23 Questions & Best Practices for Your Next Startup Job Interview

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

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Table of Contents

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?

Successful candidates show that they can hit the ground running on Day 1. Asking about what your immediate impact could be in the first 90 days shows eagerness to add value quickly.

2. What characteristics are needed to be successful in this role and company?

Some roles require strong leadership skills; others focus on organization and communication. Even if the interviewer doesn't ask about your strengths and weaknesses, leverage this to understand if the role's aligned with you.

3. To the hiring manager: How would you describe your management style?

Some managers are very hands-on, while others like to give you autonomy and visibility while supporting you behind the scenes. Know what you want from your manager to evaluate if the team is right for you.

4. If successful, what does my career progression & growth path look like?

Hiring managers don't just want an ambitious candidate, they want a successful teammate that can hustle alongside them. Showing that you care about your career growth reflects your dedication and helps you understand what opportunities are ahead.

Role Work

1. What are the biggest needs at the company today?

Understand and express enthusiasm in the challenges that are important to the company and think about whether those challenges are exciting for you to dedicate time towards.

2. What are some of the first projects I'd work on?

You're already thinking about what you'd do once you start and helping the team see you in that position too.

3. What other functions and stakeholders would I be working closely with?

No role works alone. Asking who you'd be working with shows that you are familiar with working cross-functionally and gives you an opportunity to understand which teams drive the company culture.

4. Why did you choose Company X?

Most candidates are interviewing at more than one company, and the job search process goes both ways (they want to impress you too!). Asking why the interviewer chose the company gives you insight into why this opportunity may be better than the rest.

5. How have you continued learning to become better at (product, engineering, design, etc.)?

Every ambitious person wants to keep learning. This can be structured through events (i.e. tech talks on engineering teams), code reviews, feedback sessions, and more. Asking this question shows that you will put in the work to improve — becoming an increasingly more valuable asset to the team.


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

This is great to ask the recruiter early, especially if they don't volunteer the information. It's better to get this out of the way in case there isn't alignment on salary to avoid wasting their time and yours. While many find this question to be uncomfortable, it's often a deal-breaker when deciding to join.

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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?

Many early-stage companies have very little information online, making this a fair question that shows you want to learn more about the broader competitive landscape. For larger companies with abundant information online, do your homework!

2. What is the business model and what do unit economics look like?

While venture-backed companies aren't always looking to turn a profit quickly, understanding the business model and a path to profitability is critical to the company's long-term success. If this information is online, be prepared and do your homework!

3. What's the vision for the next 5 to 10 years? What are the company's growth plans for the next year?

You want to grow with the company, which means the company needs to grow too. Taking time to understand the company vision shows that you are invested in the company beyond day-to-day work and team-level decisions.

4. To founders: what keeps you up at night?

This is purposefully a very open-ended question and shows you want to know not only about the highlights but also potential lowlights and concerns.

Company Operations

1. What is the culture of ownership and autonomy like?

For more junior roles, ownership and autonomy may be for a smaller project or task. For senior roles, ownership and autonomy become a higher priority requirement. If you want to learn by doing, this is a great question that shows just that.

2. What metrics do leadership look at to assess company-wide success?

Some companies are most focused on users (i.e. MAUs for a consumer app) while others are more focused on revenue (i.e. ARR for SaaS). Show that you care about the highest priority metric(s) and can envision yourself helping to move that needle.

3. Given the pandemic, how does the company approach in-office and remote work?

If a company already has this on their website, there's no need to ask again.

Company Culture

1. How would you characterize the company culture?

Some companies offer lots of flexibility as long as you get your work done, while others expect you to work weekends. Some companies like to give junior-level employees visibility while others prefer making quick decisions, involving others on a need-only basis. You want to know what you're getting yourself into and show that you want to positively contribute to the culture.

2. What do company all-hands look like? How transparent is leadership?

Especially for those looking to be future founders, hearing how founders approached fundraising, landed new customers, dealt with supply chain issues etc. are great learning opportunities outside your role. If this is important for your growth, ask!

3. How do you think about scaling the company in the context of diversity & inclusion?

Be prepared for some companies to not have a great answer here, especially early-stage ones. However, data has backed that diverse teams lead to diverse approaches and come out on top.

4. What makes someone unfit for the team?

This question always yields interesting answers. A common answer is "ego". You want to ensure that you're aligned with their sentiments and can show that you will not fall into that category.

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?

Showing that you manage time well is critical in any role. This also shows your appreciation for their time and allows you to hop off on time if you have to be somewhere too.

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".

This shows that you can communicate effectively at various levels — high level when meeting with leadership and in detail when collaborating with peers.

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.

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