20 Unconventional Interview Questions to Ask as an Executive Candidate

20 Unconventional Interview Questions to Ask as an Executive Candidate

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April 2024

In today’s competitive job market, standing out as a candidate is more important than ever. Gone are the days when traditional interview questions could give employers an accurate insight into a candidate’s potential. Today, nearly every job interview invites the opportunity for a two-way conversation where executive candidates can ask questions of the hiring manager or panel participant to learn more about the team, role, and company that they could potentially be stepping into.

As an executive candidate, it is crucial to ask bold questions throughout the interview to showcase your unique abilities and also assess the company culture and your fit within it.

Here are 20 unconventional questions that every executive candidate should consider asking in an interview to gain valuable insights about the organization.

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?

This question provides valuable insights into the organization's culture and strategic direction. By exploring recent decisions made, you can gain a deeper understanding of the organization's core values and operational priorities. This knowledge can then be used to assess your compatibility within the organization's ecosystem.

Understanding the decision-making process also helps reveal the leadership styles, collaboration dynamics, and the company's commitment to strategic thinking, offering clarity on the decision making environment within the firm.

By asking this question, you, as the candidate, have the opportunity to demonstrate your business maturity and seniority as a decision maker. Learning from past decisions equips you with insights to navigate any future challenges effectively, further emphasizing this question as a proactive approach to gauge the alignment between your decision-making style and the organization's business decision environment.

Question 2: How do decision makers 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?

As an executive candidate, asking this question during the interview showcases your readiness and capability to make crucial decisions in the new role. It highlights your maturity as a leader looking to understand the organization's decision environment and culture. Asking this question provides critical insights into the organization's decision-making process and its commitment to inclusivity, transparency, and collaboration.

Understanding how decision makers solicit input from diverse parties with varying perspectives and knowledge further sheds light on the organization's values and priorities. Learning about the communication strategies employed when considering divergent input allows for assessing the organization's capacity to manage dissenting opinions constructively, and foster trust and engagement among employees. By posing this question, you demonstrate your interest in fostering an environment where every voice is heard and valued, empowering your potential fit within the organization.

Question 3: Can you trace your businesses’ success or lack thereof to certain decisions that have been made? Have you ever done this kind of decision making post-mortem? If so, what was learned?

Asking this question not only gauges your ability to glean insights from past decisions but also illustrates your aptitude for critical thinking and self-reflection. This question provides a platform to exhibit your analytical skills, business acumen, and capacity for self-assessment. Such attributes are indispensable for executive leaders who are continuously entrusted with making pivotal decisions that shape the trajectory of their organizations.

By posing this question, you demonstrate a proactive approach to understanding the dynamics of decision making within the organization and emphasize your commitment to fostering an environment where diverse perspectives are valued. Additionally, it offers an opportunity to assess the organization's transparency and openness in considering differing viewpoints, which in turn fosters trust and engagement among employees. Ultimately, diving into these aspects of decision making empowers you to evaluate your potential fit within the organization and make well-informed decisions about your executive journey.

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

This question challenges you to think critically about the decision-making process within the company and identify areas for improvement. It also showcases your proactive mindset and willingness to constantly improve and drive change. This is an important quality for executive leaders who are responsible for driving growth and innovation within their organizations.

Question 5: What are the next 2-3 major decisions that you (individually, or as a company) need to make?

This question serves as a powerful tool for you as an incoming executive. It highlights your strategic thinking and planning skills. By asking about the company's future direction, you demonstrate your understanding of forward-thinking and your readiness to contribute meaningfully from day one. The company's answer, in turn, provides valuable insights on multiple fronts. First, it offers a window into the company's future trajectory and the upcoming challenges they anticipate. This allows you to assess potential roadblocks and gauge how well these challenges align with your professional goals and values. Second, the answer reveals the company's level of transparency and willingness to share strategic information. This transparency is crucial for fostering collaboration and informed decision making within the organization. Ultimately, by asking this question, you not only showcase your strategic mindset but also gain valuable insights into the company's future outlook, potential roadblocks, and cultural alignment.

Unconventional Business Strategy Interview Questions

Question 6: What have you defined as your “playing field”? In the process of focusing, have you concluded that there are certain areas where you don’t compete?

This question provides a clearer understanding of the company's strategic positioning and competitive landscape. As an executive candidate, this information helps you assess if your core competencies and experience align with the company's strategic focus. The question also uncovers the company's ability to identify areas where they do not compete, crucial for strategic decision making and resource allocation.

A clear understanding of the company's 'playing field' helps anticipate potential challenges, and opportunities, and better prepares you for the role. It also provides insights into the company's strategic thinking and planning processes. This question reveals the company's self-awareness about its positioning and gives you a snapshot of its competitive strategy, critical to your decision-making process as a potential executive.

