The Power of Questions

Why great executives know what questions to ask

When I was a junior software manager and had the opportunity to sit in meetings with senior executives, I was pretty overwhelmed. Despite not understanding everything that was being discussed I noticed something. The best executives could get to the heart of the matter with a few simple questions. I was enthralled by how they consistently were able to do this. The subject of the meeting or topic being bantered about, didn’t seem to matter. Whether it was a review of a very technical project or a detailed financial review, these folks could see right through the technical jargon. If someone was trying to gloss over an issue, they could practically sniff it out. They would ask two or three questions and have the entire issue laid out. With that done, everyone could begin to dig in and hopefully resolve the issue. Given that these meetings were almost three decades ago and it stuck with me after all these years, I was very impressed.

Of course, wanting to emulate these executives, I asked myself, how do I get better at asking questions? It turns out that I wasn’t the only one asking this question. Researchers Alison Wood Brooks and Leslie John have been asking questions about questions for a while and stated in an Harvard Business Review article:

Questioning is a uniquely powerful tool for unlocking value in organizations: It spurs learning and the exchange of ideas, it fuels innovation and performance improvement, it builds rapport and trust among team members. And it can mitigate business risk by uncovering unforeseen pitfalls and hazards.

The authors continue suggesting that most people don’t ask enough questions and instead we make too many statements. They suggest the reason is that we are eager to impress other people with our own thoughts, stories, and ideas. Stephen R. Covey, author of The 7 Habits of Highly Effective People, wrote that, “Most people do not listen with the intent to understand; they listen with the intent to reply.” Research backed this up, demonstrating that people have conversations to both exchange information but also to manage other’s impressions of themselves. The good news is that more recent research has demonstrated that asking questions can accomplish the same thing. The researchers found not only are question askers more liked in a corporate environment but also in more casual situations, stating that, “people who ask more questions are better liked, and speed daters who ask more questions get more second dates.”

There is even some evidence that people who ask more questions are more intelligent. Research published in the ​​The International Journal of Early Childhood Learning stated that, “Children with higher intelligence ask usually more questions with both visual and linguistic stimuli. It was found that the number of questions generated by the indifferent visual stimulus is a good predictor of IQ, especially its verbal component.” This suggests that curiosity, as demonstrated through questioning, is closely linked to cognitive abilities. The study highlights the importance of encouraging questioning not only as a means of acquiring information but also as an indicator of intellectual development.

This insight implies that a culture of inquiry could be equally beneficial in the corporate world, particularly among executives. The connection between curiosity and cognitive abilities, as evidenced in early childhood learning, can be extrapolated to suggest that executives who cultivate a habit of asking more questions may also demonstrate higher levels of intelligence and strategic thinking. Encouraging a questioning mindset in business leaders can foster an environment of continuous learning and innovation. This approach not only aids in personal intellectual development but also enhances decision-making and problem-solving skills within the organization. By valuing and promoting inquiry at the executive level, companies can leverage the power of curiosity to navigate complex business landscapes more effectively, driving growth and adaptation in an ever-evolving market.

Despite the apparent simplicity of asking questions, formulating ones that are both insightful and impactful is no small feat, particularly for executives delving into areas outside their expertise. This skill hinges on a nuanced understanding that great questions often transcend the immediate technical details, focusing instead on broader implications, strategic alignment, and potential obstacles. The challenge lies not in acquiring exhaustive knowledge of every subject—which is impractical for any leader—but in mastering the art of critical inquiry.

Executives adept at this form of questioning possess a unique blend of humility and curiosity, acknowledging their own knowledge gaps while leveraging their strategic acumen to probe deeply. They rely on their experience to draw parallels, identify potential pitfalls, and question assumptions, regardless of the domain. This ability to navigate unfamiliar terrain through effective questioning is a testament to their strategic thinking and leadership qualities. It requires a delicate balance of listening intently to understand the essence of the matter and asking questions that guide the conversation toward uncovering underlying issues and opportunities. Such questions often open avenues for innovation and problem-solving that would remain obscured without this level of inquiry.

I think one way executives who are great at asking questions accomplish this is through pattern matching. This is a cognitive process where past experiences and knowledge are used to identify similarities or patterns in new information. This technique enables them to quickly connect dots across different domains, applying lessons learned from one area to another, even when they lack deep expertise in the new area. They intuitively recognize patterns in business scenarios, strategic challenges, or operational issues that resemble past experiences, allowing them to ask questions that cut through the surface to the heart of the matter.

Interestingly, this process of pattern matching is not unlike the mechanism through which artificial intelligence, particularly large language models (LLMs), operates. LLMs analyze vast amounts of data to identify patterns, correlations, and associations. They use this understanding to generate responses that are contextually relevant, despite not possessing consciousness or genuine understanding. Just as an executive uses pattern matching to navigate unfamiliar topics through strategic questioning, LLMs leverage their extensive training data to provide insightful answers across a wide range of subjects. This parallel underscores the power of pattern recognition in both human and artificial intelligence as a tool for navigating complexity and fostering innovative solutions. By drawing on this capability, executives and LLMs alike can bridge gaps in knowledge, offering perspectives and solutions that might not be immediately apparent through conventional analysis.

Mastering the art of asking the right questions isn't just about filling your head with more information; it's about sparking curiosity, embracing the unknown, and being okay with not having all the answers. If you're leading the charge or aspiring to, the real game-changer is your ability to ask questions that open doors and shed light on new possibilities. Think of it as matching patterns like a pro, using what you've seen and learned before to navigate what's in front of you, much like how AI sifts through data to find gold. So, here's a nudge for all the execs and future leaders out there: make it your mission to get better at asking those questions that get to the heart of the matter quickly. Dive into the depths of your experiences, draw inspiration from the world of AI, and remember, sometimes the smartest move is to ask the question no one else is asking. Get curious, stay humble, and turn questioning into a way of driving innovation and leading with confidence.