The 239 interview questions technical startup founders should ask every candidate

There are few things as exciting as meeting with amazing new people who might be the right one to join your team. You found some great candidates, now how do you figure out if they are the one?

You have to assemble a team of people that can create a world changing product, a team that will work relentlessly together even when things are tough, and a group of people who are motivated by your vision as the founder to do what they never thought they could do over and over again. 

None of that is about the tech. It’s about the combination of the people you bring together. You have to balance technical skills and people skills. 

Can they build the product and talk about the product?

Can they identify the roadmap and get everyone’s buy-in that this is the right path?

Can they read the signals in the market and know what to do with them?

Can they build a process and motivate others to see why it is valuable?

Can they connect tasks to strategic objectives?

Evaluation of these core competencies requires thorough data collection. The primary source of that data is the interview with the candidate. You’ve got to ask the right questions, for the right reasons, aligned to the skills required for the role and the competencies needed for your team. 

We’ve been collecting questions in this interview bank from across our portfolio of companies for the last five years and thought it was about time that we share it out for others to put to work. 

The questions are organized by competencies — adaptability, analytical skills, behavioral skills, communication, conflict management, creativity, cultural fit, customer service, grit, initiative, leadership, learning, motivation, presentation skills, problem-solving, remote work habits, rigor, self-awareness, teamwork, time management, and social skills — and in role-specific collections for interviewing a few key, particularly complex roles including developers, marketing leaders, sales leaders, and sales engineers. 

Use this question bank as a guide to put your interview plans together.


Introduce yourself, share a bit about how or why you started the company or why you decided that it was the right time to hire for this role. Open the conversation with questions that are expected and an anchor to get the candidate comfortable speaking with you. 

  • Tell me about yourself.
  • Walk me through a day in the life of you.
  • What did you have to be good at to be good in your last role?
  • What are the Top 3 Skills for a [insert job here]?
  • How would you organize your day as a [insert job here]?


Once you’ve broken the ice, it’s time to dig in and get your candidate telling real stories about their experiences. Competency-based interview questions are designed to assess how a candidate’s experiences have shaped the skills, behaviors, and processes that they use in their work as individuals and in their leadership guiding others. 

Use this as a guide to pull from based on the competencies that are most important to the role you are hiring for and the work environment that you are creating. 


  • Provide an example when you had to adapt your approach due to shifting priorities.
  • Tell me about a time when you had to adjust to a colleague’s working style in order to complete a project or achieve your objectives.
  • Can you tell me about a time when things didn't go according to plan? How did you cope?
  • Recall a time when you were assigned a task outside of your job description. How did you handle the situation? What was the outcome?
  • Describe a situation in which you embraced a new system, process, technology, or idea at work that was a major departure from the old way of doing things.
  • Describe a time in which you had to adjust quickly to changes over which you had no control. What was the impact of the change on you? On your work or project?

Analytical Skills

  • Give an example of a time you identified a new approach to a workplace problem.
  • ​What was one of the toughest problems you ever solved? What process did you go through to solve it?
  • How do you analyze different options to determine which is the best alternative?
  • Describe for me how your prior positions required you to be proficient in the analysis of technical reports?
  • How have you approached solving a problem that initially seemed insurmountable?
  • Where do you go to research a decision?

Behavioral Skills

  • What inspires you to be good at your job?
  • What do you do to stay motivated?


  • What team communication tools have you used? What was your experience with them?
  • How would you overcome communication challenges on a remote team?
  • If you're presenting your ideas during a meeting and your audience seems disengaged, what would you do to get their attention?
  • Have you ever worked with someone you struggled to communicate with? If so, what was the obstacle and how did you handle it?
  • What would you do if your manager gave you unclear instructions for a new project?
  • Describe a time you had to share bad news with your team or have a difficult conversation with a coworker.
  • If hired, how would you introduce yourself to your new colleagues? How would you get to know your team members?
  • Can you walk me through your process of how you’d explain a complex topic to someone who was unfamiliar?
  • Tell me about yourself in 2 sentences.
  • Explain to your 95-year old grandmother what you do for a living.
  • Your colleague is publicly belittling your work achievements. What do you do?
  • Which one is more important to you and why: to be a good listener or a good communicator?

