15 Astute Questions To Ask Other Leaders

Jennifer Herrity

Updated September 30, 2022

https://www.youtube.com/embed/gvsiYHr573c?controls=1&autoplay=false&enablejsapi=1&origin=https%3A%2F%2Fwww.indeed.com&widgetid=1Show Transcript

Video: Top Leadership Styles – Definitions & Examples

Jenn, an Indeed Career Coach, explains the top leadership styles in management and how to identify the one that’s right for you and your team.

In the realm of your profession, you may have a rare opportunity to meet another leader whom you admire. Both of you may be seated side by side on a long haul flight or share the same table for refreshments at a conference. This a good opportunity to ask this leader questions that could lead to a breakthrough in your company or field. Speaking with your leaders is vital for your growth and is one of the best ways to improve your processes and strategies.

Questions to ask leaders for career growth

Having a list of questions ready can help make for a successful encounter with other leaders. Whether you save these in your phone or learn them by heart, make sure to have questions like these on hand so you can take advantage of the moment you come face-to-face with one of your leaders.

Doing so not only makes you look prepared, but also makes you stand out from others as someone who is passionate about their career and is looking to excel. To help you get started, here are 15 top questions to ask leaders you respect:

1. Who do you look up to for inspiration or mentorship?

As a leader, it is important to maintain connections with role models and mentors. Regardless of a leader’s success, these are the individuals they go to when they need advice themselves.

Perhaps this question can encourage you to find mentors in your profession who have overcome trials you are currently facing. By learning from their experience, you can avoid potential pitfalls along the way.

The leader’s answer may even be surprising. You may follow the same role models. This can be a point of connection to start a rewarding, lasting relationship.

2. What is one decision you wish you didn’t make?

Part of growth is learning from other people’s mistakes. Even if you have done a SWOT analysis, there is always more to learn about your own abilities. You can save yourself time and resources by speaking with leaders who have made mistakes while encountering situations similar to your experience. It may also be helpful to inquire about the thought processes and the actions that led to said mistakes. This will allow you to learn from the wisdom of those who have experienced failures.

3. How do you keep your team motivated despite conflicts and obstacles?

This is one of the most insightful questions to ask senior leaders because it involves their vision and how they help their organization achieve its goals. Good leaders know that people need more than financial incentives to commit to long-term goals.

Regardless of your industry, this question can reveal actionable strategies that will motivate employees or fellow team members to work toward the same vision. It takes more than astute leadership to do this, it involves providing a source of motivation, which your leaders are more than likely experienced in. Speaking about the right motivation for teams can help you learn how to approach this with your team’s specific needs.

4. What are the most important attributes of successful leaders today?

Some people are natural leaders. They can bring people together behind their ideas and manage them to achieve a common goal. If you don’t have this natural trait, you can still become an exceptional leader by studying the habits of successful leaders in your industry.

This question can demonstrate the power of communication skills, empathy, vision, strategic thinking and other desirable qualities in a leader. It can also show you the best combination of traits to enhance your leadership style and deliver top quality guidance for your team or organization.

5. What qualities are lacking among today’s leaders?

Again, this is a powerful question that can reveal your own shortcomings as a leader. Being in a leadership position can create a feeling of invincibility, but it helps to check in with others to improve upon things you are not aware of. Chances are, asking this question will allow you to receive a response that helps you identify your own strengths and weaknesses.

6. What are your current goals?

Leaders who excel generally have goals they are currently pursuing, even if they are already successful or hold a position of stature.

When you ask this question, note the number of goals, the scope and how they plan to accomplish the goals. Compare your procedures and strategies to see how to improve your goal setting for optimal growth in your career. Additionally, knowing how to best prioritize goals can help you focus on the things that matter most for your organization.

7. What one thing makes you most proud?

This response could reveal a side of the person you never knew existed. While people may respect leaders for their professional achievements, many of them do not see these accomplishments as the epitome of self-actualization. Things like family, their spouse, the ability to speak a language or an artistic skill may be the thing they are most proud of.

Questions like these often help put life into perspective, as they reveal the things that are most important aside from business. If anything, they can help balance the way you view your time at and away from the office.

8. What’s the most important risk you took and why?

Leaders sacrifice a lot to reach their position. When they answer this question, some risks may bring fond memories while others may elicit strong emotions of opportunities lost. Take away lessons on how to choose risks to avoid making the wrong decisions on your career journey. Allow yourself a moment to reassess your priorities and how you are approaching them.

9. How do you continue to grow and develop as a leader?

The most respected leaders know how to stay ahead in their industries. They continue to upgrade their skills, make new connections, improve their relationships and take advantage of worthy opportunities. Some leaders retain these skills by reading books; others teach staff and find better ways of solving old problems.

Even if you already have a process for refreshing your skills, you can expose yourself to different ways to approach your position when you ask others questions regarding their own leadership practices.

10. How do you align your organization with your vision and mission?

Successful leaders are not supernatural. These individuals achieve more than others because they know how best to utilize people and resources for the sake of accomplishing their common goals. Some do this by rallying their team members to increase production. Others may use their leadership to gain the support of important stakeholders.

You can use the insights from this question to improve your strategies for things such as starting new programs in your organization or changing the way your organization processes information.

11. How do you generate great ideas in your organization?

Different organizations use a broad range of idea generation techniques. Some companies have an organizational culture that encourages dialogue, sharing of information and feedback. Others have a procedure for stimulating and documenting new ways of solving problems and reward systems to encourage creativity.

By asking this question, you can discover enhanced methods to make your employees or team members better idea-generators. A great idea can come from the lowest ranking employee or a senior executive. Making sure everyone has access to things that help optimize different ideas makes way for growth in your organization. What’s more, this question can reveal weaknesses in your employee feedback policy and how to make this more effective.

12. What are the most important traits to look for when hiring a new employee?

Employees are the foundation of any organization. It is vital to be thorough when hiring, as these potential employees can either help or hurt your organization. Even with a great resume and cover letter, some candidates could lack the necessary skills or techniques needed to excel on your team.

Ask this leader how they handle hiring and what to look out for. This will likely introduce you to new hiring strategies to implement and employee qualities to seek out.

Related: How to Find Good Employees

13. What three books can you recommend on leadership?

Books are some of the best sources for gaining wisdom and knowledge from other leaders, as they can guide successful new processes and methods. This said, each leader often has their own recommendations, so ask the one you are interviewing for theirs.

14. What do you consider before promoting someone?

You may not be in a position to promote people now, but it helps to know the factors to consider when choosing between two or more similarly-qualified employees. The answer to this question can reveal an effective guideline to use when you need to promote a team member. What’s more, it can teach you how to become a team member worthy of promotion in your organization.

15. What is the most dangerous trait in a leader’s career?

There may be personality traits you possess that could unknowingly hinder your professional growth. However, it can often be difficult to identify these traits in yourself, objectively. Speaking with someone else about these attributes can be revealing for the better, and is likely to assist your professional development long-term.

When you meet another leader you find interesting, it may be difficult to come up with questions that can have a far-reaching impact on your career. Even if you are nervous, you can avoid anxiousness by having a list of questions to ask when you meet such a person. The short time you spend together can produce deep insights that will help you advance in your career.