When I was in high school I was in this work-study program where I would go to school for half a day and work in an office environment the other half.  It was supposed to help us mimic the “real world” while getting some hands on experience in our desired career path.  My first official “white collar” job was that of receptionist at this law firm.
 
The lawyers only dealt with civil matters so most of the people that showed up either wanted to talk about some contract or some title dispute.  It was pretty benign so it’s not like people were there because they were accused of killing someone. 
 
Even though the lawyers each had several years of experience, this was a new firm (I was employee #9) so although we had a good amount of appointments, the phone didn't ring much. That meant I spent my day in a reception area waiting for someone to show up. 
 
Sometimes the clients would get there earlier than their appointment by 20 minutes.  I would offer them something to drink and let the lawyer’s respective secretary know that their appointment was there.  So now we had 20 minutes to kill. 
 
Since the phone didn’t ring much I would end up in a waiting room by myself with nothing else to look at than the waiting client for 20 minutes.

It got awkward.
 
Probably after my first week of doing this, I decided to make small talk.  So it went something like this:
 
17 year old me (after staring at client for 5 minutes without saying anything): “It’s pretty hot outside, right?”
Client (who has bigger things on their mind than some 17 year old receptionist):“Yup.  It’s hot”

Silence for next 15 minutes.
 
You know what’s more awkward than 15 minutes of silence?

Asking a question and THEN getting 15 minutes of silence. 
 
I tried different variations:
 

  1. How are you? Typical answer: Good

  2. How’s the weather?  Typical answer: Hot

  3. Did you have a hard time finding us? Typical answer:No/Yes
     
    And all of them were met with a one word answer and 15 minutes of awkwardness.
     
    I tried keeping the conversation going but it usually died down after 2 or 3 more one-word answers and I would give up.  
     
    So I kept on trying.  I didn’t know how to keep the conversation going no matter how many more things I said.  Turns out people aren’t too interested in hearing what a part-time teenage receptionist has to say.

A 17 Year Old Conversation Master

A 17 Year Old Conversation Master

 
Then I stumbled into the answer:
Instead of me trying to talk for 15 minutes, I would have the other person talk for that time. It works for two reasons: 1. People love talking about themselves and 2. You make them feel important. 

On top of that, I didn’t have to do the heavy lifting.  They had to entertain me and not the other way around.  All I had to do was ask the right questions and these people would blab for the rest of the 15 minutes.
 
I also noticed that these people coming to see their lawyers for private matters would spill the beans if you asked them.  You didn’t even have to be sneaky about it.  All you had to do was ask and people would tell you. 
 
So here is a sample conversation:
 
Me: “It’s really hot outside, isn’t it?  Is this the hottest you’ve ever seen it?”
Client: “No.  I remember once when I was little that lake over there dried up.  That was probably around 1973”
Me: “So you’ve lived around this area since then?  How was it different than now?”
Client: “Well it wasn’t as crowded as it is now. We used to live……” and they would fill up the rest of the time. 
 
My job became a lot more enjoyable after that since I didn’t have to deal with 15 minute blocks of silence anymore and people actually enjoyed my company. 
 
So you’re probably saying “Well how does that help me?”  Well I’ll show you.
 
Even now I still have go to “Primer” questions I like to pull out when I’m meeting strangers.  For example, in the elevator you have to ride for several floors with at least one stranger and it’s usually pretty weird just being in a moving box with someone else.  You know you should talk but you don’t know what to say.
 
If I’m in that situation, I like to ask something about what they’re wearing (Hey, that’s a really pretty necklace you’re wearing.  Where did you get it?” and follow it with “Is that your favorite store?”.  

Another favorite that is always good is asking about their lunch plans especially if they’re holding a to-go bag from somewhere.  “What’s for lunch?” and followed by “What would you recommend that’s nearby for lunch?” always get people to turn from strangers to a really elevator buddy.
 
One you can use regardless is “What’s on X floor?” where X is the floor they’re going to.  You can then ask them about what they do and how long they’ve done it.
 
  
You can use the Primer Questions I gave you above or you can make your own.  
 
How To make your own "Primer Questions:

Here is the formula to follow:
 
Step 1: Make sure the question can’t be answered in one word:
 
Bad Question: “Are you having lunch?”
Good Question: “What’s your favorite thing from that place?”
 
Step 2: Follow up with another question where their opinion is the center of attention:
 
Bad Follow Up Question: “My favorite sandwich is the tuna” (that’s not even a question!)
Good Follow Up Question: “Which is your favorite tuna sandwich in town? (Assuming they said tuna was their favorite sandwich)
 
Even better, I realized that by the 2nd or 3rd question, it was completely normal and natural to ask them what their name was and introduce myself. Insta-friend!
 
So the conversation would go something like this:
 
Me (Pointing to their Jack in the Box bag): What’s for lunch today?
 
Random Stranger in elevator: “Um, a Jumbo Jack. Nothing fancy”
 
Me (with a smile): Is that your favorite burger from there? Or which one is your favorite burger in the city?”
 
Random Stranger (that is starting to warm up to me): “Well I really like The Broken Spoke.  Their cheeseburger is really good but the fries are ok”
 
Me: “Really? By the way, I’m Ramon. What’s your name?”
               
Stranger who feels important that someone would ask them their opinion: “I’m Rob.  Nice to meet you”

Me: “So Rob, which place has the best fries?”
 
And so on and so forth.  That stranger became an acquaintance and possibly a friend in just a couple of minutes. 
 
Now that you know how to do it, you’re going to have to go out and practice it.  It’ll be a little weird at first but don’t get discouraged. 

You’ll notice that people will open up a lot faster than you thought.  Don’t worry if you completely fall flat on your face the first few times.  You will become more relaxed and quicker on your feet with questions the more practice you get under your belt. This works no matter if you’re on the spectrum or not. It works very well.
 
Let me know any struggles and/or success you have.  I’m eager to hear about them. 
 
Ramon
PS:I'm looking to attend a gala or fundraiser in the next month or so.  If you have one you're attending, let me know.  I'd love to support causes my readers believe in.