Conflict Management

  • What would you do if you disagreed with the way your manager wanted you to handle a situation or problem?
  • Have you ever had a team member who kept raising objections on projects? How did you (or would you) manage them?
  • Have you ever faced a conflict of interest during a cross-departmental project? What did you do?
  • How would you advise a team member who complained about a coworker’s behavior?
  • You've noticed that a team member is aggressive or arrogant toward the rest of the team. How would you approach this person?
  • How would you react if a coworker blamed you for something that wasn’t entirely your fault (eg. missing a deadline) during a meeting?


  • Tell us a story about something that’s happened in your life?
  • How do you facilitate creative thinking within your team?
  • What is your relationship with chaos?

Cultural Fit

  • Describe the work environment or culture in which you are most productive and happy.
  • When working with people, in general, describe your preferred relationship with them.
  • Do you have a best friend at work? How do you feel about becoming friends with your coworkers? Is this a wise practice?
  • Do you prefer working alone or as part of team? Please explain your answer.
  • What is your opinion about taking work home with you? Do you usually take your work home? Is it good practice in your opinion?
  • What are, in your opinion, the key ingredients in maintaining successful business relationships?
  • Tell me about a time you had to work with someone difficult?
  • What are the three things that are most important to you in a job?
  • What does the day in the life of (Name) look like? Walk me through your wakeup to bedtime.
  • Tell me about your relationship with ambiguity.

Customer Service

  • What does customer service mean to you?
  • How would you reply to a potential customer who claims that our competitors offer better prices?
  • Provide an example of a time when you went out of your way to delight a customer.
  • Tell us about a decision that you made that was made based primarily on customer needs and input.
  • Whose responsibility is the satisfaction of customers?


  • Tell us about a time in your career that you wanted something so badly that you were unstoppable in pursuing it. What obstacles did you overcome to get there?
  • Tell me about a time you took a risk and failed. What did you do?
  • Tell me about your biggest professional failure and what you learned from it. 
  • Have you turned a dream into reality?
  • How have you dealt with failure and bounced back from it?
  • Tell me about a time you had an idea to improve a process at work and what was the result?
  • Describe a project that you had to work on for an extended period of time and how you stayed engaged?
  • How hard will you work? 
  • How well have you dealt with routine or administrative work in the past? How do you motivate yourself to do it?
  • Tell me about a time when you made a mistake, how did you overcome it?


  • Tell me what are the challenges our company faces?
  • Describe a situation where you faced serious challenges in doing your job efficiently. What were the challenges, and how did you overcome them?
  • What kind of relationship do you expect to have with your boss?
  • What do you want to accomplish with this job? What are your goals?
  • When you had extra time available in a previous position, describe ways you found to make your job more efficient, or what techniques you learned to make yourself more effective or productive?
  • How did you reach the decision that you wanted to change your job and work for us?
  • Tell me about a time when you took initiative or were internally motivated to do something you weren't instructed to do.
  • Think back to high school or college. Who were you in a group project team? How did you approach a group project?
  • Why did you apply?
  • Tell us about a time you experienced what you perceive to be an injustice.
  • What do you know about the company?
  • What's your definition of hard work?
  • Who is the smartest person you know? Why?
  • What made you excited to get up and come to work at your last job?
  • What's your favorite non-professional activity?
  • Talk me through a bad professional relationship you've had. Why didn't it work?
  • If you've previously reported to multiple supervisors at the same time, how did you get to know each person's preferences and juggle conflicting priorities?
  • Tell me about a workplace conflict you were involved in, either with your peers or someone else in the company. How did you manage that conflict, and were you able to resolve it?
  • What would a previous boss say is the area that you need to work on most? Have you taken steps to improve in this area, and if so, what have you tried to change?
  • What do you want to do differently in your next role?
  • Tell me something you are learning right now.
  • What do you read?


