This is Why You Failed Your Startup Interview

Understand the other side

Tim Chen
The Art of Business
2 min readJun 16, 2016

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Having hired for non-technical employees at an early-stage startup, I bucket candidates into two pools:

  1. Shotgunners: candidates who are looking for a job — any job.
  2. Serious: candidates who have an idea of what they want and want to learn more about the position.

Right off the bat, if you’re shotgunning your resume to various job listings, you’re going to get weeded out, fast. Desperation translates to “I don’t know what I want,” or “it’s going to be hard to keep me motivated and I might leave in 6 months.” No bueno.

Here are the 5 most common reasons why I rejected you:

  1. Do your homework on the company beforehand. The questions you ask DO matter and demonstrate your interest and knowledge. I want to see you actually put some work in beforehand.
  2. Network, network, network. A strong referral gets you to the top of the list. It won’t get you an automatic pass but will get you at least an interview. If my colleague is an all-star and he or she can vouch for you, then you are definitely going to be on my radar.
  3. Your story matters — if you can’t communicate clearly why your experiences led you to wanting to join that particular startup, you’re not going to get the job. I want to know why and how you made the choices you did; i.e. I want to learn about your thinking process.
  4. Understand how the role fits within the team — is the team looking for an analytical member or more generalists? Is the team looking to round out its skillset or focus deeply on one function? Knowing this beforehand could help you frame your pitch or understand if the role is right for you.
  5. Understand your search timeline and the company’s hiring timeline. Some Early stage startups hire on a rolling-basis but will pull the trigger if and when the right candidate comes around…at the right time. Understand how quickly the startup is looking to hire, and know beforehand how quickly you can move on your end. This is oftentimes a large obstacle for early-stage startups .

Doing the above won’t guarantee you the job. But understanding how the interviewer thinks will provide you tremendous advantages.

Conversely, here’s “How to Hire Entry-Level at an Early-Stage Startup”

If you enjoyed this read, please recommend ☺

Follow me on Twitter at @timothyxchen for more stories like this

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