A complete guide to startup interviewing

In a behavioral interview, you will showcase your knowledge and functional skills by giving specific examples from your professional experience. That's it.

It's a fancy way of saying you're going to tell a series of stories that demonstrate a set of characteristics your interviewer is looking for. It sounds pretty straightforward, but telling good stories isn't easy. Crafting compelling stories on demand is really difficult.

Good storytelling takes practice and preparation. But how can you prepare if you don't know what they're going to ask?

Prepare stories, not specific answers

Most people prepare for interviews by doing a quick Google search for interview questions online and preparing to answer them.

While this can be helpful, you can never fully prepare for the near infinite number of questions an interviewer might ask.

You could also spend an enormous amount of time preparing for specific questions that you may never be asked and be totally unprepared for a few questions that you didn't happen to rehearse.

Instead of preparing answers to a specific set of questions, you should prepare a series of stories that targets what those interview questions are trying to uncover.

After analyzing thousands of interview questions, we can definitely say there are only a very small number of traits that all of those questions were fundamentally driving at.

If you can prepare a solid story for each of the following themes you will be able to handle almost any behavioral interview question.

Theme-based interview preparation

This section will go through an exhaustive list of behavioral interviewing themes as well as example questions to show how someone might pose a related question.

Let's get after it!


"Trust is the glue of life. It's the most essential ingredient in effective communication. It's the foundational principle that holds all relationships." - Stephen Covey

First, and probably the most basic skill that any startup is going to be looking for is stellar communication. In the fast-paced startup environment, being able to effectively sell your ideas, listen to and persuade teammates, have tough talks, and resolve conflicts is paramount. There are three main areas in communication:

1. Pitching/Selling

The ability to sell your ideas and persuade teammates to help you.

"Describe a time when you needed the cooperation of a peer who was hesitant. What did you do?"

2. Tough Talks

Can you be direct and honest during sensitive conversations?

"Tell me about a piece of direct feedback you gave to a co-worker or classmate? How did that person respond?"

3. Conflict Resolution

Can you be diplomatic when your teammates/managers/customers disagree with you? Especially when don't get your way in the end.

"Tell me about a time that you strongly disagreed with your manager on something you deemed to be very important to the business. What was it about and how did you handle it?"

"Give me an example of your most difficult customer interaction and how you worked through it. What was the outcome?"


"Creativity is just connecting things. When you ask creative people how they did something, they feel a little guilty because they didn't really do it, they just saw something. It seemed obvious to them after a while." - Steve Jobs

Startups need employees who live for the opportunity to pave their own path when they run into a roadblock using more established methods. Creativity is the lifeblood of startups. These questions will directly ask for something you have done that you consider creative, usually involving creative problem solving.

"Give me an example of a time when you came up with a creative solution to a problem"

Decision Making

"Wherever you see a successful business, someone once made a courageous decision." - Peter Drucker

Learning about how interviewees make decisions gives a vital glimpse into how their minds work. Employers need to know that you have exemplified sound decision making skills under various constraints in the past. There are five main areas here:

1. Trade-offs/Prioritization

Do you have good judgement about how to prioritize decision considerations?

"Have you ever had to balance the needs of a customer vs. the needs of the business. How did you handle this situation?"

2. Time constraints

Can you make good decisions under time pressure?

"Have you ever been working against a deadline and didn't have the time you needed to consider all options before making a decision? What was the time constraint? How did you make the decision?"

3. Under Information Constraints

Do you have a good intuitive judgement to make decisions without all the data?

"Have you ever made a decision where the data and research weren't enough to provide the right course and you had to use your judgement?"

4. With Lack of Authority/Guidance

Can you make good decisions when the boss is unavailable?

"Have you ever made an important business decision without talking to your manager first? How did it go?"

5. Sunk Cost

Do you know when to cut your losses?

"Have you ever been working towards a goal and you were nearly finished when you realized it was not actually the right goal? What did you do?"

