Jennifer Van Buskirk, a seasoned leader who has dedicated more than twenty-five years to AT&T, stands as one of the company’s most experienced and influential executives. Over the course of her long tenure, she has taken on significant leadership responsibilities, guiding a workforce of approximately twenty thousand employees with strategic oversight and operational insight. Given her extensive history in managing people across various levels of the organization, she has developed a deep familiarity with the complex art of identifying, recruiting, and nurturing top talent.
Several years ago, during a pivotal moment in her career, Van Buskirk spearheaded the creation of a new business initiative that eventually evolved into Cricket Wireless, which now functions as a dynamic and fast-growing subsidiary under the AT&T umbrella. What began as a forward-thinking startup concept has grown into a major player in the telecommunications market, valued at over six billion dollars and serving an impressive customer base exceeding thirteen million subscribers, according to an AT&T spokesperson. This entrepreneurial endeavor provided Van Buskirk with the unique opportunity to assemble what she referred to as her “dream team” — a carefully chosen group of individuals who shared her vision for innovation, growth, and agility.
Throughout that transformative process, Van Buskirk discovered that constructing a team capable of driving large-scale change required far more than technical skill or professional experience. It demanded people who possessed a deeply ingrained willingness to think beyond conventional limits, to confront uncertainty head-on, and to pursue ambitious goals with courage. Through considerable experimentation and reflection, she refined her hiring philosophy and identified two core interview questions that have since become central to her approach. Even today, she continues to rely on these questions as reliable indicators of a candidate’s potential to thrive in challenging, fast-moving environments.
In describing her own mindset, Van Buskirk has characterized herself as “a bit of an adrenaline junkie” — a phrase that succinctly captures her appetite for both personal and professional challenges. She approaches leadership with an adventurous spirit, embracing risks that others might shy away from. When interviewing potential hires, she deliberately seeks out individuals who exhibit that same combination of energy, boldness, and resilience. In her view, the best employees are those “courageous enough to take the bold move, the big risk,” because such traits often signal the capacity to persist through instability and to innovate under pressure.
Her first major interview question, which she has relied on time and again, cuts straight to the essence of a person’s relationship with risk: “What’s the greatest risk you’ve ever taken — and why?” Van Buskirk believes this deceptively simple query exposes how candidates respond to uncertainty and illustrate whether they possess the mindset required to build something new. She explains that in roles involving constant change or rapid innovation, success depends heavily on an individual’s ability to flourish in unpredictable environments rather than retreat from them.
According to Van Buskirk, acceptable answers may come from either the professional or personal spheres of a candidate’s life; what matters is the scale and intention behind the action. She listens closely for examples that demonstrate what she calls a “big, bold move,” the type of decision that pushes someone outside their comfort zone. For instance, she has heard compelling stories of individuals who relocated across continents, pursued entirely new careers, or switched industries in pursuit of greater purpose. Such answers suggest a level of adaptability that she values deeply.
Van Buskirk can speak authentically about this topic because she herself has taken notable risks — everything from launching an entirely new line of business to engaging in physically demanding adventures like skydiving. These experiences have taught her that growth rarely occurs within the confines of predictability. Consequently, she prizes candidates who display the same fearless curiosity she has shown. Those lacking such experience, she observed, often struggle to succeed in roles that demand comfort with ambiguity. As she put it, “You have to be okay living in that land of uncertainty.”
She recalls one particularly memorable instance when a candidate, when asked about their greatest risk, responded that it was getting married. Van Buskirk admits the answer gave her pause. To her, it suggested that the individual might either possess questionable judgment or exhibit a strong aversion to taking meaningful risks — neither of which aligned with the qualities she sought for her dynamic, fast-paced team.
Her second key interview question explores another dimension of self-awareness and ambition: “If you started all over again, what would you do differently — and why?” Van Buskirk uses this inquiry to gauge how expansively a candidate can think about their life and career trajectory. She regards the willingness to reimagine one’s path as a sign of intellectual flexibility and visionary thinking. In her experience, the best answers reveal not only humility and reflection but also an appetite for bold, strategic imagination. A candidate who can candidly acknowledge that they might have chosen a completely different professional route, or drastically reshaped their responsibilities, signals an ability to think beyond conventional limitations.
Van Buskirk emphasizes that the scale of the candidate’s response is telling: the bigger and more daring the answer, the better. When she first began using these questions more than ten years ago while launching Cricket Wireless, the business world looked very different. Yet, she notes, with the rapid evolution of technology — particularly the rise of artificial intelligence — the capacity to think broadly and creatively has only become more essential. As routine tasks become automated, the defining human advantage will be, as she puts it, an individual’s “ability to dream big enough.”
Conversely, a narrow or overly cautious response — for example, a statement focused on altering one minor aspect of a past role — suggests limited vision. Van Buskirk views that as a missed opportunity, explaining, “That’s a fail, because there’s always some improvement that can be had if you can think big enough.” In her assessment, effective leaders and innovators never settle for incremental tweaks; they constantly imagine how systems, strategies, and entire organizations might evolve toward a more ambitious future.
Ultimately, Van Buskirk’s hiring philosophy reflects a belief that boldness and self-reflection are not optional attributes but essential components of professional excellence. Her two core questions — about risk-taking and reimagining the past — serve as practical tools for uncovering the depth of a candidate’s ambition, adaptability, and capacity for growth. In her view, the individuals most capable of driving transformation are those who thrive on challenge, embrace uncertainty with composure, and possess enough vision to continuously redefine what success can mean within an ever-changing corporate landscape.
Sourse: https://www.businessinsider.com/att-executive-shares-favorite-interview-questions-redflag-answers-2025-11
