Startup Interviewing: The Fundamentals

Short and sweet

Having been on the other side of the table, there's nothing more annoying than a candidate rambling on for five minutes when one minute would have sufficed.

Taking more time does not mean you're giving a more complete answer, in fact, usually the opposite is true.

Listen completely first

You will naturally want to start thinking about potential answers while your interviewer is asking a question but resist that urge.

Questions generally come in multiple parts and if you start searching for an answer before your interviewer is done speaking you may miss something important.

Think before you speak

The most common error I see with green interviewers is that they are afraid of silence. It is absolutely fine to take a moment to think through a question and plan how you want to answer it before speaking.

Too often candidates jump straight into the answer and think out loud until they reach a conclusion they like. It's confusing for the interviewer and it makes it look like you lack clear thinking. Take a breath, think, then speak.

Keep it simple, stupid

Big words and complex sentence structure isn't going to fool an experience interviewer if the content and structure is lacking. In fact, the only thing worse than someone who doesn't know what they're talking about is someone who speaks like what they're saying is insightful when it isn't.

Save your profound language for late-night existential conversations with your friends. The simpler you can make your answer, the better.

Start high level

In keeping with the theme of short and simple, you should always start by answering a question in the clearest high level way possible. If interviewers want to know more, they can probe. The easiest way to confuse your interviewer is by jumping straight into the weeds.

Here's an example:

"What was your proudest accomplishment at your internship?"

Overly detailed answer

"What's my proudest accomplishment? Well when I joined the team it was just me and one other salesperson, Peter, under our sales manager. We had to do a lot of cold calling but it wasn't very successful. We were calling people and using a sales script but it wasn't very effective. I thought it was my inexperience that was the problem. One day I went off script because I was just having such an interesting conversation with this potential client. He owned this burger restaurant called Secret Sauce in Los Angeles, but he was having trouble getting his restaurant to show up in Google search results because there were so many other results for Secret Sauce. I realized that our SEO optimization service would help him start ranking in Google. Once I told him that he was more opening to our product and eventually signed. I realized that our script needed to start by getting potential clients to outline their business problems first before we started talking about our features. I rewrote the sales script and our lead conversions went up significantly!"

High level answer (better)

"In my sales internship at ChowNow, my proudest accomplishment was developing a new sales script that resulted in 25% more lead conversions. I’m happy to explain how I was able to accomplish that if you’d like."

They both eventually got around to the same information but one took significantly more time. The interviewers eyes were probably glazing over.

Sometimes an interviewer wants more context and sometimes they may be satisfied with the key takeaway and want to move on. Give the interviewer the option to make this decision by starting high level and then getting into more details if they probe.

Avoid company or industry specific references

Interviewee: "When I went to pitch the company to the portfolio fund committee they said the sell-side IR rep had not made a convincing case for why the multiple was so high, especially for that industry"

Interviewer: "Huh?"

Building on the theme of starting high level, you also want to keep what your audience knows in mind.

College students are notorious for jumping into an answer and assuming the interviewer knows everything about their past experience. As an interviewer, I have no idea how the company you worked for was organized and I certainly don't know your company-specific jargon.

This also applies if you're coming from a different industry. If you had a summer internship in finance at a bank and you're applying for a Product Analyst position at a tech startup, there's a good chance your interviewer doesn't know what EBITDA means and you should be accommodating.

There is an I in interviewing

Contrary to almost every other area of your life, talking about yourself is exactly what you're supposed to be doing when interviewing.

I'm always skeptical when candidates throw around the word "we" or "the team". "We implemented a new referral marketing process..."

The interviewer wants to know what you did specifically. Be upfront and clear about your individual contribution.

Non-professional experience is better than nothing

If you're stumped on a particular interview question and can't think of an answer from your professional life it is better than nothing to give an example from your academic, extra-curricular, or even personal life.

We think of our professional lives as a distinct area of our lives but in reality, the skills and experience from every area of our lives carry over into every other area.

If you're in college and you have limited professional experience, your interviewer knows that, and will understand if you dip into examples from your personal life to answer an interview question.

Interviewers are human

For the time being, interviewers are still human. As much as we would like to believe they are infallible and logical decision makers, they are not. If you happen to catch an interviewer on a bad day, it could affect your chances of making a favorable impression.

The interview is about more than just getting the right answers, it's about making a connection with your interviewer. People hire people they like.

You're an interviewer too

The job interview is a two-way street. It’s an opportunity for the interviewer to learn about your qualifications and for you to get a feel for the company culture and specifics of the role. As an interviewee, it is crucial that you do your homework and come prepared to an interview with creative questions.

Note of warning though, don't be that person that tries to turn the interview around. It's annoying. Questions are appropriate when the interviewer specifically gives you time to do so or if you need to clarify something about a question they have asked.

Interview with your dream company last

Just like anything else, practice makes perfect. No matter how much you prepare it takes some time to get used to the format of interviewing, it's very contrived and unnatural.

Take some practice runs by applying to roles at companies that you're interested in but where you may be overqualified. You should interview with a few different companies and get comfortable with the process before taking a shot at your dream job.

Communicate other interview deadlines

If you're in the process of interviewing with multiple companies at once, be sure that all the companies know about your interviewing status and are aware of any offer expiration dates from other companies. This is also a great way to get your interview process expedited.

Be nice to everyone

I hope this goes without saying, but from the moment you arrive at the office you are interviewing.

If the office receptionist thinks you're an asshole you can bet that information is going to get around. A thoughtful compliment about the office aesthetics wouldn't hurt either.

Dress to impress

Tech startups are notorious for their laid back office attire but on gameday, you should be dressed to impress. It shows that you respect the process and put in the effort. A full suit is probably overkill (depending on the industry and office culture) but you should look sharp and professional.