20 Unconventional Interview Questions to Ask Executive Candidates as a Hiring Manager

20 Unconventional Interview Questions to Ask Executive Candidates as a Hiring Manager

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April 2024

When it comes to executive recruitment, a well-structured interview process can be the linchpin that determines the success of your hire. While traditional interview questions can provide a fundamental understanding of a job, a candidate’s capabilities often fall short when it comes to assessing crucial elements such as their decision-making style, creativity, problem-solving skills, cultural fit, and untapped potential.

That’s why, today, we’re sharing 20 unique and unconventional executive interview questions designed specifically for hiring executives. These questions intend to allow hiring managers dive deeper into a candidate’s thinking process, approach toward team dynamics, attitude toward corporate culture, and perspective on business strategy.

Importance of Asking Unconventional Questions in an Executive Interview

Filling an executive role requires identifying the very best talent. Standard interview questions often provide a limited view and hiring managers need to go deeper to assess a candidate's true potential. It is important to ask unconventional questions to avoid:

Limited Insight into Creativity and Problem Solving

Most traditional interview questions primarily focus on past experience and skill sets, leaving little room to explore innovative thinking or the candidate’s approach to challenges. As hiring managers, it's crucial to recognize that past performance isn't always indicative of future potential. By incorporating the below unconventional questions, you give candidates the opportunity to showcase cognitive flexibility, innovative problem-solving, and thinking outside the box. This is particularly valuable when hiring for executive positions. These thought-provoking questions prompt candidates to share instances of creative problem-solving, providing a more comprehensive understanding beyond a resume.

In addition to these unconventional questions, it's also important to include common interview questions. These questions help assess a candidate's basic qualifications and can provide insights into communication skills, work history, and motivation. By combining both unconventional and common questions, hiring managers can gain a well-rounded perspective of a candidate's abilities and potential fit for the role.

Inadequate Assessment of Cultural Fit

Conventional interview questions for leaders often emphasize skills and experience, while crucial aspects of cultural compatibility such as values, beliefs, attitudes, and behavior are frequently overlooked. To better evaluate alignment, a hiring manager should incorporate unconventional questions into the interview process, such as questioning candidates about past contributions to team environments or ethical dilemma resolutions. Understanding a candidate's response to a company's dynamics can aid in assessing cultural fit. These unconventional questions provide a more nuanced perspective on integration and influence on company culture, which are aspects often disregarded in traditional interviews.

Inefficient in Uncovering Hidden Talents and Potential

Traditional interview techniques focus on documented skills and experiences, potentially overlooking valuable latent abilities. This is especially significant in executive hires where the potential to grow and deliver strategic value outweighs experience. Unconventional interview questions bridge this gap by revealing a candidate's adaptability and future potential. For example, asking how to navigate unfamiliar business challenges can showcase the ability to learn, innovate, and lead outside an executive’s comfort zone. Leveraging unconventional questions unlocks insights into a candidate's latent potential, aiding in identifying future leaders.

Risk of Encouraging Prepared Responses

Predictable questions make it easier for candidates, including seasoned executives, to rehearse answers that highlight experience and skills. However, these rehearsed responses often lack genuine insight into a candidate's capabilities, hindering an accurate evaluation of suitability for the role. Introducing unconventional questions disrupts this predictability, encouraging spontaneous and honest responses.

This approach, aligned with recruiting best practices, allows hiring managers to observe candidates' problem-solving skills and thought processes in real-time, offering a more authentic view of their potential. Unconventional interview questions reveal a candidate's true persona beyond rehearsed narratives, creating a comprehensive and effective executive recruitment process.

Unconventional Decision-Making Interview Questions

Question 1: What is a recent important decision you made? What process or approach did you use to work through it?

Directly engaging with candidates about recent decision-making processes offers a profound glimpse into their strategic acumen and leadership style—qualities paramount for C-suite executives. By sharing decision-making journeys, candidates unveil analytical prowess, risk assessment methodologies, and stakeholder engagement strategies. This question enables hiring managers to discern not just the outcomes but also the depth of the candidate’s decision-making rationale, providing invaluable insights into suitability for executive roles.

Question 2: How do you go about soliciting input from various parties with different perspectives and different knowledge? How do you communicate when that input is taken into consideration but differs from the decision being made?

