When I was in my twenties at some point I realized that I was fundamentally terrible at small talk. The uncomfortable idea of meeting someone new and having nothing to say lived so large in my mind that I mostly avoided it all together. At the time I’d rather have been under the table than across it from someone searching for common ground.

However, as a photographer in Boston I was starting to get assignments that required me to go out into the world and connect with people in a meaningful way to take their portraits. Magazines started hiring me to take photos of politicians, and business people, and chefs. While companies started hiring me to take professional headshots of their employees.

I knew that there was a skill I lacked and that I needed to learn it, fast. I’d go to parties and practice being interesting or funny, but it didn’t really seem to solve my problem.

Then I started asking questions. A lot of questions. What’s your story? How’s your Friday going? I like that shirt where did you get it? Where are you from? What are you drinking? Really raining out there! How ‘bout those Patriots? Just kidding I’m not a sports guy. Where are you from? Did I already ask that? Pretty much anything I could ask people to keep the spotlight off me and keep the conversation going. As soon as the conversation hit a lull, I’d ask a new question.

It turns out people really like talking about themselves, but I also learned that I really liked it too. By asking random questions I would end up in places so far from where we started but would learn so much along the way. I’d start by asking someone about some random thing and twenty minutes later we’d be talking about our shared love of folk music, or shiny things, or pie. It went from practicing a skill to a genuine interest in knowing more about the people around me.

It seems kind of silly to say that I needed to learn to ask people questions but I really did, and learning that skill changed everything for me as a portrait photographer. People would start to forget about the photographer, the lights, the camera, posing this way or that, and I started getting much more natural reactions from people.

These days most of the people in my life know me as someone who is so easy to talk to. Some of my newer friends say it’s the first thing they noticed. It’s become a part of my life but it wasn’t always that way.

Next time you see me at a party around Boston ask me about the weather. Who knows where we’ll end up. (In the mean time check out some corporate portraits I shot for OTJ).