Senior leaders have tons of experience and strategic wisdom. Whether you are looking for career advice, leadership insights, or just want to understand their vision, asking the right questions to ask senior leaders can unlock a world of perspectives.
In this guide, we have rounded up 56 unique questions that go beyond the usual small talk. These conversation starters will spark meaningful discussions – and even leave a lasting impression. Let’s explore what you can ask to make the most of your time with them.
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Strategic Questions To Ask Senior Leaders
Talking to senior leaders can feel overwhelming, but asking sharp, strategic questions opens doors to their world. Here are strategic questions to ask senior management that will uncover some gold.
1. What’s the biggest strategic priority for the organization this year?
Why Ask This: It reveals the company’s focus and how it aligns with the broader goals.
Follow-up Questions You Can Ask:
- How will success in this area be measured?
- What challenges do you anticipate while pursuing this priority?
2. How do you decide which initiatives receive the most resources?
Why Ask This: It provides insight into the leader’s decision-making framework.
Follow-up Questions You Can Ask:
- What criteria do you prioritize the most?
- How do you address pushback when reallocating resources?
3. What role does innovation play in your strategic planning?
Why Ask This: It highlights how much importance the leader places on adaptability and change.
Follow-up Questions You Can Ask:
- Can you share an example of a recent innovative change that worked well?
- How do you encourage innovation among your teams?
4. How do you balance short-term goals with long-term strategy?
Why Ask This: This explores the leader’s approach to handling competing priorities.
Follow-up Questions You Can Ask:
- Which area tends to require more focus lately?
- How do you communicate this balance to the team?
5. How do external market trends influence your strategic decisions?
Why Ask This: It demonstrates how responsive the organization is to external factors.
Follow-up Questions You Can Ask:
- Which recent trend has had the biggest impact on your strategy?
- How do you stay informed about emerging market trends?
Unique Questions To Ask Leaders
If you are tired of asking the same old questions, here are some good questions to ask leaders that will shake things up and actually spark fresh conversations.
6. What’s a leadership lesson you learned the hard way?
Why Ask This: It reveals personal growth and resilience.
Follow-up Questions You Can Ask:
- How did that lesson change your approach to leadership?
- What advice would you give to someone facing a similar challenge?
7. What’s a decision you made that you wish you could revisit?
Why Ask This: It offers a glimpse into their reflective practices and humility.
Follow-up Questions You Can Ask:
- What would you do differently now?
- How do you handle decisions when outcomes are uncertain?
8. What’s one misconception people often have about leadership?
Why Ask This: It uncovers hidden aspects of leadership that aren’t obvious.
Follow-up Questions You Can Ask:
- How do you correct this misconception in your organization?
- How has this misconception impacted your career?
9. If you weren’t in your current role, what would you be doing?
Why Ask This: It provides a personal and creative look into their passions.
Follow-up Questions You Can Ask:
- How does that passion influence your current work?
- Have you ever pursued that interest in a small way?
10. What’s the best advice you’ve ever received?
Why Ask This: It distills their core philosophy into a single impactful takeaway.
Follow-up Questions You Can Ask:
- Who gave you this advice, and how did it influence you?
- Have you passed this advice on to others?
Questions To Ask Leadership About Decision-Making
Want to know how leaders make those tough calls? The right questions can give you meaningful insights into their thought process.
11. How do you ensure decisions align with the company’s mission?
Why Ask This: It connects decision-making processes to overarching goals.
Follow-up Questions You Can Ask:
- How do you communicate this alignment to teams?
- What’s an example of a tough decision you made with this in mind?
12. What role does data play in your decision-making?
Why Ask This: It uncovers their reliance on evidence versus intuition.
Follow-up Questions You Can Ask:
- What types of data are most influential?
- How do you handle situations where data is incomplete?
13. How do you handle disagreement during decision-making?
Why Ask This: It reflects their collaborative and conflict-resolution skills.
Follow-up Questions You Can Ask:
- How do you ensure all perspectives are heard?
- How do you decide when to move forward despite disagreements?
???? That’s right!
83% of companies say developing leaders is crucial.
(Source)
14. What’s the most challenging decision you’ve made recently?
Why Ask This: It provides insight into the complexity of their role.
