• Jonno White

150 Leadership Questions To Ask Your Senior Leaders

Updated: Nov 17

When it comes to leadership, there are a lot of questions that can be asked in order to help improve the effectiveness of a team or organization. By asking the right questions, you can gain valuable insights into your own strengths and weaknesses from your senior leaders.


These questions can also help identify areas where more training or development may be needed. Below are 150 questions I'd recommend you ask your senior leaders to help you get started on the path to better leadership.


1. How often does the whole team get together?


2. How do you promote career development for employees?


3. How do you promote new ideas and innovation?


4. How do you measure success for you as a leader?


5. What are successful leaders today missing?


6. What is a leader’s best asset?


7. Are you more comfortable with verbal or written communication?


8. Have you ever been a member of a successful team? What was your role in the success of the team?


9. What's the key to building organizational effectiveness as a leader?


10. What can I do to be a better leader?


11. Who inspires or mentors you?


12. How do you ensure that your company is operating in accordance with your vision and mission?


13. How do you recommend someone like me invests in my leadership development in a role like this?


14. How do you ensure that your company is operating in accordance with your vision and mission?


15. What are the most critical characteristics of today's effective leaders?


16. Can you recommend three books on leadership?


17. How would you deliver bad news to your team?


18. Can you give me a valuable insight into what it's like day-to-day in this role?


19. What characteristics do today's leaders lack?


20. Is there a real-life example you can give of how you've coached one of your team members to become better?


21. What do you think makes a successful leader?


22. What type of support is given to new employees?


23. Which leadership qualities do you feel are the least important?


24. How does your company develop outstanding ideas?


25. As a new hire, what would be the onboarding process?


26. What sort of leader would your team say that you are?


27. What are the most important leadership values to you?


28. What are the most critical characteristics to look for in a new employee?


29. What factors do you examine while making a promotion?


30. How do you manage employee engagement here?


31. What are the most critical characteristics to look for in a new employee?


32. Which three leadership books would you recommend?


33. What leadership style do you use?


34. How would you go about praising a team member in public?


35. How do you lead through change?I am good at getting teams excited to work together and achieve common goals.


36. How do you motivate your team?


37. How have you rallied your team in the past in difficult projects/tasks?


38. What does a successful leader need to do in a role like this?


39. I'd love to get a sense of the bigger picture for your team and company. What's the thought process when cascading high level goals and strategies through the company?


