Ask good questions
Some personal tips about having conversations from me to you :)
Yesterday, I was at a New Year’s Eve party with my family when we started running out of things to do. My cousin, brother, and I had already finished reading the books we brought, played an entire game of Risk (I won), and were left sitting on the couch, wondering what to do.
It was still only 10 pm.
We ventured upstairs to find some other way to entertain ourselves, and discovered a foosball (table soccer) table hidden in a back room. We dusted it off and began playing a game to pass the time.
Since we only had three players, I decided to venture downstairs and recruit a 4th player to join us for an epic 2x2 match. There was no one else at the party under the age of 25, so I tapped on the shoulder of a random gentleman and asked if he wanted to join. His name was Bill, and he enthusiastically responded, “Yeah, I’d love to! I played foosball all through college and it’s the reason my GPA was so low.”
Even though Bill must’ve been 60+ years old, I knew we were cooked.
We had such a fun time playing 2x2 games upstairs, and Bill showed us the crazy skills he picked up playing foosball in his college dorm 40 years ago. He was doing things like this and this, (so-called “holding” the ball), which I had never witnessed in person. The team he was playing on didn’t lose a single game.
The crazy part about this entire situation is that I had no idea Bill was a foosball wizard because looking at him, he seemed like just a normal guy at the party. Yet hidden underneath was a foosball dragon waiting to be unleashed.
But this pattern of discovering cool things about people is not confined to the New Year’s Eve parties of family friends. In every single extended conversation with someone I’ve ever had, I’ve learned something interesting about the other person and the world. Every single time.
What all these experiences over the years have shown me is that every person has something special about them, whether it be an awesome accomplishment, an interesting skill, or a very niche passion (if you know the relevance of the term “niche passion”, you know). Your job as the listener is to figure out what that special something is.
The key to doing this is asking good questions.
“So Dennis”, you’re wondering right now. “Funny story about foosball and all, but you just said a vague thing about asking good questions and I have no idea how to apply that in my life.”
That’s a valid concern! Below, we’ll look at some practical tips for good conversations and asking great questions.
The first thing to recognize is that conversations are always smoother when you and the other person have something in common, so one of your biggest goals when talking to someone new is finding what that thing in common is as fast as possible. This can be achieved immediately (“Whoa, I love your duck shirt, I love ducks too!”) or it may take a bit of time (more on that later).
In the case of Bill, our commonality was foosball!
The second thing to recognize is that conversations with strangers need to start somewhere, and that somewhere is almost always small talk.
“Fuck”, you’re thinking. “I hate small talk.”
But there’s a reason that small talk exists: you can’t just walk up to a random person and start asking them deep, personal questions. Imagine someone you’ve never met before walking up to you and asking, “Hey, what’s your biggest regret about college?”
You’d be standing there thinking:
“Do I know you?”
“Damn that was a crazy question”
And you’d promptly walk away, thinking that person was a bit strange.
However, by starting off conversations with, “How’s the weather?”, “Where are you from?”, “What do you study?”, “What’s your job?”, and all these other minute things, people are actually trying to find out if you two have something in common. This is so hardwired into us that we don’t even consciously think about it — we just use these questions to find people similar to us. This is exactly why most conversations between college freshmen start with, “What’s your name? Where are you from? And what’s your major?”
These little points of small talk make the other person feel more comfortable around you, setting the stage for further conversation. Yes, small talk is small. But it’s very, very important.
Once you get the small talk out of the way, it’s time to step up your game to more interesting questions, inspired by what you learned in the small talk. This is where more exciting information can be revealed and learned!
For me, the most helpful way to think about this process is as a series of stepping stones across a pond. Each question you ask is somehow based on what the other person just said, moving the conversation further and further along. Eventually, one of these conversations will reveal something interesting to you, and you’re all set! The conversation will be smooth from there.
Let’s look at this strategy by examining another conversation I had yesterday, this time with another person at the New Year’s Eve party (not the foosball legend Bill).
This dude’s name was Alex, and my mom made me go talk to him because he had just arrived at the party and he didn’t have anyone to talk to. I reluctantly agreed, and invited him upstairs to play foosball with me.