Follow-up Questions You Can Ask:
- How did you navigate through the challenge?
- What was the result, and would you approach it differently now?
15. What’s your process for evaluating the success of a decision?
Why Ask This: It highlights accountability and continuous improvement.
Follow-up Questions You Can Ask:
- How often do you review outcomes?
- What happens if a decision doesn’t deliver the expected results?
Open-Ended Questions To Ask Leaders
Open-ended questions can lead to stories, insights, and lessons you’d never expect. Let’s explore some good questions to ask senior leaders that really get them talking.
16. What motivates you to keep growing as a leader?
Why Ask This: It uncovers their personal drive and approach to continuous development.
Follow-up Questions You Can Ask:
- How has your source of motivation evolved over time?
- What advice would you give to someone struggling to find motivation?
17. What do you think defines great leadership in today’s world?
Why Ask This: It provides their perspective on modern leadership qualities and priorities.
Follow-up Questions You Can Ask:
- How do you embody these qualities in your role?
- What challenges make achieving this standard difficult?
18. What’s a skill you’re currently working to improve?
Why Ask This: It shows their willingness to grow and self-reflect.
Follow-up Questions You Can Ask:
- How are you going about improving this skill?
- How do you measure progress in personal development?
19. What do you consider your most impactful achievement as a leader?
Why Ask This: It highlights moments of pride and their contributions to the organization.
Follow-up Questions You Can Ask:
- What lessons did you take away from that achievement?
- How has it shaped your approach to leadership?
20. How do you maintain a work-life balance while leading a large organization?
Why Ask This: It provides insight into their priorities and personal well-being strategies.
Follow-up Questions You Can Ask:
- What practices help you stay balanced?
- How do you support work-life balance for your team?
Questions To Ask A Leader About Challenges & Failures
Every leader has faced challenges and failures that shaped who they are today. Let’s see how you can get to understand their journey.
21. What’s the toughest challenge you’ve faced as a leader, and how did you overcome it?
Why Ask This: It offers lessons in resilience and problem-solving.
Follow-up Questions You Can Ask:
- What resources or support helped you the most?
- What did you learn from that experience?
22. How do you handle failure within your team or organization?
Why Ask This: It explores their approach to accountability and learning.
Follow-up Questions You Can Ask:
- How do you ensure the team moves forward constructively?
- Can you share an example of turning a failure into success?
23. What’s a risk you took that didn’t work out as planned?
Why Ask This: It reveals their risk tolerance and adaptability.
Follow-up Questions You Can Ask:
- How did you manage the aftermath of that decision?
- What would you do differently if faced with the same situation again?
24. How do you support team members who face setbacks?
Why Ask This: It shows how they foster resilience and empathy in their team.
Follow-up Questions You Can Ask:
- How do you balance accountability with encouragement?
- What resources do you provide to help them recover?
25. What’s your process for learning from past mistakes?
Why Ask This: It emphasizes their focus on growth and improvement.
Follow-up Questions You Can Ask:
- How do you ensure lessons are applied organization-wide?
- How do you communicate these learnings to your team?
Questions To Ask Executives About Diversity & Inclusion
Here are diversity and inclusion questions to ask senior leaders and start conversations that matter with them.
26. What steps are you taking to create a more inclusive workplace?
Why Ask This: It highlights their commitment to fostering diversity.
Follow-up Questions You Can Ask:
- How do you measure the impact of these initiatives?
- What challenges have you encountered while implementing them?
27. How does diversity contribute to the success of your organization?
Why Ask This: It connects diversity to business outcomes.
Follow-up Questions You Can Ask:
- Can you provide specific examples of where diversity made a difference?
- How do you celebrate and leverage diverse perspectives?
28. What’s the biggest barrier to achieving true inclusivity, and how are you addressing it?
Why Ask This: It uncovers challenges and their proactive solutions.
Follow-up Questions You Can Ask:
- How do you ensure accountability in this area?
- What role does leadership play in overcoming these barriers?
29. How do you ensure diverse voices are heard in decision-making?
Why Ask This: It focuses on their approach to empowering underrepresented groups.
Follow-up Questions You Can Ask:
- What processes are in place to facilitate this?
- How do you handle feedback from diverse teams?
