Today my colleague, Dani, and I visited with high school freshmen at Comp Sci High to share a bit about what we do for work.

Obviously both of us work in the venture capital industry, but as far as industries go, I find this one to be particularly obtuse in explanations.

So rather than spend the hour long lunch period talking about ourselves, we asked ourselves: “What’s something important we can share or teach these students?” We landed on asking questions.

Questions breed curiosity. They help you learn. The answers feed you information and help you establish a growth mindset in life.

Of course all of this is easier said than done. But I often find, in the moment as somebody is explaining something, it takes a very sharp and quick-witted human to jump back in with an immediate question. After all, as the best VCs, recruiters, and journalists know, it’s never about the first question you ask. The art of question-asking is all in the follow-ups.

So Dani and I decided to teach this progressive art of question-asking. (This was a particularly convenient topic as she is the best question-asker I know.) Her idea was that we kick off with some questions, then break into groups and have each set of students answer personal (as opposed to professional) questions with each other. With each answer given, as the moderators, we would help lead and guide follow-up questions.

For this exercise we keep the prompt simple with three options adapted from the classic guide of questions you ask to fall in love:

  1. Would you want to be famous? Why or why not?
  2. What is a perfect day for you?
  3. What are you most grateful for?

As each question was asked in small groups, we encouraged the students to probe deeper. “He enjoys video games on your perfect day. What’s a question we can ask?” Or: “She wants to be a photographer one day but doesn’t want to be famous. What else are you curious about?”

After 30 minutes of these questions, I finally turned to my group and said, “Alright, I’ve been asking you questions. Now I’ll let you ask me some in return. Which question should I answer?”

“Number two!” they said.

So I described my perfect day, which included art, coffee, lunch, and reading. They all asked me follow-up questions: What kind of art? What do you like about it? Where do you go? Why?

Then I finally jumped into the career side of things.

“Okay,” I announced to my group. “In my day job I work at a venture capital firm. Let me tell you what that’s like.”

After a few minutes of explaining the complexities of the world of VC, I stopped and posed my real question. “What questions do you have?” I held my breath and waited.

A few beats passed.

So…have you given money to any ‘famous’ companies? I mean, anything we may have heard if?” asked one student. I racked my brain to think of the most relevant choice before answering.

“…have you heard of Amino?”

“Oh! Amino I know! Wow you guys helped make that possible? I browse graphic design ideas there sometimes!”

I exhaled deeply and smiled. We were on the right track.

“Wait…” interrupted another student. “So you said you could give a company $2 million, right?” I nodded. “But what if that’s not enough?”

I almost doubled over. Talk about an excellent question.

“REALLY good point. Many times it’s not enough. But if things are going well, and they are making more money or attracting more user subscribers, we might give them more money in a few years.”

“But does it ever happen that they don’t make more money? Sometimes companies don’t always…” another student trailed off.

“What do you mean?” I asked. “Go on.”

“No, it’s stupid…”

“I’m sure it’s not. What are you thinking?”

“I’m thinking about Toys R Us. Like, they shut down right? Why did that happen?”

I literally almost gave that kid a hug.

“That’s an amazing question,” I validated him. “We didn’t invest in Toys R Us specifically but one thing I think about is how expensive it must be for a company like that to run so many stores. Think about another place where you can buy toys, like Amazon. They can also sell millions of toys but they don’t have to pay to rent retail space or to pay sales people at the stores. So I imagine overall in the end, it’s easier for Amazon to make money selling toys than Toys R Us.”

“I have a question!” interrupted another kid. “Well, but it’s related to history class so I’m not sure it’s relevant…”

“Let’s hear it.” I encouraged.

“Well…we were learning about these things called monarchies that take over everything. Is that what you would say Amazon is?”

“YES.” I cried. “Except in business we call that a monopoly. And we don’t always like that because it can discourage innovation.”

“And creative ideas” interjected the artist.

“And that’s why we try to invest in companies that can do something totally different. Or companies that can maybe take down a part of that in some way.”

Let me tell you, these kids were rapt. By the end of this conversation, we were talking about pricing strategy, hardware and software costs, and privacy and security online. Their questions blew me away.

It’s hard to ask easy questions. But with a little warm up and practice, you’d be surprised what can come out of a good conversation.

We left the session with an encouragement to keep doing what they did today: Ask one more question than they would otherwise. I hope it sticks.

VP @ BolsterTalent, alum of @USV, @StackOverflow and @NorthwesternU, board member at @CompSci_High and @NUalumni, co-founder of #BeyondCodingNYC