“In the future, there will be no female leaders. There will just be leaders.” 
― Sheryl Sandberg

Question Everything: Asking Your Way to Success

Question Everything: Asking Your Way to Success

Written by Hillary Kirtland


One of the best things that ever happened to my dad was the invention of Google. Rather than deal with the relentless questions his curious daughter had, Google provided my father with an avenue for sanity. His favorite response soon became: “I don’t know. Google it.” Fast-forward 20 years, and now we live in a world where we no longer have to search very hard for the answers we seek. Knowledge is power. And in the workplace, information can give you a leg up. So, here is a brief list of scenarios in which questions can help you stand out and make all the difference in your career—and some additional questions to make you stand out in those moment:

When Networking
Ask: How did you come to be who you are? 

I start every networking opportunity by trying to understand the other person’s journey. Not only does it actually start the conversation (which can sometimes be the hardest part), but it also skips the often monotonous—and sometimes annoying—small talk. This kind of question opens the door for the other person to share whatever they want about themselves, and people love sharing their stories. When people answer the question of “who” they are rather than “what” they do, conversations get much deeper, much more quickly. I find this makes me much more memorable in the long run. Recently, I connected with someone on a flight from Washington, D.C. to Chicago this way. Not only did we connect on LinkedIn before the flight was even over, but we’ve also managed to keep in touch.

Other useful networking questions:
What do you do for fun?
Who is someone you consider your role model?
If you could do anything else, what would you be doing?

When Negotiating
Ask: What do you need from me? 

Whether you’re negotiating a promotion or raise with your boss or negotiating a contract with a client, gathering information is key. Information will help you find common ground and subsequently frame your case. When I worked in sales, clients often needed something specific to be able to move forward on a proposal, sign off on a contract or renew business for the next year. The most successful sales managers could find out what that “something specific” was and actually deliver on it. This way they didn’t waste time doing what they thought the client needed; instead, they could spend their time working to gather what the client actually wanted. Asking the right questions got them the right answers, and everyone walked away feeling like they had successfully achieved a win-win.

Other useful negotiating questions:
What is most important to you?
What do you need in order to make this happen?
What are you willing to talk about or compromise on?

When Interview for a Job
Ask: What about this company keeps you here?

Asking the right questions can not only provide valuable information, but it can help you stand out in a job interview. Good questions really show that not only do you understand the role you’re applying for, but you also understand how this role fits within the company’s bigger picture. Don’t be afraid to follow up on the interviewer’s responses to your questions with additional questions. It can become an opportunity for conversation and a chance to show that you “get it.” 

One time, in a carpool ride back to the airport after a full morning of group and individual interviews, another candidate talked about how she ran out of questions to ask. Her interviewer chose to share an answer to a question someone else asked. It was an answer to one of my questions. The fact that the interviewer was so impressed with what I wanted to know that he shared it with another candidate left a strong impression on me. From then on, I took even more care to craft just the right questions for every interview that came my way. 

Other useful job interview questions:
What keeps you up at night?
Who on your team is the most successful, and why?
Did I answer all your questions and is there anything I can clarify?

When Receiving a Performance Review
Ask: What do you recommend as next steps?

Performance reviews are designed to help you grow; to identify what you do well and where you have opportunity to be even better. These conversations are a significant opportunity to better understand how management views success and what recommendations they have for your future growth. Although we may be reluctant to accept the critiques at times, we shouldn’t be afraid to ask for recommendations. During an internship I held in grad school, I was told I needed some better project management skills to achieve the next level in my consulting career. After clarifying with my boss what she meant, I signed up for an introductory course to build foundational knowledge in project management the very next semester. Going into interviews that fall, I was even more prepared to address some of the gaps in my experience because I took steps to proactively fill them early.

Other useful performance review questions:
How do I do even better with what I do well?
Did I meet your expectations from when we did this last?
Could you explain that in more depth so I make sure I address it appropriately later?

At the end of the day, the old adage is true: You don’t know what you don’t know. Questions help you figure that part out. While Google can provide you with many answers, it doesn’t matter if you don’t know how to find the ones you need. If you take time to cultivate your ability to ask more meaningful questions, you’ll find the information you receive in return also becomes more meaningful. It can make the difference in everything you do; in work, and in life.


Hillary works as a Senior Strategy Consultant at IBM. She found her passion for her new job in the two years she took off work to pursue a full-time, Global MBA degree at George Washington University in Washington DC. She is driven by her constant curiosity and her truest love is for travel and adventure. Outside work you can find her playing in two of the local DC kickball leagues, taking Jiu Jitsu, boxing, and yoga classes at her gym, reading a book, or binge watching a new show (Currently obsessing over Outlander, because Jamie). Find her other contributing pieces here and here.

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