  • Describe a situation you were in when you motivated a difficult member of a team?
  • What qualities are needed to be an effective leader?
  • Describe your leadership style?
  • How would you motivate a team?
  • How do you monitor the performance of the people that you have to lead?
  • Describe a time when you failed as a leader.
  • How do you delegate responsibilities efficiently?
  • You know your manager is 100% wrong about something. What do you do?
  • Your team members are quitting one after another. What do you do?
  • What do you expect from a manager?
  • Your company is in financial difficulties and you have to cut down salary costs. How would you decide who to fire?
  • How do you navigate the fine line between coaching and telling?


  • In your previous position, what specific skills or competencies did you seek out to better yourself and to help others better themselves?
  • Describe a time when you realized you needed additional skills or knowledge to be successful. What was your approach to gaining these skills?
  • Can you give me a time when you changed your mind based on evidence and reason?
  • What do you see as your areas for improvement?
  • What did you learn about yourself in your past job?


  • Describe your ideal work environment. 
  • Why do you want to work here?
  • Have you ever been excited about a major project and learned that it was canceled? What did you do?
  • What are the limits of your authority in your job? Have you ever gone over those limits?
  • What would you want to do if you didn't have to work?
  • Describe your ideal role and your ideal company culture.
  • We finish the interview and you step outside the office and find a lottery ticket that ends up winning $10 million. What would you do?

Presentation Skills

  • How do you prepare before delivering a presentation?
  • Describe a memorable presentation you’ve attended. What made it successful? 
  • How do you modify your presentations for different audiences? 
  • Describe how you would present our company/products to a prospective client.
  • What tools do you use to create a presentation?


  • How many ways can you think of to find a needle in a haystack?
  • How have you dealt with taking negative feedback in the past?
  • Tell me about a time you predicted a problem with a stakeholder. How did you prevent it from escalating?

Remote Work Habits

  • What's your experience in working with distributed teams across time-zones?
  • Have you ever worked with a remote team or employee? Describe your experience. How will you deal with the challenges?
  • How do you picture coordinating and communicating with your team and coworkers if you’re not all in the same office?
  • Describe one of the biggest challenges you picture facing working with a remote worker? How do you plan to deal with it?
  • How do you plan on getting past slumps in productivity?
  • Tell me about a time when you had to respond to a problem from a communication failure.
  • What do you bring to the table that would help you excel as a remote worker?
  • What tools have you used in the past to work effectively while remote?
  • What activities do you do that help you maintain a work-life balance?


  • Tell us about a time you used data to make a decision.
  • Tell us about a person or organization that you admire. Why do you think they have made an important impact?
  • Tell us about a time you had a measurable (read: quantitative) impact on a job or an organization.


  • What is the biggest mistake you've ever made at work? 
  • What makes you the best candidate for this job?
  • Describe a situation where you demonstrated confidence in your viewpoint despite opposition.
  • How do you build relationships?
  • What is the biggest compliment you have received in your current role?
  • The last time you left a team, why did you leave?
  • What do you think is your peers’ biggest criticism of you? What do you think is your peers’ biggest appreciation for you?


  • When have you worked as part of a team to complete a difficult task?
  • When working on a team, what's hardest for you?
  • What about a time you worked on a difficult team? What was your role and experience? Do you know where the other people involved were coming from? Tell us about the situation from their perspective.
  • What makes you happiest and most effective when working with others?
  • Can you tell me about a time when you had to work with someone you weren't compatible with?
  • Which one do you prefer and why: teamwork or working alone?
  • Your teammates are all in agreement on how to approach a task but you disagree. How do you react?
  • How would you deal with a teammate who wasn’t doing their share of work?

