ali khan
Ali Khan
Published On
April 19, 2024
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70 Best Questions To Ask Leaders in 2024

Ever bump into a leader while grabbing coffee, or found yourself sharing an elevator with the CEO?

It’s not as uncommon as you think! And when that moment comes, having the right questions ready could be a game-changer for your career or business.

Imagine you're armed with questions that not only show you’re informed but also genuinely curious about their journey and insights.

That’s where we come in. Our list is designed not just to impress, but to spark meaningful conversations that could lead to fresh insights and opportunities.

Leadership isn't just about guiding teams and making decisions; it's about constant learning, adapting, and connecting. Whether they're voracious readers, strategic thinkers, or creative problem-solvers, every leader has a unique approach to staying ahead.

What better way to discover their secrets than by asking them directly?

We'll give you our top 10 questions right here at the top and then we'll even give you a way to ask your leader an anonymous question using our platform! (you can also use it to give them anonymous feedback).

Top 10 questions:

  1. What’s the most important leadership lesson you’ve learned and how has it proven invaluable?
    • Gathers insights into personal growth and leadership evolution.
  2. How do you stay ahead of major industry changes and position your organization to take advantage of them?
    • Reveals strategies for innovation and adaptability.
  3. Looking back, what one decision would you change if you could, and what did you learn from it?
    • Provides a candid look into reflective practices and learning from mistakes.
  4. What do you believe is the most significant barrier facing our industry today?
    • Offers perspective on current challenges and how top leaders perceive them.
  5. Can you describe a time when you had to make a tough decision without all the information you needed? How did you handle it?
    • Explores decision-making skills under pressure.
  6. How do you foster creative and innovative thinking within your team?
    • Provides insights into cultivating a culture of innovation.
  7. What are your top strategies for maintaining work-life balance, and how do you encourage your team to do the same?
    • Offers personal insights and advice on maintaining balance.
  8. What book has influenced your leadership style the most and why?
    • Reveals influences and personal preferences that shape their leadership.
  9. How do you ensure your organization’s activities align with its core values?
    • Delves into integrity and alignment in leadership practices.
  10. What goals do you have for the next year, and how do you plan to achieve them?
    • Provides understanding of forward-looking strategies and goal-setting.

What are some good questions to ask leaders?

There are a lot of questions that can run around your mind when meeting a leader. But despite your willingness to make the most out of your meeting you can easily make the conversation weird and sound rude at some point. 

Start easy with small talk, introduce yourself, and ask them questions related to the place or wherever you happen to meet. When the introduction is being made along with other small talk continue to tell him/her about your work.

Tell the leader what you do, be honest, and share what you love and look forward to achieving in your future.

This way you will let the other person know that you are a potential future leader and will make it easier for them to engage in your conversation. Personal drive is infectious, and a leader can tell when someone has it almost immediately.

Ask important questions like the importance of professional development in the workplace. Communication, information exchange, and feedback are valued in specific organizations.

If your workspace utilizes platforms like Slack or Microsoft Teams, you can integrate's suggestion box into your channels. This feature allows you to pose questions to your leadership either directly or anonymously.

The option to remain anonymous is particularly valuable, as it empowers you to raise sensitive or challenging questions that you might hesitate to ask openly.

Being able to ask such questions without fear of repercussions can foster a more open and communicative work environment.

Below is an attached screenshot demonstrating how you can use Wrenly to anonymously gather feedback from leaders, enhancing the overall feedback process within your organization.

use Wrenly to collect feedback anonymously from leaders

What are good questions to ask leaders? Here we have listed a few good questions you can ask leaders.

  1. What inspires you?
  2. What do you consider as core values within your team? 
  3. Do you consider leadership a good career path?
  4. If you could have made a different choice, what would it have been?
  5. Despite disagreements and adversity, how do you encourage your team?
  6. In today's world, what are the most critical characteristics of effective leaders?
  7. Is there anything lacking in the leadership of today's generation?
  8. How do you plan to achieve your immediate objectives?
  9. What is your proudest accomplishment?
  10. If you had to choose one significant risk to take, what would it be?
  11. How do you maintain your leadership development and growth?
  12. Which steps do you take to ensure that the vision and mission of your company are being followed?
  13. What is your company's process for generating outstanding ideas?
  14. When looking for a new employee, what are the most critical qualities to look for?
  15. What are some of the industry trends you keep up with?
  16. What are the three best leadership books you recommend?
  17. When making a promotion, what factors do you consider most important?
  18. What is the most dangerous attribute a leader can possess?
  19. How would you improve our product or service?
  20. How do you set up a plan to grow and develop further? 
  21. What is your process of goal setting?
  22. Do you prefer individual one on one meetings with every team member in your company?

