Mastering the Art of Strategic Interviewing: A Guide for Leaders

Written By Penelope Quinn
Job interview panel.

Hiring the right talent is one of the most important investments an organization can make. But according to the Monster Global Report, employers are struggling to fill jobs. Moreover, the potential risks of a bad hire can be immense, from lowered productivity to poor cultural fit. That’s why crafting strategic interview questions is essential for identifying top strategic thinkers who will drive your company forward.

Too often, interviews rely on predictable, surface-level questions that don’t reveal much about how a candidate will actually perform. Asking questions like “Tell me about yourself” or “What was your most interesting project?” has become cliché and easily rehearsed. To gain meaningful insights into a candidate’s ability, you must go beyond the basics and apply strategic thinking to your interview approach.

This article will provide an in-depth guide to developing impactful, strategic interview questions that dig deeper into a candidate’s experiences, competencies, and motivations. We’ll explore the different types of strategic questions and how each category can help assess key qualities you need on your team. You’ll get examples of incisive behavioral, situational, and skills-based questions to incorporate into your hiring process.

With strategic interview questions, you can evaluate problem-solving ability, leadership potential, cultural fit, and technical competencies. This helps paint a complete picture of how a prospective employee will likely perform and contribute. Asking thoughtful questions about specific competencies for the role will improve your ability to select candidates that move your organization in the right direction.

By being intentional with your interview questions, you gain actionable insights from a candidate’s response, allowing you to make well-informed hiring decisions. This article will provide tips and strategies to create an interview process that surfaces the strategic information needed to identify and attract top-tier candidates ready to tackle your most pressing business needs. With strategic planning, we can start crafting strategic interview questions that uncover the intel you need to build a stellar team.

Decoding the Interview Process

Strategic interview questions generally fall into three key categories: behavioral, situational, and skills-based. Each type of question serves a purpose in assessing critical qualities and competencies required for the role. Let’s examine the distinct goals of each strategic question category:

Behavioral Interview Questions

Behavioral questions focus on how candidates handled past work experiences and situations. This reveals telling insights into their natural behavioral tendencies, decision-making skills, and capability to navigate challenges on the job.

Here are some examples of behavioral interview questions:

  • Tell me about a time you had to solve a difficult problem at work. What was the situation, and how did you approach finding a solution?
  • Describe a situation when you had to manage multiple priorities with tight deadlines. How did you prioritize and organize your work?
  • Give me an example of when you had to coordinate with other teams or departments to complete a project. How did you communicate effectively and ensure alignment?

The value of behavioral questions is uncovering how candidates will likely act in similar circumstances based on their past actions. It demonstrates their judgment, work style, communication ability, and problem-solving skills applied in real-world contexts.

Situational Interview Questions

Situational questions present hypothetical scenarios and ask candidates how they would respond. This reveals critical thinking, judgment, and the ability to quickly analyze information to make strategic decisions.

Examples of situational interview questions include:

  • If you noticed consistently low morale among your team members, what strategies would you use to improve engagement?
  • How would you handle a situation where a client was upset about a delay in a deliverable caused by another department missing a deadline?
  • If you discovered an error in an important report right before it was scheduled to be presented, what steps would you take?

Situational questions demonstrate how candidates gather data, evaluate options, and consider impacts when faced with complex hypothetical scenarios resembling those they may encounter on the job. This provides insight into their strategic thinking skills and how they think on their feet.

Skills-Based Interview Questions

Skills-based questions focus directly on assessing the technical competencies required for the specific role. This allows you to evaluate hard skills and specialized knowledge.

Some examples of skills-based interview questions include:

  • This role involves developing financial models in Excel. Can you walk me through the key steps you would take to build a financial forecast model?
  • How would you go about debugging a problem in a large codebase you were unfamiliar with?
  • Tell me about a time when you had to analyze large amounts of customer data to draw insights. What tools and techniques did you use?

The goal of skills-based questions is to determine whether candidates have mastery of the technical competencies and specialized knowledge needed for the job functions and responsibilities. It demonstrates both their hard skills and how they apply those technical abilities.

