Ask better to talk more.

Phil At Asymmetric Creativity
5 min readFeb 12, 2024

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Boring questions are exhausting to answer.

I asked an employee during a one on one, “how was their day”. All I saw next was them dragging their face as we went through the usual pleasantries.

Hell, I am even guilty of doing that with my parents.

I am guilty of asking questions that cause this reaction. Photo by Sander Sammy on Unsplash

Although harmless, monotonous or predictable questions can cause some mental and emotional exhaustion. These questions often generate a lot of mental work in the form of repetitive fatigue. A mixture of cognitive demands and cognitive processes may explain this paradoxical phenomenon.

Psychologically, the lack of cognitive stimulation leads to disengagement and decreased cognitive functioning. Like untapped muscles, the mind thrives on novelty. Given questions without these features, it goes into a non-motivational state. This can make us feel bored and depressed. In addition, the low effort to answer these questions leads to an underutilization of one’s cognitive abilities.

Emotionally, non-questions feel monotonous and exhausting. This reflects the fatigue associated due to the lack of variety or challenge. This type of repetition can motivate a lack of motivation and fulfillment. Furthermore, unengaged and dull conversations further contribute to emotional drainage. It leaves the individual feeling less productive and mentally stronger.

So, what can I do to avoid asking boring questions? How can I make others think more clearly?

Socratic Questioning.

Socrates himself. Creator: GeorgiosArt | Credit: Getty Images/iStockphoto Copyright: GeorgiosArt

Socratic questioning, named after the Athenian philosopher Socrates, is more than information gathering. It creates a pedagogical and philosophical approach designed to stimulate critical thinking. This breaks down complex ideas and reveals underlying assumptions. Unlike questions that demand definitive answers, Socratic questions facilitate discussion. It fosters rational insight over factual declaration.

Sometimes, questions need to end with definitive answers. But it should not be the only tool we use.

Socratic questioning hinges on open-ended queries that prompt individuals to think deeper. These questions don’t just rely on the recall function of the brain. It scrutinizes beliefs, considers alternative viewpoints, and articulates the rationale behind their positions.

The interviewer uses a series of probing inquiries to guide the participants. The purpose is to deconstruct preconceived notions, identify inherent biases, and engage in deeper analysis.

Central to the Socratic method is the concept of elenchus. This is a process of critical examination that uses questions to interrogate arguments and unveil inconsistencies.

By asking clarifying questions like “What do you mean by that?” or “Can you explain in more detail?”, it encourages others to refine their thinking. Probing questions such as “How do you know that?” or “What evidence supports your claim?” encourage individuals to justify their statements and consider alternative explanations.

Photo by Uladzislau Petrushkevich on Unsplash

Here are some key characteristics of Socratic questions:

Open-ended: Socratic questions don’t have a single “correct” answer. Instead, they prompt further thought and discussion.

Probe deeper: They go beyond surface-level understanding. It challenges individuals to examine their reasoning and evidence.

Clarify meaning: They aim to ensure everyone agrees by asking for definitions or examples.

Consider alternatives: They encourage exploring different perspectives and viewpoints.

Uncover assumptions: They expose biases that might shape someone’s thinking.

This approach allows managers and executives to delve beyond superficial answers and ideas. These questions provide a deeper understanding of team members’ perspectives and concerns.

By “unlocking the why”, managers and executives can do a lot. They can challenge bias, dig into blind spots, and explore solutions. Often, this will lead to well-rounded, impactful decisions. Collaborative inquiry fosters deeper understanding, challenges assumptions, and identify blind-spots.

Socratic questioning has a higher probability of getting to the root cause. By asking “why” repeatedly, managers and executives can understand the reasoning behind team members’ issues. This often leads to more informed decisions.

Because of the biases and assumptions, they must challenged without causing defensiveness. Socratic questions help challenge these by fostering open-mindedness and encouraging fresh perspectives.

I wrote an article about biases.

Experienced managers and executives can sometimes miss important information. Socratic questions can prompt team members to highlight potential risks or overlooked opportunities. By considering different angles, managers can explore options before choosing.

Sometimes superficial solutions address the symptoms, not the root cause. Socratic questions help us probe deeper, leading to more lasting and inspiring solutions. By engaging with Socratic questioning, managers can create a sense of shared ownership.

While Socratic questioning holds many benefits, it’s important to consider its potential drawbacks. In the wrong hands, the Socratic question can manipulate or belittle others. Especially in hierarchical settings such as workplaces, people can exploit power dynamics.

If the interviewer dominates the discussion with probing questions, others may be reluctant to share information. This can stifle opinions and create groupthink. Especially if done rigorously, repetitive questioning can make one feel critical or vulnerable. This can hinder open communication and trust.

Not everyone is comfortable with deep self-reflection or questioning their fundamental assumptions. Imposing this approach can cause discomfort and amplify resistance.

Socratic questioning relies heavily on the willingness and ability of the respondent to take part actively. It may not be effective for individuals who are reluctant to think deeply or lack critical thinking. The interviewer’s own biases and assumptions can influence how answers are interpreted. Often, this leads to misunderstandings and missed opportunities.

While the theoretical foundations of Socratic inquiry provide a valuable foundation, it is nothing without practical application. The following section presents a selection of Socratic questioning templates from my experience.

What it can possibly look like. Photo by Austin Distel on Unsplash

Clarifying Meaning:

  • Can you explain that concept in simpler terms?
  • What do you mean by “X”? Are there different interpretations?
  • Can you give me an example to illustrate your point?

Probing for Evidence:

  • How did you arrive at that conclusion?
  • Are there any alternative explanations for this phenomenon?
  • What data would change your mind about this issue?

Considering Implications:

  • What are the potential consequences of taking this action?
  • Who might be affected by this decision, and how?
  • Are there any unintended side effects we should consider?

Exploring Different Perspectives:

  • Can you see this issue from another perspective?
  • What might someone with opposing views say about this?
  • Are there cultural or historical factors that influence our understanding of this topic?

Uncovering Assumptions:

  • What are some underlying assumptions you’re making here?
  • Are there any biases that might be influencing your thinking?
  • What values are shaping your approach to this situation?

Others

  • What is the most important thing we need to understand about this?
  • What question haven’t we asked yet that might be crucial?
  • How can we connect this idea to what we already know?
  • What are the implications of this for future actions?
  • If you could give one piece of advice on this topic, what would it be?

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Phil At Asymmetric Creativity
Phil At Asymmetric Creativity

Written by Phil At Asymmetric Creativity

A writer who looks beyond the surface, explores the terrain, and finds the insights.

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