How to use Wrenly to ask questions from leaders? 

Using Wrenly to ask questions from leaders in your organization can be a straightforward process, especially if your workspace uses Slack or Microsoft Teams.

wrenly for slack

Here’s how you can set it up and start engaging with your leadership:

  1. Integration: First, integrate into your Slack or Microsoft Teams. This typically involves adding the Wrenly app from the respective app store or marketplace and following the setup instructions to install it in your workspace.
  2. Setting up the Suggestion Box: Once Wrenly is integrated, set up the suggestion box feature within the app. This might involve configuring settings to suit your team’s needs, such as who can see the questions and whether they should be anonymous.
  3. Asking Questions:
    • Directly: If you choose to ask questions directly, you can simply type your question into the suggestion box and submit it. Your identity will be visible to the leaders.
    • Anonymously: If you prefer to remain anonymous, ensure the anonymous feature is enabled in your settings. Then, post your question in the suggestion box without revealing your identity.
  4. Notification and Access: Leaders will receive notifications when new questions are posted. They can access these questions directly from the suggestion box and can respond accordingly.
  5. Feedback and Responses: Check the suggestion box or your notifications for responses from leaders. Some setups may allow for open discussions, while others might be more controlled with direct responses from the leadership.
  6. Review and Follow-up: Regularly review the questions and responses to ensure that all concerns are addressed. If necessary, follow up on specific questions if the initial responses were not satisfactory.
Asking questions to leader with real name using Wrenly

This tool can be particularly useful for fostering open communication and ensuring that all team members, regardless of their position or comfort in speaking openly, have a chance to voice their concerns and questions to the leadership.

Wanna test out on your own for Free?

Try Suggestion Box for Free!

Test out every feature for 2 weeks, no credit card needed.
Start asking questions from today!
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Questions to ask organization leaders

Every person is different therefore every organization or workplace is different from each other. There are endless questions to ask respected leaders.

An organization leader's role is to guide and manage the activities of a team in a broad sense. 

Questions to ask organization leaders should reflect the unique dynamics of every team and organization.

From strategic planning to boosting team productivity, understanding the leader's approach to guiding their team towards a common goal can offer valuable lessons. 

An organization's leaders focus on both the company and its employees. Some open ended questions you might ask include:

  1. What guidance would you offer a person taking their first leadership position?
  2. How do you maintain calm in stressful situations?
  3. What are some new ways you started implementing?
  4. What methods do you use to boost productivity within the team?
  5. How do you recruit new team members?
  6. When hiring what should we be looking for?
  7. How to keep track of all the achievements?
  8. How do you keep your team focused on the most important objectives?
  9. What do you understand about "self actualization" within the company?
  10. How do you work toward decision making?
  11. Do you receive and give constructive criticism?
  12. How would you rate your communication skills and why? 
  13. In your organization, where do great ideas come from?
  14. Which abilities are most crucial when it comes to leadership?

Open-ended questions allow for deeper insights into their management style, decision-making process, and how they foster a culture of growth and innovation.

Questions to ask corporate leaders

Corporate leadership extends beyond daily operations, embodying the core values and guiding principles that steer the company's future. It, however, goes beyond only monitoring workers.

They create declarations of basic principles and give orders to staff members at all levels. However, on a more personal level, it promotes team building and employee retention when workers believe that their leader is familiar with them and aware of their own objectives.

Since they are involved in a lot of things at once you might have a lot of questions to ask such leaders too. Here are some of the best questions to ask corporate leaders:

  1. If you were a first-time leader, what advice would you give?
  2. Which teams do you think are the most engaged inside the organization?
  3. Why do you think that exact team is engaged?
  4. What can make the other teams like the team he/she just mentioned?
  5. How critical is employee energy to the organization's success?
  6. How well do you listen to your staff?
  7. What, in your opinion, makes employees happy and engaged?
  8. How can one inspire others to go above and beyond?
  9. Could you explain how social networking and social media have impacted your business?
  10. In your organization, how do you generate great ideas?
  11. What are the major challenges to career growth in our market?

Asking corporate leaders strategic questions can reveal how they inspire engagement, foster employee happiness, and leverage social media for business impact.

Strategic questions to ask HR leaders 

When it comes to HR leaders and teams there are a lot of questions they can answer from many aspects of the organization or company.

Since they are considered to be the bridge between the staff and the leading team.

You can ask the leader how they manage to work on their leadership qualities while doing daily work.

