25 Strategic Interview Questions to Ask Candidates | Toggl Hire
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25 Strategic Interview Questions to Ask Candidates

Juste Semetaite Juste Semetaite Last Updated:

Few business tasks are as important as recruiting the right people. But what happens when you reach the interview stage and have to choose between several great candidates with rockstar resumes?

You can toss a coin or go with your gut instinct. Or, you can look at a list of strategic interview questions to ask candidates and use those to get a better idea of who’s got the skills and qualities needed to become your next team member.

Strategic interview questions assess behavior, experience, skills, and goals. When chosen wisely, these questions allow you to assess and filter candidates with more precision than using general interview questions.

Sound appealing? They’re certainly better than leaving your next hire up to a coin toss. Read on to improve your interview process and find the perfect fit with 25 strategic questions that get results.

TL;DR — Key Takeaways

  • Poorly structured interviews waste time and ultimately result in bad hires or skills mismatches. Strategic interview questions boost hiring efficiency and meet unique role requirements.

  • Strategic interview questions can be behavioral, situational, or career-oriented. Choose a mix of question types to assess ability, character, and commitment.

  • While strategic, these interview questions are still quite broad. Hiring teams can drill down into specifics by adapting these questions to explore leadership, teamwork, or other relevant skills needed to close skills gaps or boost a certain aspect of a team.

  • Skills assessment tests focused on soft skills are a great way to start the interview process and often include strategic interview questions that you can customize to develop interviews tailored to every job role.

What are strategic interview questions?

Strategic interview questions enable companies to find employees with the right personality traits, experience, values, and skills. Expertly written questions lead to valuable answers and make the interview process far more efficient.

Strategic questions also supply information-rich answers to enable informed hiring decisions. They help hiring managers avoid confusing situations that include long, generic interview transcripts that make it hard to accurately identify strong candidates.

Instead, when asking the right questions, hiring teams gain a shortlist of potential hires. Following up strategic questions with skills and cognitive ability tests is a great way to further filter that shortlist.

Types of strategic interview questions

Strategic interview questions fall into three main categories: behavioral, career-oriented, and situational. A successful interview process balances these three topics to gain a comprehensive portrait of every candidate.

If you’re new to these kinds of questions, here’s a brief overview of each of these categories before we explore the 25 of the best strategic interview questions to ask candidates.

A brief overview of different types of strategic interview questions.
A brief overview of different types of strategic interview questions.

Behavioral interview questions

Behavioral interview questions are all about discovering more about a candidate’s personality traits, values, and skills. They allow you to learn more about what drives their behaviors and what their personalities could add to your existing team.

Examples include questions about dealing with workplace disputes or about the candidate’s approach to tough ethical situations. Ultimately, you’d use these strategic interview questions to understand a candidate’s approach to various realistic situations they might face on the job.

Behavioral questions are among the best strategic interview questions to ask candidates because they produce revealing answers. They also allow hiring managers to gain insights into the candidate’s personality.

Career-oriented interview questions

Career-oriented interview questions are the kinds of questions you’d ask to get a better understanding of a candidate’s career aspirations and work ethic. They help you understand why an individual is applying for the role and how the role can help them reach their future goals.

For example, recruiters might enquire about the applicant’s “dream job” or their ideal company. In this sense, career-oriented questions help recruiters identify potential long-term employees and reduce the risk of hiring someone who doesn’t fit your company culture (or vice versa).

Situational interview questions

Situational interview questions ask candidates about past or future work-related scenarios. They’re based on imaginative role plays or situations and challenge interviewees to explain how they perform under pressure or in their everyday work environment.

These questions usually focus on problem-solving and give insights into how candidates use their skills in real-life situations. For example, you might ask a few questions about dealing with workplace disputes or inquire about adopting new technology to meet business goals.

25 strategic interview questions to ask candidates

Ready to test everything from strategic thinking to self-awareness and work style? Based on our internal hiring processes, we’ve chosen 25 strategic interview questions to ask candidates that deliver relevant information and spark discussion.

Tip: Use this list to build effective interview scripts and processes. However, this list isn’t exhaustive! Check out our other suggestions for follow-up questions or more inspiration.

Download this list of strategic interview questions to ask and use it during interviews.
Download this list of strategic interview questions to ask and use it during interviews.

