Conversation Skills Essentials

A teacher friend of mine told me that this year students were different. If she asked to see a hall pass from a freshman, they’d give her the finger. They swore at her and were generally rude. The behavior was so out of line that seniors would step in and tell them not to talk to her like that. I asked why she thought that was happening, and she said, “Covid”. The lack of socialization, especially at such a key time in life, had made this incoming class the first one that lacked basic manners and social skills.

Nearly all of us has had less social interaction over the past few years. For many months my primary social outlet was VR games with friends. It feels like people have really lost their social skills over the past few years. I notice it all the time and am bewildered by how many people aren’t even doing the basic things correctly. Once in a while I think that maybe I’m just too sensitive to social “errors”, but then I’ll have a conversation with someone with good social skills and it feels like being on a vacation.

I have written an entire book on social skills, but I wanted to write a separate post about the top mistakes I see people make consistently during conversations. If you master these core skills, you’ll be better off than the vast majority of people.

Don’t Interrupt

In text based messaging, interrupting doesn’t really matter. You can have two or three topics going at once and jump back and forth between them. It may not be ideal, but it’s not rude and it doesn’t kill the conversation. Too many people take this habit into real life conversation, where it has disastrous effects.

A conversation is best when both parties are interested, engaged, and want to share. If you interrupt you show that you are uninterested and you blunt the other person’s motivation to share. If they don’t feel like their input is valuable, they will either fight you for the spotlight (by interrupting you) or they’ll stop investing in the conversation because they know that there’s no point in trying to get full thoughts across.

Accept, Don’t Seek

Accept whatever reaction someone gives you, and treat it as though it were correct. If you said something hilarious and they didn’t laugh, act as if it wasn’t funny. Either it wasn’t, or they didn’t pick up on it, but in either case trying to get them to laugh will make them feel uncomfortable.

If you tell a bunch of jokes and the person doesn’t seem to find them hilarious, stop telling them jokes. You may be funny, but you may not share a sense of humor.

Seeking laughs is one of the most obvious ways in which people seek reactions, but there are many others. They usually come in the form of follow-up statements fishing for a specific reaction.

Imagine someone tells me a story about some crazy thing they did when they got drunk. As a non-drinker who can’t relate I might not find it that interesting, but would still try to say something positive like, “Wow, sounds crazy.” If they really want validation from the story, they might try to tack on statements to get a bigger reaction. “Yeah, it was wild!” or “My friends couldn’t believe it!”, to which there is no possible response other than a bigger reaction or awkward silence.

This sort of behavior puts a huge burden on the listener because it makes them responsible for your emotional state. Their options are to deny you the emotional state you want, or to give it to you by lying. This is exhausting and will cause people to limit the amount of social time they spend with you.

Gauge Interest

This is more of an advanced technique, but is one that has a huge impact. At all times you should be gauging interest in what you’re saying, and modulating what you say to fit the recipient’s interest level.

I could tell a story about building my pinball machine. A crafty technical friend might be very interested in hearing every step, but my mom might not be interested in more than about 10 seconds of detail on it. If I adjust the depth of the story for my audience, it adds to any conversation.

In general the best thing to do is to tell the quickest version of your story, and leave out any tangents or details. This puts the other person in the driver’s seat and lets them ask about the things that most interest them. They are also motivated to ask questions because they can see that I will not bog them down with uninteresting details.

“I spent last month building a virtual pinball machine…”

“Cool! That sounds fun!”

If that’s the response I get, I’m totally done and moving on. Even if I’m really excited about my pinball machine, it does neither of us any good for them to hear more details if they don’t care. If you’re confident that you have a lot to offer, you don’t mind cutting a thread short and looking for another one.

“Huh? What’s a virtual pinball machine?”

Here the listener is showing interest, so I’ll answer their question AND give them a little more that they can ask about.

“It’s a physical machine that looks like a pinball machine, but instead of a playfield it has a high res screen to simulate pinball games. It ended up being a huge project, but it’s super fun to play”

Now they can easily bail from the topic as before, or they can ask why it ended up being a huge project. If they like pinball they might ask what games I like to play. If they’re technical they might ask about the software or what kind of computer it needs. By giving them the option to ask about things they’re interested in, or to exit the conversation, they feel no pressure and there’s only upside.

Ask Questions

An ideal conversation is a mix of listening, asking questions, and sharing in a way that allows the other person to politely guide the conversation. You must ask questions so that the other person knows that you are interested in them and what they are saying.

The worst conversations are those where both parties are waiting their turn to talk, saying as much as they can before getting interrupted, and then being forced to listen to the other.

Asking questions signifies investment. Besides allowing you to hear about what most interests you, it proves that you were listening and shows that you value the other person.

You don’t have to ask questions every single time someone says something, but it’s probably correct about 50% of the time. Err on the side of asking more questions. Factual questions are good, but questions that deepen the conversation are even better. “What were you thinking when she said that?” “Was that as hard as it sounds?” “How did you learn how to do that?” “What made you decide to go that route?”

Verbalize when you change your mind

People love to teach and persuade others. When someone has taught you something or changed your mind on something, let them know. Say things like:

“Wow, I would have never thought to do that, but that’s a great idea.”

“Ok, maybe you’re right. I hadn’t thought about that before.”

