40 Startup Interview Questions to Ask Potential Hires

As a startup, one of the most important things you’ll build is your team. Assess potential hires more effectively and improve your hiring process for candidates by following these interview guidelines.

• Ask interviewees the same set of questions. Reduce bias and increase equity in your interview process by asking candidates interviewing for the same role the same questions.
• Listen for the STAR method in response. Situational and behavioural interview questions are often best answered using the STAR method—Situation, Task, Action, Result. Listen for candidates to provide the context of a professional situation, describe the task they undertook, explain the action taken to accomplish something specific, and the result of that action.
• Grade responses against a rubric. Prepare a scorecard or response scale before the interview and grade all candidate answers against it. This will allow your team to more effectively (and fairly) rank candidates.
• Limit the length of the interview process. Respect the time of candidates by limiting both the length of interviews (under one hour), the time spent on test projects or assessments (under three hours), and the number of total interviews (three total interviews maximum).
• Leave room for interviewee questions. Treat interviews like the two-way evaluation they are: candidates will be assessing you, too. Leave ample time at the end of the interview for candidates to ask questions about the role and company.

Everyday at a startup is different than the last. Aim to understand if candidates are comfortable with ambiguity and have experience thriving in dynamic work environments.

1. Can you describe a time when you had to complete a project without clear instructions or a playbook? What was the result?
2. How do you approach planning your day or week in fast-paced work environments?
3. Can you provide an example of a situation where you had to take on a responsibility outside of your comfort zone?
4. When was the last time you had to alter your approach to a problem at work?

Between swiftly building new features based on customer feedback and quickly iterating on growth experiments to see what works, startups often don’t have the luxury of time. Seek out hires that can balance thoughtful strategy with rapid execution.

5. Can you describe a situation where you had to make a decision without all the information you needed?
6. How do you approach prioritization when you have multiple competing deadlines at once?
7. How do you balance strategy versus execution when kicking off a new project?
8. How do you approach learning something you need to know quickly?

Fill your team with employees who don’t shy away from learning what they need to know (and beyond) to succeed in their role—whether that’s a Google deep dive or getting on the phone with customers. Assess candidates on their propensity to seek out knowledge and their ability to learn quickly.

9. How do you stay up to date with information about your industry and/or profession?
10. What’s the last investment of time or money that you made in your professional development?
11. What’s the last piece of software or technology you had to learn to use? How did you approach the learning process?
12. What’s something interesting you learned about the company while preparing for this interview?

In the early days of a startup, everyone works together closely—from software engineering and design to customer support and marketing. Build a cohesive and collaborative team by evaluating candidates on their interpersonal skills and ability to work well on teams.

13. Can you describe a time where you had to work with a teammate that had a different working style than you? How did that turn out?
14. How would you approach communication when collaborating with colleagues remotely?
15. What strategy would you use for providing critical feedback to a teammate?
16. Can you describe a time you were part of a large collaborative project at work? Who was involved and what was your specific role in making the project a success?

In a fast moving startup environment, micromanagement is a misallocation of time and resources. Seek out startup employees who can operate with independence and are driven to take on responsibilities without close supervision.

17. Can you tell me about a time when you took initiative to solve a long-standing problem at work or improve a broken process?
18. Can you describe a time you needed to work independently to complete an important task at work?
19. Do you have an example of a time when you went above and beyond the expectations of your role?
20. What is your ideal working relationship with a manager?

Often it’s generalists that form the foundation of a founding team, not specialists. Get a measure of whether a candidate is keen to hone in on the micro or is comfortable broadening their focus to the macro.

21. Can you tell me about your professional background and how you came to be in your current role?
22. If you had to switch careers today, what profession might you pursue?
23. How do you balance the big picture and small details when working on a project?
24. Do you have any hobbies or interests outside of work?

When building a company from scratch, it’s not uncommon to encounter problems without quick-fixes and questions without obvious answers. Discern through the interview process how a candidate approaches problem-solving and their strategies for getting to the right answer.

25. When’s the last time you had to convince someone at work of something they were hesitant about? What was the result?
26. If we saw a spike in user churn, how would you approach identifying the problem?
27. What would be your approach if you had a disagreement with a colleague about a work issue?
28. Can you tell me about a time when an unexpected problem arose at work? How did you approach the situation?

Standing out in a crowded industry and differentiating yourself as a startup often means doing what other companies aren’t. Hire for employees with creative and innovative mindsets to come up with ideas that set your company apart.

29. Based on your understanding of this company, what’s one idea you have for how we could attract new customers?
30. How do you approach creative brainstorming and coming up with new ideas?
31. Do you have an example of an out-of-the-box idea you pitched at work? How was it received?
32. Where do you go when you’re feeling uninspired and in need of inspiration?

From product pivots and budget cuts, unfortunately many startups have to face stormy weather. Ask questions that assess whether a candidate can handle times of turbulence.

33. Can you tell me about a time you experienced a professional setback or failure? What lessons did you learn?
34. Have you ever received critical feedback from a manager? How did you approach resolving the issue?
35. Do you have any go-to methods for dealing with stress or pressure at work?
36. How do you stay the course on a project that feels like there’s no end in sight?

The road from startup inception to exit or IPO is far from straightforward. Seek out pragmatic employees who still manage to operate with positive optimism on the winding road ahead.

37. What aspects of this role and this company excite you?
38. Can you provide an example of a time when you had to stay positive in spite of a challenging situation?
39. From your perspective, what are some qualities of positive and healthy work environments?
40. What’s one professional milestone or goal you would love to achieve during the course of your career?

Hiring the right employees is only one of many steps in making your startup a success. Check out all of DigitalOcean’s resources for startups and SMBs in The Wave, our startup resource hub, for more company-building advice. Also, sign up for a DigitalOcean account to start building your product on DigitalOcean’s virtual servers, databases, and more.