1. What are your short and long-term career goals?

Question type: Career-oriented

Strategic role: This question works well because it asks candidates to be candid about their career aspirations and current goals. It also helps hiring managers identify candidates who want to grow their skill set as part of your team.

What to look for in a candidate’s answer: Look for candidates with a clear sense of where their career is heading and how they can contribute to the team in the position you’re hiring for.

A good candidate should be able to describe how your position fits into their professional development plan. The right person will know how they can contribute to your company (and understand what your company can offer them professionally, too).

2. What attracted you to this role?

Question type: Career-oriented

Strategic role: This is a clever question because it highlights candidates who have read the job description and familiarized themselves with what your organization’s mission and goals are.

What to look for in a candidate’s answer: Answers should be specific to the role. Apart from that, good responses vary. For instance, applicants could talk about how they connect to the business mission. They might mention the desire to learn new skills. Or they may have a passion for the work itself.

On the other hand, negative responses can identify weaker candidates. Look for answers only about pay or a desire to work close to home. If candidates only talk about superficial things, you can safely strike them off your shortlist.

3. What’s a change you proposed in a previous job, and how did it impact the workplace?

Question type: Situational

Strategic role: This question helps you find employees who are proactive and confident enough to fix problems when they arise. The second part of the question also forces candidates to reflect on their actions and sheds light on their ability to understand how those actions impact others.

What to look for in a candidate’s answer: There are many strong responses to this situational interview question. Candidates should discuss an example where they identified a problem, notified managers, and devised and implemented a solution.

The actual nature of the problem isn’t important, so if you’re a hiring manager, don’t get stuck on that detail. Instead, look for evidence of candidates wanting to improve business processes or products. Answers explaining the benefits of their solution are even better.

4. Can you teach me something new in five minutes?

Question type: Behavioral

Strategic role: This question encourages candidates to explain something simply and creatively without preparation. It helps identify candidates who are creative, highly adaptable, and have strong communication skills.

What to look for in a candidate’s answer: Great answers prove interviewees can think on their feet and communicate ideas in ways that colleagues or clients easily understand. Look for answers that convey key points while avoiding complex jargon. Ask a follow-up question to gauge their knowledge of the topic.

5. How would your current or previous colleagues describe you?

Question type: Behavioral

Strategic role: This question is strategic because it requires candidates to truly consider the perspective of others. This task provides invaluable evidence of social skills and teamwork capabilities. If you pay close attention to their answer, it might also reveal a bit about what they think of themselves, too.

What to look for in a candidate’s answer: Candidates have a choice to make here. They can be self-critical and explore potential conflicts, or they could avoid painting themselves in a negative light and minimize the question altogether.

A good candidate’s response will be honest and reflective. It should be clear that they understand interpersonal dynamics and are unafraid to talk openly about disputes or even their shortcomings (because, spoiler alert, we all have them, and that’s okay!).

6. Describe a difficult situation you had with a co-worker. How did you overcome it?

Question type: Situational/Behavioral

Strategic role: This question tackles one of the most common workplace challenges: resolving disputes and improving relations with colleagues. Interviewers learn what the candidate sees as a “difficult situation” and their definition of a successful resolution. This knowledge helps you anticipate how they will act in your work environment.

What to look for in a candidate’s answer: Behavioral interview questions like this provide valuable insights into how hires will adapt to new colleagues and workplace dynamics.We like to hear about genuine scenarios (not wafer-thin disputes that could have happened to anyone). Good answers demonstrate the candidate’s ability to negotiate, see both sides, and turn disagreements into learning opportunities.

7. What is something unique about you that’s not on your resume?

Question type: Behavioral

Strategic role: This question is great because it ventures into a completely different aspect of the candidate’s personality that’s, well, not on their resume. It gives them a chance to sell themselves, and it helps break the ice in interviews so they’re not entirely resume-focused.

What to look for in a candidate’s answer: You never know what you’ll get with a question like this. Look for something unpredictable but relevant, and try to understand which related soft or hard skills they’re demonstrating when talking through their answer.

For instance, a job candidate might talk about how they coach their child’s sports team. Activities like coaching or volunteering are closely linked to teamwork and project management. You can also use this question to gauge cultural fit and personality — don’t get too stuck on skills if it’s not relevant.

8. What are your strengths?

Question type: Behavioral

Strategic role: It might be a cliché, but this timeless question will always be relevant. You can use candidate strengths to build a skills profile, which helps you match individuals to business roles.

