Organizational Wellness

Hire the Best Leadership: 28 Strategic Questions to Ask Senior Leaders in Interviews

Mar 12, 2024
Last Updated Mar 12, 2024

When you are on the hunt for a senior executive, asking relevant questions in an interview can reveal key details. What is their perspective on employee wellness? How will their leadership style add to your workplace culture? Getting a sense of who this leader is and what they can do is one of HR’s most important responsibilities. 

The top brass are at the heart of decision-making and the direction of your organization as a business. These executives have a major impact on employee performance, influencing everything from trust to retention.

To find leaders that your teams will trust and thrive under, you can start by honing your interview inquiries. The best ones are more than just conversation starters — they allow candidates to put their best foot forward. These strategic questions to ask senior leaders can help HR leaders conduct insightful interviews.

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28 Strategic Questions for Leaders

With such limited time with your candidates, forming clear categories can help HR ask questions that will have the most impact. This ultimately facilitates a more structured and insightful conversation. Some of the most common and relevant categories include:

  • Questions about employee engagement
  • Questions about strategy and performance
  • Questions about company success and vision
  • Questions about company culture
  • Questions about the importance of employee wellbeing
  • Questions about career growth and development
  • Fun questions

Questions about Employee Engagement

Employee engagement is a top concern for organizations, and for good reason. Engagement indicates how invested and motivated employees are regarding their contributions to an organization. 

There is also a strong correlation between employee engagement and positive performance outcomes including profitability, productivity, wellbeing, and retention. And employees are 14 times more likely to be fully engaged if they trust their team leader, according to an ADP Research Institute Global Workplace Study survey. Given how much of an impact engagement has on a business, it’s important to learn how your candidate approaches engagement. Especially competitive candidates will have ideas about how to not just maintain employee engagement, but boost it. 

Consider questions that prompt examples and new opportunities, like these:

  • How do you measure and evaluate employee engagement within an organization?
  • Can you share a specific example of a time when you identified a dip in employee engagement and how you addressed it?
  • What role do you believe senior leadership plays in fostering engagement, and how have you embodied this in your past?
  • In your view, how does employee engagement impact organizational performance?

Questions about Strategy and Performance

Senior leadership largely influences your company’s direction, from analyzing performance indicators to implementing a long-term strategy. With the right questions, HR interviewers can identify how a candidate will contribute to their organization’s future success.

This requires asking questions about strategy and performance. Strategy questions shine a light on the “why” behind organizational decisions, while performance questions indicate how effectively that strategy is working. 

From market conditions to organizational structure, these questions help candidates share how they tackle these high-level tactics:

  • How do you ensure that your strategic goals are aligned with the overall objectives of the organization?
  • Can you highlight akey performance metric that you use to measure success? Why that one?
  • Can you provide an example of a strategic risk you took based on your understanding of the market, and what was the outcome?
  • Can you give an example of a time when a strategy you implemented did not perform as expected? How did you respond?

Questions about Company Success and Vision

One of the major responsibilities of leadership is to provide a clear vision of the organization’s future. The company vision guides the organization through tricky markets and tough decisions, about both business and workforce management. 

It’s helpful when senior leaders can break down their primary priorities so that the workforce can bring the vision to life. Solid questions can help candidates share how they envision the company’s future.

You can consider asking:

  • How do you define success for our organization, and what role do you see yourself playing in achieving that success?
  • Looking ahead three to five years, what major milestones would you aim to achieve within our organization, and how would you approach these goals?
  • How does our company vision align with the needs and expectations of its customers or clients?
  • What are the biggest challenges our industry will face in the coming years, and how should our organization successfully adapt?

Questions about Organizational Culture

Companies that neglect their culture often struggle to meet business and operational goals. Culture is all about collective values and behaviors, which inform the performance of teams and individuals. From communication styles to diversity and inclusion, culture shapes the effectiveness of the workforce. Discussing culture with senior leadership in interviews can show what policies and values a candidate prioritizes — or help identify gaps. 

With that in mind, HR has the important job of hiring executives who will best support or improve the company culture. Consider these questions:

  • How would you describe your ideal organizational culture, and how have you worked to cultivate such a culture in your previous roles?
  • Can you give an example of a time when you had to address a cultural issue within your team or organization?
  • In your experience, how does an organization's culture impact its success? How does leadership play a role in modeling that culture?
  • Can you share examples of successful team collaborations and how they exemplify high-performing team culture?

Questions about the Importance of Employee Wellbeing

Employee wellbeing and organizational success are another pairing that go hand in hand. Eighty-seven percent of workers say they would consider leaving a company that does not focus on employee wellbeing. This goes to show just how important wellbeing is to encourage employee loyalty and morale. 

A leader’s perspective on wellbeing in the workplace, such as what work-life wellness looks like, says a lot about how they view employees. Wellbeing is often influenced by factors like benefits and wellness programs, which leaders also have a lot of influence over.

Questions that touch on these topics can reveal how senior decision-makers incorporate wellness into their strategic planning.

