When preparing for interviews, most people anticipate the classic “Tell me about your background,” or “What are your greatest strengths and weaknesses?”
Those are always fair game — but some executives have developed their own favorite questions to evaluate specific traits, whether they’re determining a candidate’s understanding of the role or looking for signs of an entrepreneurial spirit.
Business Insider asked five executives, including chief people officers at Walmart and Dayforce, about their go-to interview question.
AT&T’s head of business operations, Jennifer Van Buskirk
Jennifer Van Buskirk has been with AT&T for over 25 years and leads a team of roughly 20,000 people.
A few years ago, the head of business operations launched a startup, now operating as Cricket Wireless. She said she discovered two interview questions in the process of building her dream team that still uses to help identify the right candidates.
The first one is: What’s the greatest risk you’ve ever taken and why?
The second question is: If you started all over again, what would you do differently and why?
For both questions, Van Buskirk said she’s looking to spot whether the candidate can make bold moves and dream big. As a risk-taker herself, she wants to see that quality in potential hires.
“When you’re driving change or starting something new, it’s really important to get people that can thrive in that kind of environment,” Van Buskirk said.
Cisco EVP and chief people, policy, and purpose officer Francine Katsoudas
Cisco’s Francine Katsoudas told Business Insider that she typically speaks with candidates at the end of the interview process, so she likes to ask what they think is the most important part of the role, based on prior interviews.
“It’s a question that allows me to understand how they’ve distilled the various conversations that they’ve had, and then how they have translated that into what’s really needed — sometimes beyond the job description,” Katsoudas said.
She said that’s usually her starting point, and it gives her “a lot of insights” about the candidate.
Dayforce EVP and chief people officer Amy Cappellanti-Wolf
Dayforce chief people officer Amy Cappellanti-Wolf asks a version of the classic “what’s your greatest weakness” question. She asks about recent constructive feedback that a candidate is actively working on.
She said she’s open to personal or professional responses. The executive said she’s excited to hear genuine answers and finds it a “problem” if they say they don’t get feedback or have nothing they’re working on.
“It reveals people’s character a bit, in terms of their ability to be vulnerable, but also to be open and honest about what they’re working on, because we’re all a work of art, right? We’re all working on ourselves,” Cappellanti-Wolf said.
IBM VP and managing director for Salesforce, Corinne Sklar
IBM executive Corinne Sklar has been asking the same question for 20 years, and it helps her identify whether a candidate has entrepreneurial qualities.
The question is: “Tell me how you first made money.”
The executive said she comes back to it every time because it helps her evaluate whether someone is a go-getter and not waiting around for a degree or a job to get started, she said.
Sklar said part of the reason she’s set on hiring hustlers is because she considers herself one. At 7 years old, Sklar said she knocked on doors to sell hand-drawn 25-cent bookmarks for Halloween. When one woman complained that the bookmark was made of construction paper, Sklar said she offered to laminate it for 50 cents.
“I’m looking for people who are not going to ask for permission; they’re going to drive their strategy,” Sklar told Business Insider at Monday.com’s Elevate event in September 2025.
Walmart EVP and chief people officer Donna Morris
Walmart’s Donna Morris typically interviews candidates at the leadership level, and her favorite question is one that’s open-ended.
The question is: “If I was to ask people who’ve worked for you before, what will they tell me?”
“You can’t really rehearse for it, even if you knew the question,” Morris said.
She said she likes to ask this because the candidate’s response naturally leads into a larger discussion. Morris said she then continues to probe the candidate further to get more details about how they position themselves in the workplace and interact with others.
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