30. What training or resources do you provide to promote inclusivity?
Why Ask This: It demonstrates their investment in long-term cultural change.
Follow-up Questions You Can Ask:
- How do you gauge the effectiveness of these resources?
- What has been the most impactful initiative so far?
Questions To Ask Leaders About Organizational Culture
Curious about what truly defines a company’s culture? Leaders have all the answers – if you ask the right questions.
31. How do you define your organization’s culture in one sentence?
Why Ask This: It offers a concise snapshot of their values and priorities.
Follow-up Questions You Can Ask:
- How do you maintain this culture as the organization grows?
- How do you ensure this culture resonates across all levels?
32. What behaviors are most celebrated in your organization?
Why Ask This: It highlights the traits and actions that drive success.
Follow-up Questions You Can Ask:
- How do you reward these behaviors?
- How do you reinforce them in daily operations?
???? Here’s another interesting fact!
Leadership training improves learning by 25% and performance by 20%.
(Source)
33. How do you onboard new employees to align them with the company culture?
Why Ask This: It reveals their process for integrating new hires effectively.
Follow-up Questions You Can Ask:
- How do you measure the success of onboarding efforts?
- What role do team leaders play in this process?
34. What’s the most challenging aspect of maintaining a cohesive culture?
Why Ask This: It explores the difficulties of preserving values amidst change.
Follow-up Questions You Can Ask:
- How do you address these challenges proactively?
- Can you share a recent example of overcoming such a challenge?
35. How does leadership embody the organization’s values?
Why Ask This: It examines how leaders serve as role models for culture.
Follow-up Questions You Can Ask:
- How do you communicate these values to teams?
- How do you ensure consistency in behavior across leadership?
Questions To Ask Leadership Panel About Team Building
Team-building is at the heart of great leadership. Let’s dig into questions that spark meaningful insights from a panel.
36. What do you believe is the most important quality for a successful team?
Why Ask This: It provides insight into the foundational principles they believe drive effective teamwork.
Follow-up Questions You Can Ask:
- How do you evaluate whether a team embodies this quality?
- Can you provide an example of a team that exemplified this?
37. How do you approach conflict resolution within teams?
Why Ask This: It uncovers their approach to maintaining harmony and effectiveness in a group.
Follow-up Questions You Can Ask:
- How do you ensure that the resolution process is fair?
- What role does team feedback play in conflict resolution?
38. How do you foster collaboration across departments and teams?
Why Ask This: It explores how they promote cross-functional work and synergy.
Follow-up Questions You Can Ask:
- What tools or processes have been most effective for you?
- How do you handle situations where departments are resistant to collaboration?
39. What’s the most effective way to build trust within a team?
Why Ask This: It reveals their strategies for creating a cohesive and reliable team environment.
Follow-up Questions You Can Ask:
- How do you monitor and reinforce trust-building behaviors?
- How do you address trust issues when they arise?
40. How do you ensure that team members feel valued and motivated?
Why Ask This: It shows how they prioritize engagement and employee satisfaction.
Follow-up Questions You Can Ask:
- What specific recognition practices do you use?
- How do you keep motivation high during challenging times?
Questions To Ask An Executive About Future Trends & Goals
Want to know where the future is headed? Ask executives about trends and goals – they love sharing their vision.
41. What emerging trends do you see shaping the future of the industry?
Why Ask This: It provides insight into the executive’s foresight and awareness of market changes.
Follow-up Questions You Can Ask:
- How are you preparing the organization to adapt to these trends?
- Which trend do you believe will have the biggest impact on your business?
42. What are the most significant goals you have for the company in the next 5 years?
Why Ask This: It offers a long-term view of their vision and strategic direction.
Follow-up Questions You Can Ask:
- How do you plan to measure progress toward these goals?
- What challenges do you foresee in achieving these objectives?
43. How do you decide which technologies to invest in for the future?
Why Ask This: It explores their decision-making process around innovation and technological advancements.
Follow-up Questions You Can Ask:
- What role does customer feedback play in your technology investment decisions?
- How do you assess the potential ROI of new technologies?
44. What do you think will be the next big disruptor in your market?
Why Ask This: It helps understand the executive’s anticipation of major changes or disruptions.
