Rotman Management

The Art of Disruptive Conversations

“ONE DAY EARLY IN MY CAREER I was doing a trade, and something didn’t feel quite right about it.” Chris Clearfield, who was working for a financial firm on Wall Street at the time, told me. “It turned out I had lost on the order of tens of thousands of dollars, which wasn’t a huge amount of money for this firm, but is no small amount either.”

The thing is, it was something only Chris knew about. What would you do next? Pretend nothing happened and hope no one noticed? Blame someone else? “After a little while, I went to my manager and brought his attention to it.” Chris owned up to his mistake and then waited for the other shoe to drop. That’s not what happened.

“I received feedback from a number of very senior people in the firm who obviously had talked about what happened. They came up to me and said, ‘Hey, it’s so great you were open about your mistake.’ I have never received more praise in my life.” When Chris admitted his costly mistake and his bosses thanked him for it, both employee and employer came out

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