Think for a minute that you are at a leadership conference, and during the Q&A session, someone asks a CEO on stage, “What’s one mistake you’ve made as a leader, and how did you grow from it?“
The room falls silent as the leader pauses, then shares a candid story about a decision that cost the company millions. But the decision or the mistake taught him a lesson that he still carries today.
Moments like these remind us that asking great questions for leaders helps uncover invaluable insights. It can help you become an aspiring leader or simply get answers about leadership. Asking the right questions can help you grow by learning from other experiences.
In this article, we’ll explore the 10 best questions to ask a leader, designed to spark meaningful conversations and provide a window into their mindset and experiences.
Why ask questions to a leader?
It doesn’t matter what experiences you’re having or challenges you’re facing; the odds are that other senior leaders have likely faced and overcome something similar. It’s, therefore, good business practice and great for your personal growth to talk to one of today’s leaders about their experiences.
A list of open-ended questions to ask leaders gives you plenty of insight because it allows them to talk without barriers. Their responses will help you analyze what made them better leaders. It will also give you ideas on how you can tackle the issues and challenges you’re facing.
But asking questions is an art! Here are some suggestions:
How to ask powerful questions?
- If you’re lucky, you’ll have the time for a long conversation with a senior leader, but most likely, you’ll be part of a group vying for attention. Make sure your question is direct.
- You need to learn from the response you get. So, don’t be afraid to ask a question that others may deem ‘trivial’ or ‘dumb.’ Seek out the information you need for your leadership journey.
- After you’ve asked your question, listen attentively to the response. Paraphrase what was said to make sure you’ve understood the context correctly. If there is something you haven’t fully grasped, ask a follow-up question.
So now that we’ve got those basics out of the way, here’s a list of:
10 best questions to ask leaders
Senior leaders have reached the top through a lot of trial and error. And they have accumulated wisdom and knowledge during their journey. However, they are always short of time. Make sure you ask questions to which they will give valuable answers, such as their secret to leading a team. Some examples of such questions are:
1. What is your leadership style?
All leaders bring their unique approach to guiding and inspiring their teams. A leader’s managing style shapes their team’s culture and success.
By asking this question, you gain insight into the principles and practices defining your leader’s operations. It’s an opportunity to understand what inspires them, how they tackle challenges and the qualities they prioritize in a team.
2. Who do you look up to for inspiration or mentorship?
Even the most accomplished leaders have people they admire or turn to for guidance. These people often serve as sources of wisdom, motivation and new perspectives for leaders also. Asking this question allows you to see who has influenced your leader’s journey and why. What qualities do they admire in their mentors? How has this guidance shaped their decisions and leadership style?
By understanding who inspires them, you gain insight into the values and principles they hold dear. It can also introduce you to new ideas, approaches, or individuals who might inspire your growth and development.
Also read: How To Be A Mentor: Tips to Lead Your Proteges to Success?
3. Looking back, what one decision would you change if you could and what did you learn from it?
Every leader has made decisions that, in hindsight, they might have approached differently. These moments of reflection often reveal some of the most powerful leadership lessons. This is one of the best leadership questions you can ask. It helps you uncover the challenges your leader has faced and how they’ve grown from them.
Hearing their story helps you see that even tough decisions, even if it’s successful or not, are all opportunities to improve. It also reinforces the idea that growth as a leader comes from embracing vulnerability, reflecting on experiences and being open to change.
4. What are three things that today’s leaders should be mindful of?
The business sphere is ever evolving and so are the challenges. Posing this question to today’s leaders will help you better understand the challenges businesses and senior leaders face.
While you will get valuable insights into how issues like yours have been resolved, you may also come across a few you haven’t encountered. This will prepare you for the course of action you could take if and when you do face them.
5. What’s your best advice for someone just stepping into a leadership position?
Stepping into a leadership role doesn’t happen overnight. You already have a lot of business experience and expertise and, of course, plenty of knowledge and skills. But leadership is a different ball game, played on a higher and more complicated platform. One of the best ways to develop and succeed as a leader is to learn from the journeys and capabilities of other leaders.