Strategic Question Best Practices

When crafting strategic interview questions, keep these best practices in mind:

  • Ask follow-up questions to gain deeper insights
  • Keep questions job-specific
  • Use a mix of question types to fully assess candidates
  • Provide enough time for candidates to fully explain examples
  • Listen for specific details and examples in responses

Using a combination of well-formulated behavioral, situational, and skills-based strategic questions will provide a multidimensional view of each candidate and how they may thrive in your organization.

Top Strategic Interview Questions to Ask Candidates

Now that we’ve covered the distinct types of strategic thinking interview questions, let’s look at some of the best questions to ask in each category:

Behavioral Interview Questions

Behavioral questions provide the opportunity for candidates to demonstrate how they’ve handled real workplace situations and challenges. Listen for specific details and examples that reveal their approach to decision-making, problem-solving, leadership, and more.

Question One

Tell me about a time you had to overcome a challenging obstacle at work. What was the situation, and how did you handle it?

This reveals perseverance and grit. Listen for step-by-step examples of how they approached the challenge analytically, tried different solutions, and achieved a successful outcome.

Question Two

Describe a situation where you had to coordinate with other departments or teams to achieve a goal. How did you ensure alignment?

This demonstrates cross-functional communication, influence, and collaboration skills. Listen to how they brought different groups together to work towards shared goals.

Question Three

Tell me about a time you received critical feedback from your manager. How did you respond?

This assesses the ability to take constructive feedback non-defensively and improve. Listen for evidence; they can admit mistakes, implement manager guidance, and develop professionally.

Question Four

Give me an example of when you motivated your team to meet an important deadline or achieve a difficult goal.

This reveals leadership ability to rally a team under pressure. Listen for unique strategies they used to motivate and gain buy-in during crunch times.

Situational Interview Questions

Situational questions demonstrate a candidate’s judgment, critical thinking, and problem-solving when presented with hypothetical scenarios. The objective is to assess analytical skills and thought processes.

Question One

If the scope of responsibilities in this role expanded significantly, how would you approach prioritizing your tasks and managing the increased workload?

This reveals the approach to time management and how they determine urgency when juggling many priorities. Listen for strategic focus on most mission-critical tasks.

Question Two

Suppose your manager was proposing a new strategy you felt could negatively impact customer satisfaction. How would you handle this situation?

This assesses persuasive communication skills and political savvy. Listen for tactful, constructive language focused on win-win solutions.

Question Three

Imagine you notice a colleague is struggling to meet deadlines and appears frustrated. What steps would you take to address this situation?

This demonstrates empathy, judgment, and discretion. Listen for supportive, collaborative approaches focused on enablement, not blame.

Question Four

How would you approach developing your team members’ skills? What strategies would you implement?

This reveals approaches to coaching, mentoring, and developing talent. Listen for concrete training programs, skill-building, and performance feedback examples.

Skills-Based Interview Questions

Skills-based questions directly assess required technical competencies, knowledge, and specialized qualifications. Tailor these to the specific hard skills needed in the role.

Question One

Customer Service Example:

  • Walk me through how you would handle an angry customer dissatisfied with our service. What steps would you take to resolve the issue?

Listen for customer empathy, de-escalation tactics, and the ability to diagnose issues and achieve win-win solutions.

Question Two

Sales Example:

  • If our main product was not gaining enough market traction, how would you identify new potential customer segments or use cases to pursue?

Listen for strategic approaches to researching, ideating, and developing new target markets and customer niches.

Question Three

Engineering Example:

  • Explain how you would troubleshoot a slow function in a large legacy codebase you are unfamiliar with. What would be your process?

Listen for a methodical, step-by-step debugging approach using tools like logging, tracing, and profiling. Values systematic critical thinking.

Question Four

Healthcare Example:

  • Walk me through how you would treat a patient presenting with chest pain and shortness of breath.