Getting results

“There are two kinds of people, those who do the work and those who take the credit. Try to be in the first group; there is less competition there.” - Indira Gandhi

Can this candidate grind? Startup work isn't always glamorous and perseverance is key. Startups are looking for candidates who keep their eyes on the prize and get things done on time no matter what.

1. Follow Through

Can you persevere on long term initiatives without losing steam?

"Give me an example of an accomplishment that took a long time to achieve or that you are still working towards? How do stay focused?"

2. Under time Constraints

Can you get the job done under a tight schedule?

"Tell me about a time you were able to deliver a big project under a tight deadline? How did you make it happen?"

3. Unexpected Obstacles

Have you dealt with unexpected challenges in delivering results?

"Give me an example of a time that you had significant, unanticipated obstacles to work through in achieving a goal? What happened?"

4. Home Runs

When have you really hit it out of the park?

"Give me an example of a time that you not only met a goal but exceeded expectations? How?"

Going above and beyond the call of duty

“The question isn’t who is going to let me; it’s who is going to stop me.” - Ayn Rand

Startups need candidates that take initiative, push boundaries, and have a bias for action. In startups, there's no time to wait around be told what to do.

1. Having High Standards

Do you insist on doing things to the absolute best of your ability?

"Give me an example of a time that would not compromise on accomplishing an excellent result when others felt something was good enough."

2. Upset the Status Quo

Is this candidate unafraid to shake things up?

"Tell me about a time when you were unsatisfied with that status quo. How did you change it?"

3. Take Initiative

Will this candidate seize opportunities to improve the business, even without being asked to?

"Give me an example of a time when you took on a project outside your are of responsibility? What was the impact?"

Failure and Learning from Mistakes

"I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not trying.” - Jeff Bezos

Startups want employees who are comfortable with failure and more importantly, can learn from their failures. Everyone needs a good failure story.

"Tell me about a significant professional failure. What led to the failure and what did you learn from the situation?"

Intellectual Curiosity

"I have no special talent. I am only passionately curious." - Albert Einstein

Startups want to hire candidates that are naturally curious. Curiosity breeds innovation. Keeping an open mind and asking the right question can be the difference between startup success and failure.

"What is the most interesting thing you have learned on your own? Outside of work or school?"

Problem Solving

"Any time scientists disagree, it's because we have insufficient data. Then we can agree on what kind of data to get; we get the data; and the data solves the problem. Either I'm right, or you're right, or we're both wrong. And we move on. That kind of conflict resolution does not exist in politics or religion." - Neil DeGrasse Tyson

Startups want to know that you have the ability to diagnosis complex problems, break them down into bite-sized pieces, and tackle them effectively.

"Give me an example of a problem that you solved that required deep thought and analysis."


"It's not the lack of resources that cause failure, it's the lack of resourcefulness that causes failure." - Tony Robbins

Can you do more with less? Startups are strapped for time, money, and people power. Being frugal is invaluable.

"Tell me about a time that you had to get something done with half the resources you thought you needed to get it done."

Self Improvement

“Take criticism seriously, but not personally. If there is truth or merit in the criticism, try to learn from it. Otherwise, let it roll right off you.” - Hillary Clinton

Are you honest with yourself about your abilities and constantly looking to improve? Startups want employees that are constantly striving towards a better version of themselves.

"Tell me about a critical piece of feedback you received? What was it and how did you respond?"

"How are you making an effort to improve a certain skillset right now?"

Team Player

"The main ingredient of stardom is the rest of the team" - John Wooden

Are you a team player? Startups often operate exactly like a scrappy sports team, and they want to know that you're the type of person looking out for the good of the entire team.

1. Helpfulness/Selflessness

Do you lend a hand when you don't have any incentive to?

"Tell me about a time when you saw a colleague struggling and you helped them out. What was the situation?"

2. Boosting Team Morale

Are you a positive person who inspires others?

"Give me an example of a time when you contributed to boosting morale on your team. Why was morale low in the first place?"

3. Building Trust

Can you build trust with your teammates?

"Give me an example of how you have built trusting working relationships in the past"