successfully convince you to keep your cat on a tighter leash. In fact, I don’t want the cat in the house at all, but you pay half the rent and we did agree when we arrived that the cat was cool. I need to figure out how to verbally amend that agreement, which means we’re going to need to negotiate. I’m going to have to concede something in order get the goddamned cat away from my delicious socks and out of the house.

In this case, I don’t know what my concession is — it’s something we need to discover via our conversation, which means there are a couple of potential topics:

1. Regarding your cat eating my socks.
2. The cat eviction negotiation.
3. Things I know that piss you off.

With these topics in mind, our conversation starts gently, in the living room. I explain, “I would like to discuss the matter of your cat eating my socks,” to which you respond, “I am sick and tired of you not cleaning the bathroom”.

Whoa. Wait. What?

In my head, the conversation looked like this:

But you just hit the pause button on our first topic and started another topic:

The second topic introduces a new element in the model — the segue. This handy line is the context that ties one topic to another, which, in the case of the sockball situation, is currently a confusing, “Wuh?”

The point: it takes at least two people to have a conversation, but the real work is in making sure you’re both having the same conversation.

I can help.

A Conversation Structure

In computer science, there’s a concept called data structures. The idea is that a data structure is a model used to organize data so that it can be used efficiently. One of the simplest structures is called a list and it looks like this:

In terms of a conversation, think of lists as the most basic and easy to follow type of conversation. Using the model I describe above, no topic can be paused or stopped until the topic is resolved. There are no segues, tangents, or sidebars.

You’re thinking conversations as simple and structured as these don’t exist, and you’re right. This type of meeting does occur, but it’s called a presentation — where the speaker is click-click-clicking through his topics on his merry way towards the undisputed end.

While this basic list of conversations doesn’t exist, there are people who want them to exist and will make this clear as part of the conversation. They sound like this:

• “Wait, wait, wait, we’re not done with topic #1. Can we talk about topic #1?”
• “Hold it, before we go there, what about the issue at hand?”
• “This new topic has absolutely nothing to do with what we’re talking about.”

The intricacies and implementation of various data structures are not the topic of this article. What’s relevant is understanding that there are different conversation models you might find yourself in and then figuring out how to adapt.

The Stack

A slightly more complex data structure, and one that is more representative of a real conversation, is the stack. This is where our Pause and Stop buttons come into play. Let’s go back to that goddamned sock-eating cat to understand. Our conversation started with the sock topic, but you immediately put a Pause on that first topic and fired up a new one. In my head that looks this:

This is a stack. The topics are literally stacked on top of each other because, in my head, we’re actually talking about both topics, and the successful conclusion of all topics is key to this entire conversation coming to a successful conclusion. The question is are we both prepared for this type of conversation?

My definition of an effective conversation is if, at any moment, you could ask any participant in the conversation to point at precisely which topic was being discussed and how that topic was progressing. Bonus points for walking through the stack and explaining how you got there.

When conversation participants lose the context of the conversation, when they lose track of where they are, they stop listening and stop participating. The conversation no longer has a chance of resolution because resolution requires their active involvement and all they’re doing is fake listening to your speech.

Conversation Tolerances

A stacked conversation, one with multiple topics tied together with segues, is where everyone involved needs to keep track not just of the complexities of the conversation, but of the tolerances of those participating. Again, this is not a meeting with a well-defined agenda and anointed leader; this is a conversation where everyone needs to keep their wits about them.

When a conversation gets complex, this is what I’m watching for:

How many open topics can we handle? Each segue moves us slightly further from the starting topic. Are you cool with that? Ok, how many topics can you keep in your head? There’s a point where everyone will lose track of where they are if we have too many open topics — what’s your threshold? Wait, now I’m lost, so I’m going to ask: “How’d we get here?”

What’s our segue tolerance? How deliberate do I need to be switching from one topic to the next? Do I need to explicitly say, “We are switching topics now,” or can you keep up? How much segue detail do I need to give? Can anyone hit Pause and pivot to a new topic? Will you? Ok, you just did, but I don’t understand your segue, so I’ll ask: “Please explain how this relates to that.”

What’s our closure tolerance? How much progress do you need to make before we switch topics? Will you get cranky if we don’t even try to resolve something? Is this topic more important to you than other open ones? Will you freak out if all is not resolved? Can the conversation totally mutate into something else? Is that a bad thing?

Understanding both your own conversation tolerances as well as the ones of those you converse with is essential to having a successful conversation, and the best way to know where they’re at is to look. Humans wear a bevy of visual cues that indicate their comfort with a conversation. Nods, sounds, and eye contact — these are potential signs of engagement. The rule is, if they look lost, you ask: “What did you just hear?” If you’re lost, you say: “I’m not following you.”

The Tree

Problem solving is the art of a finding a solution acceptable to everyone in the conversation. If everyone knew the solution to the problem, you wouldn’t be having the conversation in the first place. If there is no problem, then, well, you’re shooting the shit. Problem solving means getting conversationally creative, and being creative means letting yourself mentally wander — eschewing structure. This is why my favorite conversation structure is the Tree.

The Tree is the pinnacle of advanced conversations. Where a stacked conversation looks like this:

The tree appears chaotic:

The simple explanation of the Tree conversation is that it’s multiple conversations. In the image above, you’re looking at three seemingly disparate conversations, except they’re not. The reality and the definition of the Tree-based conversations are the inspired segues. Think of a conversation with your best friend. Would anyone listening to this conversation actually be able to follow it? Could they diagram it? Of course not.

Could you? Of course.

For qualified participants, the Tree is pure conversational joy. Topics vary wildly, being held together by only the thinnest of segues that are often unspoken, but there is a structure. And more importantly, there is mutual understanding and appreciation of this wonderfully chaotic verbal mess, because it’s in this mess where you have the most potential to resolve the topic.

Remember, this is a conversation; it’s not a story and it’s not a meeting. There is a topic to be resolved and no one is happy until that topic is resolved. If this was a trivial topic, if we could just tell your cat to stop eating my socks. Resolution might be easy, but it’s not. My spoken frustration about your sock-eating cat has triggered your response about my inept cleaning skills, which means now we’re going to do some heavy-duty roommate therapy.

The resolution might be tricky and it might involve verbally wandering to disparate topics, but you and I have known each other for years. We’re ok with a deep stack of topics that eventually transform into a forest of conversations. We know that part of big discovery is verbally wandering into strange mental places.