I concluded my regularly scheduled meetings with Karrie Kohlhaas this evening. As always, there was much ado and many great questions raised for me to consider.
But my favorite question of the night goes to the imaginary businessman that Karrie impersonated, who asked, “Well, this looks like a good enough idea I suppose, but let’s be honest: you’re 27, you’ve never done this before, so what the hell do you know about anything?”
She got me. I think I’m cool no matter the line of questioning, but it was a little startling to pretend as though I were being asked that question in real time. In that sort of situation, even the smallest pause before your answer can be interpreted as doubt. If you do pause, the answer you give must answer the original question and reassert your confidence. I think the trick to answering “tough questions” like this is to know they are coming, and when they do, to give a straightforward answer that belies confidence.
When I think about how to go about answering tough questions with confidence, I think back to the first couple seasons of The Apprentice (before I re-learned to ignore Trump). With a few exceptions (ahem, “Street Smart” Chris), I was consistently impressed by how well each of those contestants could quickly and cooly respond to intense personal attacks by each other and Trump himself. As season 3 Alex said, in one of my all-time favorite interviews,
“People know how to argue more or less from their upbringing but the biggest thing being an attorney did was to prepare me to go into the boardroom and not take arguments personally.”
I thus engage the process of assimilating quick logic robot.