11 Useful Questions To Ask Senior Leaders for Growth

Knowing what questions to ask senior leaders in your field is the best way to learn. Networking with senior leaders is how you grow. If you put both together, you’re paving a great career path for yourself.

Often leaders want to share their experiences and they are a vital resource to our success! Their hardships and growth have not happened by chance so we have an opportunity to grow ourselves through asking leadership questions.

Why Should I Care About Asking Questions to Senior Leaders?

Asking questions shows your team members, including senior leaders, that you care about what you’re doing. It also shows them that you are ambitious, and that you want to continue learning and continue growing.

Having a connection to senior leaders will also help your professional development. They are valuable assets to your network. Great leaders can help you move around, and up, in your current organization.

Senior executives even have connections hiring externally and be able to recommend you there, too. Senior leaders can have a strong impact on your career, which is why establishing a strong relationship with them is important.

How can you establish this relationship with senior leadership? By asking them good questions! Not only will it show them that you want to grow in your career, but it will show them that you value their expertise, knowledge, and experience, too. All of this will help you create and foster a relationship with them.

So, How do I Know Which Questions to Ask Senior Leaders?

Here are 11 creative questions to ask senior leaders that will spark meaningful conversations which inspire your growth. Whether you are wanting to become part of a senior leadership team, or improve in your everyday work, their answers to these strategic questions are all things you can learn from.

How did you get into this field of work?

We all know that everyone loves talking about themselves, and senior leaders are no different. Let them tell you their story! You just may find it interesting, too. Sometimes getting started in a field of work is one of the biggest challenges we face.

Everyone’s career path is so different. Especially when talking with senior leaders who are in older generations than we are – their career path to a leadership role is vastly different than what ours is like.

They didn’t have LinkedIn or digital job boards. Their whole application process was so different. What was their first step into leadership development? You may learn something from the path they took to get to where they are, too.

What advice would you give to your younger self?

Senior leaders know a thing or two both about the company you’re working at, the industry you’re working in, and life, in general. They have life and career experience you don’t have just yet.

Asking them the advice that they would give to their younger self is basically asking them what their advice would be to you. It’s asking them to reflect on things they may have done while they were your age that they either regret or would do differently.

You can learn from this and make sure not to do it – or to do it, whichever way their advice may go. Undoubtedly, there will be something you can take away to apply to your own life.

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

Along the same line of insightful questions, this holds a similar value of advice. It may seem like a personal question but part of growing is learning from your own mistakes, and also from the mistakes of others. Everyone has made mistakes in their lives, senior leaders included.

They have probably even made some mistakes in the workplace, too. Learn about their mistakes so you can look out for them and to not repeat them.

Once they tell you which decision they regret, ask them about the thought process behind them. What actions led to that decision being made? How did you handle the repercussions? This is the best way to let you learn, and show them that you care.

What professional organizations are you part of?

You’ve probably heard the saying that your network is your net worth. Having a strong network is so important! These senior leaders should also be part of your network.

But they also have their own networks, too, that are vastly larger than yours. It’s a good idea to try and get embedded into their network too, to have theirs become yours. Bam! Your network is already growing larger.

Most senior leaders are part of professional organizations. Not only does this strengthen their network, but it also provides them with continuous learning and growing opportunities too. Ask them which ones they’re part of and which ones they’d recommend.

See if they are a good fit for you, and if it is, circle back with the senior leader asking for their insight on whether you should join it or not. They may even be able to help you get in!

What are the most important attributes of successful leaders today?

If you want to be a good leader one day, asking this question will show the leader you’re speaking to that it’s on your radar. Plus, their answer to this question will give you insight into the type of leader they are.

If they are a leader you may be working with one day, it’s good to know how they define valuable leadership skills. It’ll show you their working leadership style. If you are looking for a mentor, asking this question would also show you whether the relationship would be a good fit.

What are your current goals?

