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5 Tips To Nail Behavioral Questions In Your Next Startup Job Interview

Interview Guides
Nearly every interview cycle includes behavioral questions to assess your communication, management, and teamwork skills. We spoke with seasoned recruiters, exceptional top talent, and Contrary's portfolio founders to put together a list of tactics to help you prepare for behavioral questions.

1. Know your story

”Tell me about yourself” is almost always the first question. In 60 seconds, share a high level overview of your experience. We recommend doing so in chronological order so it’s easy for the interviewer to follow, and finish with how that leads you to speak with the company. If your experience includes companies that aren’t easily recognizable (i.e. an early stage startup), be sure to include 1-2 sentences on what the company does and the relative size of the company. You won’t have time to share every detail but offer to expand with “happy to elaborate if you have questions”.
Q: Tell me about yourself.
A: My name is Jane Smith. I love connecting and helping people share resources. I developed this passion 2 years ago when I was a product manager at a venture studio that launched a company every single month. There, I built several marketplace startups including a platform that connected over 5,000 fitness instructors with students.
From that experience, I realized that I wanted to continue building marketplaces to increase access to education and resources so I joined a 3D laser printing company where I currently work on building a 2-sided marketplace connecting 3D laser printer owners with prospective customers.
I'm excited to potentially help launch a new marketplace at —insert company name—. Happy to elaborate on anything I just mentioned!

2. Know why you’re passionate about the company

”I saw the job posted on Startup Search” or “my friends love it there” won’t fly. Early stage startups aren't just looking for people who check a set of boxes. They want people who understand and believe in the product and mission. Have a compelling story for what makes you passionate about the company and be sure to research the company’s story, founders, and culture.
Q: Why are you interested in our company?
A: I've had experience launching a service marketplace at the venture studio and also scaling a more mature one with the 3D laser printer company. I'm excited about the opportunity to spearhead the new marketplace at your company. In addition, I’ve chatted with A, B, and C at your company and they mentioned X aspects of the company's culture, and that really resonates with me.

3. Have a story in mind for something you’re proud of

Interviewers want to understand your accomplishments and envision how your skills can contribute to their company. Pick a story that highlights your strengths and individual contributions. If you have quantitative results, even better (i.e. “this feature resulted in +5% increase in conversion”).
Q: What accomplishment are you most proud of?
A: My proudest accomplishment is launching the virtual fitness marketplace within a month at the venture studio. Coming in, I had a hypothesis that gyms that had shut down due to covid would increase demand for online fitness. From there, I conducted customer interviews with fitness instructors and regular gym attendees to validate whether this opportunity was worth pursuing. After receiving converging positive responses, I manually posted fitness classes online and matched them to interested students. Eventually, I worked with a team of engineers to transform this pilot into a product that now helps more than 5000 fitness instructors teach every day.

4. Have a story for a time you made a mistake

No one expects you to be perfect. However, having the awareness to understand where you’ve made a mistake and how you’ve moved forward reflects your seniority. For example, for product managers, this could be a feature you advocated for that didn’t have intended results. Why did you have conviction when you advocated for it? What did you do when the results weren’t optimal? What did you learn and how will you apply those learnings to the next feature?
Q: Tell me about a time you failed?
A: At the 3D laser printer company, I designed a new section of 3D laser printer classes for advanced printers. My reasoning was that our experienced laser printer owners would be more likely to purchase classes given that many are looking to to start part-time laser cutting businesses. However, after putting together a pilot of advance printing class, we found that the traction was really poor. After chatting with our laser printer instructors and members of our laser printer community, I realized that the barrier for laser printer owners to starting their business wasn’t lack of technical printing skills but instead lack of marketing and operational knowledge. To improve, I designed a new line of classes around laser cutting business creation which now out performs our beginner classes.

5. Be ready to ask questions

Many interviewers will dock points if a candidate doesn’t have any questions because it shows lack of interest, preparation, and/or understanding. Here’s a list of 23 questions & best practices to ask.

Looking for additional resources? These are resources geared towards startup founders and hiring managers. Get prepared by understanding what they’re looking for.
  1. 40 Favorite Interview Questions from Some of the Sharpest Folks We Know (from First Round)
    All the questions come from leaders in the tech industry, and the article is split into different sets of questions, each assessing different things. Check out the "Questions on Their Fit for the Role" section in particular.
  2. What to Ask When Interviewing Your First Employees (from Gusto)
    A guide with five specific questions to assess key traits for startup employees: resourcefulness, adaptability, what motivates them, accountability, and customer focus.
  3. Nontechnical Interviewing (from Holloway)
    A section from the Holloway Guide to interviewing. Has a long set of sample questions to ask to assess different areas. Note their difference between "values alignment" and "cultural fit".
  4. *Whom Should You Hire at a Startup? (Attitude Over Aptitude)* (from Both Sides)
    A great piece by Mark Suster, an investor and successful founder with multiple acquisitions. He describes the key things he looks for in startup job candidates.

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