Interviewing at a Startup: The 20% that Everyone Screws Up

I just sat through another shoot-me-in-the-face interview.

For the sake of all future interviewers and interviewees, I’m hoping to save the world from at least one less terrible interview with this post.

This blog post is going to cover the last 20% that will make or break your future job at your dream startup. I’m going to go out on a limb here and assume that you’ve taken care of the first 80%, that you’re a talented, hardworking and smart human being. I know, it’s like I read your mind or something.

Anyways. Back to the 20%.

I did some research on the articles out there right now about interviewing for a job at a start up. There’s a lot of advice on studying the product, knowing what you’ll contribute on day 0, and how to prepare your resume infographic or 2-minute video so that you stand out from the crowd.

I’m not going to say that stuff won’t work. It probably would. But again, we’re talking about the last 20% so you already have your foot in the door, passed a couple interviews and you’re about to close the deal at the “culture” or “team” interview. Congratulations on making it this far, but listen carefully.

The last 20% is strictly about 3 things:

  1. How do you think and make decisions?
  2. Do I like you as a person?
  3. Do I trust you?

These are 3 things that every interviewer is asking themselves when they’re making their decision about you.

How do you think and make decisions?

You need to show that regardless of what it is, a problem you’ve never seen, an impossible situation, that you have both the logic and the right priorities (which align with the company’s…) to figure it out.

You’ll likely be given impossible hypothetical situations and be asked to pick between two even more impossible answers. Don’t panic. They’re not trying to scare you, they just want to understand how you think, how you handle stress and pressure and at the end of the day, whether or not you’re a good person that will get shit done. Make a rational decision from an irrational scenario, don’t get distracted by how absurd the question is. Pick an answer and explain your logic, do not just pick an answer because they asked you to, if you really don’t know – tell them you don’t know. Honesty is the only policy at startups and trust me, they’ll know if you’re full of shit.

Do I like you as a person?

The sunday test is something we ask every team member after an interview. Every time. Would I want to come in on Sunday and work with this person alone? Because 1) it’s a plausible scenario and 2) sundays are reserved for company you actually enjoy.
You don’t have to be super funny or witty to be likeable. You can be quiet, introverted and still really likeable. If you’re normally a shy person, say so.
“I can be in my own head a lot, but that doesn’t mean I don’t like talking to other people, I just find it easy to get really deep into my work.”
is much better than
“If I have to come into work and actually talk to people everyday, well maybe I’ll reconsider… kidding.”
Showing a little self-awareness can go a very long way when you’re trying to come across as a genuine human being.

Do I trust you?

Most people believe that if an employer likes you, they’ll hire you. 

89% false. 

Lets take your college best friend who never went to class. Do you really like them? Yes. Would you trust them to take notes for you after a really crazy night of partying? Not in a million years. 

Like does not equal trust. Startups are modern day business warriors, the Davids of the corporate world. They’re looking for people who are willing to wake up at 4 am in the morning to put out a fire. You need to show each person that they can go to bed without worrying about waking up to 1000+ support tickets about the app being broken for the last 5 hours.

At the end of the interview, each potential coworker is going to ask themselves: Do I want to go to war with this person? Do I TRUST them to have my back when I’m about to be speared by a crazy Spartan man?

The only answer you can afford is yes.

If you’ve made it to the end of this post, you’re likely looking to or about to work at a startup – I wish you the best of luck because everyone should be able to wake up everyday, excited and happy to be doing something they love. I know I do. As a bonus, here are two likely behavioural questions that you should knock out of the park: 

“If you and Johnny get into a disagreement about how to build a product, how would you resolve the situation?”


“If given no instruction and you’re not allowed to ask anyone, how would you know what to work on next?”

The two ideal answers? Look at the data and talk to customers.

I’ll go into more detail about specific questions and answers in a later post.

Til then, let me know how I can help you get to where you want to go.

Moonshots @insidePN. Growth Alumna @OpenCareHQ. Member of @Growthhackers. Lifelong Student. Collector of Experiences. Can be seen writing on a good day.

Start typing and press Enter to search