Asking the right questions during an interview is key to finding the best fit for your team. Yet, we often rely on surface-level questions that don’t give us enough insight into a candidate or questions that give us cliché responses.

It’s time to level up your questions.

By asking thoughtful questions, you can gain the deeper insights needed to make confident and informed hiring decisions.

We’re going to share some of our favorite categories of interview questions, along with tips to help you go beyond the resume and help you learn about your candidates.

Icebreaker Questions: The Perfect Start

Why they work: These questions help candidates relax, making for a more natural conversation. Though more casual, these questions can still offer valuable insight into the candidate. Plus, most likely, a candidate hasn’t rehearsed this question and will offer an authentic response that lets you really get to know them.

Examples

• “What’s your favorite Disney character and why?” – Sean McQuade, Account Executive
• “If you could instantly master a skill, what would it be?”
• “What’s a fun fact about you that surprises people?”
• “If you were a movie character, who would you be and why?”

Recruiter Tip: Share with the candidate why you are asking these unique, fun questions. It’ll set the tone for a positive interview.

Cultural Fit Questions: Matching Values, Not Just Skills

Why they work: Candidates need to align with your company’s mission and environment. The most skilled candidate can still hurt your team’s culture if they aren’t the right cultural fit.

Examples

• “What percentage of people have you worked with that do not like you?” – Christina Yu-Eisenberg, CMO
• “What’s the best company culture you’ve worked in, and why?”
• “How do you prefer to receive feedback?”
• “What excites you about our mission, and how do you see yourself contributing?”
• “How do you measure success?”
• “If the person who had the most difficulty working with you were to describe you, what do you think they’d say?”

Recruiter Tip: Negative experiences with previous employers aren’t always a red flag. Be sure to listen to their responses and get to understand how they act even when in an environment that isn’t suited for them.

Creative & Curveball Questions: Uncovering Personality and Imagination

Why they work: These questions break from the monotony of typical interviews and give candidates a chance to think on their feet. When the role requires a candidate to show personality, ingenuity and imagination, these questions help to see if they possess the skills to be successful in the role.

Examples

• “What’s the biggest marketing myth out there?” – Steve Gradman, CMO
• “You’re being asked to create a proposal to clean up all the stray golf balls on every golf course in California. What price would you quote?” – Charles Stumpf, Account Executive
• “If you were a kitchen appliance, what would you be and why?”
• “How would you explain ChatGPT to someone from 1992?”
• “If you could redesign a famous product, what would it be?”

Recruiter Tip: Let the candidate know why you’re asking these questions. Highlight how these questions can provide surprising insights about problem-solving, personality, and communication. Letting them know upfront will allow them to know the purpose and help them fully and authentically answer.

Scenario & Skill-Based Questions: Show, Don’t Tell

Why they work: At this point, you should know what is on their resume. It’s one thing for them to talk about their experiences but let’s see how they can use those experiences in a potentially new role. These questions go beyond theoretical answers to evaluate how candidates apply their skills in real-world situations.

Examples

• “Imagine you’re leading a project with conflicting deadlines. How would you prioritize tasks and communicate with stakeholders?”
• “If you discovered a mistake in your work after submitting it, what steps would you take to fix it?”
• “You’re given a new tool to use that you’ve never seen before. How would you approach learning it?”
• “Tell me about a time you had to figure out a solution to something outside of your usual responsibilities.”

Recruiter Tip: Pair these questions with a brief discussion of the specific skills (e.g., time management, adaptability) you’re assessing. Also, asking them to provide specific examples in their past related to the scenario is a huge bonus.

Leadership & Problem-Solving Questions: The Decision-Maker Test

Why they work: Leadership and problem-solving skills aren’t just for managers—they’re crucial for any role. Even if the role isn’t a leadership-level role, it’s a good way to see how they use critical thinking and problem-solving when someone may not be available to provide them with answers.

Examples

• “Convince why we shouldn’t hire you.” – Lester Chen, Group Product Manager
• “Tell me about a time you had to navigate conflict on a team. How did you approach it, and what was the outcome?”
• “What’s the most challenging problem you’ve solved, and how did you arrive at your solution?”
• “Can you share an example of when you took the initiative to improve a process or project?”
• “What decision have you made in the last couple of years that made the most impact professionally?”

Recruiter Tip: These questions may be tricker for the candidate to answer, so it’s always a good idea to give them time to process these questions and provide thoughtful responses instead of answering them for the sake of speed. Remember, whoever you choose to fill the role, you’ll want them to be as tactful and thoughtful.

Personal and Motivational Questions: Getting to the Heart of the Candidate

Why they work: These questions provide deeper insights into a candidate’s personality, values, and motivations. They help reveal what drives the candidate. Understanding their aspirations and influences can also give you a sense of how they might fit into your team.

Examples

• “What is the one thing that you want us to remember about you when we make this hiring decision that you may or may not have brought out in this interview?” – Paul McDermott, Senior Account Executive
• “What’s something you’re proud of (professionally or personally), and why does it make you proud?” – Janet Pittock, CAO
• “Why are you interested in this role? What would be most exciting to you about taking this role?”
• “Tell me something about you that is not on your resume.”
• “Tell me about a person you admire and how they have influenced you.”
• “What are your top 3 book recommendations?”

Recruiter Tip: These questions give candidates a chance to showcase their individuality. Pay close attention to the “why” behind their answers—it can reveal what motivates them and whether their aspirations align with the role.

A Few More Tips About Interview Questions

• Great questions can uncover a ton about a candidate that goes beyond the resume or cover letter. Be thoughtful in creating and asking questions during the interview.
• Interviews are conversations. You want to build rapport and give them a sneak peek into what it’s like working for your company. Make it engaging and enjoyable.
• Take time to review the questions your team asks candidates. Being aligned as a team on the types of questions you ask helps you ensure you’re finding the best fit for both the role and the company.
• If you need help figuring out what questions you need to ask, reach out, and let’s chat.