What to look for in a candidate’s answer: Strong answers depend on the job description. Candidates should list abilities in line with role requirements. Try to encourage applicants to list technical skills and soft skills separately.

Never take what candidates say as the gospel truth. They probably aren’t lying. However, what they see as “strong” may not meet your internal standards, which is why skills testing matters as part of the next interview steps. Targeted tests let you verify every claim made by candidates.

Top tips to enlarge those brains Top tip:

You can use hard skills testing to verify that a candidate’s skills are as strong as they say they are. For example, if they talk a lot about JavaScript skills while answering this question, you can have them take a JavaScript skills test.

JavaScript Skills Test Toggl Hire

9. What are your weaknesses?

Question type: Behavioral

Strategic role: Nobody enjoys listing their weaknesses. We often list minor flaws and gloss over gaps in our experience or abilities. So, asking about weaknesses challenges people to speak frankly about uncomfortable things, and this is one of the greatest strengths an employee can have.

What to look for in a candidate’s answer: Good answers are direct and honest. Interviewees should know their limitations and discuss how they work to overcome them. A great answer flips the question into something positive. For example, a strong job candidate might ask about personal development opportunities to turn their listed weaknesses into strengths.

10. What is your ideal company?

Question type: Career-oriented

Strategic role: You’re not asking this question to fish for compliments or test how well an applicant knows your company. Instead, the goal is to see whether the job candidate has thought about how businesses work and assess the kind of mindset your hiring managers need.

What to look for in a candidate’s answer: Good answers show independent thought. The right person won’t regurgitate the “about us” section from your website. If the candidate’s ideal company resembles your own, great, but it’s not essential. Instead, you’re looking for answers that show awareness of ethics, business structure, and workplace management.

11. What leadership style are you looking for in an employer?

Question type: Career-oriented

Strategic role: Everyone is different. Some of us love self-directed work, while others thrive in close-knit teams. Responses to this question will help you understand whether a candidate will fit into your company culture or a specific team.

What to look for in a candidate’s answer: Good answers are role and company-specific. Regardless of their answer, you’re looking for someone who answers this question honestly and demonstrates an understanding of their preferred work environment.

Unless you probe deeper with follow-up questions, take each answer with a grain of salt. People who like autonomy and independence may still be very manageable, while those who prefer to work in a team environment may still be great independent workers.

12. What role do you typically play when working in a team?

Question type: Situational

Strategic role: Strategic interview questions like this illuminate the candidate’s ability to contribute to teams. However, this question goes a bit deeper. Candidates must explain why they tend to adopt that position when working in a collaborative environment (such as group leader, creative thinker, or problem solver).

What to look for in a candidate’s answer: Responses to this question reveal a lot about who candidates are and whether their future lies in leadership positions. A solid answer demonstrates how the applicant will contribute to team projects and shows you how they accept responsibility and integrate into a team setting.

13. Talk about a time when you made a big mistake at work. How did you handle the experience?

Question type: Situational

Strategic role: This is one of the best strategic interview questions to ask candidates because it forces them outside of their comfort zone. Everyone makes mistakes, and responding positively to personal errors is a critical working skill. Asking about failures identifies people who are ready to learn from mistakes (and can help reveal candidates who tend to blame others during stressful situations).

What to look for in a candidate’s answer: A great candidate won’t likely respond to this question with an answer that is either too confident or simplistic. Strong answers show self-awareness and a sense of honesty about what caused the mistake and how it affected colleagues and the wider business.

14. Can you talk about a time when you had to motivate a team to work together?

Question type: Situational

Strategic role: This is one of the best strategic interview questions to ask candidates applying for leadership roles. It gives candidates the freedom to look back over their careers, asking them to identify challenging but manageable team environments.

What to look for in a candidate’s answer: A good answer shows creativity and empathy. Maybe the candidate organized an ad hoc party or away day to unify the team. Perhaps they found a way to reconcile two opposing viewpoints. Detailed examples of dealing with team colleagues always score well.

Less impressive answers exaggerate teamwork challenges and spin run-of-the-mill management achievements as career-defining moments.

15. Describe some of the setbacks you’ve had in your career. How did they shape your current career goals?

Question type: Situational/Career-oriented

Strategic role: This question helps identify people with ambitious career aspirations and those who understand how to deal with adversity. Answers provide insights into the direction candidates have chosen and what career success might look like to them.

