10 Questions to Ask the CEO: Uncovering Business Insights

As a CEO myself, and a key figure in the boardroom for several successful businesses, there is one thing that I would advise everyone to do: before you enter into business with someone, do your research. A little “due diligence” is all it takes, and more often than not the information is there for all to see through their online footprint: the type of person they are, the sort of people they associate with. And ultimately, through Companies House and other portals, you’re able to see whether they have a good history or bad history in previous business dealings.

I don’t just jump feet first into business. It takes time to build trust and to find out what my associates and prospective partners are about, and I understand the importance of asking the right questions when given the opportunity to interact with the CEO of a business.

These questions can help me gain valuable insights into the company’s vision, goals, and expectations, as well as learn from the experiences and knowledge of a highly accomplished individual, figuring out how they have got to the position they’re in today.

Assessing Company Vision and Strategy

As I delve deeper into understanding the company’s vision and strategy, I find it crucial to ask the CEO certain questions that can give me insight into the organisational goals and objectives.

Understanding the Company’s Mission

Getting to know the company’s mission helps me understand the core values and principles driving the business. To assess this aspect, I may ask the CEO:

  • How would you describe the company’s mission in a single sentence?
  • What inspired the creation of this mission?
  • How does the company’s mission align with the daily operations and decision-making process?
  • Are there any plans to revisit or update the company’s mission in the near future?

Asking these questions will allow me to comprehend how the CEO views the company’s mission and its impact on the overall functioning and growth of the business.

Discussing Long-Term Goals

Beyond the company’s mission, understanding its long-term goals is essential for evaluating the plans and strategies being employed for sustainable growth. Some insightful questions to discuss with the CEO could be:

  • What are the company’s top three long-term goals for the next five years?
  • How do these goals align with the overall vision for the company?
  • What strategies are in place to achieve these goals?
  • How do you evaluate the progress towards meeting these goals, and how often is this evaluation done?
  • Are there any external factors or market trends that could significantly impact the achievement of these goals?

Positive and informative responses to these questions can give me a deeper understanding of the company’s long-term objectives and the measures being taken to achieve them.

Evaluating Leadership and Management Style

As a vital component when inquiring about any CEO’s objectives and values, understanding their leadership and management style can offer insights into how they operate and influence their organisation’s culture.

Personal Leadership Philosophy

In my pursuit of gaining insight into a CEO’s personal leadership philosophy, I would ask questions like:

  • What motivates you as a leader, and what drives your leadership approach?
  • What are your core values, and how do they shape your decision-making process?
  • How do you strike a balance between driving performance and supporting employee well-being?

These questions can help me obtain a better understanding of the CEO’s guiding principles, which in turn have a significant impact on the company’s direction.

Approach to Employee Engagement

Another important aspect I’d like to uncover is their approach to employee engagement. To do this, I would ask the following questions:

  • How do you foster open communication within the company, and what strategies do you use to ensure employee voices are heard?
  • What methods do you employ to identify and develop talent within the organisation?
  • How do you measure employee engagement and satisfaction, and how do these metrics inform your management decisions?

By asking these questions, I can gain insight into the CEO’s efforts in maintaining a healthy employee relationship and motivating their workforce to perform optimally.

Company Culture and Values

In this section, I am going to discuss company culture and values by exploring how culture influences decision-making processes and the importance of promoting diversity and inclusion. Both of these components are crucial to the success of any organisation and worth understanding by asking specific questions to a CEO.

Role of Culture in Decision Making

Company culture plays a significant role in how decisions get made within a business. It is essential to ensure that the company culture fosters an environment where employees feel comfortable speaking up and sharing their thoughts.

You might want to ask the CEO, “How have you fostered a company culture that encourages open communication and effective decision-making?” Another question to consider is, “How do you promote a culture of innovation and risk-taking in your organisation?” You can also inquire about the CEO’s views on the role of culture in making business decisions by asking, “Do you believe that the company’s culture impacts decision-making? If so, how?”

Promoting Diversity and Inclusion

Having a diverse and inclusive workforce not only contributes to a fair working environment but also positively affects a company’s performance. A CEO should be aware of the significance of embracing diversity and ensuring equal opportunities for everyone. As such, some potential questions to ask the CEO related to diversity and inclusion could be:

  • What steps have you taken to increase diversity and inclusion in your company?
  • How has promoting diversity and inclusion benefited the business?
  • What challenges have you faced in fostering an inclusive work environment, and how have you addressed them?

