Jonathan’s modus operandi is to ask candidates to reflect on a past mistake. In the early 2000s, he used to ask candidates “What big trend did you miss about the Internet in 1996? What did you get right, and what did you get wrong?” It’s a deceptively tricky question. It makes candidates define what they expected, link it to what they observed and explore the revelations, and forces them to admit a mistake—and not in the lame, my-biggest-weakness-is-that-I’m-a-perfectionist sort of way. It’s impossible to fake the answer.
