How to get past boring small talk, have interesting conversations, and make people look forward to talking to you.

On top of being the 26th US president, Theodore Roosevelt was an expert conversationalist.

His guests ranged from diplomats to cowboys. But they all walked away amazed by his extensive knowledge and conversational skills. 

His secret?

The night before the meeting he would stay up reading about a subject he knew interested his guest.

Because he knew 2 important things:

1. People are most invested in conversations about things they treasure.

2. The best conversations happen between people sharing the same interests. 

I’m not saying you need to read encyclopedias to have interesting conversations. But you do need to learn to get past boring small talk.

Most people say they hate small talk. What they mean is they hate the stage of exchanging factual information.

• How are you?

• What do you do?

• Where do you live? 

The conversation ends up feeling like a job interview, forced and uninteresting. 

Small talk isn’t bad, it's like testing the waters by dipping your toe in the pool. Most people are uncomfortable talking to new people. Small talk helps you build basic trust before delving deeper. But like a ripe fruit, if it lingers too long it gets stale. 

Small talk is like the spark lighting a fiery conversation. But without the right fuel, it fizzles out. 

How to make people interested in talking to you (even if you're not an interesting person)

People think they're bad at conversations because they have nothing interesting to share.

• My job isn’t interesting

• I don’t have cool hobbies

• I don't have cool experiences like traveling. 

The truth is people with amazing stories can be the most boring to talk to. 

You know that friends who came back from a trip abroad? The one who only ever talks about all the cool things they did. Remember how tired you got of hearing about it?

People don’t want you to go on about yourself. Sorry to break it to you, but most people's biggest interest.

If you want to get people dialed into your conversation you need to talk about what they're interested in.

How do you figure out what people are interested in?

The holy grail of get-to-know-you questions: What do you do for fun?

I love this question:

Asking about what people do in their spare time is an amazing glimpse into the kind of person they are. Given the chance people will talk about what they like for hours.

Dale Carnegie tells a great story about meeting this woman at a bridge party.

After inquiring about her trip to Africa she went on while he sat there listening. In the end, she was telling her friends how great a conversationalist he was.

Even though all he did was listen.

But how do you ask “What do you do for fun?” without it coming off as forced?

Simple, whenever you ask “What do you do?” add “for fun”. Asking about their job won’t yield much interest because most people aren’t in jobs they care about. Plus after being asked about their job a million times they’re bored of answering it.

Start replacing “What do you do?” with “What do you do for fun?”

Fun conversations are much easier to come by when the topic is literally about fun. 

But what if what interests them bores you?

How can you find something you’re both interested in?

2-step blueprint to probing for shared interests and creating engaging conversations.

In Roosevelt's story, he didn’t just listen to his guests talk about their interests. 

To become a contributor he learned as much as he could on the subject. You could do the same but it's much easier to find a topic you're both already interested in and familiar with. If you do, conversation becomes a breeze. Think about the last time your passion came up in conversation. I bet you didn't have trouble coming up with stuff to say.

The problem is finding what interests you have in common.

Do so by probing for shared interests:

Step 1: Make a list of 5 things you like to talk about.

(*NOTE: not everything you like doing is something you like to talk about)

Keep them broad to make finding people who share the same interests easier.

It is harder to find someone who likes talking about the surrealist art movement than it is to find someone interested in art in general.

But don’t make the topic so broad you lose interest in it. 

If you like talking about basketball but not sports in general then keep basketball as the topic. 

Once you have your list you can practice probing these topics in conversation. 

Step 2: Probe for shared interests

During the conversation, think about how the current topic relates to one of your interests.

Probe by telling them how your interest relates to the current topic. If they share your enthusiasm they’ll jump at the chance to go down your conversational path. If not, look to probe a different interest of yours as the conversation is going

For example: 

I love talking about AI. I like to probe for interest by bringing it up whenever I can.

After learning a bit about what the person does for a living I’ll probe by saying:

•  How do you think AI will affect that kind of job?

•  Do you take advantage of AI at all at your job?

Often I’ll get a short answer indicating low interest. But sometimes they share my enthusiasm and we get to rave about AI. 

All you’re doing is opening a conversational path and seeing if they'd like to walk down it.

Continue until you find a path you both like and see where it takes you. Finding similarities with others is how you’ll find people you love spending time with.

Get them invested by asking “What do you do for fun” and form a connection by probing for shared interests. 

Now you can find interesting topics for conversation but if you want to learn how to keep talking about them click here: 📢 Never run out of things to say ever again

P.S. This was all about having interesting conversations, but if you want to learn how to have deeper conversations and form connections be on the lookout for next week’s newsletter.