By asking these questions, you can gain valuable insights into the company culture, values, and the CEO’s perspective on these essential aspects of the business. Ultimately, these inquiries will help you better understand the organisation and its leadership.

Performance and Growth

In this section, let me discuss a few questions that can help you understand the performance and growth aspects of the business from the CEO’s perspective.

Key Business Metrics

One critical question to ask the CEO would be, “How do you measure the success of the company, and which key performance indicators (KPIs) do you focus on?” This enquiry can provide insights into the CEO’s priorities and the company’s strategic objectives.

For instance, they might mention metrics like revenue growth, customer satisfaction, or employee retention as essential indicators of success. Remember, these metrics might vary depending on whether the business is a startup, an established company, or in a transition phase.

Another question I find useful is, “In your opinion, what have been the most impactful decisions that have improved the company’s performance?” This question encourages the CEO to share their thoughts on crucial decisions made within the company, such as innovations, market strategies, or leadership appointments, which can give you an insight into their decision-making process and future plans.

Opportunities for Expansion

When it comes to exploring the growth potential of a business, asking the CEO about the strategies and plans they have for expansion is essential. You may want to enquire, “What key markets or industries do you plan to target for future growth?” This question can help you understand the company’s target audience and growth sectors as well as specific opportunities they are currently exploring for expansion.

Another question that brings clarity to the growth plans is, “What do you see as the most significant challenges that your company faces when expanding and how do you plan on overcoming them?”

Understanding the CEO’s perspective on the barriers to growth can offer a better understanding of how prepared the company is for expansion and any proactive measures they are taking to manage potential setbacks.

Innovation and Adaptability

In my experience, innovation and adaptability are critical aspects for any company’s success. It’s essential to know how the CEO perceives these areas; here are some questions to ask about embracing change and prioritising technological advancements.

Embracing Change

1. How do you foster a company culture that encourages innovation and adaptability?

Creating an environment where employees feel empowered to explore new ideas and make bold decisions is essential for a thriving business. Understanding how the CEO achieves this can provide insights into the company’s mindset and approach to innovation.

2. How do you handle setbacks or failures related to innovative projects?

Innovation often involves taking risks and learning from failures. Knowing how the CEO views setbacks – as opportunities for learning or barriers to success – can reveal their attitude towards business growth and development.

3. How do you ensure that innovative ideas are not stifled by bureaucracy or “yes, but” attitudes?

Developing a culture of “yes, and” can be crucial in ensuring that potential breakthroughs are brought to fruition. A CEO’s strategy for mitigating resistance can offer valuable insights into how the company promotes creative thinking.

Prioritising Technological Advancements

1. How does your company stay ahead of industry trends and emerging technologies?

It’s vital to determine whether the CEO keeps abreast of new technologies and how the company ensures it remains competitive in a rapidly changing landscape.

2. How do you allocate resources to research and development?

Funding plays a crucial role in driving innovation. Asking about the CEO’s approach to resource allocation can offer insight into the company’s commitment to research and development and whether it’s adequately fuelled by the necessary investments.

3. How do you balance traditional business methods with technological advancements?
Incorporating technology into a business often requires a delicate balance between embracing new tools and maintaining tried-and-true practices. It’s essential to know how the CEO strikes the right balance, ensuring that innovation doesn’t come at the expense of core business operations.

Corporate Social Responsibility

As I researched different CEOs and their approach towards corporate social responsibility (CSR), I found that these topics are crucial to include in the conversation: commitment to sustainability and community involvement. By asking these questions, we can gain a better understanding regarding the company’s values and priorities.

Commitment to Sustainability

How important is a sustainable business to your company? In today’s business climate, understanding a CEO’s commitment to sustainability plays a crucial role. Many stakeholders are focused on the triple bottom line of people, planet, and profit.

I would ask the CEO to explain their approach to sustainability and identify the key pillars of their sustainability strategy. This will provide insights into their company’s long-term goals and shed light on the importance given to ESG and sustainability efforts.