Time Management

  • How do you cope when you have too much work on your plate?
  • Describe a time when you recognized that you were unable to meet multiple deadlines. What did you do about it?
  • If you woke up and had 2,000 unread emails and could only answer 300 of them how would you choose which ones to answer?

Social Skills

  • What’s your go-to karaoke song?
  • What is your most-used app on your phone?
  • What actor would play you in the movie version of your life?
  • If you could describe yourself using a character from a popular television show, who would you choose and why?
  • What non-role related initiative would you be interested in pursuing at our company? (Examples: mentoring new employees, community service, employee resource groups, etc.)
  • If we gave you time off to be involved with the community, what would you do?
  • What's the last thing you really geeked out about?
  • What do you think of garden gnomes?
  • Are you a hunter or gatherer?
  • What are you really good at, but never want to do anymore?
  • How would you solve problems if you were from Mars?
  • What is the color of money? 
  • If you had to be shipwrecked on a deserted island, but all your human needs—such as food and water—were taken care of, what two items would you want to have with you?
  • What was the last gift you gave someone?

Role Specific Collections

Technical founders are extremely good at knowing what they want when they see it, and often recruit early team members from their previous companies. In fact, the ability to do this, to bring people along with you as a founder, is something that is extremely favorable to venture investors. However, this means there is often very limited experience in hiring developers that they have not worked with before, so getting beyond the technical capability through story-based questions is critical to determining success in a collaborative team environment. 

When it comes to sales and marketing, technical founders have the least personal experience in these functional areas of the business, and need to view themselves as the marketing leader and the sales leader first, before hiring anyone else. Marketing and sales people are good at selling and marketing themselves, they’ll be great at telling their own story. With these questions you’ll get into the more mechanical, tactical, and the work explicitly related to why you’ve decided to make these hires at this moment in time, a crucial step in achieving alignment.  

When Interviewing Developers

  • Tell me a little bit about you and your recent work experience. What have you been up to the past few years?
  • Why are you looking for a new position?
  • We endeavor to be TDD whenever possible. Please speak to your experience with Test Driven Development and Continuous Integration.
  • Tell me about your experience working on a team with other developers. How did you compartmentalize work and assign duties and make sure you were working together recently?
  • At your last position, how did you know what to work on at any given time? What PM tools and strategies did you use?
  • Tell me about your experience managing projects and serving as the buffer between your internal stakeholder or your client.
  • Give me some examples of times when you've pushed back on requirements that were given to you. Examples of times where you materially improved a software product with your own ideas.
  • What’s a personal opinion you’ve had and changed in the last year?
  • What’s the best (or worst) piece of advice you’ve gotten?
  • What’s your timeline for starting a new position?
  • What would your preferred tech stack be for an in person interview?

When Interviewing Marketing Leaders

  • Talk about the importance of brand management? Why do you think it is important?
  • What are some of your favorite marketing campaigns?
  • What metrics are important to you as a brand manager?
  • How do you know when a branding strategy isn’t working?
  • Do you have any hobbies or interests that have added value to you as a marketer?
  • Give us an example of how you have managed a marketing campaign on time and under budgets?
  • Assuming we hire you, how would you jump in as a project manager for an upcoming product launch? Can you walk us through that process?
  • How would you describe your own personal brand?
  • Which three marketing skills would you like to improve or learn more about?
  • How would you reply to a negative online review about our company?
  • What would you consider to be good or bad website content?
  • How does website content influence the company as a whole?
  • How do you know if the company's website content is successful in its mission?
  • How do you decide what kind of content to write or display on the website?
  • How often do you post on social media on a personal or professional level?
  • How do you talk about a dry or technical subject without relying on buzzwords?
  • How would you capture our company’s voice?
  • What do you need to know about a project before you start writing?
  • How did you determine the style, tone, and voice for a recent piece of content you wrote?
  • What online communities have you managed in the past?
  • What do you think of our current social media efforts? What could we be doing better?
  • What metrics do you use to measure the success of your social campaigns?
  • What strategies would you use to generate leads?
  • Tell me about SEO and its relationship with social media.
  • What are the relevant metrics for tracking ROI on social media?
  • What channels do you think are most relevant to our business? How do you use each channel differently?
  • How do you deal with negative comments or a brand reputation crisis?
  • How would you allocate our social media budget?
  • How would you communicate with the rest of the company?
  • Do you have your own blog or do you regularly publish content on your own social media platforms?
  • What tools do you use to manage your channels?
  • Give me a couple of examples of social media experiments you’d like to run with our business.