Everyone has goals. Well, everyone should have goals. Goals shouldn’t just stop once you reach a certain age or reach a certain position. A senior leaders goals will likely be different than your goals but you can still hear some great ideas from them.

Pay attention to what they say. See if there’s anything you can do to help them achieve this goal, especially if it’s a company wide one. It’ll show them that you listen, care, and are willing to be proactive in helping.

Also be sure to ask them how they plan on reaching this goal. Knowing the strategic planning path they take when it comes to achieving goals can help you figure out a path to achieving your own strategic goals, too.

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

Taking risks can be scary, but it’s how we grow and learn. To get to a leadership position, some sacrifices likely had to be made on their end. By asking them this question, you are again learning from them.

You are also getting insight on what it takes to become a leader. Their answer can really paint a picture for you as to whether you want to be on a similar tract as they were… or not.

Also use this question as an opportunity to learn how to properly choose risks, and how to make the right decisions on your career journey. That’s the importance of including the “why” at the end of this question.

What was your biggest hardship and how did you overcome it?

Without fail, they will have endured a difficulty that required some creative navigating. And ultimately, if you haven’t already, you will too.

Hearing their strategies to overcome their biggest challenges could give you some valuable insights. Understanding the different ways they managed getting back on their feet may give you new ideas for the next time you encounter something difficult.

Additionally, you can glean some understanding of what characteristics embody a resilient person. This is an example of asking the right questions to help you along the path of reaching your personal goals.

What are some great books you can recommend on leadership?

If becoming a leader is on your radar, or if you’re just an avid bookworm always looking for a great read, ask them about any leadership books they have read that they recommend. In addition to chatting directly with a leader, books are also a great way to gain knowledge, wisdom, and insights.

Most leadership books are written by leaders, or provide firsthand accounts from leaderships. You’ll learn about their successes and failures. Additionally, their thought processes and methods will become part of your arsenal to develop your own leadership style.

You’ll learn a lot from reading a leadership book. Every leader will likely have their own “top three” leadership books, so you can easily ask this question to many leaders and have a whole bunch of books to add to your TBR!

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

If you are a new employee, this is one of the key questions that would be super beneficial to you personally. Even if you’re not a new employee, this can also be incredibly helpful in learning how to become one of the top team members.

The traits that they say in response to this question are traits that you should look for in yourself and start integrating any that you are not already doing. This will also help give you insights into the new hiring process that is happening at your company, and likely beyond that.

If you are interested in the hiring side of things as well, this can be an opportunity to ask a follow-up question to see if there’s any chance for you to shadow on an interview or learn how to get more involved in that process.

Do you have any projects I can contribute to?

Is the senior leader in question someone who’s team you hope to be on one day? Are they working on projects that you hope to one day be working on? If you answered yes to either of these questions, get your foot in the door!

Assuming you have the capacity within your time management, ask if they have any projects happening that you can help on in any way, shape or form. If they don’t, or if you don’t have the capacity for that, ask them if there’s upcoming calls that you can sit on or meetings that you can shadow.

This will help you learn what they do, and can better your chances of moving to that team or project down the line. This is an effective communication showing an initiative and passion for investment in both your and your company’s goals. Leaders admire this kind of employee engagement and employee morale.

Final Thoughts on Useful Questions to Ask Senior Leaders for Growth

All of these are great questions to ask senior leaders you come in contact with. Another thing? If your company offers a leadership series or leadership panels, or if you know of any networking organization that does, go!

Most leadership talks or panels have time allotted at the end for a Q&A session. Use that time to stand out and don’t be afraid of asking questions to pursue your growth. You now have 11 perfect questions to ask senior leaders up your sleeve, ready to use!

About the Author

Michelle graduated from Fordham University with a Bachelors of Arts ’13 and a Master of Arts ’14. She’s currently working in corporate America with a side of freelance writing. She wants you to learn from her experiences and mistakes so your 20s can be your best decade. When she’s not working, she’s likely planning her escape to a tropical island.