Questions Startups Should Ask in Interviews
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In short
To design an effective candidate experience, you need to take the time to think about your goals for each step of the interview process.
What you should ask
Now that you have an idea of what the interview process looks like, the question arises of exactly what you should ask candidates. If you’ve ever applied for a job, you may already have an intuitive idea of what kinds of questions worked well for you and which didn’t. You might even disagree with many of the questions you’ve been asked. Chances are, the questions have become so ingrained that you don’t question their validity.
When candidates are bombarded with questions for three, four, or even more than six interviews, it can be attributed to a lack of strategy and, instead, to conversations that overemphasize one aspect of assessing a candidate’s suitability (i.e., personality) at the expense of others. When you don’t have a strategic plan for each stage/interview, especially as a founder with a myriad of other tasks, you might end up conducting the interviews accurately, but ultimately feeling like you don’t have enough information to choose one candidate over another, leaving you in what feels like a hiring limbo.
What are the goals for each step?
To design an effective candidate experience, you need to take the time to consider your objectives for each step of the interview process and the questions that will help you evaluate the response against those objectives.
So, instead of a prescriptive list of must-have questions, here are three categories you should incorporate into your interviews, with sample questions you can draw from.
Three Categories of Startup Interview Questions
- Assessing the Startup’s Overall Profile
“First hires should be startup people: they’re good with ambiguity, have an innate ability to execute, aren’t afraid to take risks and fail, and are willing to work hard to help find solutions to problems as they arise.” —Gale Wilkinson, VC
As we mentioned in our article on what makes a good employee at a startup, there are specific traits and qualities that favor individuals most likely to thrive in a startup environment.
Part of the interview process should include assessing these traits with questions such as:
What do you value in a job?
What was your last failure and what did you learn from it?
What aspects of your current role cause you the most stress?
Where would you like your career to take you at ___? (An updated version of “Where would you like to be in five years?” with the added benefit of identifying specifically with your company and understanding its motivation.)
Think of something you’re deeply passionate about. Take a few minutes to prepare it and show it to me in a few minutes. (Chamath Palihapitiya, CEO of Social Capital, with a review on why this type of question, also used by Google, can be effective)
Original questions like this one are excellent for assessing whether a startup is a good fit, as they allow you to better understand a person’s personality, thought process, and ability to think quickly, among other things like self-awareness, creativity, and determination.
Here are some creative ideas gathered from Twitter and other platforms:
What question should we ask you that we haven’t asked you yet? (@jereshiahawk)
What experience do you think you can gain here that you can’t get anywhere else? (@MrPeopleOps)
What secret project or idea are you working on or thinking about that few people know about? (@SALBshow)
A screwdriver and a screw together cost $2.20. The screwdriver costs $2 more than the screw. How much does the screw cost? (Mark Anderson, CEO of Complete Express Foods. Try it yourself: it assesses critical thinking and active listening.)
Tell me about a time you were successful. (@Pam_Rubin1)
During the interview, you should also try to find out if they are proactive
people, someone who genuinely enjoys development and isn’t just intellectually interested in the idea of growth. They may be future leaders in your startup, but for now, they need to execute. What you’re really looking for is proof of this execution ability. So, for example, when you ask them what they value, do you get the sense that they genuinely enjoy doing and developing things, and not just sitting around talking about strategy? Andrew Chen writes here about not hiring anyone with more experience than a team leader or director for this very reason.
- Assessing Values Compatibility
Your first employees not only influence the culture, but they largely shape it. And while culture evolves over time, values are the foundation of any company and brand. Values are what differentiate one company from another, and a strong reflection of them will be evident throughout the product, managed by you and your first employees. Here are some general questions to help you assess values compatibility to get started:
Tell me your story. (Shopify, with an explanation of how this conversational approach allows you to get to know yourself, your values, and how you might align with their values of impact, preparedness, trust, commitment, and self-awareness.)
What stood out about our company that led you to apply? (Listen carefully: Are they mentioning the things that truly matter to your company, or are they mainly focusing on superficial aspects?)
For a closer, more personal perspective, work backward from your company’s values and then formulate your questions. Examples:
When have you worked with a diverse group of people? What do you think are the 3 to 5 most important steps for building rapport and credibility with a new team member? Share an example of how you built credibility with a new group. (Unity has an excellent article on why they ask this and how it helps them assess the company’s core value: building relationships.)
How would you do it? (Airbnb, to help them identify candidates who fit their «builder, not maintainer» value; it’s also excellent for assessing that startup star quality mentioned earlier.)
What feedback do you have on our interview process? (An example of a good question if your company values trust, feedback, growth, and transparency.)
Tell me about a time you gave your boss critical feedback. What was it, and how did you handle it? (Jeff Tetz, CEO of Results. Another example of an excellent question to assess the ability to be constructive and kind—something that doesn’t come easily to many people.)
- Assessing Job Fit
This is where companies typically focus most of their interviews, especially with behavioral and situational questions, which often go something like this: “Tell me about a time you did ___.”
These types of questions help companies learn from someone’s past experiences. You should include some, but keep in mind that they often rely on a good memory; a well-prepared candidate may perform better. Preparation matters, but in the startup world, it certainly doesn’t tell the whole story.