Assessing a candidate's ability to manage diverse perspectives and incorporate them into decision-making processes is one of the most insightful interview questions. Crucial for senior leadership roles, this inquiry enables observation of navigating complexities in gathering feedback from stakeholders and making decisions that may not align with everyone's viewpoints.

This approach also allows the executive to demonstrate their communication skills, especially when conveying the reasoning behind a decision that may not be well received by all. By asking this unconventional question, the hiring manger can gain a fuller understanding of the candidate's leadership approach, commitment to collaboration, and capability to balance various perspectives while making critical business decisions.

Question 3: Can you trace your success or lack thereof in a given role to certain decisions that you have made? Have you ever done this kind of decision making post-mortem?

Reflection and self-evaluation are crucial for successful leadership. This unique question encourages analyzing past decisions, learning from successes or failures, and applying insights to future scenarios. It provides insight into decision-making processes and the capacity for growth and resilience in challenging situations. For hiring managers, understanding the ability to self-reflect and draw lessons from experiences is vital.

This question helps assess adaptability and evolution in dynamic business environments, essential for senior leadership roles. Introspective questions enable gauging suitability for executive positions, making them valuable additions to unconventional interview questions.

Question 4: What could be improved to make your own personal decision making even more effective? What’s holding you back?

Challenging the interviewee to demonstrate self-awareness and introspection, this inquiry helps the hiring manager assess the candidate’s vital qualities for effective leadership. Candidates are prompted to critically assess decision-making processes, identify areas for improvement, and articulate potential constraints. The responses provide valuable insights into commitment to personal growth and approach to overcoming obstacles.

It allows interviewers to gauge capacity for self-improvement and a proactive nature in addressing limitations. Additionally, it offers a glimpse into how the candidate might handle professional challenges, change, and growth within the company.

Question 5: What are the next 2-3 major decisions that you think we need to make, as a company or team, given what you know about us?

Serving as an effective tool for discerning a candidate's strategic insight and understanding of the organization's current state and future challenges, this approach evaluates not only past decisions but also the ability to envision future scenarios and make informed choices.

By asking candidates to identify the 2-3 major decisions that the company or team needs to make, hiring managers can gauge the candidate’s strategic thinking, their research of the company, the ability to understand industry trends, and a potential alignment with the company's goals. Additionally, their response provides insights into adaptability to the organization's culture and commitment to long-term success. This question adds to the arsenal of unconventional interview questions for hiring effective leaders.

Unconventional Business Strategy Interview Questions

Question 6: What trends are you seeing in the space that you think we might not be aware of?

Asking executive candidates about industry trends unknown to the company can provide valuable insights into understanding the competitive landscape and the ability to stay ahead. This question is particularly useful in rapidly evolving or highly competitive sectors. The responses reveal awareness of market dynamics, anticipation of changes, and strategic thinking skills – crucial for effective leadership.

This answer can also highlight the potential to bring fresh perspectives and innovative strategies. In a changing business environment, leaders who identify and leverage emerging trends position the organization for sustained success. Therefore, it's a powerful addition to unconventional interview questions for hiring forward-thinking executives.

Question 7: How do you think we define our competitive landscape? What new entrants or threats should we be thinking about?

To evaluate candidates' understanding of the market and strategic planning abilities, hiring managers can gauge knowledge of the company's industry, competition, and potential challenges. This includes identifying direct competitors, as well as assessing threats from new entrants, substitutes, changes in buyer behavior, and industry trends. Insights into strategic thinking and risk assessment are crucial for senior leadership roles, making this question a valuable addition to unconventional interview techniques for selecting competent leaders.

Question 8: What excites you and what makes you nervous about joining a company with our specific objectives and strategy?

Inviting executive candidates to discuss enthusiasm and concerns about joining a company with specific objectives and strategies can provide valuable insights. Asking what excites and what makes them nervous helps assess alignment with the company's vision, motivation to contribute to goals, and fit into the company culture. Inquiring about concerns reveals the ability to identify challenges, assess risks, and mitigate them. Ultimately, these responses provide a well-rounded understanding of the candidate's perspective and potential to navigate the company's objectives and strategies. This question is crucial for selecting the right leaders.

Question 9: What metrics do you think we should be tracking given our objectives and our strategy?

