How do I have fascinating conversations? | The anti-patterns

How good are you at conversations? I think I’m in the “OK, but not great” group of people. I know people who are brilliant at turning even the most mundane encounter into a fascinating interaction, I also know people who struggle with conversing and some who are conversation murderers.

I can have fascinating conversations, but I’m not great at it. I can also find myself in the conversation wilderness wondering where the best route out is.

Conversations are a skill which I believe can be developed and improved. I’m expecting this post to be the first of a series, I’ve not planned the series out (which is unusual) but I know that I have more to say than this single post, at least. Hopefully, we’ll learn some new skills along the journey.

The Fascinating conversation Anti-Patterns

Before we understand how we have fascinating conversations, let’s start with the opposite, the characteristics of terrible conversations. As I’ve been thinking about conversations in recent weeks and months I’ve come across a number of anti-patterns that interrupt an interaction and leave it flapping around with nowhere to go, I’m sure that there are plenty more and each of these is just a caricature, but sometimes those caricatures teach us something.

The Soakers

You are placed next to someone at a dinner who you don’t really know and you think that it might be fun to get to know them. You turn and say “Hi” or something equivalent.

They say “Hi” back and all appears to be good. They haven’t snarled at you which is always a bonus and they aren’t so shy that they can’t enter a conversation.

Having made the initial advance it’s time to get started and you reach for one of your semi-interesting opening questions: “What do you do?” or even “How long have you know {name of host}?” perhaps “Do you have family?” may be appropriate.

Whichever question you choose will be answered, but the answer will give little away. The respondee may talk for several minutes, but somehow what they say gives you no footing for a follow-on question about their answer.

You wait a second to see if they want to ask you a question, but that doesn’t appear to occur to them.

Your left with few options and decide to pick another question from the list while still hoping to gain an insight that opens up an avenue of insightful conversation.

Again it is answered, but still little is revealed.

You wait a few more seconds to see if they will ask you a question, again nothing. Your inner voice wonders why they don’t want to ask you a question.

The list of semi-interesting opening questions is starting to look a bit depleted, but you persevere.

Another answer, still no opening.

Still no question in response. Your inner-voice wants to shout at them “ASK ME A QUESTION!” but you are far too polite for that.

You return to your list of questions and decide that the next one on the list is just too boring to ask.

The conversations dies from lack of interest and you look around the rest of the table for someone, anyone, to talk to.

The Smart Bomber

You are stood with a group of people you know reasonably well and the conversation is OK, but not quite fascinating. You’re enjoying the interaction and everyone is contributing.

Then someone joins the conversation.

Within seconds they have contributed to the conversation.

The conversation is now dead.


The flow of the conversation was stopped by the contribution of the newest member of the group.

Everyone looks at each other desperately seeking a way of restarting the movement of words but time is running out fast. The conversational heartbeat is flat-lining. Quick, someone, do something, but no rescue is coming and everyone stands there in a silence that gets ever more uncomfortable.

Eventually the silence becomes too painful and the group disperses or breaks own into factions that each start their own, new, flow.

What did the newcomer say? There’s no simple way to define what was wrong with their contribution other than to characterise it as smart. Like many English words smart has a positive and a negative meaning – I’m using the negative meaning in this context. I’m talking here about statements for which there is no reply other than to say “Pardon? (You Muppet)” Politeness precludes anyone from saying this, politeness also stops us ignoring the comment and returning to the state we were in a few seconds earlier.

Notice that I describe these contributions as statements, because they are very rarely questions.

The smarts bomb has exploded and we are all left picking up the pieces.

The Agenda Enforcer

You join a teleconference early and discover that a number of your colleagues are also on the call early and so you say “Hi” and ask a question “How is everyone today?”

One of your colleagues chooses to respond with an insight into some planned special events in their office where things are going particularly well, they’ve been working on this for weeks and are quite excited about the outcome. Another colleague comments in a similar way and asks others in the group about their experiences. Other excited responses follow.

This is when the Agenda Enforcer enters the conversations and says “Today we are going to go around the call and I want each of you to report on how you are getting on with the planned special events? Who wants to start?”

