Questions You Should Be Asking

After interviewing of founders, bankers, lawyers, engineers, and execs in every industry, one thing became clear:

Everyone has a favorite question.

In every interview, I ask “Whats a question you love to be asked (or love asking others)?”

Below is a collection of the top hits, organized so you can best prepare for your next coffee chat or introspective moment.

The Rundown:

"What’s something you wish you knew when you were in my position?” (Betsy Bass, Litigation Paralegal, Sullivan & Cromwell LLP)

“Of all the things you could be doing, why this?” (Paul Vann, Co-Founder, Validia)

“What should I have asked that I didn’t?” (Melanie Seidner, VP of Digital Storefronts, Warner Bros)

“If you could give a TED talk on anything, what would it be about?” (Matt Fickel, Risk Management Lead, U.S. Navy)

“What’s something not a lot of people know about you?” (Shelby Brachmann, Founder, Funky Fads)

“What’s a hobby you’ve spend time and energy getting better at?” (Doug Etts, Patent Litigation Associate, Fenwick & West)

When I first thought of Hoo You Know, The Foundry — UVA’s free startup space above Coupes — helped me figure out what to do next.

They offer advising from seasoned founders, resources, and mentorship whether you have a 3 a.m. idea or are scaling a business. They helped get me started — and they can help you too.

Got a startup idea? Book A 30-Minute Advising Meeting

"What do you bring to a team that no else will bring?” (Adam Cohn, CFO & EVP, CNN)

“Are you hunting antelope, or chasing field mice?” (Jared Tewodros, Software Engineer, Meta) ← click here to understand this question

“What are you most proud of, and what are you least proud of?” (Todd Albert, Surgeon-in-Chief Emeritus, Hospital for Special Surgery)

“What do you see our of yourself in this role?” (Ryan Eagan, Investment Banking Analyst, Lazard)

“Tell me about your soul.” (Romeo Sarmiento, Veteran / IB Analyst, U.S Marines / KippsDeSanto & Co)

Reading is great — but putting yourself out there, meeting new people, and finding opportunities is what this is all about.

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