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Which headline are you more likely to click on? Headline A: “Stocks Plunge Amid Global Fears.” Headline B: “Markets Decline Today.” Online publications frequently test headline options like this in what’s called an A/B test. In this case, a publication shows headline A to half of its readers, headline B to the other half, then measures which receives more clicks. Marketers have long used A/B tests to determine what drives engagement. Generative AI is now positioned to accelerate the process, automating the tests and iterating rapidly on headlines—or any other content—to optimize outcomes like click-through rates. But sometimes, according to Yale SOM’s Tong Wang and K. Sudhir, simply knowing what works and shaping content accordingly leads to bad outcomes.