Follow-up Questions You Can Ask:
- How is the company positioning itself to manage this disruption?
- How do you stay ahead of these shifts before they become mainstream?
45. How do you ensure that the company’s goals align with your vision for the future?
Why Ask This: It connects personal leadership vision to broader organizational goals.
Follow-up Questions You Can Ask:
- How do you communicate this alignment throughout the company?
- How do you handle misalignments when they occur?
Fun Questions To Ask Senior Leaders
Conversations with leaders don’t always have to be serious. Fun questions can break the ice and show their human side.
46. What’s something most people don’t know about you?
Why Ask This: It helps humanize the leader and provides a personal touch.
Follow-up Questions You Can Ask:
- How has this personal interest or trait influenced your leadership?
- Is there a story behind this lesser-known fact?
47. If you could have dinner with any historical figure, who would it be?
Why Ask This: It reveals personal interests and inspirations.
Follow-up Questions You Can Ask:
- What would you ask them?
- How do you think that person would have approached today’s challenges?
48. What’s your go-to strategy for dealing with stress?
Why Ask This: It shows how the leader manages pressure and maintains well-being.
Follow-up Questions You Can Ask:
- Do you think stress management is a skill leaders should teach others?
- What advice would you give to a leader who struggles with stress?
49. What was your first job, and what did you learn from it?
Why Ask This: It provides a look into their humble beginnings and early lessons.
Follow-up Questions You Can Ask:
- How did this job shape your career path?
- What advice would you give your younger self at that time?
50. What’s the most adventurous thing you’ve done outside of work?
Why Ask This: It adds a personal, fun element and can highlight their interests outside leadership.
Follow-up Questions You Can Ask:
- How did that experience challenge you?
- Would you recommend others take similar risks?
Questions To Ask Senior Leaders About Career Development
Ever wondered how leaders got to where they are? Let’s uncover their secrets to career growth with a few simple questions.
51. What do you believe is the most important skill for career advancement?
Why Ask This: It reveals the leader’s perspective on essential professional growth areas.
Follow-up Questions You Can Ask:
- How do you develop that skill in yourself and others?
- What resources would you recommend to strengthen this skill?
???? That’s promising!
Women’s representation in senior management rises to 28%.
(Source)
52. What was a turning point in your career, and how did you capitalize on it?
Why Ask This: It uncovers significant moments that shaped their professional journey.
Follow-up Questions You Can Ask:
- What challenges did you face during that time?
- How did you prepare for that moment before it happened?
53. How do you maintain a work-life balance as your career progresses?
Why Ask This: It helps understand their strategies for maintaining a balanced life as responsibilities increase.
Follow-up Questions You Can Ask:
- How do you ensure your team members also achieve this balance?
- How has your definition of work-life balance changed over time?
54. What advice would you give to someone looking to transition into leadership?
Why Ask This: It provides practical guidance for individuals aspiring to take on leadership roles.
Follow-up Questions You Can Ask:
- What common mistakes should one avoid during this transition?
- How do you identify the right leadership opportunities?
55. What’s the best way to position yourself for promotion within an organization?
Why Ask This: It sheds light on effective strategies for career growth and organizational navigation.
Follow-up Questions You Can Ask:
- How do you evaluate employees for potential promotions?
- How can someone demonstrate readiness for greater responsibility?
56. How do you identify and nurture high-potential employees for leadership roles?
Why Ask This: It reveals the leader’s approach to spotting and cultivating future leaders within the organization.
Follow-up Questions You Can Ask:
- What specific qualities do you look for in these individuals?
- How do you support their development over time?
How To Prepare What Questions To Ask Senior Leaders
When preparing strategic questions to ask senior leaders in an interview, you don’t have to use the exact words or ideas above. Adjust them to suit your situation and the information you need with these tips:
1. Identify Your Objectives
Clearly define what you want to achieve from the conversation. This helps you come up with questions that match your goals, whether it’s gaining industry insights, learning about leadership strategies, or understanding organizational goals.
2. Research The Leader’s Background
Start by learning about the senior leader’s professional background. Explore how they progressed in their career and identify key milestones and transitions. Next, take note of the leader’s recent achievements and contributions to their organization or industry.
