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10 Strategic Interview Questions to Ask Candidates

Here are some of the best strategic interview questions to ask candidates to ensure they’re a good fit for the position.

By Kate Dagher  •   September 13, 2022  •   8 min read

It can be challenging to put together strong questions to ask job applicants. The goal with interview questions is, of course, to try to get the most out of the interview, which is why you should be asking specific, strategic, and pointed questions. Strategic interview questions to ask candidates should be a mix of open-ended questions focusing on behavioural, situational, and goal-oriented factors. 

By evaluating the candidate’s previous behaviours, problem-solving abilities, strengths, weaknesses, and aspirations, you’ll typically gain a strong understanding of whether the individual is a good fit for you and your team. Because it’s not always easy to compile questions to ask job applicants, this article will cover how to prepare for an interview as an interviewer, outline 10 strategic interview questions to ask candidates, and provide you with some free meeting agenda templates you can try for yourself. 

How to prepare for an interview 

It’s important that, as an interviewer, you feel adequately prepared to interview the applicant. Because you only have a short window of time to gain an idea of who somebody is, the interview time needs to be used wisely; you want to be able to gain a sense of their personality, their work ethic, and how they may fit in with the rest of your team. Typically, interviewees prepare themselves for more common, basic questions, which is why it’s a great idea to come up with a few unique or unusual questions to ask when interviewing a candidate so you avoid getting rehearsed lines as answers. 

Take time to really consider what you need for the role for which you’re hiring, what you would like to see in the new addition to your team, and what your company values from a cultural standpoint. Once you determine these details, you’ll feel more prepared to put together some strategic interview questions that will yield the types of responses you’re looking for. When individuals apply, begin by analyzing their resumes to look for the types of experience and background that make a candidate attractive for the position that you’d like to fill. Take note if the effort has been made to write a cover letter and if the candidate has come prepared with references to offer you. Keep in mind that to hear good responses, you’ll need to ask good questions.

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10 strategic interview questions to ask every candidate 

1How would you be described by your coworkers?

This is a great interview question because candidates tend to take some time to think about how to respond. Typically, people don’t want to come across as full of themselves, but they also don’t want to sell themselves short. The answer to this question requires introspection, self-awareness, and good communication skills, since you’re asking someone to describe themselves from another person’s point of view. This question provides you with some insight into the individual’s personality and what kind of a relationship they had with their previous team. Usually, you can tell if the candidate will fit well within your team and within the role by listening to how their previous coworkers would have described them. 

2What is one thing you want me to know about you that is not on your resume?

While resumes are an essential part of qualifying a candidate for a role, they are often polished and can’t portray a true depiction of someone’s skills, abilities, and personality. This question is a good one to ask because it allows you to gain a solid first impression of the candidate and gives the individual an opportunity to be more candid with you. A resume typically shows you a lot of what you want to hear, but by asking this question, you foster a more genuine interaction so you can learn more about the job applicant as a person. 

3What led you to your latest role?

This is a great interview question for a few reasons. First, it helps you understand how the candidate got to where they currently are, whether it was by knowing someone, getting a referral, or working from the ground up. This also gives you a good insight into individuals who are managers because you have the opportunity to learn about how and why they want to move their career into a leadership role. Further, this question often gives you a clear understanding of whether the individual has been promoted once or more during their time with their previous employer. 

4How do you take criticism from a superior?

While you hopefully practice and preach constructive criticism with your team, criticism is a part of any job. This is an important question to ask because you want to ensure that the person you’re hiring is open to continuous learning and growth. In fact, without any criticism, it becomes very difficult to evolve. This question is also helpful in identifying the best-suited candidate for your job opening because while knowing how to take criticism is important, so is knowing how to stand up for oneself, and especially knowing how to do so with a superior. 

5Can you tell me about a time when you had to overcome a difficult work challenge?

This is a helpful question to ask because it’s important to identify how candidates handle obstacles and challenges at work. Like criticism, our challenges help us learn and grow to reach our highest career aspirations, while promoting personal growth as well. It’s important to listen attentively to the way the candidate responds, and to note if they become defensive or can’t seem to come up with anything. These reactions are both red flags—we’ve all faced challenges that have needed to be overcome. The green flag response to this question is a response in which the candidate provides several ways a challenge helped them grow into the person they are today. 

6What are your career growth goals?

Asking about career growth is a good idea because it helps you comprehend if the candidate is confident, organized, ambitious, and open-minded. Through the candidate’s answer to this question, you’ll be able to identify if the job applicant has strong goal-setting abilities and demonstrates the ability to identify areas in which they can improve. Perhaps even more important is that through this answer, you can identify if the individual’s career aspirations and goals align with the goals of your team and of the business as a whole. It’s essential to be able to truly support someone in their career development, and to do so, there needs to be goal alignment between the employee and the organization. 

7In what type of company culture do you best thrive?

When you ask a job applicant about what kind of company culture they work well in, you identify what it is the person is looking for in their next position. From this takeaway, you can determine if what they’re looking for aligns with the type of culture that your company provides. As an interviewer, this question also gives you the opportunity to speak about your company culture, benefits, perks, and describe the synergy that exists in your team so the candidate can gain a better idea of what it may be like to work with you. 

8What would you say is your biggest strength and weakness?

Discussing strengths and weaknesses is one of those expected interview questions. That said, this question is an important one. Giving someone the opportunity to self-identify strengths will very clearly help you determine if they’re a good fit for the role. After listening to the candidate’s strengths, be sure to see if these skills align with the job responsibilities. Equally important to discuss are weaknesses. Pay special attention to the candidates who have trouble identifying any weaknesses or who lose confidence when you ask this question. What you’re looking for in someone discussing their biggest weakness is a follow-up explaining how they have improved, with examples, to make the weakness a strength. 

9Can you share a time when you were wrong?

Asking someone to share a time they were wrong is really important; people don’t often anticipate this question to be asked, so their responses are more authentic. We all make mistakes, but the ability to own up to them and to adjust the way we work moving forward is a very desirable trait in any employee. In the Supermanagers podcast with Melissa Rosenthal, the Chief Creative Officer at ClickUp, Rosenthal further explains why this question is so important to ask: 

“I like to see what they were wrong about. I like to see how vulnerable they are in an interview to admit that, and I like to see how they course-corrected. There are a lot of benefits, I think, to understanding that question…I’ll admit, when I’m wrong to the team, or I made a mistake. I think that shows that I’m human and I’m vulnerable. You know, we all make mistakes, we all do, and that’s okay, as long as we fix them moving forward, and we create a process or a system where they don’t break or something doesn’t happen again.”

Listen to the full episode here:

10What has been your favourite project you’ve worked on?

Asking what the potential employee’s favourite project has been to work on gives you an in-depth explanation of the employee’s experience, highlights what they’re most passionate about, and tells you what kind of work they would like to be involved in should they be successful in securing a position with your team. This question also allows you to gauge how much the candidate will enjoy the role you’re trying to fill, what they prefer to work on, and perhaps responsibilities they may enjoy less. 

Free interview meeting agenda templates

Parting advice

We hope that these strategic interview questions to ask candidates have been helpful and are impactful in your recruiting endeavours. Remember that if you want candidates to set themselves apart from the rest, you also need to stand out as an employer and demonstrate a genuine interest in the individual. If you found this article valuable, be sure to send it to a friend or a colleague so they can best prepare themselves to interview for the role they’re seeking to fill. It’s always a pleasure to see you on the Fellow Blog. Until next time!

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