How to Interview a CEO in 100 Questions

March 22, 2023

The selection process is highly stressful for companies and recruiters. However, the challenge raises to a whole different level when interviewing CEO job applicants. The Chief Executive Officer is the highest-ranking individual in an organization.

They make the principal and most impactful decisions in a company, driving its profitability, expansion, and market share. CEOs typically have extensive experience, knowledge, and wisdom that makes them both powerful and intimidating.

For instance, their average annual salary is 107,680 USD, and C-Suite professionals must work in their industry for at least five years to reach this position. Because of that, recruiters have a demanding task when interviewing candidates who apply for executive roles.

The best way to do it right is to prepare well and establish a thorough selection process. There’s no place for mistakes or hesitation when identifying a CEO because they will make the principal decisions in a company and determine its future.

Not getting the selection process right could jeopardize an organization’s market capitalization, stock prices, reputation, and longevity. Recruiters and hiring managers should avoid mistakes by establishing comprehensive interview questions that help them determine the compatibility of each candidate.

How to Prepare for an Interview with a CEO Candidate?

When preparing for interviews with executive candidates, it’s advantageous if you weeded out underqualified applicants in previous stages. Only those who fit the profile of your envisioned ideal candidate should get to the interview phase.

However, first, you should determine what makes someone a perfect CEO of this specific company and in this industry.

An executive should lead by example. Because of that, they must embody a company’s mission, principal objective, culture, and values. Yet, that’s not enough.

Your ideal CEO should meet the technical requirements and expectations to be successful in this role. They should have an all-encompassing knowledge of the industry, understand the trends, and predict challenges.

Moreover, an executive should be goal-driven and focused on achieving results. They don’t settle for the average and have an innovative approach.

The ideal CEO candidate will express its passion for the industry in their job application and showcase achievements and projects that prove their expertise. They should have the capacity to share their knowledge within the organization and stimulate innovative solutions and strategies.

Hence, your perfect applicant is a stellar cultural fit who has the required technical and soft skills.

That should make it easier to understand what kinds of questions you should ask. Center them around the vision of your ideal CEO and design the questions with this in mind.

Strive for an in-depth assessment as you’re interviewing people who applied for a role with the highest level of responsibility and accountability. Because of that, you should pay attention to nuances in their answers that could make the final selection easier.

Simplify the process by identifying criteria that will guide your interviews and help you recognize candidates with the highest potential according to their answers. Seek the input of other executives and board members to determine the question flow and detect job applicants who meet company expectations.

When selecting the future CEO, it’s not enough only to look for technical abilities and soft skills. Go beyond the elementary aspects to find well-rounded candidates who could be stellar executives.

What Makes a Well-Rounded CEO?

Interviews with executive candidates are a challenge even for the most experienced recruiters, especially if they don’t have a vision of what makes a great CEO. According to an SHRM report, executive selection boards and staffing directors typically look for characteristics similar to their own, using attributes from previous searches or relying on instinct and intuition.

Yet, that can result in disastrous aftermaths because it’s essential to select candidates who match the current imperatives of the company. CEO accounts for 45 percent of an organization’s performance.

Hence, profound scrutiny in choosing the most compatible candidates isn’t only understanding but mandatory. But how can an interview reveal which individual comes closest to what a company needs?

First, remove gut feelings, instincts, and prejudices from the selection process. Rely strictly on facts, behaviors, and skills one can prove.

For instance, SHRM identifies four categories of executive attributes:

  • Cognitive skills – These abilities center around problem-solving, intelligence, critical thinking, creativity, and absorptive capacity.
  • Interpersonal skills – These abilities include communication, social awareness and judgment, negotiation and persuasion, collaboration, relationship-building, and multicultural sensitivity.
  • Business skills – Business acumen, finance management, organization management, and global networking are among these capabilities.
  • Strategic skills – These capabilities include visioning, systems-level perceptiveness, innovation, talent management, and adaptability.

However, SHRM also notes that today’s ever-changing world requires a new kind of executive – the one who can balance multiple roles and possess behavioral complexity. Because of that, interviews with executive candidates should focus on absorptive capacity, ability to change, and managerial wisdom.

