Sitting on the curb drinking a slurpee

Justin Jackson skateboarding at the skatepark rocking Vision Streetwear t-shirts

This post is a part of this week’s Startup Edition: “How do you discover what people really want?”

I used to be a youth worker.

Our team’s mandate was to connect with at-risk teenagers, and figure out how we could improve their lives. The problem in youth work is that you can’t follow the traditional social work playbook: set-up a center, come up with programs, and have people come to you.

With teens, you have to go to where they’re at.

And so that’s what we did. We went to skateparks. But we wouldn’t show up, and be those goofy adults that stand on the sidelines in a button up shirt and khakis. We would actually skate with kids. Jeans, t-shirt, skateboard. We’d spend time. We’d stay until city’s night lamps turned on.

There was no judgment from us. Kids could be themselves. They could swear. We mostly just asked questions and listened. We were trying to figure out: “what’s it actually like to be a teenager in this town?”

Here’s what we discovered: adults don’t listen to teenagers. Most programs targeted at teens are laughably awful. It’s because bureaucrats have never sat with a kid on a curb, drank slurpees, and actually listened.

Surprisingly, what kids needed most was meaningful relationships with adults. That became the foundation of our program: having adults (parents, volunteers, staff) build meaningful relationships with kids.


Now I’m working in the software industry. That might seem like a funny career transition, but the foundations are still the same.

I’m working with real human beings, who need help.

I think the question isn’t: what do people want, but rather, what do people need(Amy Hoy recently reminded me of this)

To figure this out we use the same method: we need to spend time in their world.

That might mean asking them about their day on a phone call. Or going to visit them at their office. Or maybe even taking a customer out for lunch and just listening. Spending time in their world.

I remember visiting the office one of our users, and being blown away: a noisy cubicle farm, with outdated hardware and impossible deadlines. Those are your customers. They’re real human beings stuck in particular situations. They’re not thinking about how you chose Rails instead of Python, or flat design vs skeuomorphism. They’re just people with problems.

The way we discover those problems is hanging out with them. Email them some questions, and engage with their responses. Instead of spending your whole travel budget on conferences, pick a city where you have a bunch of customers and take them all for dinner (Freshbooks does this). Go to online forums, find people in your niche that need help. Spend time in their world.

The professional term for this is customer development. I don’t like it. Let’s just call it hanging out. Go hang out with customers, and just listen. Do that, and you’ll discover insights that will make your product, much, much better.

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Published on July 7, 2013