Diving into the evolving landscape of human inquiry in an AI-dominated era, I’m thrilled to sit down with Ling-Yi Tsai, a seasoned HRTech expert with decades of experience in leveraging technology for organizational change. With her deep expertise in HR analytics and talent management processes, Ling-Yi offers a unique perspective on how we can ask better questions to navigate uncertainty and foster meaningful human connections. In this conversation, we explore the challenges of questioning in a world flooded with instant answers, the personal risks and rewards of asking tough questions, and the profound value of embracing big, existential inquiries to enrich our daily lives.
How has the rapid rise of AI and its ability to provide instant answers influenced the way we approach asking questions in professional settings like HR?
The speed of AI has been a game-changer in HR, no doubt. It can churn out data-driven insights on recruitment or employee engagement in seconds, which is incredibly useful. But this speed often tricks us into skipping the deeper, messier process of questioning. We might accept an AI-generated report on turnover rates without asking why certain patterns exist or what cultural factors are at play. In my work, I’ve seen teams lean on these quick answers and miss the human nuances behind the data. It’s a shortcut that can dull our curiosity and prevent us from digging into the root causes of issues.
What do you see as the biggest risks when we rely too heavily on AI for answers instead of honing our own questioning skills?
The primary risk is losing our critical thinking edge. In HR, if we just take AI’s word on, say, candidate fit or performance metrics, we might overlook biases in the algorithms or miss unique human potential that doesn’t fit neatly into data models. I’ve witnessed organizations make hiring decisions based solely on AI recommendations, only to realize later that they’ve passed over candidates who could have brought fresh perspectives. Over-reliance on AI can also erode trust—employees and leaders start to feel like decisions are impersonal, which damages relationships and morale.
Why do you think there’s no simple formula or tool, even AI, that can fully teach us how to ask better questions?
Asking better questions is inherently a human skill tied to context, emotion, and experience—things AI can’t replicate. Tools can provide prompts or data, but they lack the intuition to understand why a question matters to a specific person or situation. In my career, I’ve found that the best questions come from reflecting on past challenges, like when I’ve had to navigate a failed onboarding process. No chatbot can tell me how to frame a question about employee dissatisfaction if I haven’t lived through those moments myself. It’s about personal growth, not a plug-and-play solution.
How does tapping into our own experiences with asking questions help us grow more than following expert advice or structured guidelines?
Our own experiences ground us in reality. Expert advice often feels abstract—it’s generalized for a broad audience. But when I recall a time I hesitated to ask a tough question during a talent review, fearing I’d look uninformed, and then later regretted not speaking up, that memory teaches me more than any textbook. It shows me my blind spots and pushes me to be bolder next time. In HR, I’ve learned to ask about employee well-being by drawing on moments when I sensed tension in a team. Personal experience makes questioning authentic and relevant.
What do you mean by the ‘ugly side’ of asking questions, and why is it something we should embrace rather than avoid?
The ‘ugly side’ is the vulnerability that comes with asking questions—admitting you don’t know something, feeling exposed or insecure. In HR, I’ve seen leaders shy away from asking about potential flaws in a new tech tool because they worry it reflects poorly on their expertise. But embracing this discomfort is crucial. It’s how we uncover blind spots and build trust. When I’ve asked tough questions about whether our analytics tools are truly equitable, even when it felt awkward, it opened up honest conversations that led to better systems. Vulnerability is the gateway to growth.
Why do you think so many people are hesitant to show ignorance or insecurity when asking questions in a professional environment?
It often comes down to fear of judgment. In professional settings like HR, there’s pressure to appear competent, especially when you’re implementing tech solutions or managing talent. I’ve noticed team members hold back on asking clarifying questions during software rollouts because they don’t want to seem out of the loop. There’s also a cultural aspect—some environments penalize uncertainty rather than rewarding curiosity. I’ve worked with organizations where asking ‘why’ was seen as challenging authority, which stifles learning and innovation.
Can you share an example of a personal or professional risk someone might face when asking a difficult question, and how that risk ties into better understanding?
Absolutely. I once worked with a manager who asked during a strategy meeting if a new HR platform was worth the cost, given early feedback about usability issues. This question risked their reputation—some saw it as undermining the project they’d championed. But it forced us to confront real concerns, leading to critical adjustments before a full rollout. The risk of looking critical or disloyal was real, yet it deepened our team’s understanding of the tool’s limitations and ultimately saved us from a bigger failure. Asking hard questions often means risking your standing, but it’s worth it for clarity.
How can someone strike a balance between the fear of risking relationships or roles and the necessity of asking meaningful questions?
It’s about intent and framing. If your question comes from a genuine place of wanting to improve or understand, and you communicate that, it softens the perceived threat. In my experience, I’ve found that prefacing a tough question with context—like saying, ‘I’m asking this because I want us to succeed’—helps. Timing matters too; asking privately first can reduce public tension. I’ve also learned to accept that not every question will be well-received, but if it’s meaningful, the long-term benefit often outweighs short-term discomfort. It’s a calculated risk.
Why is it so vital to care deeply about the questions we ask, beyond just seeking answers, especially in a field like HR?
Caring about your questions shows investment in the outcome, which is huge in HR where human lives are impacted. When I ask an employee about their experience with a new onboarding system, and I genuinely care about their struggle, it builds trust and often reveals insights no report can capture. If I’m just going through the motions, the question feels hollow to both of us. Caring transforms a question into a bridge for connection and problem-solving—it’s not just about data, but about showing you value the other person’s perspective.
Why do you believe asking big, existential questions can have a practical impact on our day-to-day challenges in professional or personal life?
Big questions—like ‘What does it mean to create a fair workplace?’ or ‘How do we define success beyond numbers?’—force us to zoom out and see the larger purpose behind our daily grind. In HR, I’ve used these questions to rethink how we measure employee satisfaction. Instead of just looking at survey scores, we started asking what fulfillment looks like for individuals. This broader lens helps reframe smaller issues, like a policy complaint, as part of a bigger mission. It gives mundane tasks meaning and guides better decision-making.
What is your forecast for the role of questioning in a future where AI continues to dominate information and decision-making processes?
I believe questioning will become even more critical as AI advances. While AI can handle data and logistics, it can’t replicate the human drive to ask ‘why’ or ‘how can this be better’ in a way that reflects our values and ethics. In HR, I foresee questioning as the differentiator—those who ask thoughtful, human-centered questions will stand out in creating workplaces that balance tech efficiency with empathy. My forecast is that fostering a culture of inquiry will be the key to not just surviving, but thriving, in an AI-driven world. We’ll need to double down on our uniquely human ability to probe deeper.