Urban Echo

When I was young I remember being embarrassed by my mother, particularly when we were standing in long grocery store lines. No she wasn’t making spit balls with her coupons or relishing a lollipop, she was making conversation. (Horrors!) She was talking with strangers.

As an adult I know the world is full of interesting strangers - everyday potential new friends are all around us – if we just knew how to break the ice and start conversations.



Every time I’m out in public chatting up a random stranger my friends can’t help but ask me “Pramit how do you start a conversation?”

So how exactly do you start a conversation? Well for in-person conversations I think it all boils down to the following:

1. You need to let go of self-conscious and judgmental thinking. Introverts - listen carefully - you don’t need to be an extrovert! It’s more important that you’re comfortable with yourself and genuinely interested in getting to know other people…like you were when you were a kid. First day in Kindergarten – you didn’t have any trouble making new friends.

For me it helps to remember that most people are happy to engaged in conversation and appreciate when someone else takes the lead.

Besides being comfortable it’s also important not to dismiss anyone or pre-judge a person by their appearance. You never know what the future will bring. Here is what Chris Yeh, a VP at PBwiki has to say

“At one event I saw slight pimply faced kid and struck up a conversation. His company was doing a $100 million a year in revenues. And as it turned out I made one of my most successful angel investments because I met the entrepreneur at my acne inflicted friends 25th birthday party.”

So that’s an important lesson…don’t dismiss ANYONE!


2. The next step is to pay attention. Pay attention to everyone and everything around you. Pay attention to your immediate environment – do you see something unusual? Is someone wearing and interesting tie or a watch?

Pay attention to the news – what’s happening on in the local news? In your industry? What’s happening in pop-culture? You can be surprised how lively those “boring” political discussions Doordarshan can get.

3. Be curious - the idea is to comment or ask a question. Just be careful not to interrogate. The key is to be GENUINELY interested and inquisitive.

I personally love to ask about peoples shoes. If I tell someone I like their shoes it makes them feel good. My favorite shoe story – a *cute* [ :P ] young girl I met on a plane.

She was wearing what was obviously a pair of expensive heels. I mentioned how I liked her style and off went a 2 hour conversation on where she got them and why and how they were made. We then began a dialogue about our colleges and chatted the rest of the flight and exchanged cards (turns out she was an entrepreneur as well). Weeks later I received by email an online purchase order for the exact same heels! All I had to do was login and select the size. I called and thanked her and asked her why she had sent a nice gesture; as there really was no professional relationship that could have resulted from us meeting. Her response “I enjoyed meeting you…you seem like a nice guy…a nice guy who has a nice girlfriend…and a nice girlfriend deserves a nice pair of heels.” Turns out the heels were worth $600!

Final tip – try to practice every chance you get, because it’s a skill that can be cultivated. Practice at your favorite coffee shops, practice at sporting events, practice at college, practice at seminars and of course you’d make my mother proud if you practiced at long grocery store lines.