Practicing Your Interviewing Skills With Strangers

It’s important to practice interviewing because it’s a skill that’s different from just having a conversation. Asking open questions, not trying to fill silence with more ideas, finding the right balance between listening and sharing – all these things are a learned skill. And learning often means making mistakes.

But how do we make mistakes without putting our projects at risk?

Last summer I read a blog-turned-book titled Talk to Strangers. The book is a collection of autobiographical posts by an anonymous  author who goes by “People Person”. The author is a shy, lonely man in Los Angeles who realizes that a few years out of university, he has no close friends and feels entirely lonely in the big city.

What he does next is pretty extraordinary. Even though he describes himself as nothing short of an antisocial a-hole, he decides to make friends by initiating conversations with complete strangers on a daily basis. What follows is a collection of hilarious, touching, and sometimes embarrassing stories that eventually land him in a completely different life to the initial lonely planet he lived on.

His successes and failures (and there are plenty of failures), made me realize this might be the most convenient, low-investment way to practice interviewing. Just like People Person, you can do this anywhere: in line at the store, on the bus, on a flight. Anywhere where you have to be in the company of people for a few minutes or longer. Be warned, however: apparently elevators are a poor place to start.

Mission: Find out one meaningful thing about a stranger

There are many detailed resources on the skills you need for effective interviewing. For these short encounters, I would suggest focusing on one thing only: finding out something meaningful about the other person. People are great at making small talk but we know that design work is best aided by meaningful insights about people, like motivations, philosophies, and attitudes. How do we find someone’s motivation? We start with a meaningful action that was driven by it.

On a flight from NYC to London, I decided to find out how the people I met chose where they lived. I started with a simple question: Where are you from? Here are some of the stories I heard.

The hair stylist who doesn’t like NYC. The woman who sat next to me on the flight was from Poland but married an American and moved to New York with him. She left on a bridal visa, had a child, and they got divorced since then. She doesn’t like NYC but is a hair stylist and doesn’t want to go through getting a license in a different state. She also loves her client base. When her daughter is old enough, she will definitely move to avoid the NYC school system.

This story is a bit more detailed than your usual small talk. It goes to show that most people are pretty happy when asked about their lives or what they do for a living. It didn’t all come from “where are you from?” I had to ask some follow up questions:

  • How did you end up here?
  • Do you like it?
  • Do yo think you’ll stay here forever?
  • Where would you move next? Why aren’t you moving there?

The Flight Attendant Who’s Never Moved. When I got up to use the rest room, I saw that the flight attendant standing near the lavatories had a band-aid on his forehand. I asked what happened and whether he’s having a good break (he wasn’t on a break!). Then whether he was from London. He was, in fact, born and raised in Glasgow and still lives there because he travels a lot and loves the feeling of a stable home base.

Here’s the entire inventory of questions I asked him:

  • Are you from London?
  • How long have you lived in Glasgow?
  • Why have you decided to stay in one place?

I didn’t get as much out of this conversation. It was pretty ambitious to ask several open ended questions while he was rushing through serving the morning tea. Eventually, he seemed to be somewhere between irritated and busy. It wasn’t the best timing.

The Student Who Has Friends Everywhere. While eating lunch at the airport, a young woman asked to sit next to me because there were no other seats available. I agreed and immediately asked to borrow her phone charger even though I had one (you gotta do what you gotta do). She politely declined and explained that it is her lifeline for the next several hours since she has two 12 hour connections. I had to ask where she was going.

She turned out to be an American college student who wanted to travel so badly that she postponed her graduation to do it (talk about a meaningful action). As a rule, she chooses to travel to places where she already knows people. What is even more impressive is how easily she opened up and began talking about her life. It took perhaps two minutes.

Mission Accomplished

This experiment was useful but also fun. It felt a little less foreign and lonely to spend ten hours in airport halls. I got to share a bit about myself and spend a lot of time listening to people’s stories. Best of all, even when it didn’t work out – I could politely get back to my reading and try again later.

What’s important here is how much more I could learn about them beyond just demographics. These were people who based their life decisions on their family, who were desperate for a constant place to call home, and who put aside a normal life plan for new experiences. Now, that’s something we can work with when thinking about personas, user journeys, scenarios, and how to plan features.