How to make meeting new people easier — ask Q’s!

Shaan Shah
4 min readOct 27, 2017

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I have found that asking how or why questions has been an effective way for me to develop a relationship with a new person.

I came to this specific discovery from reading How To Win Friends and Influence People and my own experience befriending a nice range of people: Uber drivers, doormen, homeless people, among others.

Since I have been subleasing out of my friend’s condo in a high rise, I have walked passed a doorman every morning. I often waive with a “morning!” And I continue on my way.

One time I was thinking to myself, “man, this dude is always smiling.”

Me: “you seem so happy!”

He smiled in agreement.

Me: “I assume you like being a doorman?”

He again smiled in agreement and said,”yep, I really enjoy it!”

Me: “I am curious. Do you mind sharing why you like your job because most people I know answer, ‘do you like your job?’ with ‘it’s not bad’ versus ‘I really enjoy it!’”

After a minute, he answered with “Two things come to mind. I really enjoy getting to know the residents, talking to them, observing there different moods, regularly seeing them. And I also really like meeting their friends and family: their kids, grandpa grandma, girlfriend boyfriend that they may or may not even like! It’s fun. I see something new everyday. Oh and their dogs!”

Gained a cool perspective from asking about asking a why question. Also, made me recognizing the value of finding a good balance of building stronger relationships and making new relationships.

Every morning, I now try to slot out at least 5 extra minutes, because I often get into conversation with that doorman, Ian, or John, the other morning doorman. It makes for a more exciting morning. Ian typically sings an oldie or drops some knowledge like:

Ian: “some people will be in your life for all of the journey, but some only for parts of your journey”

Me: “Interesting. I often have a hard time with letting go. Cool quote!

Learnings from How to Win Friends and Influence People

Author Dale Carnegie has a story about how he went to a party one time and a woman wanted to talk to him about botany — a subject he was well versed on. The two talked for two hours and she walked out of the party raving about how great a conversationalist Dale Carnegie was.

Carnegie told his friends later that he had only asked two questions and that the woman had filled the rest of the conversation.

God gave you two ears and one mouth — some old saying

With Dale Carnegie’s perspective (aka his 15th principle) in mind, I responded to a homeless person that asked me for money.

Me: “I am curious, why are you homeless? Why don’t you have any money?”

Him: “Well, I was in jail for 7 years and just got out

Me, in my head: “man, that sucks”

Me: “Why were you put in jail?”

Him: “Well, I was out of money and a teenager. My parents didn’t have money either and they were both drug dealers so I started that. I made a mistake and got caught.”

Me: “Here’s a few bucks man. I will try to give more another day. It’s crazy cause my dad ran a small business and I helped out. Eventually, I started my own business as well. I am just lucky my parents weren’t drug dealers.”

Many times a week I see this guy, Jerome, and we shake hands and exchange a good morning or good evening. It’s pretty awesome having friendly faces in the neighborhood.

It’s cool to be yourself and share what you’re thinking!

I’ve found it valuable to be okay with expressing myself when I have genuine curiosity. Questions I’ve asked:

“Hasan, why did you choose to move to New Jersey?”

David, how did you go from living in the south side to the life you have now?”

Do share if you enjoyed reading this, what thought it provoked feedback, any questions you’ve enjoyed asking, or anything you do to build a new relationship!

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