Question 7: How do you define your competitive landscape? How do you know that that’s broad or narrow enough and are there any new entrants you are anticipating who could disrupt your business?

This interview question aims to test the company's self-awareness regarding its market positioning and competitive strategy. As an executive candidate, gaining insight into how the company defines and navigates its competitive landscape is critical. It helps you assess if the company has a keen understanding of its market, competitors, and potential disruptors, which are crucial aspects of strategic decision making.

The company's response can give you a sense of its strategic agility and preparedness in handling market changes or disruptions. The response can also hint at the company's corporate foresight, a trait vital for innovation and long-term sustainability. Therefore, asking this question positions you as a strategic thinker and can provide valuable insights into the company's strategic approach toward competition and innovation.

Question 8: How would you describe the company’s current lifecycle stage and what are the implications?

This unconventional question provides insight into the company's self-perception regarding its development stage and implications. As an executive candidate, understanding the current lifecycle stage is crucial, as it influences decision-making, planning, and resource allocation. You can infer the level of risk, innovation, and change you might encounter, and gauge whether it aligns with your ambitions and competencies.

For instance, a startup may require more risk-taking and innovative thinking, while an established firm may require change management and strategic planning skills. The company's response can reveal the leadership's strategic foresight and understanding of the business's potential trajectory. Posing this question exhibits your big-picture thinking and enables you to evaluate if the company's growth stage aligns with your aspirations and capabilities.

Question 9: What metrics have you chosen as the most important and what are the consequences of those metrics, for example, do they shape behavior in any meaningful way?

This question helps you understand the company's performance measures and their impact on employee behavior and organizational culture. It shows your understanding of the role metrics play in driving performance and shaping behaviors. As an executive candidate, it's crucial to identify the key performance indicators (KPIs) that the organization values most and the resulting behavior they encourage.

Do these metrics promote teamwork, innovation, and customer satisfaction? Or do they inadvertently encourage unethical practices or short-term thinking? The company's choice of metrics reveals its values, culture, and strategic direction. By asking this question, you demonstrate strategic thinking and assess if the company's performance measures align with your values and leadership style.

Question 10: What is the expected pace of innovation that you are targeting and how do you measure/ensure that pace is maintained?

This non-traditional question uncovers the company's innovation strategy. Understanding the expected pace of innovation is crucial for executive candidates as it impacts the organization's dynamism, agility, risk appetite, and commitment to continuous learning. How a company measures and maintains innovation reveals its creativity promotion and adaptability to market dynamics. The response provides insights into the company's commitment to innovation, procedures for encouraging new ideas, and how it recognizes innovative efforts. Asking this question shows your interest in the company's innovation strategy and evaluates its alignment with your leadership style and capabilities.

Unconventional Interview Questions About the Current Team

Question 11: Given the business strategy and objectives, how equipped is the current team to get the company where it needs to be?

This question assesses the correlation between team capabilities and strategic objectives. As an executive candidate, it helps you evaluate leadership skills, talent development, and potential team restructuring. The company's response reveals its commitment to employee development and talent management strategy. Asking it demonstrates your understanding of alignment between workforce and strategy, and whether it aligns with your leadership approach.

Question 12: What are the team’s greatest strengths? What are the gaps? And how are you trying to take both of those into account when hiring for this specific role?

This question reveals insights about the team you may lead and the organization's view of its talent pool. As an executive candidate, understanding team strengths is vital for driving results and achieving objectives. Identifying gaps provides clarity on areas needing development or reinforcement. This knowledge forms the foundation for post-hire talent management and leadership actions.

Additionally, it helps evaluate the company's understanding of the role and qualities required to maximize team strengths. Asking this question demonstrates your interest in effective leadership and aligning team dynamics with your expectations.

Question 13: How does the current team handle conflict? What examples can you offer?

This insightful question aims to examine conflict resolution strategies within a team. Understanding how a team handles conflict is integral to assessing dynamics, communication style, and emotional intelligence. Conflict management significantly influences team cohesion, productivity, and the work environment.

By asking for specific examples of conflicts and their resolution, you gain insights into problem-solving abilities, negotiation skills, professionalism, and leadership approach. It demonstrates a commitment to fostering a harmonious work environment and evaluates if conflict resolution aligns with your leadership style.

Question 14: Where does the team need to improve? Has this goal been made explicit?

This question is crucial as it uncovers areas of improvement and communication within the organization. As an executive candidate, you can influence change and inspire growth. Understanding areas for enhancement enables you to develop strategies to address them. By asking about explicit improvement goals, you assess transparency and communication. How a company communicates its goals indicates its culture of feedback and improvement. Asking this question highlights your commitment to team development and open communication, and helps you evaluate cultural alignment.

