A 51-year-old chief marketing officer from Chicago came to me excited about a rapidly growing company she had been researching. She had built a successful corporate career by trusting her instincts and making decisive judgments. Over time, she consumed every positive article she could find, followed bullish analysts online, and listened to podcasts that reinforced her conviction. Whenever someone raised concerns about competition or valuation, she dismissed those views almost immediately.
As our discussions progressed, it became apparent that she had become emotionally invested in the story long before investing any money. The company represented innovation, vision, and future success. Criticism felt like an attack on an idea she already believed in. Rather than challenging her directly, I encouraged her to devote equal time to the strongest bearish arguments. Initially, she resisted because she found negative opinions uncomfortable. But gradually, she began engaging with opposing viewpoints.
Over time, she developed a more nuanced perspective. She still invested in the company, but with more realistic expectations and an appropriate position size. Later, she told me that the exercise improved not only her investing decisions but also her leadership style at work. Confirmation bias thrives when we only listen to information that supports what we already believe. Some of the best decisions begin when we’re willing to seriously consider the possibility that we might be wrong.