“You know, I used to really think X, but you’ve convinced me Y”

You should only say these things if they are true, but when they are it is a great gift that you can give to the other person. It seems that these days everyone is so focused on being right and believes that changing their mind shows weakness, but in reality it is the opposite. Only confident people feel are able to change positions without affecting their self image.

Disagree Positively

While you want to be an agreeable person, it’s important to share your real thoughts and to express them in proportion with their weight. One of the best things you can do is to engage in positive disagreement.

Imagine that I tell you I live in Vegas and that you don’t think that you would like living in Vegas. There are three routes you could take. The first is to try to be agreeable, even though it’s not genuine.

“Oh cool, I bet it’s great there!”

This is ok, but it can really only lead to a superficial conversation where I say something like, “Yeah, I really like it. Where do you live?”. That’s fine, but if you do this habitually, your entire conversation will be surface level. The other person will eventually realize that you don’t seem to have any independent opinions, which is uninteresting.

The second approach could charitably be called brutal honesty.

“Wow, I would never live there. It’s too hot and there are no trees.”

What can I say to that? I could argue about the weather and trees, but that’s a pretty miserable conversation. I could tell you why I like it, but you haven’t shown any interest in knowing why, so why would I bother?

The last option is positive disagreement.

“Vegas? Casinos and desert? What made you choose that?”

Here you’ve pushed back and expressed that you wouldn’t want to live in Vegas, but you’ve also given me a great opportunity to talk about something positive and to try to sway you in a friendly way.

I have a friend who has somewhat extreme political views, but he will always say things like, “I believe X, but I bet you believe Y and you always have interesting takes, so I’d love to hear your thoughts”. It’s a great way to disagree in a positive and constructive way, and I always enjoy conversations with him. In our conversations we also usually both concede points, as described in the previous tip, which makes the conversations even more engaging.


It’s VERY difficult to know how well you’re doing in conversations, especially in polite company. I will let someone violate every rule on this list and will do my best to give them the conversation they want. I just won’t seek out more conversations in the future.

There are some indicators you can look for to figure out which mistakes you’re making. Look at them in aggregate rather than worrying too much about any individual conversation.

“Nice” “Cool” “Ok”

If you get a lot of single word answers, you are not keeping the other person interested. They are trying to prevent you from saying more, either because you habitually talk too much or because the topic isn’t interesting to them.

50% Talk Time

Conversations should be just about 50/50, especially if you know each other reasonably well. It is your responsibility to get the ratio correct, either by talking more or by asking more questions to induce the other person to talk more. Of all the people I know, I can only think of a couple people who I believe really don’t want to be 50% of the conversation. Topic introduction should also be split pretty evenly.


Conversation should frequently be making it to a depth where you are learning more about the other person and they are learning more about you. This is what makes conversations exciting. Real depth doesn’t happen unless both parties are sharing, so you must be willing to be vulnerable and share things about yourself, and must also have the awareness to ask questions to induce the other person to do the same.

If I wanted to set someone up for a good life and they could focus on only one thing, I would prioritize getting social skills, especially conversational skills. Our experience on earth is largely defined by our interactions with others, so improving those interactions pays off massively.


Photo is Vegas from just the right angle as I flew out. You can see the mountains and Lake Mead in the background.

The gear post is coming soon. Probably with an accompanying Youtube Live. I was going to rush and get it done today but I don’t have good photos of some of the new things.





23 responses to “Conversation Skills Essentials”

  1. erik Huijsmans Avatar
    erik Huijsmans

    A highly under rated topic. Great blog!

  2. Taylor Levinson Avatar
    Taylor Levinson

    I love this post, and I learned a lot from it. Thanks for taking the time to articulate it Tynan!

  3. Flavio Avatar

    Thanks for the great work. We can learn valuable social skills

  4. Kellan Avatar

    Great post, thanks! Will be referring back to it, I’m sure.

    1. Pelan Avatar

      Please do forgodsake kellan! 😉

  5. markus enriquez Avatar
    markus enriquez

    very insightful and useful post. thanks for the valuable post.

    i would love to hear more about your pinball project! i, too, love real and virtual pinball and have thought quite seriously about having a go at building a table, and if you happen to be sharing your code and insights i sure would love to hear them and see how your approaching the build…

    i know im asking a lot, but if you could maybe send me an email with any info you are willing to share tips and ideals about your virtual pinball project, i sure would love to hear them.


  6. Jochen Goerdts Avatar
    Jochen Goerdts

    Significant and advancing conversational skills pleasantly distilled. Thank you

  7. JCK Avatar

    Well written and useful post. I bet you are part of engaging relationships with many interesting people.

  8. Tha Fox Avatar

    Thank you for writing this post! I got some ideas about how to enhance my conversations.

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  12. Denis Howe Avatar

    My son jokes that I’m autistic. As I read your article, I was thinking, this is just the kind of advice an autistic person needs to learn in order to function better socially. Keep up the great work!

  13. Esse Hennessey Avatar
    Esse Hennessey

    Perfectly articulated for me, thank you. Look forward to more.

  14. Adam Ruggle Avatar
    Adam Ruggle

    Succinct and helpful with examples to bring the concepts to life. Thanks Tynan!

    P.S. I’m psyched for the gear post.

  15. Aleks Avatar


    Just kidding, great post!

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