This way, you can come up with relevant questions that reflect your genuine interest in their experiences and insights.
For example, if you’re meeting with a VP of Marketing who recently led a digital transformation initiative, recognize this in your questions. You might ask, “I saw that you led the digital transformation project that increased the company’s online engagement. What were some of the biggest challenges you faced, and how did you overcome them?”
3. Align Questions With Current Challenges
When preparing questions to ask senior leaders, research the company’s latest news, recent financial reports, and any public statements from leadership. Identify challenges like market competition, regulatory changes, technological advancements, or internal restructuring.
For example, if the company is currently on a major digital transformation, you could ask, “With the ongoing digital transformation, what strategies are you implementing to ensure a smooth transition for your teams and maintain productivity?”
This question shows that you’re aware of the digital transformation challenge and are interested in understanding the leader’s approach to managing such change. The leader can share their insights on strategy, team management, and overcoming obstacles, giving you valuable knowledge and practical advice.
4. Prepare Open-Ended Questions
Craft open-ended questions to get detailed responses. For example, instead of asking “Did you face challenges in your career?” ask “What significant challenges did you face, and how did you overcome them?”
5. Be Ready To Follow Up
A follow-up question can help clarify their initial response. It shows that you’re actively listening and engaged in the conversation. For this, you need to pay close attention to their answers and be flexible in your questioning. Don’t just stick to a script – be adaptable and think on your feet.
Use this simple formula to create effective follow-up questions: Acknowledge + Explore + Relate.
- Start by acknowledging their initial response to show you’ve understood their point.
- Then, explore a specific detail or ask for an example to deepen the discussion.
- Finally, relate it back to your own experiences to make the conversation more meaningful.
For example, if a senior leader mentions that team communication was really important during a recent project, you could follow up with, “You mentioned that team communication was key during the project. Can you share a specific strategy or tool that helped facilitate this communication? How do you think this approach can be applied to other teams or projects?” This keeps the conversation flowing and reveals useful information.
6. Practice Active Listening
Active listening means paying close attention, showing genuine interest, and responding thoughtfully to the leader. This ensures you understand the leader’s message correctly and can engage in a more meaningful conversation. It also shows respect for the leader’s time and insights, making them feel valued and understood.
Active listening involves several techniques:
- Maintaining eye contact
- Nodding to show understanding
- Using verbal affirmations like “I see” or “That makes sense”
- Avoid interrupting the leader while they’re speaking
- Take mental notes or jot down key points to remember important details
- After they finish speaking, paraphrase their main points to confirm your understanding
7. Be Respectful of Their Time
Make sure your questions are concise and to the point. Respect their time by not asking too many questions and being mindful of the conversation’s length.
Conclusion
Having conversations with senior leaders is a great opportunity where every minute you spend can help with your career and business operations. Take note of the questions to ask senior leaders and prepare well with the tips we discussed above. Make sure you don’t miss this opportunity and remember, showing up on time is key – it is a sign of respect for their time.
Genius, a headhunting agency, can connect you with senior leaders if you need consultants for your company. You gain access to a network of experienced professionals who can provide valuable insights and guidance for your business. Whether you’re looking for strategic advice, leadership development, or industry-specific expertise, Genius will find the right consultants.
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FAQs
1. How to communicate with senior leaders?
To communicate effectively with senior leaders:
- Be concise and clear
- Avoid unnecessary details
- Use data and evidence to support your ideas
- Be prepared to answer questions
- Show respect for their time by getting to the point quickly
2. In what situations is it most appropriate to ask senior leaders unique questions
Ask unique questions during strategy meetings, performance reviews, or when seeking insight into company vision. It’s ideal when you need clarity, innovative ideas, or guidance on big decisions. Make sure the question adds value to the conversation.
3. What are some common mistakes to avoid when crafting questions to ask senior leaders in an interview?
Avoid asking vague or irrelevant questions. Don’t ask questions that can be easily answered by others or through basic research. Be mindful of the timing and avoid interrupting important discussions.
4. What are the benefits of asking senior leaders unique and thought-provoking questions?
It shows you’re engaged and proactive, builds stronger relationships, and can spark innovation. Thought-provoking questions often lead to valuable insights that help shape strategy and improve decision-making.