What to look for in a candidate’s answer: Answers to situational questions like this always generate valuable insights because setbacks change us as people. Sometimes, they make us more selfish and desperate to succeed. Hopefully, however, they teach us lessons about humility and cooperation.

The definition of a good answer depends on your company’s culture. However, most organizations seek people who balance ambition with a desire to improve their relationships and skills.

Top tips to enlarge those brains Top tip:

Use this question to separate self-driven candidates from those building careers around teamwork, ethics, and personal relationships.

16. Are there any skills you’re interested in learning in the coming year?

Question type: Behavioral/Career-oriented

Strategic role: We rank this among the top strategic interview questions because it allows candidates to showcase their current understanding of their skill set as well as how they would like to develop skills in the future to further their career path. It also filters out the few individuals who are content with their existing skills or are not inclined to retrain or upskill.

What to look for in a candidate’s answer: The hiring manager should look for mentions of specific goals and skills — the more specific, the better. Does the candidate have a strategy to meet role-related skill profiles? Are they building a skills profile in line with company needs? Could the individual plug urgent skills gaps?

This question also prompts a discussion about self-improvement. Feel free to ask follow-up questions about learning and the candidate’s goals. In some cases, you may find that somewhat “weak” candidates lacking certain skills have a strong interest in upskilling. With help, they could become a productive part of your team.

17. What do you do to make yourself a better employee?

Question type: Behavioral

Strategic role: This is one of the best strategic interview questions to ask candidates at the beginning of the interview process because it allows you to gain a better understanding of whether the potential hire has thought about their personal development plan.

What to look for in a candidate’s answer: The right job candidate for most roles always seeks self-improvement. Answers to this question cast light on how interviewees try to achieve this.

A candidate’s approach should be realistic. For instance, they might set aside one afternoon per month to audit their internal processes. Look for candidates who learn from managers but challenge leaders with constructive criticism. These individuals are probably good team members and have an eye on leadership roles.

Good answers also mention specific skills they’d like to improve. Answers might mention courses to sharpen a candidate’s problem-solving skills. Or candidates may mention that they make a point of asking team leaders for relevant feedback after every project.

18. How do you stay up to date on the latest trends and technology?

Question type: Behavioral/Career-oriented

Strategic role: This question isn’t about asking whether the interviewee keeps up with tech and trends. Instead, the answer should reveal their methods for learning new information and putting that knowledge into practice. This makes it one of the best strategic interview questions for assessing intellectual curiosity and knowledge-acquisition skills.

What to look for in a candidate’s answer: There’s no right answer here. This question is about exploring how candidates approach self-improvement. Look for answers showing curiosity and a passion for continued learning.

19. How do you prioritize deadlines, and what do you do if you fall behind on a project?

Question type: Situational/Behavioral

Strategic role: Project managers will instantly understand why this is part of our list of strategic interview questions to ask candidates. Companies rely on diligent employees who meet project milestones, attend meetings, and notify managers if problems arise. Capturing this information in the interview process isn’t easy, but it helps if you include this question in your interview structure.

What to look for in a candidate’s answer: The best candidates are self-aware enough to admit when they’ve fallen behind (or, if you hire them, they’re self-aware enough to admit when they’re struggling to stay on track).

The best answers include examples of candidates working with managers and colleagues to plan ahead and avoid project delays. What you don’t want is a candidate who says they’d simply work twice as hard and face problems or setbacks alone. While seemingly noble, that doesn’t really demonstrate strong communication or organizational skills.

Top tips to enlarge those brains Top tip:

If organizational skills and meeting strict deadlines are super important to the role, include a time management skills test as part of the interview process. It helps assess applicants’ time management, task prioritization, and goal-setting capabilities.

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

Question type: Behavioral

Strategic role: We should all take pride in genuine achievements. However, what we feel proud of reveals a lot about our values and personalities. This interview question, therefore, allows you to see whether a candidate leans more towards the “lone wolf” category of worker or is a team player.

What to look for in a candidate’s answer: Interviewees focused on gaining promotions or hitting personal sales targets show ambition and competence. Interviewees who cite delivering team projects or helping colleagues through personal difficulties expose a different side to their personalities. It’s up to you which form of accomplishment carries the most weight.

21. What are the most important values and ethics that you demonstrate as a leader?

Question type: Behavioral

Strategic role: Phrasing strategic interview questions for potential leaders is tricky. Recruiters expect self-confidence on the surface, but they need to probe deeper to discover those with the best management talent skills. This question explores a candidate’s ethical approach to leadership, requiring candidates to explain what drives them as they lead projects and encounter challenges.

