I learned about empathy at 80 miles an hour, on a highway between Columbus and Cincinnati back in 2010. I had hitched a ride with one of our sales guys and he'd teed up an endless series of conference calls for the trip. So with one hand on the wheel and the other on his phone, he worked his calendar, dialing the conference number, then flipping back really quick to his calendar for the passcode. But of course he could only remember half the passcode at a time, so I watched him go "7412, 7412" and he would type it in and then he would flip back to the calendar for the other half: "316, 316." All the while weaving between semi-trailers. I just about lost my mind.

That night, I went to my hotel room and in three hours I wrote an app that used regular expressions to scrape your calendar for conference calls, get all the bridge information--the 800 number plus the passcode--put it into a single screen, and allow you to dial in with a single touch. I called it Beamer. And it was the hottest thing that I ever wrote and my fellow Apple employees freaking loved it. Why? Because I was sensitive to what the salesperson was going through, to what we've all been through. I saw his pain. (I felt it, actually, like my head going through a windshield.) Steve Jobs baked empathy into Apple's DNA and this app was all about being empathetic to the end user.

Empathy Begins at Home

My current company suffered from an empathy problem a while back. Instead of figuring out how to give customers what they need (namely, something that helps them sell stuff), we were too focused on building something amazing, and assumed everyone would be powerless to resist it. So we created something shiny and gorgeous and trusted that the rest would take care of itself. Then we got out in the real world.

Early on, we had identified realtors as an obvious (and massive) use case for our product, which is a newfangled kind of presentation software. So we set up meetings with some big agencies, and Scrollmotion's co-founder, Josh Koppel, who puts on one hell of a magic show, wowed them with all our features and how shiny and fabulous the thing looks on an iPad. What buyer could say no to a split-level ranch that looked so damn fine? The realtors nodded their heads. Then they said, "Have you guys heard of Zillow? Redfin, maybe?"

Walk in the Other Guy's Shoes

We'd made a classic mistake. We'd confused our needs--showing off our work and getting them to pay us for it--with theirs. In other words, they didn't give a rat's ass how pretty something looked on an iPad; tell them how they move more merch and you'll get their attention. Software, after all, is supposed to make your life easier, better.

So we started listening more carefully. And we started hearing a new message: Our software didn't make sense for listings, but it made a ton of sense for the initial, crucial process of winning a listing--the presentation realtors make to sellers to convince them to become a client in the first place.

Lack Empathy? Buy It

So we went back and retooled our whole pitch around the realtor, not the property. And because we not only empathized with the realtor but also helped her empathize with the seller, the whole narrative arc of our pitch suddenly worked for them. And for us. As IDEO's David Kelley once put it, "Deep empathy for people makes our observations powerful sources of inspiration."

That experience taught us a critical lesson: Don't guess. Learn. And the way we learned was by bringing actual expertise into the company in the form of what I call an ambassador--someone from inside the world we were trying to enter; people who have real knowledge and real connections who can essentially bring you to those places intellectually and emotionally. Since then, we've brought in ambassadors in real estate, pharmaceutical sales and enterprise sales. They don't have to be full-time employees. But they help you internalize the needs of the people you're trying to win over, make you feel their pain. And as you learn, you hone your pitch. You find a language that describes their world. And eventually, with a little luck, you become part of it.