Question 15: Would everyone on the team describe the company, the team, and the strategy the same way?

This question, though seemingly simple, is a powerful way to assess team cohesion. As an executive candidate, understanding consistency in perception is crucial. If team members describe the company's mission, team role, and strategy uniformly, it signifies a well-communicated vision. However, variations in descriptions might indicate communication gaps or misalignments, impacting your leadership approach. The company's response to this question reveals its openness to addressing inconsistencies and fostering a unified culture. Asking this question reflects your interest in team alignment and helps you evaluate cultural fit.

Unconventional Corporate Culture Interview Questions

Question 16: Some people define culture as the rules of how work gets done that are unwritten but followed by everyone. What are some of the things that you think constitute the “unwritten rules” here?

This question dives into the essence of organizational culture, focusing on the implicit norms and behaviors that govern how work is accomplished within the company. It offers an opportunity to discover unspoken expectations and values that shape interactions and decision-making processes among employees.

Exploring these unwritten rules provides insight into the underlying cultural principles and dynamics that offer a deeper understanding of the shared beliefs, attitudes, and practices that influence daily operations and interactions within the workplace.

As an executive candidate, understanding these unwritten rules is vital for effectively navigating the organizational landscape. It enables alignment of behavior and decision making with the prevailing culture, fostering collaboration, trust, and mutual respect among team members. Additionally, it empowers contribution to shaping and reinforcing the desired cultural norms within the organization.

Question 17: Are there any elements of your culture that are unique, in other words, something that no other company does?

This question is a creative interview inquiry that explores the distinctive aspects of the company's culture. As an executive candidate, it's important to understand the unique attributes that differentiate the organization. This perspective helps to assess if the company’s uniqueness aligns with your personal values and leadership style. Cultural uniqueness often signifies innovative practices, unconventional approaches, or unique traditions that enhance employee engagement, satisfaction, and loyalty. It also provides insight into how much the company values differentiation and uniqueness in its work environment.

By asking this question, you demonstrate a desire to appreciate and contribute to the unique cultural elements that define the company. The response to this question can serve as a measure of the company's authenticity, its commitment to preserving its uniqueness, and how it fosters a distinctive work environment. Such a question underscores your eagerness to be part of a unique and vibrant company culture.

Question 18: Where are you trying to take the culture in the future? Ideally, what does the culture look like 1 year from now?

This question helps gauge the company's vision for its organizational culture. Understanding their cultural aspirations provides insight into growth strategies and alignment with your leadership philosophies. Inquiring about the company's vision for its operating culture offers you valuable insights into the organization's growth strategies as well as the potential alignment with your own leadership style.

By gaining a perspective on their approach to change, specifically the steps they take to implement it and how you can contribute to those efforts, you can assess their commitment to becoming a forward-thinking organization that embraces continuous evolution. Their response will also reveal their level of agility and responsiveness to change, and how your role fits into their broader cultural development strategy.

Question 19: How does the culture support the business strategy?

This interview question can reveal insights into how the organization's culture aligns with its business objectives. Understanding the relationship between culture and strategy is crucial for organizational success. The culture can either propel strategy execution by fostering alignment, engagement, and innovation or hinder it by creating friction. By asking this question, you show an understanding of the relationship between culture and strategy and your interest in cultivating a culture that supports the business strategy. The company's response can provide insight into its strategic alignment and its commitment to leveraging culture for success.

Question 20: Are you open to new employees coming in and adding their own distinct flavor to/changing the culture? It’s easy to say “yes” but can you point to an example of when this happened recently and how the company reacted.

This interview question assesses the company's openness to diversity, change, and fresh perspectives. It helps understand the company's willingness to embrace new employees and reveals how inclusive and adaptable they are. Asking for a specific example compels the interviewer to provide tangible evidence, showing how the company handles change and integrates new influences into its culture. It also assesses the freedom and support you'll have to implement your ideas. By asking this question, you demonstrate your intention to actively participate in the company's culture and bring your unique value.

Confidently Navigate Your Next Career Move

Incorporating unconventional interview questions significantly enhances an executive candidacy. Each question serves as a strategic tool, revealing insights into the company’s culture, and business objectives, offering you an understanding of the organization’s decision environment. These questions not only provide a glimpse into the company's inner workings but also demonstrate your proactive approach to comprehending and contributing to its success.

The insights gained from these questions are invaluable for making informed decisions about your career journey as an executive leader. They offer clarity on whether the organization's values and culture resonate with your professional goals and working style. Armed with this understanding, you can confidently navigate opportunities that align best with your long-term career aspirations and personal fulfillment.

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