Another quality a stellar CEO should possess is to work well across cultures because that could become essential in the future.

McKinsey also conducted a study to identify what makes an excellent executive mindset. The results have shown that well-rounded CEOs have a bold corporate strategy and reframe the reference point for success.

Moreover, they think systematically about their people, put team dynamics ahead of mechanics, help the company board create long-term value, and act on a corporate purpose while also thinking about how it benefits society.

Keep these in mind when creating a set of questions for the interview with CEO candidates. Ensure that you cover various categories that help you understand their qualities, behavioral traits, and whether they could achieve success in this position.

Here are the best questions you can ask executive candidates during an interview.

100 Questions that will Help You Identify the Best CEO Candidate

Leadership Vision

  • If you become the CEO of our company, what would be your long-term strategy and vision?
  • What actions would you take to ensure the executive board and employees develop a connection with your strategic vision?
  • What would you do to inspire other executives and employees to drive and fulfill your vision?
  • Share what would be your principal four objectives for the company if you become a CEO.
  • What do you see as potential threats standing in your way to accomplishing those objectives?
  • Reflect on your past experiences and describe your response to encountering challenges in achieving company goals.
  • What is the principal thing our company is going well now?
  • Explain what our organization could do better?
  • If you become the CEO of our organization, what actions would you take to improve those issues?

Strategic Potential

  • What would you highlight as crucial strategic concerns for our organization for the next five years?
  • If you were the CEO of our organization, what actions would you take to ensure success in managing those priorities?
  • Describe the strategies and methods you used in the past to address and neutralize competitive threats?
  • How did you measure your success in responding to these threats?
  • Reflect on your past experiences and explain what actions you took to guide the creation and implementation of new business products, services, models, or strategies?
  • How did your strategic vision transform in the process of adjusting to a new business model?
  • What steps have you taken in the past to ensure buy-in from stakeholders while the organization was transforming?
  • What do you see as the principal threats to our company?
  • What actions would you take to mitigate those threats?

CEO Objectives

  • As a leader, what actions would you take to guide the company in setting objectives?
  • Describe how you would make sure that objectives across all levels align well, including organizational and department goals.
  • How would you lead our company in prioritizing its objectives?
  • How would you identify the information you need to launch the goals across all levels?

Handling Competition

  • Explain how you would analyze our competition.
  • Describe how do you keep up with what the competitors are planning or introducing?
  • What would be your response if our main competition is achieving success with a project or service that we didn’t?
  • What strategies would you use to stay ahead of our competition?

Initial Integration in the Company

  • Describe your priorities in the first three months if you become the CEO of our company.
  • What actions would you take to gain the trust and buy-in of other executives and staff?
  • What factors and trends would influence your plan in the first three months?
  • Describe how you would get an in-depth knowledge of our company, business, and objectives?

Accelerating Business Expansion

  • What strategies would you use to improve our position in the market?
  • What steps would you take to establish the core competencies of our company?
  • Describe what actions you took in the past to drive business towards growth acceleration, a higher EBITDA margin, and profitability boost?
  • Reflect on the past and describe when you accelerated business expansion through a joint acquisition or venture?
  • Describe the long-lasting impact of this joint undertaking?
  • Describe the strategies you used to ensure new revenue streams from starting new services or launching an innovative product?

Leadership Style

  • How would you describe your leadership philosophy?
  • What actions do you take to materialize that philosophy?
  • What is your leadership style?
  • What makes our company an environment where your leadership style can thrive?
  • What actions would you take to improve the performance of your executive team?
  • Looking back to the past, how did you motivate your employees?
  • What strategies would you implement to create tight-knit connections and teamwork across the company?
  • Remember a team when you had to lead your team through challenging circumstances. How did you leverage your leadership abilities to overcome the difficulties?

