Crafting the Perfect Strategic Interview Questions: A Guide for Hiring Managers

If you want to hire someone who not only has the skills and experience you need but also wants to work for your company, you need to make sure you ask the right interview questions. You only have a short time to talk to someone, so the answers to your questions should tell you two things: first, how well the candidate will do in the job, and second, how well their goals, interests, and values fit with your company.

Here are 15 strategic interview questions you can ask candidates at different stages of the interview process, whether you are a recruiter or on the hiring team.

The type of questions you ask a candidate in an interview will depend on the role (i. e. , what you ask a software engineer will be quite different than what you ask a marketing manager). As long as the questions aren’t about the specific job, you can learn more about the candidate’s work style and general skills (e.g. g. , problem solving and communication).

We asked two SeekOut recruiters what their favorite strategic interview questions are, and Laszlo Bock, who used to be Senior Vice President of People Operations at Google and now works as an advisor for SeekOut, helped us put this list together. There are also some questions from people who watched our recent webinar with Laszlo, which you can see by clicking on the link below.

Conducting interviews is one of the most critical parts of the hiring process. As a hiring manager the interview allows you to dig deeper beyond what’s on the candidate’s resume to understand their experience, skills and whether they will be a good culture fit.

Asking the right strategic interview questions is key to eliciting the information you need to make an informed hiring decision. But what exactly are strategic interview questions? How do you formulate questions that go beyond the standard interview questions most candidates expect?

In this comprehensive guide we’ll cover everything you need to know about crafting strategic interview questions. including

  • What are strategic interview questions and why are they important?
  • Different types of strategic interview questions
  • 10 examples of strategic interview questions to ask candidates
  • Best practices for developing strategic interview questions
  • Common mistakes to avoid when creating strategic interview questions

What Are Strategic Interview Questions?

Strategic interview questions are open-ended questions designed to reveal key information about a candidate beyond their skills and experience

Unlike common interview questions such as “tell me about yourself” or “what are your strengths and weaknesses”, strategic questions aim to provide insight into a candidate’s:

  • Thinking process
  • Problem-solving abilities
  • Personality and motivations
  • Cultural fit within the organization
  • Leadership capabilities
  • Response to real-life work situations

Well-formulated strategic questions give you a more in-depth understanding of whether a candidate will thrive in the role and align with your company values.

Asking strategic questions is important for several reasons:

  • Gives you a sense of the candidate’s cognitive abilities, communication skills, and emotional intelligence.

  • Reveals their approach to challenges, how they think through problems, and their decision-making process.

  • Provides insight into their self-awareness, growth mindset, and ability to receive feedback.

  • Helps assess cultural fit and whether their work style and values align with your organization.

  • Indicates their strategic vision and capability to drive innovation or change.

Let’s look at the different types of strategic interview questions you can leverage.

Types of Strategic Interview Questions

There are three main categories of strategic interview questions:

1. Behavioral Interview Questions

Behavioral questions focus on how a candidate responded to specific work situations in the past. They aim to reveal their approach to real-life scenarios relevant to the open role.

Examples include:

  • Tell me about a time you had to rapidly learn a new skill to complete an important project. What was the situation and how did you handle it?

  • Describe a challenging situation where you had competing priorities. How did you approach prioritizing your work?

  • Give me an example of when you had to convince a resistant colleague to support an idea or initiative. How did you gain their buy-in?

2. Situational Interview Questions

Situational questions present hypothetical scenarios the candidate might encounter in the role and ask how they would respond. These aim to reveal their judgment, critical thinking, and problem-solving abilities.

Examples include:

  • If you discovered your team was struggling to meet a tight deadline on a high-priority project, what steps would you take to get it back on track?

  • Imagine you strongly disagreed with a new process change implemented by your manager. How would you share your concerns and suggest alternatives?

  • If our largest client was considering leaving for a competitor, how would you convince them to stay?

3. Culture Fit Interview Questions

Culture fit questions provide insight into whether a candidate’s values, mindsets, and work styles align with your company culture. They aim to assess compatibility and screen for any red flags.

Examples include:

  • What type of work culture do you thrive in?

  • How would your colleagues describe your work style?

  • Tell me about a time when you had to adapt your style to work effectively with someone quite different than you.

10 Strategic Interview Questions to Ask Candidates

Now let’s look at 10 examples of highly effective strategic interview questions to ask candidates:

  1. How do you typically approach preparing for a big presentation or important meeting?

    This reveals their process for an essential responsibility in most roles. Listen for preparation, strategic thinking, and communication skills.

  2. Tell me about a time you had to rapidly adjust your priorities to meet changing demands. What challenges did you face and how did you handle them?

    This assesses adaptability and ability to thrive in changing environments. Listen for problem-solving, critical thinking, and communication abilities.

  3. Describe a situation where you had to influence someone resistant to your ideas. What tactics did you use to gain their buy-in and how did you ensure the relationship remained positive?

