23 Questions And Best Practices For Your Next Startup Job Interview

We spoke with seasoned recruiters, exceptional top talent, and Contrary's portfolio founders to put together a list of questions to ask during your next job interview to better understand the role, position yourself as a strong candidate, sound prepared and land the job.

Questions to ask about the role

These are positive signal questions that show recruiters your thoughtfulness and help you understand the role you're interviewing for.

Role Expectations

1. What would success look like in the first 90 days?
2. What characteristics are needed to be successful in this role and company?
3. To the hiring manager: How would you describe your management style?
4. If successful, what does my career progression & growth path look like?

Role Work

1. What are the biggest needs at the company today?
2. What are some of the first projects I'd work on?
3. What other functions and stakeholders would I be working closely with?
4. Why did you choose Company X?
5. How have you continued learning to become better at (product, engineering, design, etc.)?

Compensation

1. What is the expected salary range for this role?

Questions to ask about the company

These questions will help you decide if the company is on a path that is worth joining and exciting on a personal level. Think like an investor, giving up your time instead of money.

Company Growth

1. For smaller companies (or those in stealth mode): Who are your main competitors and what's your most significant competitive advantage?
2. What is the business model and what do unit economics look like?
3. What's the vision for the next 5 to 10 years? What are the company's growth plans for the next year?
4. To founders: what keeps you up at night?

Company Operations

1. What is the culture of ownership and autonomy like?
2. What metrics do leadership look at to assess company-wide success?
3. Given the pandemic, how does the company approach in-office and remote work?

Company Culture

1. How would you characterize the company culture?
2. What do company all-hands look like? How transparent is leadership?
3. How do you think about scaling the company in the context of diversity & inclusion?
4. What makes someone unfit for the team?

Time Management

1. When you think the interview may run over: I want to be respectful of your time, do you have a hard stop? Any chance I could email you a few follow-up questions?
2. Best Practice: Know how long your interview is and tailor your answers accordingly. For a 20 minute interview, you likely can't give long answers per question. Instead, answer in 60-90 seconds and then follow up with "feel free to ask me to dive deeper into any part of that".

These questions and best practices will help you better understand the expectations for your role, who you'll be working with, and whether or not this is a company worth spending your time with.




Recruiting for top startups where online information may be sparse makes it difficult to assess which company best fits your needs. At Startup Search, we work with the Contrary team to help you discover startups with exceptional teams in fast-growing industries.