From this question, you can expect several points to consider as you embark on your journey as a leader. It also helps you understand what concerns other leaders face as learning leaders.
6. As a leader, what are you doing to encourage and foster diversity, equity and inclusion in your teams?
Diversity, equity and inclusion (DEI) are becoming increasingly important in determining who the employers of choice are. Employees are now looking behind the curtains for natural and sustainable initiatives in organizations. Successful leaders understand the importance and benefits of having a diverse workforce. They lead the change – introducing and actively monitoring initiatives that foster an all-inclusive culture.
A Gallup survey highlighted different experiences among people of various sexual orientations, races and genders in the workplace. Learning how these initiatives are being managed at other organizations will help you understand how you can be a better leader on your own.
7. How do you keep your team motivated despite conflicts and obstacles?
Leaders show their true potential in times of challenge. Whether it is internal or external, whether it is interpersonal or inter-functional conflicts or the obstacles that can block the path, the leader can rally the team and keep spirits high.
By asking this unique question, you gain insight into the strategies your leader uses to maintain focus, foster collaboration and ensure morale stays strong. This will teach you how to get through difficult situations and remind you that resilience and adaptability are essential qualities for a leader. It’s a chance to learn how great leaders turn challenges into opportunities to foster growth and unity.
8. How do you align your organization with your vision and mission?
Any successful organization requires a strong vision and mission, but at its core, it is the leader who breathes life into it. Aligning your teams with the realization of such goals requires clear communication, consistent actions and sharing a sense of purpose.
This unique question will show you how your leader connects the big picture to everyday decisions. Their answers can give you valuable insights into the importance of purpose-driven leadership. It also helps you see how aligning your efforts with the organization’s vision can lead to greater impact and shared success.
9. What three books can you recommend on leadership?
Great leaders are influenced and inspired by the books that they read. You definitely should ask for book recommendations to understand the knowledge that has shaped your leader’s thinking and approach. These recommendations also give you a glimpse into the philosophies your leaders value most.
You never know, you might learn something through reading, from principles of leadership and management to personally inspiring stories that can help you better resonate with incidents and see what you need to change to become a better leader.
10. What do you believe is the most significant barrier facing our industry today?
Every industry comes with its own set of challenges and leaders are often at the forefront of identifying and addressing them. By asking this question, you gain a deeper understanding of the hurdles your leader sees as critical.
Their perspective not only gives you insight into the industry’s current landscape but also prepares you to think proactively about solutions. It’s a chance to learn how visionary leaders navigate uncertainty and turn challenges into opportunities for growth.
Conclusion
In the American author and speaker John C. Maxwell’s words, ‘A leader knows the way, goes the way and shows the way.’
So, please make the most of other leaders’ willingness to share their knowledge, experience, and formula for success. Use their knowledge and lessons to prepare for your success as a leader. Asking thoughtful questions is a skill that can deepen your understanding of leadership and inspire your own growth. The 10 questions above aren’t just conversation starters. They’re pathways to uncovering the mindset, values and experiences that shape great leaders.
FAQs
What are fun questions to ask a CEO?
There are many fun questions you can ask your CEO based on your repo with them. But here are a few you can consider starting with:
- If you weren’t in this role, what would you be doing?
- What’s the most unconventional piece of advice you’ve ever received?
- How do you unwind after a stressful day?
What are the top 5 powerful questions?
There are so many questions that you can ask a senior leader to help your professional journey, but out of all these 5 questions are the most powerful, in our opinion:
- What’s the most important lesson you’ve learned in your career?
- How do you handle failure?
- What drives your decision-making process?
- What advice would you give to your younger self?
- How do you measure success?
How do you talk to senior leadership?
As senior leaders have limited time, it is important to quickly get to the point and have any data that you might need to show them. Here are a few tips to consider while talking to a senior leader:
- Be concise and focus on key points.
- Back up your ideas with data and evidence.
- Show understanding of their goals and challenges.
Ask insightful questions to demonstrate engagement.
