6 Questions to Ask Exceptional Women in Leadership

Indira Gandhi once said, “The power to question is the basis of all human progress.” This quote illuminates the idea that when we listen, we learn and when we learn, we equip ourselves with the tools and confidence we need to evoke change in the world.

What we don’t always realize is that being inquisitive is a skill, one we need to cultivate, practice and sharpen over time. We teach the listen-and-learn technique during Syracuse University’s Women In Leadership Cohort Experience, a program that supports the professional development of women on campus through education, awareness, and mentorship. Much of our programming is offering participants the opportunity to hear from other women in order to glean lessons from their experiences and insights. Through asking questions, we hope that cohort participants hear stories that make them think, feel, and ask Why?

If you’re feeling stuck, unmotivated, or unsure of your “what’s next,” getting curious is a solid first step in charting a path forward. Reach out to the women you admire most — supervisors, mentors, colleagues, friends, or family members. Set up time to chat and ask questions that will help you learn about their journey and their best advice for navigating challenges along the way.

Below is a list of six questions to ask women in leadership roles.

Question 1: What are some of the leadership skills that helped you move up in your organization?

When you ask this question, a leader will likely share details about her career trajectory. Maybe she’s a natural-born leader who captained sports teams and headed up committees in high school. Maybe her leadership skills took time to develop and are the result of her expertise on a given subject in her industry. Whatever story she shares, you’ll get a sense of what got her to where she is today. Listen for specific leadership skills and traits like communication, organization, problem-solving, creativity, out-of-the-box thinking, emotional intelligence, delegation, and having a strategic mindset. Compare what she shares with your own skills — if there are gaps, think about courses and professional development opportunities that may help you round out your leadership skillset.

Question 2: What are some leadership challenges that are unique to women?

As you build up your leadership skills, work to gain awareness of potential roadblocks that lie ahead — especially obstacles that are specific to women. By asking this question, you can learn about how a leader navigated issues like the double bind, likeability conundrum and pay inequity. You may follow up by asking her when she encountered these challenges and what strategies she used to overcome them.

Depending on your relationship with the leader, you may also ask about how she’s experienced leadership through other parts of her identity — specifically ones you share, like being a mother or having a specific racial or ethnic background.

Question 3: Was finding a mentor part of your leadership journey?

Chances are the leader you’re having a conversation with had some help along the way. Inquire about her support system. Did she have a supervisor who championed her success or a seasoned colleague who showed her the ropes? Learn about how she built her network and how she’s made valuable connections over the years. She may offer to make some introductions to help you grow your own professional circle.

Remember, you can find “informal mentorship” by simply observing dynamic leaders in action. I had the privilege of watching a woman leader with a calm demeanor be focused and decisive in the face of a crisis. In a critical moment, she galvanized our global team in a response, and in doing so modeled outstanding leadership. This can be seen as mentorship in action.

Question 4: What is the best leadership advice you have ever received?

No two women will answer this question the same way, so use this question frequently and soak up the wisdom that comes with each response. You’ll likely learn about the advice that leaders wish someone had given them earlier in their careers.

I still remember the best piece of leadership advice I ever received: choose progress over perfection. For high performers and goal-oriented leaders, it’s easy to strive for perfection. Particularly for those leading transformational change, it’s important to achieve small victories early on. In early days, progress has a lot of value.

Question 5: What is your leadership style?

If she’s done any sort of formal leadership assessment, she might share that she’s a transformational, delegative or servant leader. Or she might explain her style in her own words. When I think of the woman I admire most, I’d describe her leadership style as authentic. That’s because there is no one way to show up as a leader. What is most important is that “you do you.” Your values, your sense of self and purpose should ground you. These north stars will also serve as a lens through which you can consider the feedback you receive. While it’s helpful to learn from other leaders, part of your opportunity is to chart your own individual path forward based on your authentic style.

Question 6: If you could do one thing differently in your leadership career, what would it be?

You can learn a lot from a leader’s successes and mistakes. Save this question for later in a conversation when she feels more comfortable opening up about a misjudgment or missed opportunity. Chances are she had a way to learn and grow from a less-than-ideal experience and can pass that knowledge on to you.

Personally, I wish I had learned earlier to ask more questions when team members brought challenges to me. Leaders are often asked for solutions, and in an effort to move quickly, respond with quick judgment calls. From one of my coaches, I saw the power that exists in helping employees find empowerment through answering questions and searching for a path forward. This brings us back to where we began. There’s a tremendous opportunity to cultivate the art of asking questions and listening with thoughtful intention.

Questions are key to life-long learning

These six questions are only the tip of the iceberg. There are hundreds more you could ask women in leadership roles to encourage storytelling that’s packed with knowledge you can apply to your own leadership journey. To turn being inquisitive into a habit, dedicate a note on your phone or a page in a notebook to questions you intend to ask those around you, particularly women in leadership. Not only will you set yourself up for life-long learning, but you’ll also never run out of things to talk about with the people you admire most.

For more thought leadership content on storytelling, brand building, and women in leadership, visit my website, dararoyer.com.