14 Strategic Interview Questions to Ask Candidates (2025)

Updated November 2024

Nearly 75% of employers admit they’ve hired the wrong person for a job, and the average cost of a bad hire is $17,000. The best way to avoid this mistake is a strong, consistent interview process. By asking strategic interview questions, you are more likely to hire the right person for the job.

Strategic interview questions are targeted, open-ended questions that go beyond what’s on a candidate’s resume and assess qualities like problem-solving skills, cultural fit, career goals, and how a candidate may handle specific work-related situations.

But how do you determine which strategic interview questions to ask candidates? After all, interview questions should be specific to the job opening, the company, the industry, and even the hiring manager. If you ask only generic questions, you’re likely to get generic answers.

No matter the case, hiring managers want to ask the best questions to get the best answers, which will help them determine whether the candidate is qualified for the position they have open.

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Interview nerves don’t just affect candidates—hiring managers can feel pre-interview jitters as well. It’s important to prepare yourself so you can conduct effective interviews that help you learn in-depth insights about each candidate.

Look at the candidate’s resume prior to the interview to help you prepare questions. If there’s anything on there that you’re curious about, use this time to ask! Form questions around anything you know from prior interviews or screening to show interest in the candidate and make them more comfortable. Try and get personal.

Our Digital Services Sales Manager, Ella Pe, highlights the importance of getting personal. “Remember that the candidate is also evaluating the company and the team just as much as a hiring manager is evaluating a candidate.”

Of course, there’ll be strategic interview questions specific to your job opening, and you’ll have to determine those. However, if you need a place to start, this article will help. We’ve put together a list of the best interview questions to ask candidates in 2025, plus an explanation of why each question will help you make the most effective hiring decision.

Preparation for Conducting Effective Interviews

Interviews are difficult because you only have a short window of time to get an accurate idea of who someone is and how they measure up to other candidates. You want to know about their:

Personality
Experience
Culture fit
Future performance

Getting all that information in 30 minutes or an hour is not easy. Getting all that information in a short window and feeling good about it is even harder. Some of this comes down to the kind of interview format you choose, but it’s mostly about the questions you ask and insights you gather.

Remember: a job candidate has already made a decent assumption about the interview questions you will ask. They have already prepared their answers for the most common interview questions.

It might be in your best interest to have a few unique questions to ask when interviewing someone. That way, you get more off-the-cuff answers, rather than the same rehearsed lines they may be using for multiple interviews.

That said, the most strategic interview questions to ask candidates aren’t trick questions. You want them to answer candidly, or even need time to think before they respond. You don’t want them to feel flustered or uncomfortable.

How to Pick the Best Interview Questions to Ask

Our Culture Analyst Elise DiMase-Nordling recommends asking yourself these questions so you can understand why you’re hiring in the first place:

From the company perspective, what is the vision, purpose, and value—why does this company exist in the first place?
What does your team do, and how does that directly contribute to achieving the company’s purpose?
For the position itself, how will this person come in and add to the company and team’s success?

Once you know the answer to these questions, you’ll be on your way to selecting the best interview questions specific to your particular job opening. You’ll want to make sure you ask at least a couple of the same general questions to each candidate to help reduce bias in the interview process.

Next, check out the candidate’s resume or any other information they’ve provided you with so far and build some recruitment questions off that. Were they part of anything unique? Do they have a particular set of skills that you’re interested in knowing more about? With these candidate details in mind, you can come up with a few good interview questions specific to that particular candidate.

Tim Kuppler, our Director of Culture Solutions, recommends using questions that allow you to keep an open mind and reduce unconscious bias. Candidates may demonstrate skills or capabilities not initially anticipated, or show they’ve successfully navigated equally challenging and unclear situations.

Types of Interview Questions

There are three main types of interview questions you can ask candidates. However, the specific questions you ask should be tailored to the position you’re hiring for and the individual candidate you’re interviewing.