Assessing the candidate's ability to align organizational objectives with measurable indicators of performance, from a hiring manager's perspective, responses can reveal the candidate's understanding of strategic goals, ability to set key performance indicators (KPIs), and familiarity with data-driven decision making. A strategic executive will focus not only on traditional metrics like sales revenue or net profit but also on employee engagement, customer satisfaction, and innovation metrics that align with the company's objectives. Hence, this question is an excellent addition to unconventional interview questions aimed at identifying leaders who can guide the organization toward achieving strategic objectives while assessing and improving performance.

Question 10: What can you do to help us increase our pace of decision making or our pace of innovation?

This question is used by hiring managers to evaluate candidates' ability to enhance decision-making pace and foster innovation. It dives into experience in streamlining processes, implementing effective decision-making methods, and fostering a culture of creativity. Responses provide insights into skills in optimizing business operations, familiarity with agile decision-making models, and strategies for encouraging problem-solving.

Moreover, the question offers a glimpse into the candidate’s leadership style, empowering teams, promoting collaboration, and maintaining open communication. Ultimately, it helps identify leaders who can swiftly respond to business demands and drive innovation for growth and competitive advantage. Incorporating this question in interviews benefits organizations aiming to expedite decision-making and foster innovation.

Unconventional Interview Questions About the Current Team

Question 11: Describe the most challenging team dynamics you’ve had to work through and what solutions you implemented.

Asking an executive candidate about experience with complex team dynamics and solutions implemented helps assess problem-solving skills, emotional intelligence, and leadership style. It provides insight into the ability to navigate difficult interpersonal situations and conflicts. The response offers valuable insight into empathy, fairness, and effective communication skills, critical for shaping a harmonious work climate.

It also reveals an approach to team building and fostering a culture of collaboration and respect. This question is essential for recruiting leaders who can transform team dynamics into a source of strength for the organization.

Question 12: Where have you seen two individuals (one could be yourself) complement each other from a skills or mindsets perspective?

In an interview, the inclusion of this question enables hiring managers to assess an executive candidate's experience with team immersion and collaboration with other people. The response provides valuable insights into the candidate’s ability to recognize and leverage complementary skills within a team, fostering a synergistic work environment. It also offers a glimpse into the executive candidate’s perspective on diversity and inclusion, often leading to creative solutions. Furthermore, it sheds light on the capacity for self-awareness and introspection.

By understanding how different individuals' skills can harmoniously mesh, leaders can strategically build and manage teams for maximum productivity. Including this question in the interview process helps the hiring manager identify leaders capable of nurturing a dynamic and collaborative team environment.

Question 13: How do you tend to handle conflict? What examples can you offer?

Understanding how an executive candidate handles conflict is crucial for assessing leadership and interpersonal skills. The question, "How do you handle conflict? Can you provide examples?" allows insight into conflict resolution strategies and the ability to maintain a harmonious work environment. It helps gauge emotional intelligence, empathy, and navigational skills in challenging situations.

Responses reveal whether to take a collaborative approach or favor authoritative decision making. Additionally, the insights also uncover the candidate’s ability to listen, understand different perspectives, and negotiate beneficial outcomes. Thus, including this question in interviews helps identify effective conflict managers who contribute to a positive team culture and a respectful workplace.

Question 14: As you reflect, what aspects of interpersonal dynamics are most challenging for you and why? What are you doing to improve here?

Understanding self-awareness of interpersonal challenges reveals emotional intelligence, a growth mindset, and commitment to personal development. By asking, "Which aspects of interpersonal dynamics are most challenging and why? How are you working on improving in these areas?", interviewers get to reflect on the candidate’s interaction patterns, identify weaknesses, and discuss strategies for growth.

The candidate’s response offers insights into relationship management, effective communication, and adaptability. Additionally, it highlights a willingness to address shortcomings, a crucial trait for leaders modeling continuous learning. Incorporating this question helps hiring managers identify proactive leaders aware of interpersonal challenges and committed to enhancing skills and competencies.

Question 15: How would past team members - peers or direct reports - describe your leadership style? What makes it uniquely yours?

Asking about past team members' perspectives on leadership style can provide valuable insights into self-perception and the impact of a leadership approach on a team. This question encourages reflection on the candidate’s leadership style from the viewpoint of those who have led, offering a multi-dimensional view of their skills. It helps reveal unique attributes, an ability to inspire and motivate, and effectiveness in fostering a team-oriented environment.