What to look for in a candidate’s answer: A good answer focuses on the “values and ethics” aspect of the question. The best responses focus on people — not results. For example, the candidate might talk about being attentive to the emotional needs of colleagues, or they might discuss cooperation and consultation as core values.

Overall, this is a broad, fascinating topic, making this a great initial question for hiring managers seeking job candidates with demonstrated leadership skills. Depending on the role, ask follow-up questions, but don’t get lost in ethical discussions. Focus on obtaining a clear image of what drives the candidate.

22. How do you handle criticism?

Question type: Behavioral

Strategic role: This question is all about honesty. It challenges candidates to tell a story about their imperfections but also allows you to gain insight into how they respond in real-world situations. Asking about criticism casts light on whether the candidate will accept advice and use it productively. It also highlights candidates with future management potential.

What to look for in a candidate’s answer: Few people handle criticism with ease. Even the most level-headed, mature individuals feel hurt by well-intended criticism sometimes. However, the best candidates demonstrate an understanding of human nature and have developed the ability to turn criticism into something positive — they know how to use it to improve and evolve.

23. Describe a situation where you worked with people from diverse cultures or backgrounds. How was that for you?

Question type: Situational

Strategic role: This is one of the best situational questions to ask candidates because it allows both you and the candidate to talk openly about diversity. The answer provides hiring managers with an idea of how comfortable candidates are when discussing cultural diversity and asks for real-world examples of handling differences.

What to look for in a candidate’s answer: Candidates should be able to provide an example of working with people from other cultures or backgrounds. Good answers bring past situations to life without using clichés. They may also describe friction between colleagues – and that’s fine.

The second part of the answer should describe how the candidate dealt with a stressful situation due to issues like miscommunication, a complex project, or other issues that stem from a lack of understanding. Look for people who successfully resolved the issue or used differences as a chance to learn about others.

24. Have you ever had to work on a project with someone you don’t get along with? How did you handle that situation?

Question type: Situational

Strategic role: Strategic interview questions can sometimes lay traps, and this is one of them. Asking about disagreements allows interviewees to showcase their interpersonal flair. But it also lets them overplay their hand. Interviewers can detect who has stellar negotiation skills and candidates who tend to inflate their diplomatic abilities.

What to look for in a candidate’s answer: Most job candidates have experienced workplace disputes. Everyone should be able to describe how a dispute affected their work and compromised project delivery. Candidates should understand the viewpoints of both parties. Good answers show the candidate knows the roots of disputes and can reduce tensions by seeing both sides.

25. Do you have any questions for me?

Question type: Open-ended

Strategic role: One of the last questions to ask candidates is if they have anything to ask you. And sure, “Any questions?” might sound like a robotic, impersonal way to end an interview, but the question serves as much more than a bookend.

For candidates, it might seem like a trick question, but it’s actually a great way to assess their understanding of the role and interview process.

Hopefully, you’ve touched on all the key factors necessary to ensure the candidate is informed, including salary expectations, but this question also allows you to assess whether potential hires are curious about their future role or if you’ve done a poor job of explaining the job and/or next steps.

What to look for in a candidate’s answer: If your hiring team has done a good job of explaining the job requirements and interview process, the best candidates show clarity and excitement. They may ask more in-depth questions about current projects or the onboarding process.

Avoid penalizing candidates for not answering this question. After all, interviews are draining and stressful, and not everyone wants to extend the process. See it as a chance for job-seekers to show something extra — a flash of originality and spontaneous thought.

Steal our strategic interview questions

Finding the perfect interview questions is an important part of working to improve your hiring process. While these are some of the best strategic interview questions to ask candidates, there are plenty of others you can use and adapt to fit your hiring needs.

And you should! You should always customize questions to ask candidates based on your internal hiring needs, business goals, and the required skills needed to succeed in the role. To help you get started, we’ve created a library of strategic interview questions.

Browse our test library to see what kinds of interview questions our experts have created to help you learn more about candidates, make an informed decision, and ultimately hire the best candidate for the job.

Full skills test library
Juste Semetaite

Juste loves investigating through writing. A copywriter by trade, she spent the last ten years in startups, telling stories and building marketing teams. She works at Toggl Hire and writes about how businesses can recruit really great people.

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