Behavioral interview questions—These questions are designed to uncover how candidates approach challenges and collaborate with others. They allow you to assess how your candidate has performed in past work experiences, and how they might perform in the future at your company.
Situational interview questions—Similar to behavioral questions, situational interview questions aim to predict how your candidate would perform at work in certain situations. However, these questions are hypothetical instead of focused on past experiences. This allows you to understand your candidate’s problem-solving abilities, decision-making skills, and ability to adapt in high-pressure situations.
Job-specific interview questions—While both behavioral and situational questions can be tailored to a specific job, this category focuses on assessing whether your candidate has the hard skills necessary to succeed in the role. You can ask your candidates to demonstrate their skills by giving them a mock assignment or asking them questions that test their knowledge.

Finally, you want to ask some general interview questions that will help you assess any candidate, for any role. In order to receive good answers, you’ve got to ask good questions.

14 Strategic Interview Questions to Ask Candidates

Here is a list of some of the best strategic interview questions to ask candidates.

1. What is something about you that isn’t on your resume?

A resume can give you valuable information about a candidate’s experience and education, but it doesn’t provide a full picture of their qualifications. Asking candidates to share something that isn’t on their resume allows them to showcase key details that they weren’t able to include on their initial application. Because this question is open-ended, the candidate can decide on the most relevant, impactful information to share.

For example, a candidate may share context about how a certain project helped them develop their skills. They may also share details about their soft skills and personality traits that would help them succeed. Their answer lets you learn important highlights of their career and shows you how they view their own qualifications.

2. Tell me about a time you had to take a risk at work. What was the outcome?

This behavioral question serves several purposes. It’s important to know how a potential employee handles adversity. In many cases, it’s difficult situations that help people grow into professionals.

In the best-case scenario, the job candidate will talk about the soft skills they learned from this situation.

3. Give an example of a time you received feedback that was difficult to hear. How did you respond?

This question allows you to determine how a candidate will handle feedback as an employee. Since receiving feedback is a part of work, it’s important to make sure a potential employee will have no issues understanding and implementing any steps they can take to improve.

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4. Describe a situation where you had to work with a diverse group of people. How did you ensure effective collaboration?

Workplaces are more diverse than ever, so it’s important to make sure employees can work well with colleagues from different backgrounds. This question can help you assess a candidate’s awareness of diversity and ability to exhibit inclusive behavior on the job.

By asking about previous situations, you can learn prior examples where candidates demonstrated these qualities.

5. Can you describe a situation where you failed to meet a goal? How did you reflect on the experience, and what changes did you make afterward?

A candidate’s ability to self-reflect and learn from disappointment is crucial for growth. This question allows you to assess how they handle setbacks, learn lessons from failures, and apply those insights to future situations.

6. What’s a professional accomplishment you’re most proud of?

By asking candidates about their professional accomplishments, you’ll gain insights into their values, skills, work ethic, and what they consider important in their career. A strong candidate’s answer should speak to your organization’s needs and demonstrate skills that are relevant to the role.

Make sure to listen for specific ways that their greatest accomplishments positively impacted their organization.

7. Tell Me About a Time When You Managed Multiple Priorities. How Did You Determine Their Importance?

This question helps you learn about how candidates prioritize their responsibilities and manage their time. By asking how candidates manage these responsibilities, you learn how they deal with multiple projects at once.

This also helps you learn about how they make hard choices when under pressure, and you can gain valuable insight into their decision-making process. Their answer can illuminate what they consider to be most important at work and demonstrate how they follow through on their choices.

For example, a candidate may share that they pushed a deadline for a flexible project to help expedite one with more rigid requirements. Or they may explain that they brought in additional resources from their team to avoid pushing a deadline.

8. 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?

Does the job candidate value good company culture? What makes a “good” company culture? By asking this question, you will understand what the candidate is looking for, and if your workplace aligns with their wants.

In addition, this question gives you the opportunity to speak to the culture of your company. Share what perks and benefits are offered. Explain what the people are like. Give the candidate a better understanding of what your company is like.

It’s possible that your company culture won’t align with what the candidate wants. In that case, you will both understand why they are not a good fit.