    Reveals their ability to read different personalities, influence effectively, and maintain relationships. Listen for emotional intelligence, communication skills, and strategic persuasion.

  4. Tell me about a time you made a mistake at work. What was the situation and how did you handle it?

    Gives insight into how accountable and transparent they are. Listen for ability to acknowledge error, course correct, and show learning from the experience. Red flags include blaming others or minizing the mistake.

  5. If you were brought in as a consultant to turn around a struggling project, what first steps would you take to diagnose issues and get it back on track?

    Assesses their strategic thinking, analytical abilities, and approach to challenges. Listen for logical sequencing of steps and insightful questions they would ask.

  6. Imagine you strongly disagree with your manager’s decision. How would you share your point of view and suggest alternatives?

    Reveals communication skills, emotional intelligence, and ability to challengerespectfully. Listen for tact, empathy, logic, and objectivity.

  7. What are some strategies you use to keep your projects and tasks organized when juggling multiple priorities?

    Provides insight into their planning, time management, and organizational skills. Listen for systems and processes that demonstrate discipline.

  8. Our company values innovation and calculated risk taking. Tell me about a time you took a creative risk or unconventional approach to solve a problem.

    Gauges comfort with ambiguity, ability to experiment, and drive for innovation. Listen for examples demonstrating imagination, vision, and the ability to sell ideas.

  9. What are some ways you stay up to date with industry trends, technologies, and best practices?

    Reveals self-motivation for continuous learning and mastery of their field. Listen for energy, curiosity, and commitment to growth.

  10. What questions do you have about the role or our company’s mission, culture, and values?

    Gives insight into how much research they’ve done and areas they want to understand better. Quality questions indicate engagement, preparation, and interest. Lack of questions can signal disinterest or lack of initiative.

Follow each strategic question with probing follow-ups to gather richer insights. Avoid yes or no questions and seek detailed examples.

Best Practices for Developing Strategic Interview Questions

Here are some best practices to keep in mind when creating your list of strategic interview questions:

  • Tailor questions to the role’s most critical skills and priorities. Ensure you have questions that reveal abilities vital for success in the job.

  • Focus on qualities that align with your culture. Develop questions that screen for alignment with your values like collaboration, transparency, accountability, etc.

  • Ask the same strategic questions consistently across candidates. This allows for an apples to apples comparison between responses.

  • Balance behavioral, situational, and culture fit questions. Using all three categories gives well-rounded insight into a candidate.

  • Use follow-up questions to probe for rich details. Dig deeper with follow-up questions like “What was the result?” or “Walk me through your exact thinking process.”

  • Allow time for candidate questions. Their questions provide insights into engagement, values, concerns, and vision.

  • Review and update your list regularly. Keep questions fresh, tailored to evolving role needs, and aligned with any culture shifts.

Common Mistakes to Avoid with Strategic Interview Questions

When formulating your strategic interview questions, be sure to avoid these common pitfalls:

  • Asking leading questions that steer candidates to the “right” answer vs. their authentic thoughts.

  • Using yes/no or overly narrow questions that limit insight.

  • Asking complex behavioral questions that set the candidate up for failure. Keep scenarios realistic.

  • Getting caught up in taking notes vs. active listening. Use a scorecard to jot concise notes.

  • Failing to standardize questions. Asking different questions throws off candidate comparison.

  • Letting poor answers slide without probing follow-ups. Dig deeper for clarification.

  • Neglecting to inform candidates of your culture. Provide context so they can assess fit.

Utilizing well-formulated strategic questions in your interviews is crucial for making insightful hiring decisions. Following the guidance in this article will set you up to create a robust list of questions tailored to your open roles.

Remember to use behavioral, situational, and culture fit questions to reveal both hard and soft skills. Strategically crafted questions lead to smarter hiring outcomes, reducing attrition and driving a stronger workforce.

What strategic questions have you found most

Can you walk me through your experience at a high level?

  • Why this question is strategic. Andy Pietromonaco, Senior Recruiter at SeekOut, says, “This question seems simple, but candidates can have trouble telling their story and how it relates to the job they are interviewing for.” “This question checks how knowledgeable the candidate is in their field, how much research they’ve done on the company and the job, and how well they can write an answer for a group.” “.
  • What to look for in a candidate’s answer. Andy says to pay attention to how well the candidate can give a short summary of their career. They should be able to highlight their experience in bullet points that match what’s written in the job description.

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

  • Why this question is strategic. The candidate’s values, skills, work ethic, and what they value in a career will become clear to you.
  • What to look for in a candidates answer. Their answer should be tailored to the needs of your company and show skills that are important for the job. Listen for specific ways that their biggest accomplishment made their company better.

LEADERSHIP Interview Questions and ANSWERS! (STRATEGIC Interview Tips!)


How to prepare for a strategy interview?

Conduct thorough research, understand the role, articulate strategic thinking, demonstrate analytical skills, highlight your problem-solving approach, communicate effectively, ask insightful questions, exude confidence and passion, highlight relevant experience, and showcase adaptability and learning.

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