The voice on the other end of the line was heavy, gravely, and slow like someone who had just woken from a deep sleep. But it was the middle of the afternoon, and I knew he hadn't been sleeping. He probably wouldn't be sleeping for days. His wife's Toyota Rav4 had launched over the guardrail on an overpass and landed 100 feet below. She died at the scene.

And it was my job to talk to this man—this widower—about fucking insurance.

It was in conversations like that, the deepest and most painful moments of someone's life, that I realized the importance of listening. I'd always felt like I knew what listening meant. I'd always thought I did a good job of it. But when I was working in a call center in Tucson, AZ, investigating insurance claims, and speaking to people who had been injured or had family members injured or killed, I realized that there was another level of listening I hadn't quite learned.

When you are speaking with someone and you have an agenda, you tend to have a list of questions you want to get through. You want to check your boxes and move on. You may find yourself asking questions that don't make sense based on prior responses from the person you're speaking with. But you ask them because they are on your list of questions to ask. You may have been able to get away with it because people are usually polite and will give you the benefit of the doubt. You won't learn as much, but you'll get by. Now, try that with a grieving widow or someone who just lost their leg when a drunk driver ran a red light. The benefit of the doubt goes out the window when people are mourning and angry. You cannot simply check your boxes and hope for the best.

You have to LISTEN.

I spent five years working in an insurance claims call center, moving from the front-line phones to investigations to management. Those five years better prepared me to be a founder and a product person at startups than anything else in my career. Those five years taught me how to talk to people.

I hadn't considered it until recently, but I can now see the impact of my time in the call center in the customer conversations I have today. Now, it feels natural to start with a loose framework of questions and then immediately go off-script because of a response. It feels natural to go into a call without any agenda at all beyond listening and learning. I've even gone so far as to apply this to hiring. When conducting a job interview with a candidate, I often have just three questions prepared ahead of time:

1. Can you tell me about your work history and background?

2. Why do you want to work here?

3. What questions do you have for me?

Despite having just three simple questions, the job interviews I conduct blossom into a half-hour (or hour) of riffing off one response after another. You can only do this if you're paying attention. You can only do this if you're listening.

I mentor startups, and the most common problem I see in the way these very early-stage companies approach customer and market research is that they treat it like a chore, like it's some job a parent has handed out to them. That, or they treat it like a sales opportunity.

In the early stages of building a company, you don't know who your customers will be. You don't know what your final product will be. You don't even know the market. The only way to learn is to talk to people. Yet, so many people miss their opportunities because they aren't listening.

You don't need to go work in a call center for five years like I did to learn how to talk to people. You can do it through practice. But you have to embrace the process and treat it like an opportunity, not a chore. Just think, you get to go out and do all of this (hopefully) without ever having to interview the husband or wife of someone taken from the world too early.

Consider your life easier, and go out and talk to customers. And listen.