Quick Summary
- 1Executives from major companies like Walmart, AT&T, and Dayforce have developed unique interview questions to assess specific candidate traits.
- 2These questions move beyond standard inquiries to evaluate boldness, entrepreneurial spirit, and self-awareness.
- 3Leaders use these methods to uncover how candidates think, act, and lead in real-world scenarios.
- 4The questions reveal a candidate's character, strategic thinking, and ability to thrive in dynamic environments.
Beyond the Basics
When preparing for a job interview, most candidates rehearse answers to classic questions about their background, strengths, and weaknesses. While these staples remain fair game, top executives are increasingly turning to more creative inquiries to uncover the true nature of a potential hire.
Business Insider spoke with five senior leaders who have developed their own go-to questions. These leaders, from companies including Walmart, AT&T, and Dayforce, use these tailored questions to evaluate specific traits—whether they're determining a candidate's understanding of the role or looking for signs of an entrepreneurial spirit.
Their methods offer a fascinating glimpse into how the world's most successful leaders identify talent that can drive change and thrive in new environments.
The Risk-Taker's Test
Jennifer Van Buskirk, Head of Business Operations at AT&T, has been with the company for over 25 years, leading a team of roughly 20,000 people. A few years ago, she launched a startup, now operating as Cricket Wireless, and discovered two key questions in the process of building her dream team.
Van Buskirk still uses these questions to identify candidates who can make bold moves and dream big. As a self-described risk-taker, 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.
Her two questions are designed to reveal a candidate's appetite for risk and their capacity for strategic reflection:
- What's the greatest risk you've ever taken and why?
- If you started all over again, what would you do differently and why?
These questions force candidates to move beyond rehearsed narratives and share authentic experiences that demonstrate their willingness to step into the unknown.
"When you're driving change or starting something new, it's really important to get people that can thrive in that kind of environment."— Jennifer Van Buskirk, Head of Business Operations, AT&T
The Entrepreneurial Spirit
For IBM VP and Managing Director for Salesforce Corinne Sklar, identifying entrepreneurial qualities is paramount. She has been asking the same question for 20 years because it consistently helps her evaluate whether someone is a go-getter.
Sklar's question is deceptively simple: "Tell me how you first made money."
She returns to it every time because it reveals whether a candidate waits for permission or a degree to get started. Sklar considers herself a "hustler," recalling how at seven years old she knocked on doors to sell hand-drawn 25-cent bookmarks for Halloween.
I'm looking for people who are not going to ask for permission; they're going to drive their strategy.
When one woman complained that her bookmark was made of construction paper, Sklar offered to laminate it for 50 cents. This early anecdote illustrates the resourcefulness and initiative she seeks in candidates today.
The Leadership Lens
At Walmart, EVP and Chief People Officer Donna Morris typically interviews candidates at the leadership level. Her favorite question is open-ended and designed to be un-rehearsable.
Morris asks: "If I was to ask people who've worked for you before, what will they tell me?"
She likes this question because the candidate's response naturally leads into a larger discussion. Morris then probes further to get more details about how they position themselves in the workplace and interact with others.
You can't really rehearse for it, even if you knew the question.
This approach shifts the focus from self-reported strengths to how a leader is perceived by their team, offering a more holistic view of their management style and interpersonal impact.
The Vulnerability Factor
Dayforce EVP and 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 is open to personal or professional responses and is excited to hear genuine answers. She finds it a "problem" if a candidate says 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.
This question assesses self-awareness and a growth mindset—critical traits for any leader in a constantly evolving business landscape.
The Synthesis Challenge
Francine Katsoudas, Cisco's EVP and Chief People, Policy, and Purpose Officer, typically speaks with candidates at the end of the interview process. Her question is designed to test their ability to synthesize information.
She asks: "What do you think is the most important part of the role, based on prior interviews?"
This question allows her to understand how candidates have distilled various conversations and translated them into what's really needed—sometimes beyond the job description.
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 this is usually her starting point and gives her "a lot of insights" about the candidate's strategic thinking and listening skills.
Key Takeaways
The interview questions used by these top executives reveal a common thread: they prioritize character, strategic thinking, and authenticity over rehearsed answers. By asking about risks, first ventures, leadership perceptions, and self-improvement, these leaders uncover the qualities that matter most in dynamic business environments.
For job seekers, this signals the importance of preparing not just for what they've done, but for how they think, lead, and grow. For hiring managers, it offers a blueprint for moving beyond standard questions to find candidates who can truly drive innovation and success.
"I'm looking for people who are not going to ask for permission; they're going to drive their strategy."— Corinne Sklar, VP and Managing Director for Salesforce, IBM
"You can't really rehearse for it, even if you knew the question."— Donna Morris, EVP and Chief People Officer, Walmart
"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."— Amy Cappellanti-Wolf, EVP and Chief People Officer, Dayforce
"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."— Francine Katsoudas, EVP and Chief People, Policy, and Purpose Officer, Cisco
Frequently Asked Questions
Executives from companies like Walmart, AT&T, and Dayforce use unique questions to assess specific traits. These include asking about a candidate's greatest risk, how they first made money, and what feedback they are actively working on.
These questions help uncover a candidate's true character, strategic thinking, and ability to thrive in dynamic environments. They move beyond rehearsed answers to reveal authenticity, entrepreneurial spirit, and leadership potential.
Modern hiring prioritizes character, self-awareness, and strategic insight over standard qualifications. Leaders are looking for candidates who can drive change, synthesize information, and lead with vulnerability and initiative.
Candidates should reflect on their past experiences, leadership style, and growth areas. Being ready to share authentic stories about risks, early ventures, and feedback can demonstrate the qualities executives are seeking.
