Outfox Competitors Through Strategic Empathy
In 2008, the first time that statistician and professional poker player Nate Silver attempted to forecast presidential election results, he successfully predicted the outcome in 49 of 50 states. That track record led to Silver’s highly touted website, FiveThirtyEight (named after the 538 votes in the Electoral College), prompting rival political pollsters to obsess over Silver’s penchant for game theory and his special method of statistical modeling.
Silver’s most recent splashy effort, tying together the worlds of high-stakes poker, Silicon Valley, and political polling, is his book On the Edge: The Art of Risking Everything. It’s clear from the book that Silver, now in his mid-40s, finds his poker career more compelling than his pollster guru fame.
If you’re not a poker player, it’s hard to relate to Silver’s breathless retelling of Las Vegas moments when, for example, the No. 3 all-time poker winner faced the No. 8 player for a five-hour showdown.
More relevant to businesspeople is Chapter 13, “Inspiration: Thirteen Habits of Highly Successful Risk-Takers.” The third habit, “strategic empathy,” describes good risk-takers as being able to “put themselves in their opponent’s shoes in adversarial situations like poker or war.”
Silver emphasizes that he’s not talking about “showing love for an injured puppy,” but rather figuring out what your opponent needs and wants in that moment. He takes it a step further, noting that real winners, facing a superior competitor, ask themselves the pithy question, “How would I kick my own a–?”
Silver’s reference to war as fruitful terrain to use empathy as a weapon is borne out by recent research. In a 2023 paper, Dr. Allison Abbey, a professor at the U.S. Army War College, argued that military officers need to learn the difference between common notions of empathy such as compassion and sympathy, and empathy as “perspective taking”—that is, maintaining enough emotional distance to accurately assess the bases on which an opponent makes decisions.
Maintain enough emotional distance to accurately assess the bases on which an opponent makes decisions.
Abbey began her study, “Understanding the Adversary: Strategic Empathy and Perspective Taking in National Security,” with a quote from CNN journalist Jake Tapper, when he asked President Joe Biden in a 2022 interview, “Do you think Putin is a rational actor?”
Read more from this issue
According to Abbey and proponents of strategic empathy, Tapper should instead have asked commander in chief Biden, “What is important to Putin?” Abbey expanded the Putin analogy, adding these questions: “How does Putin define success and failure, and what time span does he talk about most? How have his successes, failures, and personal experiences shaped his views of risk?”
Fostering that kind of deep reflection of decision-making intelligence—how the enemy thinks and not simply standard “military intelligence” such as troop strength and combat locations—will make for smarter officers and better military outcomes, according to at least one branch of the U.S. military.
Although Nate Silver doesn’t cite the War College research, he liberally quotes from former U.S. national security advisor H.R. McMaster, an enthusiastic practitioner of strategic empathy. McMaster, a Ph.D. in American history and a highly decorated war tactician, told Silver that figuring out “what the war looks like to the enemy on the ground” is the starting point. “Treating your adversaries as intelligent,” according to McMaster, is at the very heart of successful military operations and, it would follow, a key to success in business, as in war.
If you’re a would-be entrepreneur trying to figure out whether your product or service will entice customers to pay more than the sum of your investment (and operating costs), the analysis starts, in the jargon of strategic empathy, by “reading the mind” of your most ruthless and risk-taking competitor.
Empathy experts, such as social psychologist William Ickes, call this “everyday mind reading,” described by Abbey as a “simple term for a complex process of inference that combines observation, prior knowledge, memory and reasoning, and self-regulation to understand and relate to others.” Or, as H.R. McMaster might put it, “Assume your competitor is smarter than you are … but only for now.”