While playing, I started asking him about work, and he told me he was a language analyst for the Air Force in Texas.
Curiosity, tickled.
I asked for what language, and he told me Spanish.
Well, Alex, you had my curiosity, but now you have my attention.
I asked how he learned Spanish, and he explained that he was sent to the Defense Language Institute to learn it. This institute is a military school in Monterrey, CA, where personnel are sent to learn foreign languages for the military.
I just so happened to have hiked right by this language institute three years ago with my family and was somewhat familiar with the area. We started chatting about how nice Monterrey is (he could hear the seals from his dorm!), and just like that, we were golden.
Interesting conversation, achieved!
We had a lovely conversation after that, where I learned that he’s going back to the institute next year to learn Farsi. How cool!
You can see that each question was built off the other (Work —> Air Force —> Spanish —> Defense Language Institute —> Monterrey —> Success!), which you should be aiming for when meeting someone new. You got this!
The last thing I want to address is those of you who have a deathly fear of talking to strangers and would rather sit in silence than start a conversation.
This fear of talking to strangers is a huge problem, since so much opportunity and happiness comes from meeting new people. By not interacting with strangers, you are automatically closing off every single new person you could possibly meet. Not good.
This is exactly what my friend Jason was experiencing last year, and this is how we went about solving it: Once a day for the next month, force yourself to speak with a stranger for at least one minute.
That’s it!
The first time, you will be shitting your pants from fear, but by the end of the month, that fear of talking to new people will have completely disappeared. That was exactly the case with Jason, and people now know him as a social butterfly. It’s crazy how quickly times change!
Places I recommend practicing talking to strangers are in line, on the walk to class, and in dorm room / apartment lounges. Really, any place where people are waiting and bored. Most people in these situations just go on their phones, but if you tap them and ask them a question, they’ll happily respond.
And if you are standing there and have literally no one idea what to say, let your go-to question be, “Hey, I know this is super random, but I have a free weekend and I’d like to do something with my friend, do you have recommendations?” They’ll tell you about some cool activities or events, and you can go from there.
95% of you reading this are thinking, “I’m not doing that” and will completely ignore the entire above section. Lit
For the other 5% who are serious about wanting to improve their social skills, let me help you personally since it always helps to have someone holding you accountable. Every single day after you have your conversation with someone new, send me an email to dennis@interosity.co with the following. I read every single one (and love reading these)!
The name of the person you talked to
Where you met them
And what you asked them / learned!
This is exactly what we did with Jason, and it worked wonders. 🫡
And if you’re still skeptical that this process works, watch this video about 100 Days of Rejection. Trust me, you won’t regret it!
Hopefully, you’ve learned something about how to improve your conversations. Remember, try to reach common ground as soon as possible, and don’t forget that small talk! We can’t skip it, no matter how much we’d like to.
Happy New Year everyone! Excited for the year ahead and to create growing Interosity with y’all.
Best,
Dennis :)
One last note:
Sometimes your social battery is dead, and you simply have no energy to talk to someone new. I get it! We’ve all been there before, and being forced into a conversation with someone you don’t know when you’re tired is usually not fun. However, it’s important to consider if you’re actually tired and aren’t able to talk right then, or if you’re just afraid to get out of your comfort zone and using tiredness as an excuse. In situations like these, it’s helpful to have an outside party (friend or family member) keep you honest. At the New Year’s Eve party yesterday, that outside party was my mom. ❤️
I published this the morning of January 1st, 2025, and then my family and I went on a hike up Mission Peak in Fremont, CA. On the way up, I saw another hiker wearing a Rivian backpack, so I struck up a conversation with him about that. Turns out he’s on their battery chemistry team, and I learned so much about batteries, Rivian, and technology. It was a perfect example of the benefit of asking great questions!
Dennis’s Picks:
This video from Dalton and Michael talks about how to make the most of your 20s. Some really great advice and things to think about in there.
This epic mushroom I saw on a hike with my cousin on Saturday:
