Why It's Hard To Predict Success

How perceptions distort our view of who might be good, the importance of having a fast and objective feedback loop, and my new initiative for 2023

Many years ago, we hired two new customer success managers who couldn’t be more different. “Taylor” sailed through the interview process. He was charming and well-liked by everyone he met. “Pretty sure that guy will be running the whole organization in less than a year,” one exec said to me.

“Amelia” on the other hand, couldn’t have been more different. It was surprisingly hard to describe her personality. Because Amelia was super low key. She didn’t say much, and seemed to prefer hanging out in the background listening to everyone else talk. “Amelia seems oddly quiet for someone in a customer facing role,” one colleague remarked. “Not sure how long she’ll last here.”

That’s because our startup was hands down the most unforgiving work environment I have ever worked for. If you weren’t good at your job, you’d be shown the door quickly. I’d been working there for less than a year, but in that time saw more employee departures than I ever did at any other job.

And I used to work in Biglaw!

That context about the atmosphere helps explain how this narrative—that Taylor would do well, and Amelia would struggle—took hold quickly. Among everyone. High turnover would lead to fast promotion opportunities. Taylor was the golden child—and it made sense that he would glide his way up the org chart. And Amelia, who seemed like she might underperform—would struggle to hold on to her job. Right?

Wrong. Amelia ended up outperforming Taylor by a mile. Within a year, Taylor was on his way out of the company. And by then Amelia became one of the company’s most valuable employees, beloved by customers, her peers, and the execs.

Watching how this all played out helped shaped the way I view the corporate world today.