Listen for properly administered diagnostic steps, exams, lab tests, and treatments aligned with medical standards of care. Demonstrates clinical experience and knowledge.

Asking the right strategic interview questions for each role will help assess the specific hard skills and specialized qualifications needed to succeed. Tailor your questions to the technical proficiency required.

Leveraging an assortment of well-crafted behavioral, situational, and skills-based questions will provide a 360-degree view of each candidate. With these strategic interview questions in your toolkit, you will be armed to attract top talent ready to move your organization forward.

Key Areas to Assess with Strategic Interview Questions

Strategic interview questions allow you to thoroughly evaluate candidates across essential competencies and attributes that align with the open role and your organizational needs. Here are key areas you should aim to assess and how certain question types can reveal these capabilities:

Problem-Solving Skills

Assess a candidate’s problem solving skills by asking situational questions that present complex hypothetical problems relevant to the role. Listen for logical, methodical approaches to gathering data, identifying root causes, and formulating solutions.

Communication Skills

Use behavioral questions that prompt examples of clear communication across different mediums and audiences, such as executive presentations, sensitive employee discussions, and email communications.

Leadership Potential

Inquire about examples of guiding teams through change or motivating others to accomplish difficult goals. Listen for inclusive, collaborative approaches focused on enablement.

Technical Competencies

Leverage skills-based questions tailored to the specific technical hard skills required for the job, like software fluency, clinical expertise, mathematical acuity, etc. Look for demonstrated mastery.

Cultural Fit

Ask about workplace values, ideal company culture, motivations, and collaborative approaches to see if the candidate is aligned with your mission, principles, and work environment.

Motivation and Ambition

Discuss interests, passions, and future goals. Listen for drive, continuous learning mindset, and desire to take on new challenges and grow in their career.

Ability to Work Under Pressure

Probe examples of delivering under tight deadlines, handling high-stakes presentations, managing unexpected crises, or competing urgent priorities simultaneously. Listen for calmness under stress.

Organizational Skills

Ask for examples of coordinating complex projects, managing budgets, or administering programs. Listen for proactive planning, contingency preparation, and process efficiency.

Critical Thinking

Present ambiguous situations or scenarios with missing data and ask for their approach. Look for inquiry, analysis of multiple options, creative problem solving, and logic.

Additional Strategic Interview Question Tips:

  • Know the required competencies and skills for the role and develop questions that map to them
  • Ask follow-up questions to gain deeper, richer examples of capabilities
  • Take notes and score candidates on essential areas to compare thoroughly
  • Use a diverse mix of question types to gain a multidimensional perspective

With an understanding of the core competencies you need on your team and the strategic interview questions that reveal them, you’ll be equipped to assess candidates in-depth and make data-driven hiring decisions. Use this intel to attract top talent that drives high performance.

Conduct Interviews that Reveal Top Talent

An interview is your opportunity to gain strategic insights that reveal whether job candidates will thrive in your organization. Asking thoughtful, tactical questions is crucial to thoroughly evaluate each candidate’s competencies, motivations, and potential fit.

This article reviewed how behavioral, situational, and skills-based strategic interview questions can provide deeper perspectives into how candidates approach challenges, exercise judgment, apply technical skills, and demonstrate leadership. By understanding key areas you aim to assess for the role, you can develop incisive questions tailored to uncovering candidate capabilities and qualifications.

Strategic interviews allow you to collect meaningful intel to make insightful hiring decisions that keep your company on the cutting edge. Taking a multidimensional approach shapes an accurate picture of how candidates will likely perform and strengthen your team. The right interview strategy attracts those ready to drive innovation, resilience, and business results.

Strategic interview questions separate the thinkers from the doers. Asking situational and behavioral questions reveals critical thinking, strategic vision, and the ability to execute under pressure – qualities imperative for long-term success.

Make every interview count. Use the strategies in this article to gain unscripted, strategic insights into your candidates. Hiring the right talent is one of the key factors that moves your organization forward and starts with asking the right questions. Conduct strategic interviews to build an unstoppable team ready to excel today and shape tomorrow.