The Art of Asking Smarter Questions

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Personal Development, Leading & Managing Section | 1

The Art of Asking Smarter Questions

By Arnaud Chevallier | Harvard Business Review Magazine | May–June 2024 Issue

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The urgency and unpredictability long faced by tech companies have spread to more-mature sectors, elevating inquiry as an essential skill. Advances in AI have caused a seismic shift from a world in which answers were crucial to one in which questions are. The big differentiator is no longer access to information but the ability to craft smart prompts. 

Indeed, leaders have embraced the importance of listening, curiosity, learning, and humility—qualities critical to skillful interrogation. “Question-storming”—brainstorming for questions rather than answers—is now a creativity technique. But unlike lawyers, doctors, and psychologists, business leaders aren’t formally trained on what kinds of questions to ask. They must learn as they go.

Based on their research and consultancy the authors offer a practical framework for the types of questions to ask in strategic decision-making and a tool to help you assess your interrogatory style.

The questions that get leaders and teams into trouble are often the ones they fail to ask. These are questions that don’t come spontaneously; they require prompting and conscious effort. They may run counter to your and your team’s individual or collective habits, preoccupations, and patterns of interaction.  You don’t need to come up with the missing questions yourself, but you do need to draw attention to neglected spheres of inquiry so that others can raise them.

All this is harder than it may sound, for two reasons. First, you may be hampered by your expertise. Your professional successes and deep experience may have skewed your approach to problem-solving.  It can be hard to escape the gravitational pull of such conditioning unless you take a hard look at your question habits. Second, the flow and diversity of questions can be hard to process in real time, especially amid heated exchanges. Often it’s only after the fact that you realize certain concerns or options were never raised.

The authors’ research reveals that strategic questions can be grouped into five domains:

1. Investigative: What’s Known?  Investigative questions dig ever deeper to generate nonobvious information. The most common mistake is failing to go deep enough.
2. Speculative: What If?  Whereas investigative questions help you identify and analyze a problem in depth, speculative questions help you consider it more broadly.
3. Productive: Now What?  Productive questions help you assess the availability of talent, capabilities, time, and other resources. They influence the speed of decision-making, the introduction of initiatives, and the pace of growth.
4. Interpretive: So, What…?  Interpretive questions—sensemaking questions—enable synthesis. They push you to continually redefine the core issue—to go beneath the surface and ask, “What is this problem really about?” Natural follow-ups to investigative, speculative, and productive questions, interpretive questions draw out the implications of an observation or an idea.  Interpretive questions come in other forms, too: “What did we learn from this?”
5. Subjective: What’s Unsaid?  Deals with the personal reservations, frustrations, tensions, and hidden agendas that can push decision-making off course. 

How to balance your question mix:  assess your current question style, adjust your repertoire, change your emphasis, and find others who can compensate.

3 key takeaways from the article

1. The urgency and unpredictability long faced by tech companies have spread to more-mature sectors, elevating inquiry as an essential skill. Advances in AI have caused a seismic shift from a world in which answers were crucial to one in which questions are. The big differentiator is no longer access to information but the ability to craft smart prompts – an art business leaders aren’t formally trained.
2. The questions that get leaders and teams into trouble are often the ones they fail to ask becasue of two reasons first, you may be hampered by your expertise and second, the flow and diversity of questions can be hard to process in real time, especially amid heated exchanges. 
3. Strategic questions can be grouped into five domains: investigative (What’s Known?), speculative (What If?), productive (Now What?), interpretive (So, What…?), and subjective (What’s Unsaid?). Each unlocks a different aspect of the decision-making process. Together they can help you tackle key issues that are all too easy to miss.

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(Copyright liew with the publisher)

Topics:  Decision-making, Curiosity, Asking Question