Questions Not Asked

“No one has ever asked me that before” — that’s what i heard last night from a job applicant and this morning over breakfast with a prominent venture capitalist. Here are the questions:

To job applicant:
> Among all your accomplishments, what’s something you’re especially proud of and why?
[note: this is my standard first interview question because it tells me a lot about what you value]

To VC:
> What have been your most contrarian investments?

Seemed like pretty basic questions to me. Maybe they were just buttering me up 🙂