When Interviewing Sales Leaders

  • Describe your process for both promotion and firing.
  • How do you deal with chronic bad behavior from a top performer?
  • What methods do you use to get the information that you need in order to make decisions?
  • How do you run your staff meeting? What is the agenda?
  • How do you manage actions and promises?
  • What do you look for in the people working for you?
  • What is your process for evaluating the people working for you?
  • The last time you left a team, what happened? Why did you leave? What did you learn from that experience?

When Interviewing Sales Engineers

  • What’s your biggest lead-generating success? How did you get the lead?
  • How do you ensure your audience understands complex technical terms?
  • What’s the biggest challenge you’ve faced in communicating technical details? How did you overcome it?
  • Describe a successful sales project you worked on. Who did you work with and what was your specific contribution?
  • How would you proceed if a client faced a technical issue but none of your suggestions work?
  • How would you explain the benefits of using [X] product over a competitor’s service?
  • A key potential client requests a feature we don’t currently offer. Who do you contact about it and how do you respond to the prospective client?
  • Your manager sets a goal that you think is unrealistic. How do you respond to it?
  • What software have you found useful for your job? Why, and how?
  • What experience do you have with remote access software?
  • Pitch to me as if I were buying your product or service.
  • How do you stay updated on the latest tools and trends?
  • Describe in your own words what a sales engineer is responsible for.
  • What makes a good demo?
  • If you had to teach a beginner an advanced concept, how would you approach that?
  • How do you handle it when a salesperson isn’t following processes that help you do your job well?
  • In your opinion, how should a sales engineer be measured?
  • What does a sales engineer need to know before conducting a prospect demo (what information should the account executive be providing)?
  • How does a sales engineer get up to speed?
  • What’s a typical sales call like for a Sales Engineer?
  • What do you know about our products? Who do you think are our customers?
  • How would you handle a differing opinion from another experienced Engineer


There’s three final questions to end every interview on, regardless of the role or competencies you feel are necessary for the job.  

  • Tell me the story of 3 people whose careers you've meaningfully helped?
  • Is there anything you thought I would ask about that I didn’t?
  • Who are 2 people who have worked for or with you that would be a reference for you? Can you introduce them to me now?

These questions, asked at the end, will bring the rest of the conversation together, giving you a comprehensive understanding of what kind of person the candidate really is, how they see themselves inside of a team environment, what they truly value, and how fast they are to trust. 

You’ll have the data you need to evaluate how they will be additive to the vision you are executing and the company you aim to build. 

We’ve been collecting questions in this bank from across our portfolio of companies for the last five years and thought it was about time that we share it out for others to put to work. We are extremely thankful for the thoughts and additions that have been made to it by every one of our portfolio company CEOs and their talent leaders. Thank you!

To be direct about a few other sources that we’d like to express our thanks to outside of Squadra: 

SmartLogic has been hiring expert technical talent for over 20 years and graciously shared their honed technical hiring process with our teams.

Adam Grant’s Givers & Takers has been one of the first resources we’ve shared with every team we’ve worked with because it shapes why you hire not just how you hire.

Ben Horowitz’s The Hard Thing About Hard Things is a work that our team goes back to over and over again, but the real hidden gem in that book is the Appendix on “Questions for Head of Enterprise Sales Force.” Do not hire a sales leader without answering every one of those questions.


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