What a Board Game Can Teach a C.E.O.

Mr. Calkins is the chairman, president and C.E.O. of Appian, a software company in Reston, Va.

MY favorite activity during childhood was camping with my parents. We traveled up and down the California coast to little campgrounds and state parks, returning dozens of times to our favorites.

Also on these trips, I got my first taste of business, because my father would take me to properties he managed as a real estate developer. He’d explain how the parties negotiated, the quality of the materials, and the struggles he had with the architect. His was a high-stakes industry because, once you’re committed to a project, you’re on a fixed track, and if the commercial real estate market goes down, everyone knows you’re going to lose money.

I skipped first grade and was first in my class in high school. I’d take courses at lunchtime and belonged to three music organizations simultaneously. I love learning and I love a challenge. At Dartmouth, I took all the economics courses I could once I discovered how much I loved the subject. I won the prize as top economics graduate in my 1994 graduating class.

I was introverted as a child, and computers were a perfect playmate. As I grew, I felt that they were at the forefront of change. I decided that I wanted to be in a constantly changing field with enough dynamism that I could rise quickly. After college, I joined MicroStrategy, a software firm in Tysons Corner, Va., and rose to director of the Enterprise Product Group. I had always wanted to start my own company, but I didn’t think I had enough expertise initially, and I was right. I stayed five years and at 26 I walked away from millions in stock options to start Appian in 1999 with three friends.

Appian automates business processes. Our clients range from Amazon to the Pepco power company to the Department of Veterans Affairs. Enterprise Rent-A-Car uses our software in its Rideshare program for van pool commuters.

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Credit...Sorensen Institute

About five years ago, I wanted to take the business to the next level, so we obtained $10 million from a venture capital company. We’ve since extended our capabilities to mobile devices and the cloud.

For some years now, I’ve been the host of history nights at my home. We meet about once a month. Each session covers a single year. We started with 1900 and have discussed 71 years in sequence.

I love the diversity of the groups. College friends, C.E.O.’s, Congressional candidates and others with an interest in history take part. We debate what was the most important birth, death, invention, disaster, political event and so forth in the year. We seem to spend an inordinate amount of time on births and deaths.

In my free time, I enjoy playing and writing games. My board game Sekigahara has won three gaming awards. It’s a war game based on Japanese history.

For me, gaming is a means to sharpen my mental life and to increase my abilities. Running a technology organization is full of collaborative accomplishments but there’s very little individuality in it, as much as I seek it. I’m always looking for individual expression. At times I wish I were an artist because my life would be a series of creations.

Playing games has helped me in running Appian. Games are exercises in appraising your position and making decisions. I’m interested in that strength-building behavior. Two hours after you make a decision in a game, it leads to victory or defeat. If you play enough games, you get a sixth sense for the quality of your position. You can see victory or a debacle before it occurs. You intuit how the various factors will accumulate, which helps in making strategic choices in business.

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