9. What Leadership Style Are You Looking for in an Employer?

Part of finding the right fit for an organization is picking candidates who can thrive within your existing team. Some people are happier working with a laissez-faire manager, while others appreciate more hands-on structure and guidance. You want to find a candidate who will work well with their manager’s leadership style—and the overarching leadership style of the company.

You can supplement this question by asking them to describe their favorite manager or share an example of a leader they admire. This allows them to highlight the leadership traits that they value in the workplace.

10. Can you provide an example of a time when you had to change your approach to a project because your initial strategy wasn’t working?

This behavioral question can show how candidates are able to adapt in different situations, as well as whether they are willing to review their perspectives and strategies when they face challenges.

Knowing if a candidate is able to come up with outside-the-box, on the spot solutions will help you assess whether they will be right for the role. Having the ability to step up and change their approach will come in handy for a potential employee.

11. What key milestones or achievements do you hope to accomplish in your career over the next five years, and how does this role support those goals?

When hiring a new team member, you typically want to find a candidate who’s interested in staying long-term. You also want to get a sense of their career goals. Some people may simply be looking for the next step in their career, and others may have a general vision of their growth beyond their next role. Both situations are totally okay.

This question helps you determine the potential longevity of each candidate by highlighting how the open role fits in with their career goals. Candidates will have the opportunity to explain how the position will allow them to grow their skill set, gain experience in a specific area, or apply their formal education to a real-world environment. Some candidates may even identify a clear trajectory from the role they’re currently seeking to another leadership position.

All of this helps empower you to choose a candidate who’s truly dedicated to the role and has strong external motivation to succeed.

12. What Role Do You Typically Take on When Working With a Team?

Even the most independent positions often require some level of communication and collaboration. Asking about how a prospective candidate works in a team environment can give you valuable insights into their ability to collaborate with others. It can help you assess the candidate’s self-awareness when working with others and learn more about how they perceive themself in a group dynamic.

This question also gives you an idea about how their personality and work style fit in with the role.

13. How do you seek out opportunities for professional development, and what specific skills are you focusing on improving right now?

A candidate’s commitment to professional development provides insight into how they plan to grow as an individual contributor and as a member of the team. A strong answer should demonstrate a proactive approach to learning and determination to stay in-the-know about relevant career skills.

14. How do you motivate yourself and stay productive in the face of difficult challenges?

An employee will face various challenges in their job duties that can impact their motivation and output. Asking this question can help you evaluate how a candidate deals with these challenges and stays productive.

It’s important to assess whether a candidate will be a self-starter and has the ability to overcome obstacles within the workplace.

Bonus: Do you have any questions for me?

Finally, you’ll want to end your interview with this question. Open the floor to anything the interviewee wants to ask!

Many times, they will ask about the day-to-day job, about the interviewer, or even about the growth opportunities within the company. They might throw you a curveball, so be prepared! If you can’t answer the question immediately, offer to follow up with the answer. (And make sure you actually do follow up).

Ideally they will have prepared multiple questions to ask, and they will use their remaining time with you to prioritize their most important questions. A strong candidate will want to gather as much information as they can during the interview.

While it’s usually a red flag if the candidate doesn’t have any questions at the end, don’t rule them out entirely. Did they ask a question earlier in the interview as a natural part of conversation? Do they look at their notes and say you already addressed their questions? Consider the entire interview when weighing a non-answer to this final question.

Use Strategic Interview Questions to Land the Best Candidate

Interviews are tough for everyone. Job candidates and hiring managers both need to prepare in advance and then present themselves in the best light. Candidates are often nervous about getting a good job, and hiring managers are often stressed about finding the right person for the job.

Decrease that stress with the right preparation. By using a list of strategic interview questions to ask candidates, you can feel more comfortable that the interview process will prove fruitful.

In summary, you want to decide on two sets of questions. The first set is unique to each candidate, based on their resume. The second set of questions to ask an applicant in an interview should be asked of all candidates for better comparison.

If you need help screening candidates for interviews, Insight Global can help. Fill out a form below and we’ll contact you in as little as 10 minutes!