"I was sweating bullets."
Phillip Leslie is founder and CEO of ProOnGo, a Chicago company that makes expense-reporting software for smartphones. He took Craig Wortmann's Entrepreneurial Selling class at the University of Chicago in 2008.

I had just started ProOnGo when I took Craig's class. For the final exam, for want of a better word, he asked who my target market was and then found a principal at a prominent consulting firm. I walk into a conference room, and here is this guy who is like a dream come true in terms of my market. I dove right in, trying to be peppy and confident, starting with what we call a "purpose-benefit check." That's a way of earning trust within the first minute of a sales conversation, by showing you can create value for them and you're not going to waste their time. I said, "I've heard people at your firm are spending three hours filing expense reports every month. I've gotten that down to 30 minutes for a lot of firms, and I think we can do that for you. Is it worth 30 minutes of your time to see if there is any way we can help?"

He walked me through his expense-filing process, but he didn't give me any pain points to latch on to. So I used techniques from Craig's class to draw them out. He kept throwing curve balls. I would ask how he got his expense report filed for a trip he'd just taken, and he would start telling me how great the trip was. I had to keep drawing him back, because the clock was ticking. He gave me a barrage of objections. For example, he didn't think the camera on his phone was good enough to take pictures of the receipts. I said, "We'll lend you a phone with a better camera for two months."

I was sweating bullets. Because I was starting a real company, and if I couldn't do a good job in a meeting Craig staged for me, maybe I needed to rethink my value proposition. The stakes were much higher than just a grade.