10 Best Questions to ask a Leader

By on September 24, 2022

Whether you’re someone who has just stepped into a leadership role or a leader who’s trying to improve your organization, even if you’ve been in a leadership position for a while now, you can always benefit from the thoughts and experiences of other leaders. 

When you finally meet a leader you’ve admired from afar and have a chance to speak to them, you might not immediately be able to think of all the questions you have for them. We, therefore, recommend that you have a list of questions ready – for when this chance arises!

Being prepared with a set of questions will spark a meaningful conversation and help you gain insight into successful leaders’ leadership qualities, skills, and styles. 

We’ve put together a few good questions to ask a leader. You may already have some of these on your list and probably never thought about others. But we’re confident that this article will help you prepare for meeting a successful leader! 

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

Tips to ask powerful questions to leaders
  1. 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. A concise and direct question will give you a well-formulated response. 
  2. It’s important to remember that 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.’ It’s a question you need to be answered to give you the information you need for your leadership journey.
  3. 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 to clear your doubts or confusion.

So now that we’ve got those basics out of the way, here’s a list of:

10 good questions to ask senior leaders

  1. Can you share details of a mentor you’ve had – the impact they’ve had on you as a leader or person? How has this experience made you a better mentor?

All leaders – no matter how senior or influential – have or have had the support and guidance of a mentor. A good mentor helps you avoid pitfalls, advises you on how to communicate your thoughts and ideas better, and enables you to be a more successful leader.

Training to be a good mentor means passing on your expertise and experience and helping shape the leaders of the future.

In asking this question, you learn from other leaders and their successful mentors, thus helping you become a better leader and mentor. 

Here are other tips you’ll find helpful in shaping yourself as a mentor

2. 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. 

3. 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.

4. In your opinion, what’s one mistake that leaders should avoid making?

Everyone makes mistakes. The more successful among us learn from those mistakes and avoid making them again… The super successful learn from others’ mistakes and are careful not to make them!

The senior leader from whom you seek inspiration and motivation has likely studied (and learned from!) the mistakes of other leaders. By asking this question, you will receive excellent advice based on that leader’s experiences (and mistakes) and those of the other leaders s/he has studied or followed.

5. 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.

Gallup surveyed to analyze the experiences of various sexual orientations, races, and genders at the workplace with some exciting and unsurprising results.  

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.

Learning how these initiatives are being managed at other organizations will help you understand how you can be a better leader on your own. 

6. How do you ensure creativity and innovation in your organization?

The entities that can move forward in today’s fast-paced environment are those that can adapt and change as needed.

A leadership style that fosters and encourages creative thinking and innovation among the ranks is a trademark of a successful leader. A leader successfully encouraging employee engagement and harnessing the best knowledge and skills among team members is sure to retain the best talent.

Appreciation of your team is equally important! Here’s a quick read on how you can achieve that. 

Learning how other leaders are doing this successfully will give you ideas on what you can do and how – in your leadership position.  

7. How do you choose between two equally qualified candidates when deciding on promotions?

Making tough decisions regularly seems to be a hallmark of senior leaders. Asking other leaders how they make important decisions is a great way to learn what factors to consider and how to make decisions yourself. 

It is also essential that leaders make the right decisions somehow. This question is not really about who was finally chosen for the promotion. It’s more about what factors were considered and how the choice was finally made. 

8. In your estimation, how important is work-life balance for yourself? For your employees?

A healthy balance between work responsibilities and the appreciation of a healthy life is essential. In fact, given the events since the Covid-19 pandemic broke out, the need for this balance has gained more importance. 

A lack of work-life balance causes tremendous stress and employee dissatisfaction. This article states that ‘only 52% of employees in corporate America believe that their employer cares about their work-life balance.’

Work-related stress impacts personal relationships and employee health and well-being. This ultimately hurts the organization. 

Understanding how other leaders manage this balance for themselves and their organization can provide invaluable insights into what you can do for your organization. 

9. How do you leverage your strengths and balance your weaknesses as a leader?

A good leader is humble and honest while introspecting and sharing their journeys. They also know what personal qualities work in their favor as senior leaders and what holds them back. 

Sharing this with you gives you insight into how they’ve become successful leaders despite their drawbacks or weaknesses. Or, maybe they’ve identified a weakness and converted it into a strength. In any event, there’s plenty of inspiration to be drawn from responses to this question.

10. Please share a few resources you consider helpful in continued leadership development.

Becoming a leader is not the end of your professional journey. It is, in many ways – just the beginning. You must develop and maintain a competitive edge and stay two steps ahead. 

Learning how other leaders face this challenge will give you some ideas and tips on the path you can take. You may choose to strengthen the path you’ve selected with input from other leaders, or you may decide to choose a different path based on the new information you have. 

Absorb all the information you get and then adapt it to what suits your situation best. Remember, there are no right or wrong answers. The responses you get all need to be taken in the context and circumstances in which the leaders were. 

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 formulae for success. Use their knowledge and lessons to prepare for your success as a leader.

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