To answer this question, they can describe how they personally organize their time in order to incorporate learning. This question focuses on time management, but at a leadership level.

When meeting an HR leader there are some strategic questions you can ask them:

  1. What would you do differently if you were once again a leader for the first time?
  2. When did you last think about what HR’s most important role is?
  3. What does the CEO do every day to establish an environment where employees may grow?
  4. What steps can you take to develop, grow, and train leaders? 
  5. When was the first time you succeeded in your role?
  6. Who do you wish was more engaged with HR?
  7. Do your existing hiring practices produce the desired results?
  8. How hard is it to keep the balance between staff in the company?
  9. When employing new staff, how much do you focus on the cover letter?
  10. Aside from the CV and Cover Letter, what is the thing that you look for in a candidate?

Good questions to ask leaders at work

The thing is that there is no bad or good question as long as you keep it professional, simple, and balanced.

Some people prefer to not talk about their work when they are someplace else and that is totally okay. 

Also, think about the leader's personality, what kind of person he or she really determines what you can get out of him or her. Focus more on their creative thinking and ideas.

You can learn more about senior leaders' strategic thinking and where they perceive the biggest dangers and possibilities by asking them how they're defining the limits of their company.

Additionally, it can help you identify the ideal attributes to add to your leadership style and provide your team or business with excellent advice. For both employers and the employees they lead, the coach leadership style is one of the most beneficial.

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You also get a free AI health score during your trial.
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On the other hand, think about yourself, if you have a friendly personality and no problem getting to know other people then that's a good skill to utilize.

Always find the right time and place, or maybe the right time and place will find you, if it does here you have some good questions to ask leaders at work. 

  1. How can you share the valuable teachings that you received from mentors?
  2. What is anything you wish you had been told earlier in your professional life?
  3. What are the leadership traits you still need to grow?
  4. Can you give an example of a situation in your career when you were scared?
  5. How do you balance leading with continuing to learn to lead?
  6. How do you continue to be motivated by the organization's objective while inspiring others?
  7. Do you think that direct reports within the team are important? 
  8. What methods do you use on a daily basis to ensure that your team is following the organization's goal and vision?
  9. What are some thought-provoking questions you ask your staff?
  10. How long does it take you to gain an employee's trust?
  11. What does a balance between work and life mean to you?
  12. Do you think you have a good reward system in place?
  13. What's going well for you and your team this week? Any wins (big or small)? Focus on what is working for their employee engagement.


The best questions for leaders to ask are those that help them learn about the people who report to them.  

These questions will help leaders discover what motivates their employees, and that information can be used to help them stay engaged.  

Additionally, and perhaps more importantly, it can help leaders lead better.

Once they know what motivates their employees, they can use that information to motivate and lead their team in a way that not only increases productivity but also makes everyone happier in the process.  Let's look at some of the questions that you might have in your mind.


1. How do leaders prefer to receive these questions (e.g., in formal meetings, casual settings, written communications), and does the context change their openness or the depth of their answers?

Leaders generally appreciate receiving questions in settings that align with the seriousness of the inquiry. Formal questions may be best suited for scheduled meetings, while more casual or personal questions can be asked in less formal settings. The context can indeed influence their responsiveness and the depth of their answers.

2. Are there specific questions that should be avoided because they might be considered too intrusive or off-putting to leaders?

It's advisable to avoid questions that are overly personal, invasive, or irrelevant to the leader's role and expertise. Questions that put the leader in an uncomfortable position or challenge their authority publicly should also be avoided.

3. How can someone follow up effectively after asking these questions to build a meaningful mentorship or professional relationship with a leader?

To effectively follow up after asking questions, consider expressing gratitude for the leader's insights and showing how their advice has been beneficial to you. Keeping the communication lines open with periodic updates on your progress or further inquiries can help build a lasting professional relationship.

There’s so much more to learn about leadership, so be sure to check out our other resources on the topic!  And if you want even more great content about leadership and management, subscribe to our free newsletter! Thanks for reading, and good luck on your own journey to leadership excellence!

It may inspire you to apply the techniques and styles they use in your own leadership efforts once you have gained a better understanding of their leadership styles. If you are headed on the leaders path, taking examples from senior leaders is always a good method. This will make your employee morale much better.

Do you have any good questions in mind? Feel free to share with us your ideas.

Send your leadership a question or feedback anonymously!
You can read their response and reply back in a private thread

More Articles From Ali Khan

Ali is a co-founder of Wrenly known for his innovative thinking and exceptional drive to create value for every Wrenly customer. His dedication, mentorship, and leadership skills have not only shaped various careers but have also made him an invaluable asset to the Wrenly team.

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