16 Engaging & Strategic Interview Questions To Ask Candidates

Cassy Aite
August 28, 2023
16 Engaging & Strategic Interview Questions To Ask Candidates

Whether you’re hiring an office manager, accountant, or entry-level associate, asking the right questions during the interview process is crucial. Yet ascertaining whether a candidate is the right person for the job is difficult — especially when you have limited time to talk to them, or you’re on a tight deadline to find a great candidate.

Around three-quarters of employers admit to hiring the wrong person for the job — an alarming figure that underscores the pitfalls of a shaky job interview and hiring process.

So how do hiring managers overcome this issue and make an informed decision on the right candidate? The answer lies in strategic interview questions to ask candidates.

By asking strategic questions, you gain a better understanding of the candidate’s job-specific acumen, soft skills, and whether they’re the right choice for your company’s values and work environment.

What Are Strategic Interview Questions?

Man smiling while conducting an interview

Carefully crafted by the interviewer or human resources, strategic interview questions are designed to assess a job candidate's qualifications, skills, experience, and cultural fit for a specific role within an organization. These questions go beyond simple factual inquiries, technical skills, and what’s on a resume. They delve into the candidate's abilities in general, thought process, critical thinking, problem-solving skills, decision-making, and overall suitability for the job.

Strategic interview questions to ask candidates should always be open-ended questions, allowing the candidate’s response to speak for itself. They provide more value and enable the interviewer to develop a keener sense of the candidate as an individual — as well as an employee or leader. Open-ended questions also give you the opportunity to ask follow-up questions afterward to clarify any gray areas.

As part of the interview process, strategic questions develop valuable insights into a person’s work style and work ethic, which can help hiring managers find the best candidate — especially when two or more candidates are equally qualified on paper.

The Three Types of Strategic Interview Questions To Ask Candidates

Strategic interview questions generally fall under three categories: behavioral, career-oriented, and situational. Each of these assesses a specific part of the interviewee’s past experiences, professional goals, career aspirations, or how they would deal with a hypothetical scenario.

  • Behavioral interview questions: These types of questions evaluate how the job candidate handled specific situations at previous jobs. Specific questions might include a candidate’s approach to a stressful situation or how they handled a new leadership role.
  • Career-oriented interview questions: As the name implies, these strategic interview questions to ask candidates deal with their career path and the near, midterm, and far-off future. Through this inquiry, hiring managers can determine if job seekers are in for the long haul, or if they’re merely using the job as a stepping stone to another company.
  • Situational interview questions: These questions measure a candidate’s problem-solving skills through a theoretical work situation or a real-life case study. Perfect for outside hires or new hires, situational questions determine a candidate’s understanding of how to apply their skills and prior work experience to resolve a problem. Good questions from a situational approach would include risk mitigation, conflict management, time management, and self-awareness.

16 Excellent Strategic Interview Questions To Ask Candidates

Great interview questions always start with preparation. To find the best person for the job and your company culture, you have to ask questions that apply to the specific job description/job role and comprehend what you’re searching for.

Strategic interview questions should attempt to understand a candidate’s:

  • Cultural fit
  • Personality and how they would interact with team members
  • Current experience and skills and the ability to develop job-specific new skills
  • Future job performance and aspirations

Again, open-ended inquiries make the best interview questions in a short time period, but listening is equally as important. Don’t just wait for your turn to speak. Genuinely listen to a candidate’s answer to the following questions, and you should come to a satisfactory job hire.

Formulating strategic interview questions to ask candidates isn’t easy, especially if you don’t have a written rubric, you’re interviewing for the first time, or you’re filling a new job role that previously didn’t exist.

For the sake of ease and your sanity, here are a few questions to streamline the interview process. Remember that these are generic questions; make sure to tailor them to the specific role to get the best answers.

Behavioral Interview Questions and Examples

Job interview candidates holding question marks in front of their faces while waiting for their interview

Behavioral interview questions analyze the background of the candidate through past experiences. When you formulate these questions, you’re trying to determine communication skills, problem-solving abilities, teamwork, leadership, and adaptability, so keep that in mind as you listen to their answers.

You should also focus on the STAR interview method during behavioral interview questions. Well-prepped interviewees typically use this method to explain the situation, task, action, and result (STAR). It’s not something that every candidate will do, but it’s certainly something to look for.

  1. Tell me about a situation where you had a tight deadline. How did you manage your priorities and tasks?
  2. Describe a difficult situation you had with a coworker. How did you overcome it?
  3. Talk about a time when you made a mistake at work. How did you handle the experience?
  4. Provide an example of a time that you had to lead a team to a specific goal. What initiatives or planning did you use to motivate the team and create cohesion?
  5. Discuss a time when your team went above and beyond and your role in the project. What did you do to inspire, and how did you reward or show appreciation to your team afterward?
  6. Tell me about a time when you had to adapt to a project. What initiatives did you spearhead?
  7. Describe a time when you identified a potential project in operations or workflow. How did you approach the problem or create a solution that had a meaningful impact?

Career-Oriented Interview Questions and Examples

With the right career-oriented interview questions, you can gain perspective on the candidate’s goals, ambitions, and commitment to future excellence. These can also help you determine if their trajectory matches the professional and growth opportunities offered at your company, as well as middle- or upper-management roles they may mature into.

Remember that entry-level interviewers may not have a clear-cut perspective on what they want in the long-term future, so keep an open mind during these types of questions. Conversely, mid-level or upper-level candidates should have a clear, lucid idea of what their future looks like. Use these career-oriented strategic interview questions to gauge their interest in the company and as a potential fit for the future of the company.

  1. Tell me about some of the principles and values that guide your professional aspirations and decisions. Have you noticed any of those aligning with the core values of our organization?
  2. Describe some of the setbacks you’ve had in your career. How did they shape your future in terms of aspirations and goals?
  3. Tell me how you’ve propelled your career forward outside of the office. What do you do to make yourself a better employee or candidate?
  4. Discuss how remote work has changed the modern workplace. How did you adjust to remote work, where do you see it in the future, and how well can you adapt between remote and onsite work environments?
  5. Tell me about how you go about using new software or technology. What steps do you take to master it?

Situational Interview Questions and Examples

Situational inquiries are another essential portion of strategic interview questions to ask candidates. Without these questions, you cannot accurately predict how a potential candidate would handle a difficult situation. Furthermore, situational questions gauge how well the interviewee would apply their given knowledge and skillset to a specific situation they may encounter in the future.

  1. Imagine you receive feedback from a client, and they’re unhappy with the results of a project. How would you rectify the situation and address the concerns of the client?
  2. You consistently see employees being careless with passwords and cybersecurity protocols. What steps do you take to amend the situation as a leader or coworker?
  3. During a project, you realize that you don’t have the manpower or resources to finish it either on time or under budget. How do you tell the client and address their concerns?
  4. You have a project that requires you to do work that you have no formal training in. How do you develop the skills necessary to complete the project and add the skills to your professional repertoire?

Make the Onboarding Process Easier

Interviewing and hiring new candidates is the difficult part. After you’ve settled on one, the path gets easier. Sure, you have to get the training and paperwork out of the way, but don’t forget to go one step further by giving your new employee a warm welcome.

Hoppier Remote Onboarding Gift Card

With Hoppier’s virtual gift cards, you can provide a small stipend or gift to your new employee that makes the onboarding process just a tad more enjoyable. With the ability to purchase food, desk supplies, or just things that make their job easier or more organized, your employee’s morale, engagement, and satisfaction are sure to start off strong.

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Make Hoppier your unfair advantage today, schedule a demo

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Make Hoppier your unfair advantage today, schedule a demo


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