Moreover, it helps interviewers assess the leadership style that aligns with the organization's culture and values - crucial for determining the potential for success. By incorporating this question in the interview process, hiring managers gain a comprehensive understanding of leadership style, impact on teams, and suitability for the organization.

Unconventional Corporate Culture Interview Questions

Question 16: How do you define culture?

Asking executive candidates to define culture can provide deep insights into understanding organizational dynamics and their approach toward shaping and promoting the workplace environment. The candidate's interpretation of culture helps reflect their values, beliefs, and priorities, offering a glimpse into their leadership style and potential impact on the organization's ethos.

The question aids hiring managers in evaluating if a candidate's definition aligns with the company's existing culture or if it possesses the right perspective to drive beneficial cultural shifts. Moreover, it illuminates a candidate's ability to foster inclusivity, engagement, and a sense of belonging among employees. Thus, integrating this question into the interview process strategically aims to identify leaders capable of enhancing and sustaining positive corporate culture.

Question 17: As a senior leader, how do you view your role in shaping and upholding a corporate culture? What have been some examples of you successfully doing this in the past and what are some things you’ve learned along the way?

Understanding the impact of senior leaders on corporate culture is a powerful way to assess commitment to organizational values. By exploring perspectives on the role in shaping culture, as well as successful efforts and lessons learned, candidates can demonstrate a sense of responsibility in maintaining the company's ethos and fostering a positive work environment.

Their response offers the hiring manager valuable insights into their leadership approach, ability to influence corporate culture, and growth experiences. This question is strategically included in executive interviews to identify individuals capable of nurturing a strong and positive corporate culture aligned with the organization's values and goals.

Question 18: What do you see as the biggest barriers to achieving an effective culture in the workplace?

Gaining insight into the executive candidate’s understanding of organizational dynamics and potential solutions is possible by inquiring about impediments to fostering effective workplace culture. This question assesses the ability to identify and address issues that hinder growth and productivity while providing valuable insights into the candidate’s problem-solving skills, awareness of human behavior, and strategies for enhancing the work environment. Integrating this question into the executive interview process enables hiring managers to select leaders capable of promoting a positive and inclusive culture. The right answer to this question would demonstrate an understanding of the importance of communication, collaboration, and creating a supportive and inclusive environment for all employees.

Question 19: What role did you have in enhancing or adding to corporate cultures at places you’ve worked previously?

Asking about an executive's past contributions to corporate culture provides valuable insights for hiring managers. It allows candidates to showcase commitment to fostering a positive and inclusive work environment and driving cultural transformation. It gives them the opportunity to highlight achievements in defining, evolving, or reinforcing corporate culture and how these experiences have prepared them for future leadership challenges.

This question reveals the candidate's understanding of the importance of culture in organizational success, strategies for cultural alignment, and ability to ensure cultural continuity during periods of change. Incorporating this question in the executive interview helps identify leaders who can champion a culture aligned with organization's vision, mission, and values.

Question 20: Are there any personal practices, routines, habits, etc. that you currently have adopted that you think could benefit the whole company?

Gaining valuable insights into an executive candidate's self-management and leadership style can be achieved by inquiring about personal practices, routines, or habits related to both job and personal life. By asking, "Are there any personal practices or routines that currently have adopted that idea could benefit the whole company?" candidates have the opportunity to share unique methods of enhancing productivity, fostering creativity, and promoting well-being in both job and personal life.

This not only provides a glimpse into values and personal discipline but also indicates a potential to inspire others and lead by example in both job and personal life. Ultimately, this question serves as a critical tool to identify leaders who exhibit personal excellence and can contribute to a positive and empowering work culture in both job and personal life.

Start Hiring Better Senior Leaders Today

In conclusion, these unconventional interview questions provide a comprehensive view of an executive candidate's potential to shape a company's corporate culture and identify the best candidates. The responses offer an understanding of leadership style, organizational dynamics, and commitment to a positive work environment. These questions shape the executive interview and help identify leaders who align with the organization's vision, mission, and values. Ultimately, an organization's success depends on leaders who build an engaging, inclusive, and belonging culture. Integrating these creative interview questions into the interview process is a strategic move toward selecting the best candidates and fostering a robust corporate culture.

For more information about Kingsley Gate’s unique approach to helping companies hire the very best senior leaders, please explore our Executive Search solutions here. To speak with an expert, please get in touch here.

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