This agenda item is exactly the conversation that you have just been having but no no-one wants to start. No-one wants to give a report, you were happy to have a conversation, but the conversation has left the call.

In your mind you are wondering why the Agenda Enforcer didn’t just let the conversation carry on flowing while also bubbling with anger for the interaction that was needlessly lost. Why did they feel the need to be in control?

The Distracted Distractor

You are sat in a one-to-one conversation in a coffee shop and have found great seats next to the window. Outside is a busy high-street and it feels like most of the rest of the world is going past the plate-glass facade.

The conversation is going well, you’ve caught up on some things and moved a little beyond the semi-interesting opening questions that such occasions demand. You are in the process of asking the person opposite you another question when they look out of the window and say “Have you seen that?”

You look out of the window to see a car driving illegally down the middle of the pedestrianised area. Your companion comments about the daftness of the person who has got themselves in such a mess.

After a few more choice words they ask “Where were we?”

You restate your question and they reply, but part way through their reply they again point out of the window “Look at that, they’re coming back the other way now!”

Again they ask “Where were we?” and you remind them.

A little further through their answer their phone rings, they take it out of their pocket and answer it. After a short conversation they end the phone call but continue to interact with the apps on their phone. You sit waiting, patiently, waiting, in silence, waiting.

Eventually they look up and say “Where were we again?” At this you stare intently at their phone. You flick a switch in your pocket and laser beams blast from your eyes instantly turning the phone into ash. Or, you reach over, take the phone from their hands and drop it into their drink. Or, something like that, or perhaps that’s just me.

A conversation is a flow of ideas and information, without the flow there is no conversation. In general the flow only goes in one direction, forwards. Stop-start is uncomfortable and going backwards is painful.

The Non-Stop Talker

Do I need to describe this person? You know who they are straight away. I suspect that you can picture them without prompting, if you can’t then perhaps this person is you.

They are the person who only needs one question to set them out on a track that gets ever more detailed in its telling, ever more irrelevant in its recounting.

They are the person who is convinced that you care whether it was last Tuesday, or perhaps Wednesday, or no it was Monday.

They know that you know how important time is and whether it happened at 11:05, or 10:45, or no it must have been about 11:15 because it was after the bus had left for town, you know the one, the one that is supposed to leave as 10:58, but always leaves at 11:08.

They know that it’s important that the item cost £11.98, or was it £11.95.

In short, they are verbally hyperactive and you only EVER ask them one question. You simply don’t have enough time to ask them more than one.

The Guessing Finishers

You are sat across the table from a work colleague. You are in a conversation and colleague asks you a question.

You steadily formulate an answer to the question because it’s a wonderful open question that requires an open answer.

Part way through your response you breath and pause a little. In that moment your colleague decides that you need help with your answer and start guessing.

Their first guess is utterly wrong and has you wondering whether they’ve been in the same conversation. You answer with a simple “No”. Their second guess is even more random and your “No” has become a bolder “No”. Why would they think that you would mean that? The third answer doesn’t even make sense and your “No” has become “NO”.

You are now stuck into the loop that uses all of your cognitive energy to answer their guesses and there is little remaining energy to find and give the answer that you were looking for in the first place.

The two of you eventually, somehow, find the missing word without you having to stand up and shout out “NO!!!” There is sweat beading on your neck from the stress.

Your corespondent then asks you another question and your anxiety levels hit max. You pause, trying to construct a whole answer so that you avoid the guessing game, but your stress levels make this almost impossible to achieve.

A wonderful, fascinating, flowing conversation has been replaced by an internal war with stress. The flow has left and the conversation will soon die for lack of freedom.

Learning from the Anti-Patterns

Recognise any of these? Perhaps you are some of these? I suspect that each of us has done each of these things at some point in our life, the wise thing to do would be to learn from these mistakes.

I’m planning to look into the anti-patterns for fascinating conversations as a way of improving my own interactions.

Header Image: This picture was taken on a recent climb up Crinkle Crags in the March snow. The snow was fresh from overnight showers completely covering any visibility of paths – interesting

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