40. Name a time when an employee disagreed with your directive and how you handled it?


41. What are some ways we can increase employee retention?


42. How do you encourage your team in the face of disagreement and adversity?


43. Have you been developed an innovative solution to a non-traditional problem?


44. What makes you the proudest of yourself?


45. How do you go about resolving conflict?


46. What can I do to help you be more successful?


47. How do you set an example to those for your team members?


48. What is the greatest significant risk you have taken, and why?


49. How do you maintain your leadership development and growth?


50. How does your company develop amazing ideas?


51. How do you manage conflict resolution in this team and organization?


52. Name a time when you had to change a decision due to new facts.


53. How do you ensure that your team is committed to the task at hand?


54. How do you build support for ideas/goals with people who do not report to you and you have no authority over?


55. If I'm successful, what would be the best book you'd recommend I read to prepare to step into your company?


56. Have you ever taken on a job that you were unqualified for?


57. Aside from time-management, what other skills are important for a senior manager/business leader?


58. When I have opportunities as a hiring manager, what are the main things I should look for?


59. If you had the chance, what’s one thing you would do to improve the product or service provided by our company?


60. What are the day-to-day challenges of being in a leadership position?


61. What are some of the best ways someone like me can grow into a good leader in this role?


62. How do you manage best practices in team development?


63. Out of interest, what do you consider to be some of your greatest accomplishments?


64. How would you like me to communicate my personal goals with you?


65. What are your immediate objectives?


66. What qualities do you look for in a senior executive?


67. What do you value more, innovative ideas or bringing new ideas to life?


68. What were some great contributions made by other team members recently?


69. What do you see as some of the biggest challenges in a role like this?


70. What are the biggest risks to a leader for failure?


71. How would you describe your leadership style?


72. How do senior managers communicaite with their teams?


73. Who are the most important members of your team?


74. What do you do when you are unsure about how to achieve the goals of the team?


75. How can we increase employee engagement?


76. What's the vision for the entire organization moving forward?


77. How can I help to create clear expectations if I'm successful?


78. Is there anything else I can provide for you to help with the hiring process?


79. What’s the best thing that happened to you this week, either at work or outside of it?


80. How often do you feel it’s necessary to meet with your team?


81. How do you best align with other leaders in the organization?


82. How did you a handle a time when you had to make an unpopular decision?


83. What is the difference between a Team leader and a Team manager?


84. How do you encourage the development of your employees?


85. What is the most difficult part of being a leader?


86. How do you formulate and present arguments to others?


87. How do you organize projects and tasks?


88. Explain a time when you were not able to meet a deadline?


89. What's the organization's mission in 5-years/10-years?


90. If you owned the company, what’s one thing you would do differently?


91. What factors do you examine while making a promotion?


92. If you could only pick one thing, what would be the first step for someone like me to become a better leader?


93. If you want others to listen to your ideas, it's important that you relay the benefits of the idea and how it can be applied.


94. How did you arrive in a leadership position yourself?


95. Which one of your accomplishments makes you the proudest?


96. What motivates you to be a leader?


97. Are you more effective in a group or one on one basis?


98. Have you ever been in a mentor to another aspiring leader? How did you go about establishing that relationship?


99. If I'm successful, will I have any direct reports?


100. Explain a time when you had to make a decision without all the relevant facts.


101. How are you feeling at work lately? How’s the morale around you?


102. What do you look for in team members?


103. I'm active on social media. Is social media engagement by employees important to you and the organization?


104. What is the most perilous attribute a leader may possess?


105. Are there any great risks for someone like me to step into a role like this in your opinion?


106. What advice do you have about effective time management in a role like this?


107. What are the next steps in the interview process from here? Is there anything else I can do to help moving forward?


108. How would you recommend I improve my management style?


109. What is the greatest significant risk you have taken and why?


110. How do you make sure the team you're leading is going in the right direction?


111. What barriers are getting in the way of your success? Where are you stuck?


112. What access, if any, does this role have to the senior leadership team?


113. Is competition among a team healthy? Why or why not?


114. How would you go about developing your team?


115. What are the over-arching goals of the organization?


116. What are the leadership abilities you're most intersted in when hiring for a role like this?


117. What kind of criticism you most get?


118. What's your perspective on work-life balance in a role like this?


119. What advice would you give me about decision making in this company?


120. What are the most difficult decisions to make?


121. How does the organization implement fresh perspectives?


122. What is the role that leadership plays to a manager?


123. How do you delegate responsibilities to your team?


124. What are the ways that you keep your team motivated?


125. How would you proceed to reorganize your team?


126. How would you go about getting cohesion among a team who disagree?


127. How vulnerable should I be front of the team?


128. What’s going well for you and your team this week? Any wins (big or small


129. On a scale of 1-10, how satisfied are you? Why?


130. What's the best way to earn the trust of your direct reports?


131. How do you achieve objectives in a fast-paced environment?


132. How did you end up on this professional path?


133. How do you maintain your leadership development and growth?


134. It is critical for a leader to maintain relationships with role models and mentors. Regardless of a leader's success, these are the people they turn to for counsel.


135. What is the most perilous attribute a leader may possess?


136. What is the most significant change that you brought to an organization?


137. team?


138. How will I know if I'm on the right track in this role?


139. What's the current top priority for senior executives?


140. What do you do to remain engaged in a conversation?


141. What are your immediate objectives?


142. How can we be a more client-centric culture?


143. Honest feedback is important to me. How do you like to give feedback?


144. When it comes to leadership skills, which ones are the most important?


145. Who are some great leaders you admire?


146. Describe a time you took a leadership position when you did not have the title of a leader.


147. What are some great leadership questions you've been asked by team members?


148. Do you recommend team members have role models and mentors?


149. What are some leadership skills you would expect me to develop in a leadership position like this?


150. What's a personal experience that shaped your leadership?


Leadership can be a challenging role to fill. However, if you have the right skills and abilities, it can also be very rewarding. In this blog post, we’ve listed 150 leadership questions for you to ask your senior leaders.


The next time you're sitting down with one of them, bring out one of these questions and take careful notes! You'll grow as a leader and they'll grow in their respect for you at the same time.

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