  • In your leadership role, how do you recognize signs of burnout in your team members, and what steps do you take to address it?
  • What policies or practices have you found effective in supporting work-life wellness?
  • Can you describe a program or benefit you've supported that directly contributed to improving employee wellbeing? What did that success look like?
  • How do you balance the demands of achieving business objectives with the wellness needs of your workforce?

Questions about Career Growth and Development

Leaders have a big role in creating an environment of continuous learning. They set the tone for professional advancement, both as the primary examples of leadership and as the people who spearhead company growth.

An interview is a great time to learn about a candidate’s take on growth and development for employees. Leaders who understand the significance of career growth also foster a culture of engagement and employee retention

These questions can help explore the ways a potential leader would prioritize development opportunities company-wide.

  • How do you think leaders should support and encourage the career growth of employees, particularly those aspiring to leadership roles?
  • Can you share an example of a professional development program you initiated or supported that had a significant impact on your team's performance?
  • What sort of training and development opportunities would you implement for employees, such as upskilling to keep up with industry trends?
  • What strategies do you use to ensure that you continually grow and develop as a leader?

Fun and Engaging Questions

Adding a touch of fun to executive interviews can help reveal the candidate's personality and ability to connect on a human level. Plus, creating a genuine connection upfront may deepen your discussion down the line. Some questions can even reveal how executives achieve work-life wellness and balance their time. Consider these light-hearted questions:

  • Do you have a morning routine, and if so, how does it impact your productivity and success?
  • Is there something new you want to learn this year?
  • What's the most memorable or hilarious team-building activity you've ever participated in, and what made it so unforgettable?
  • What's one hobby or activity you're passionate about, and how does it influence your professional life?

How to Craft Strategic Questions for Senior Leaders

Of course, every company is unique. This means you will want to know things about your potential leaders that can only be learned by asking questions tailored to your organization. Fortunately, there are simple guidelines you can follow to write effective questions for a leadership interview. 

Test Business Strategies

Holding a leadership role at your organization will call for more than ambition — it requires anticipating market trends and potential issues, too. Consider what changes you are likely to arise in your industry in the coming year or two, and write questions about how the candidate thinks the company should adapt. This will help you evaluate the candidate’s market knowledge and what role they see the company playing in the future.  

Evaluate Problem-Solving Skills

The ability to confront and navigate complex challenges is paramount to leadership. To test a candidate’s problem-solving acumen, pose scenarios that your organization might face or has encountered. Questions should prompt the candidate to outline their thought process, from identifying the root cause to implementing a resolution. This exploration will illuminate their capacity for analytical thinking and creativity under pressure, essential traits for navigating the uncertainties of the business landscape.

Identify Leadership Qualities

Leadership transcends mere management — it's about inspiring, guiding, and uniting a team towards common goals. To assess a candidate’s leadership style, focus on how they have motivated a team or and fostered an inclusive culture. Ask for specific examples where they have demonstrated resilience or empathy. This line of questioning reveals much about their potential to positively impact your organizational culture, employee morale, and the overall effectiveness of the team they're looking to lead.

Encourage Self-Reflection

A leader’s ability to self-reflect is indicative of their capacity for growth and adaptation. This quality is crucial in today's fast-paced business environment, where feedback loops and continuous improvement are part of daily operations. To gauge this, ask candidates to share experiences where they had to reflect on their actions or decisions, whether it led to a positive outcome or a lesson learned. This not only provides insight into their humility and openness to learning but also their resilience in the face of setbacks or failure.

Spark Dialogue

The most revealing conversations are more likely to emerge from discussions than a straightforward Q&A. Crafting questions that ignite thoughtful dialogue allows you to peer into how a candidate processes information, considers various perspectives, and communicates their ideas. Propose complex issues or ethical dilemmas relevant to your industry or organization. The aim is to engage in a dynamic exchange that sheds light on the candidate’s values and ability to articulate nuanced thoughts. This approach can be particularly illuminating, offering a deeper understanding of how they might interact with stakeholders in your organization.

Using Strategic Questions as a Catalyst for Organizational Wellness

A structured and focused set of interview questions can be one of the most effective HR tools in your arsenal. Inquiring about relevant subjects can not only lead to insights about the candidate but the organization, too. It’s all about asking the right question to glean the most impactful information — which can help HR make an informed decision when hiring.

Some of the most important topics during these interviews are how to streamline operations and prioritize employee engagement. Both of these concerns can be addressed with employee wellness programs. A focus on wellness can boost productivity by taking care of employee needs. Eighty-eight percent of C-suites consider wellness programs a competitive advantage — and your program can be just as competitive with the right resources. 

Equipped with solutions for physical, mental, and emotional health, Gympass can help organizations build a wellness program that moves the needle for employees. Talk with a wellbeing specialist to learn more!

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Gympass Editorial Team

The Gympass Editorial Team empowers HR leaders to support worker wellbeing. Our original research, trend analyses, and helpful how-tos provide the tools they need to improve workforce wellness in today's fast-shifting professional landscape.


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