Fostering Leadership Skills

  • Describe when you lacked experience or competencies, resulting in a less effective result than you wanted.
  • What did you do to enhance your expertise in this field?
  • How would your past executive team describe you?
  • What do you see as your most threatening weakness regarding leadership abilities?
  • What do you do to mitigate that weakness and use it to your advantage?
  • What do you think your previous employees would highlight as your principal leadership strength?
  • What areas are you trying to enhance to be a more well-rounded leader?
  • What actions do you take every day to be a great CEO?
  • How do you respond to feedback?
  • Describe how acting upon constructive feedback helped you evolve as a leader.

Managing Finances and Budget

  • Explain how you would manage profit and loss and the company budget?
  • What steps would you take to ensure your team centers its efforts around organizational investments?
  • How would you respond to teams and departments causing costs that exceed the budget?
  • How has cost-benefit analysis helped you make better leadership decisions in the past?
  • What financial reports should your staff prioritize?
  • What actions did you take to reduce costs in the past?
  • How do you go about difficult decisions such as hiring freezes or budget cuts during challenging times, such as the pandemic?

Enhancing Processes

  • What methods did you use in the past to improve total shareholder return and boost efficiency?
  • If you become the CEO, how will you detect and track threats in the company?
  • Describe a time when you and your team implemented a procedure change of greater scope, causing improvements in the company across all levels.
  • How did you lead your team during this process?
  • How did you gain a buy-in from key stakeholders to implement that change?
  • How did you identify whether the change was successful?
  • What methods and strategies would you use to solve a problem with your executive team?

Tracking and Measuring Key Metrics

  • What metrics would you want every department and team to establish?
  • What steps would you take to ensure your team leaders are accountable for accomplishing these metrics?

Managing Performance

  • How would you reinforce accountability among your leaders for fostering leadership abilities?
  • How would you measure employee performance?
  • How did you react to subordinates who failed to meet your standards and expectations in the past?
  • Why do you think rewards and appraisal programs are significant for the company?

Choosing Top Talents

  • What strategies and initiatives would you implement to attract high-quality candidates?
  • How would you leverage your professional network to source qualified talents?
  • What steps do you take to ensure the HR departments select the most compatible candidates?
  • What do you think are the main qualities of leadership-oriented employees?
  • When selecting leadership team members, how do you ensure they’re the right cultural fit?
  • What do you think about candidate background screening?
  • How do you think artificial intelligence can improve the recruitment process?

Bonding with the Team

  • As a new CEO, how do you establish rapport and encourage employees to commit to your objectives?
  • How do you foster diversity within your organization?
  • Why do you think having a leadership team with a mix of personalities and backgrounds matters?
  • What strategies would you implement to ensure every employee feels a sense of belonging in the company?

Navigating Failure

  • How did you respond to situations when your efforts or initiatives failed?
  • What lessons did you get from those situations?
  • How would you lead an organization to recovery after it encountered an impactful failure?

Handling Conflict

  • Describe a time when you helped your team overcome a conflict.
  • Talk about a time you encountered a challenging customer and how you responded.
  • What actions would you take to solve conflicts in your leadership team?

Talent Management

  • How do you support your staff in reaching their full potential?
  • What actions did you take in the past to increase employee retention?

Culture Fit

  • What principles guide your career?
  • How do your principal values match the mission, culture, and objectives of our company?
  • What experience had the highest impact on who you are today?

Work Across Cultures

  • Describe a time when you collaborated with international partners. What were the outcomes?
  • How would you manage an international company expansion?

Technology and Innovation

  • How would you ensure the organization is using the most efficient technology that accelerates the processes?
  • What actions would you take to reinforce innovation in the company?


Identifying a CEO among many candidates is one of the most challenging tasks any hiring manager could have. This decision can determine your company's future, making it crucial to prepare for the interview thoroughly.

That includes making a list of comprehensive questions that can point to what job applicant has the necessary technical abilities and soft skills. But you don't need to do this alone.

JB Hired can help you find world-class talents thanks to their in-depth understanding of profiling and network of CEOs. Being recognized as the leading headhunting agency in the tech industry, JB Hired has access to the largest global database of tech talents.

Whether you are a large organization undergoing a digital transformation or a fast-growing tech company or simply trying to fill a challenging role, our experience and active headhunting approach guarantees you will get the best candidates in the market!

Reach out to our consultants for more information on how we can support finding your next best hire.