Here are some examples of other questions that assess the purpose of behavioral questions, while also providing a more complete picture of how well candidates might actually fit the role you’re hiring for, along with the results of skills tests, of course.
What drew you to the position and made you apply?
What’s one of your favorite projects you’ve worked on?
Questions that reveal your way of thinking, especially when it comes to challenging questions and topics related to the position or industry.
For example: How do you think we can attract an even larger customer base? (From Netflix, which is currently facing the challenge of a declining subscriber base.)
Questions that reveal your deep knowledge and strategic and analytical skills related to your industry. For example: Which brands do you think are doing a great job and why?
What not to ask
While the following are considered standard interview questions, they tend to be filler questions that most people expect and have a well-rehearsed answer that may or may not be the truth, but is likely just an interpretation of what they think you want to hear.
For example:
What is your greatest weakness? (For example, «I’m a perfectionist» or «I worry too much about my work.»)
Do you prefer working alone or in a team? (Say, «It depends! I enjoy both.»)
Instead, think about what you’re trying to find out about them and work backward to find the answer as part of the flow of an authentic conversation. This is usually achieved by asking open-ended questions or being a skilled interviewer.
For example, if the position is very independent and you really need someone who can manage themselves and work alone, instead of asking, «Can you work alone?»—where the signal of what you’re looking for is obvious in how you’ve phrased the question—you could ask, «What does an ideal workday look like for you?» To make the question more realistic, you could make a variation: «Think about your best day at work. What was happening, and why was it your best day?»
You’ve disarmed the candidate with a question that has a positive association and given them an answer that’s difficult to fake because you’ve asked them to recall something good. When they do this, under the pressure of an interview, it’s very difficult not to tell the truth, and that’s what you’re looking for. You’re looking for real information, not perfectly rehearsed answers.
«Instead of overwhelming your candidates with the same old question, ‘What are your strengths?’, this is a more organic way to discover their strengths.» —Darren Bounds, CEO of Breezy HR
Asking the Right Questions Matters in an Interview
The following interview is from Crescendo, which describes itself as: Developing Leadership That Accelerates Growth
Driven by knowledge, experience, and collaboration, we help organizations acquire the leaders who define business results. Our leadership recruitment consulting model delivers strategic value through efficiency, precision, and depth. With a proven track record, Crescendo Global helps multinationals strengthen their leadership in India.
Author: Team
In today’s interviews, the questions you ask are often just as important as the answers you give. Thoughtful questions demonstrate preparation, business acumen, and intent.
Recruiters and hiring managers use this opportunity to assess how seriously you are evaluating the position, not just how responsive you are. Top candidates use this stage to demonstrate clarity, curiosity, and alignment, rather than asking questions out of obligation.
Here’s how asking the right questions can strengthen your interview and how to prepare effectively.
It helps you understand the role beyond the job description.
Job descriptions rarely capture the full scope of a role.
Asking specific questions allows you to understand the real expectations, daily priorities, and challenges that may not have been addressed previously. This helps you assess whether the role fits your work style, strengths, and career path, while also demonstrating a practical understanding of the position.
It demonstrates business and job knowledge. Well-formulated questions reflect that you have researched the company and understand its context. Hiring managers pay close attention to whether a candidate’s questions are relevant to the company, the team, and the job objectives. Questions that link responsibilities to results demonstrate maturity and business acumen—highly valued qualities when hiring mid- and senior-level staff.
It reinforces your career intent. Getting to the interview already confirms your technical skills. What sets candidates apart at this stage is their intention. Asking questions with a specific purpose reinforces the idea that you are seriously evaluating the position and interested in making a meaningful contribution, rather than simply securing an offer. This makes a stronger impression than generic or superficial questions.
How many questions should you prepare? Quality matters more than quantity. Preparing two or three well-thought-out questions is usually sufficient. Avoid asking questions that have already been answered during the interview. Instead, listen carefully and tailor your questions to the conversation. This demonstrates attentiveness and adaptability.
Examples of effective interview questions: Instead of focusing solely on tasks, look for questions that clarify expectations, success criteria, and growth opportunities.
How do the priorities for this role evolve during the first few months?
What distinguishes high performers in this role?
How does this role contribute to the overall goals of the team or company?
What are the next steps in the hiring process?
Conclusion: Interviews are two-way assessments. The questions you ask reflect your thinking, your preparation, and your assessment of the opportunities. Well-thought-out questions help you make informed decisions and leave interviewers with a clear impression of your professionalism and intent.
Preparing the right questions ensures you leave the interview clear and confident, regardless of the outcome.
About Crescendo Global
At Crescendo Global, we help people and organizations find common purpose. We specialize in recruiting senior and leadership personnel for our clients across India. We have created a culture of people passionate about changing the lives of others. We focus on the growth and learning of our employees and believe in the power of teamwork to achieve great things. Here, you have the opportunity to exert a greater influence than many people do in a lifetime. Crescendo Global takes pride in bringing people together through celebrations.
The Art of Discovery Questions in Recruitment: How to Ensure You Ask Candidates the Right Questions
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Author: Allison Todd. Allison Todd is a coach and consultant with over 20 years of experience transforming the operations and profitability of small and large businesses. Whether starting, launching, or scaling a business, Allison founded her coaching and mentoring business wit
