On the surface, Zocdoc seemed like the ideal startup: solid funding, a seaworthy business model, and the requisite daycare provisions techies-who-wish-they-were-still-in-college have come to demand from an employer (free lunch, play area, unlimited diaper changes, etc.). That said, it is unfortunate the company leadership leaves much to be desired in terms of personality and amiability. The first round of interviews were standard meet-and-greet affairs, encompassing fit, skills assessment, etc. I met with the CTO during this initial round. His questions were focused on testing my technical knowledge and verifying skills. Like a previous reviewer, I’m not going to disclose his questions;) All I will say is make sure you know your stuff. I met with several people during the second round of interviews. The interviews focused on assessing fit and did not touch upon technical skills. Highlights: Director of People/HR: Make sure to prepare questions to ask, because he will not bother to prepare ANY questions for you (aside from asking “Do you have any questions for me?” ten seconds after the introductory handshake). This interview was like a bad date where you ask all the questions and the other person does ALL the talking. CEO: Presuming that your patents of nobility are in order, you will ultimately have the displeasure of meeting this prickly, arrogant, unsmiling man. Did you graduate from an elite university with good grades? Did you work at top companies everyone has heard of? Of course you did…but no matter! This unsavory misanthrope will delight at disparaging your background and insulting your intelligence. Brace yourself for put-downs framed as questions. For example, in response to hearing my SAT score, he asked “How did YOU ever get into THAT college?” And he actually waited for an answer(!). After a couple of these zingers I realized that this interview had only two purposes. First and foremost, in classic power-playing b-school tradition, the point was to highlight my clear inferiority before this thoroughbred executive specimen who sat before me. Second, he wanted to assess my pedigree (high quality, of course), as if I was applying to join a golf club. This CEO-cum-glorified-college-admissions-officer only cared about my test scores, where I attended college, and my GPA, which I think reveals a lot about the company culture. It was clear that accomplishments in the real world did not matter to him (similar to how client results don’t matter at Mckinsey-type consulting companies, but I digress…). In short, if arrogance and self-importance could inflate blimps, ZocDoc’s CEO could singlehandedly launch a thousand Hindenbergs. The fact that he lists his prep school in his bio should have been a tip off. COO: Like the CEO, but very intelligent. He posed a fair, straightforward business problem, though he seemed irritated when I asked him to clarify one point, and he grew impatient when I asked to use the whiteboard for one minute to outline my thoughts. In any event, ask him to tell you about the chip on his shoulder as a result of not working in his field of training. It’s an interesting and irrelevant story that serves to underscore his greatness. Don’t forget to clap politely at the end;) A company’s culture is a reflection of its leadership. If your dream is to spend long hours working at a startup run by bloated, arrogant grouches, then ZocDoc is your kind of paradise. I really didn’t intend for this review to be as negative as it has turned out, but I think future interviewees deserve a fair warning.