Connecting with leaders is an important part of growing in your career, whether you’re already in a leadership role or working your way up the ladder. Learning about different leadership theories helps you shape your own leadership style. Here, we’re sharing a variety of situational leadership questions to keep in mind the next time you’re at a corporate event, networking social, or in a skip-level meeting.
Be ready with questions to ask when networking with a leader
Having questions in mind to ask leaders is an indispensable part of networking. When you’re caught up in the moment of meeting someone new, it’s natural to blank on some—or all—of the questions you might want answered. Preparing and practicing questions in advance helps you maximize the opportunity to learn about various leadership styles and managerial roles. Even if you aren’t in leadership yet, talking to successful leaders can give you a better idea of how to meet this goal.
“I’ve recently been assigned a mentor, who is a very senior leader. I didn’t ask for a mentor, nor was I aware that my company had such a program, so I feel somewhat unprepared. Looking for advice on how to jump into this process and make it count.”
– Senior Project Manager
What to ask a leader: Preparation pro-tips
Leaders value efficiency. If there’s a leadership topic you want to learn more about, think of a few questions that you can keep handy in a file or folder on your phone so you don’t waste time when an opportunity arises. After you prepare your list, practice asking your questions out loud. You might realize that there’s a better way to state your question to get a clearer response.
Top 16 questions to ask leaders
The questions you choose to ask when talking with leaders will depend on your interests, but they’ll generally fall within one of four categories:
- Personal development
- Management style
- Career development
- Leadership insights
To help inspire your own questions, we’ve divided the 16 best questions to ask leaders into those categories.
What to ask a leader about personal development
Questions in this category are specifically about the leader’s personal experience. This category is useful for big-picture, get-to-know-you queries.
1. What is the biggest risk you have taken?
People in leadership roles typically aren’t passive; they make bold decisions that have the potential to pay off big. Get to know what kind of risks this person took to get to where they are today, and be prepared to respond with your own story of risk and reward in the workplace.
2. What is your greatest accomplishment?
Knowing other leaders’ accomplishments can give you a better idea of whether you’re on the right track to becoming a leader yourself. It’s also a nice way to learn a leader’s values and priorities. Some leaders will take a more sentimental approach to this question, while others will stick to business. Again, think about your own response, in case the person you’re talking to wants to hear about your greatest accomplishment, too.
3.What are your biggest goals right now?
Continuously creating goals is an important part of advancing your career. Use this question to discover the kind of goals leaders have, and think about how your own goals compare. Other people’s answers can serve as inspiration when deciding which goals you want to set.
4. What is the best book you’ve read this year?
Effective leaders are constantly learning new things. Asking this question can help you find books to add to your reading list and give you insight into the ideas that are shaping other leaders’ thought processes. Don’t forget to bring a title or two of your own to the discussion!
5. Who have been your most influential mentors?
Mentors can help you plot your career path, grow into a new role, or offer peer-to-peer advice. Learning about a leader’s mentors can be helpful as you try to find your own. Plus, it opens the door for later conversations about establishing a mentoring relationship.
Career development
Whether as a co-founder, a college grad, or a copy room assistant, every leader has an origin story. Use these questions to help design your own career roadmap.
6. How did you get into this industry?
There are two approaches to this question. If you currently work in the same industry as the person you are talking to, you will learn more about this person’s educational background, interests, and aspirations, and can find common ground with them. On the other hand, if you’re trying to transition into that leader’s industry, this question might give you ideas for additional education or training, or help you think about transferable skills from your current field.
7. What resources did you use when just starting out as a leader?
When moving into a leadership position, you’re not going to know all the answers right away. Using resources is an important part of improving your leadership style and thriving in your role. Get to know what courses, certifications, how-to guides, forums, mentorships, and publications this person recommends.
8. Did you always know you wanted a leadership role?
Not everyone is born a leader. They may discover their desire to guide others later on in their career. This question is a way to learn more about what influenced their decision, as well as the challenges they may have overcome along the way.
Management Style
Save these questions for skip-level meetings or for networking outside of your current company.
9. How do you decide to partner with someone?
Leaders have different criteria when deciding which clients and colleagues to work with. This question can be useful when you have to make such decisions yourself. For instance, you may find out that this leader gravitates towards people with good communication skills. Their response can also help you learn which skills and characteristics to improve in yourself.
10. How do you encourage creative thinking in the workplace?
Getting your team to step outside its comfort zone takes skill. Leaders have a variety of techniques to facilitate innovative thinking. By learning these techniques, you can use them while you’re brainstorming your own ideas. Knowing these strategies is especially helpful if you’re in charge of a team. Because leaders are always learning, don’t be surprised if they ask you what sparks your own creativity at work.
11. What qualities do you look for in a new hire?
People in leadership roles are often in charge of the hiring process. When looking for a new job, you want to know how they decide who would be a good employee. Then, you can start to work on these skills, qualifications, or characteristics.
12. What factors do you consider before promoting someone?
If you’re looking for ways to fast-track your career, ask the top leaders in your field this question, and follow their advice. This is a particularly useful question to bring up in meetings with your manager or in skip-level meetings at your company.
13. What is your best piece of advice for a new leader?
In order to get into a leadership role, start looking for support and guidance from other leaders. Getting advice from the top people in your field can help you decide how to move forward in your career. This question also shows this person that you value their opinion, which may strengthen your connection.
“Hey all, for the people leaders out there: how do you run 1:1s with your employees? I am a brand new people leader in a brand new team, and I really want to set my team up for success. What kinds of topics do you talk about? How do you track feedback or progress? I really don’t want these meetings to turn into ‘what did you do this week?’”
Leadership insights
If you want to make your way into management, make sure some variation of these questions is on your list.
14. What are the most important characteristics of a leader?
If you want to be a leader, then you need to act like one. By going straight to the source, you can learn which characteristics you should work on. You could even ask a follow-up question to learn how to improve such traits. Be ready to respond with your own take on the most important qualities in a leader.
15. What mistake do you see leaders make frequently?
No leader is perfect. Since this person has likely been in their field for a while, they may have strong opinions about the kinds of mistakes other leaders make. Learning about the traps others have fallen into can help you avoid those mistakes.
16. If you could do anything differently, what would it be?
Learning what someone with years of professional experience would do differently can help you save time and resources in your own career. In addition to avoiding mistakes, this response might help you identify situations where you can be more mindful.
You can learn and grow from other leaders at any stage of your career, so don’t be ashamed to ask questions when you meet a leader you admire.
Prefer to keep your questions online? Get more leadership tips from professionals on Glassdoor Community in the Leadership Bowl.