Community Involvement

What is your company’s approach to community engagement and philanthropy? Many CEOs understand the importance of giving back to the community and integrating philanthropic efforts into the fabric of their organisation.

By inquiring about the company’s community involvement, I can gain an understanding of their corporate values and alignment with social issues. Moreover, this will provide an insight into the CEO’s personal values as a leader.

Asking these critical questions is essential when discussing CSR with a CEO. Their responses will enable us to better comprehend their company’s values and priorities while fostering a transparent dialogue about social and environmental issues.

Handling Challenges and Crisis Management

In my experience, it is essential to address the CEO’s approach to handling challenges and crisis management. This section covers two significant sub-topics: past experiences and risk management strategies. By understanding these aspects, one can better appreciate how the CEO guides the organisation through various situations.

Past Experiences

When I discuss past experiences with a CEO, I often inquire about their most significant challenges in previous roles and how they overcame them. To gain valuable understanding, I might ask:

  • Can you share an example of a significant challenge you faced in a previous role, and how did you resolve it?
  • How has your experience in navigating past crises shaped your leadership style and decision-making?
  • What lessons have you learned from handling previous crises that have proven useful in your current role?

By asking these questions, I can grasp how the CEO’s experiences have honed their ability to manage difficult situations, providing valuable insight into their leadership.

Risk Management Strategies

Understanding the CEO’s approach to risk management strategies is crucial, as these can greatly influence their company’s resilience amid challenges. To gain this understanding, I might ask:

  • How do you identify and assess potential risks to the company? Are there specific tools or processes you rely on?
  • What action steps do you take to mitigate these risks, and how do you ensure they are effective?
  • How do you ensure the entire organisation is prepared for potential crises, and how is this incorporated into the company culture?

By focusing on past experiences and risk management strategies in conversations with a CEO, I am better equipped to comprehend their approach to handling challenges and crisis management. This, in turn, allows me to appreciate their leadership style and potential impact on the organisation’s overall success.

Personal and Professional Development

In this section, I’ll discuss the importance of personal and professional development and how asking the right questions can help both the CEO and employees in their growth.

CEO’s Continuous Learning

Engaging with the CEO on their continuous learning journey demonstrates curiosity and can open up an insightful conversation. One question I might ask is, “What are your personal goals, and how do you work towards achieving them?“. By understanding their motivators, I can adapt and align my own goals to the organisation’s vision.

Another useful question I could discuss with the CEO would be, “How do you keep yourself updated with the latest industry trends and innovations?” This would give me an insight into their preferred learning methods and potentially help me stay updated as well.

Supporting Employee Development

Asking the CEO about their approach to employee development can provide clarity on the company’s expectations for growth. A question like, “What do you expect from the company’s team members in terms of personal development?“, can help me understand the desired qualities that can lead to success within the organisation.

Another key question in this area could be, “How can I best support my colleagues and contribute to a positive work environment?” This demonstrates my willingness to collaborate and invest in the company’s success.

Finally, a practical way to address employee development is to ask, “How can I help?“. Knowing the areas where the CEO would appreciate support shows initiative and a desire to make a difference in the workplace.


Having considered several thought-provoking questions, I believe that it’s crucial to engage in productive conversations with CEOs to better understand their perspectives and learn from their experiences. In this article, I explored key questions such as expectations from team members, company culture and goals, and the biggest challenges the company faces. These questions can indeed help employees and stakeholders make informed decisions and contribute to the company’s growth.

Moreover, focusing on an executive’s view of the number one trait they look for in their employees (source) and diving into decision-making processes and challenges faced by the company can offer valuable insights. Reflecting on these discussions, I believe that fostering an open and curious mindset towards business leaders can drive innovation and inspire success.

Constantly seeking knowledge and demonstrating the willingness to learn from the CEO has the potential to significantly impact both personal and professional growth. Asking the right questions can lead to increased understanding, alignment with company values and objectives, as well as stronger connections with the CEO and other team members.

As such, I encourage everyone to think about the variety of questions presented in this article and consider which ones resonate with their own personal and professional journey.

Related Posts

How to Self-Reflect

Self-reflection is a vital process for personal growth and emotional well-being. It involves taking time to consider one’s actions, thoughts,

Read More