The Art of Asking Questions

In any situation — technical or non-technical — the ability to frame proper questions determines your ability to progress.

Most people don't understand what makes a question "right" or "wrong." They're uncertain how to ask questions effectively. Yet questioning is foundational to learning, investigation, and problem-solving.

A question serves multiple purposes:

• Gathering information — obtaining facts for decisions
• Finding orientation — understanding your position and possible next steps
• Building overview — seeing how pieces connect

Once you know the right question, finding the answer often becomes straightforward. The difficulty lies in formulating questions when you don't understand the domain or have no knowledge of the area.

The Myth of "Good" and "Bad" Questions

Before proceeding, we must dissolve a myth:

Let's examine this carefully. Consider: "What are the best practices for secure coding?"

Suppose the answer is X, Y, and Z. Is this question "good" or "bad"?

The labels are irrelevant. "Good" or "bad" are states we assign to the question. Do these states affect the answer? No. The answer remains X, Y, and Z regardless.

If something doesn't affect the result, it's irrelevant. Assigning moral judgment to questions doesn't change their answers.

However, questions do have meaningful states:

Rough vs. Precise

• Rough: "How can I hack Windows?"
• Precise: "How can I use the SMB service on Windows Server 2019 to enumerate valid user accounts without administrative credentials?"

Precision greatly affects the quality of answers you receive. A precise question targets specific information. A rough question gets vague answers.

But precision is different from "good." A precise question isn't morally superior. It's simply more likely to produce useful answers for your specific situation.

Questions in Daily Life

You ask questions constantly. On average, 3-5 per minute, though this varies by situation.

Try this experiment: set a timer for one minute. As you read, mark each time you ask yourself something or something becomes unclear. Notice how many questions your mind generates naturally.

Most people are surprised by the frequency. Questions are inseparable from thinking itself.

Questions are essential to learning because they create links between information nodes in your brain. Remove questions from learning, and you remove the learning process itself.

Consider a cooking recipe. The core question is implicit: "How do I cook this dish?"

A recipe contains two components:

1. Ingredients — what you use (corresponds to learning content)
2. Method — how you prepare it (corresponds to your questions, which determine your approach)

The ingredients alone don't create a good dish. The method — the specific steps, the order, the technique — matters tremendously. Your questions function as the method. They determine which step you take next and define your approach.

A professional chef's recipe might work perfectly, but copy it exactly and your dish might be mediocre. Why? Because you lack the experience and intuition the chef has. You need to practice, adjust, ask questions, and develop your own understanding.

The Three Aspects of Questioning

Every question is built from three foundational aspects:

1. Origin — where the question comes from (your position, experience, knowledge gap)

2. Process — the thinking path that leads to the question

3. Result/Goal — what you're trying to achieve with the question

Questions vary enormously based on:

• Duration (How long? When?)
• Reason (Why?)
• Action/Reaction (What happens if...?)
• Location (Where?)
• Specification (Which?)

This variety reflects the diversity of human inquiry. Questions are as varied as imagination allows.

Examining the Official Definition

The official definition: "A question is a sentence worded or expressed to elicit information."

This definition has two core elements: "sentence" and "information."

But here's where it breaks down. Consider the shortest questions:

• "Why?"
• "How?"
• "Where?"

Are these questions? Yes. Are they single words? Yes.

Yet the definition emphasizes "sentence" — typically multiple words with subject and predicate. Single-word questions challenge this definition.

More problematically, the definition claims questions "elicit information." But consider:

"How is Host A connected to Host B?"

Did this question itself provide information? No. The question identified what information you're seeking, but asking the question didn't produce the information.

The definition describes what happens after the question is answered, not what the question itself does.

The Relationship-Oriented-Questioning Model

Given these gaps, we need a better framework. We call it the Relationship-Oriented-Questioning (ROQ) Model.

The model is based on a crucial insight: all questions have a commonality — they explore relationships between components.

The ROQ Model has five components:

To ask any question correctly using this model:

1. Identify the object — the core element of your question
2. Define at least two components (more are optional)
3. Establish the relationships between components

You always have one component automatically: your own position.

Establishing Relationships

Relationships between components are expressed as connections:

Solid Line — Direct connection: "How is X connected to Y?"

Dashed Line — Affection/Influence: "How does Y influence the state of X?"

Different relationships have different names depending on the components:

• "Operating on" — using something to achieve goals
• "Provides functionality" — offering capabilities
• "Listening Service" — a service that waits for incoming connections
• "Remote Access" — enabling management from distance
• "Allow to interact with" — enabling interaction between components

Example: Remote Access to Windows

Let's apply ROQ to a practical question:

Question: "What are all the methods available to remotely access Windows operating systems?"

Components:

• Your Position — Your need to manage Windows remotely
• The Object — Windows operating system
• Known — Some remote access methods (RDP, WinRM, SSH)
• Unknown — Methods you haven't encountered
• Other Position(s) — Not directly applicable here

Relationships:

1. Your Position → Windows: "Operating on" (You use Windows to complete tasks)

2. Your Position ← Windows: "Provides functionality" (Windows offers capabilities)

3. Windows → Known Methods: "Listening Service" (Windows must run services that enable remote access)

4. Known Methods → Windows: "Remote Access" (Methods enable remote management)

5. Your Position → Known Methods: "Using" (You use these methods)

6. Known Methods → Your Position: "Allow to interact with" (Methods enable your interaction with Windows)

7. Unknown Methods → Windows: "???" (You don't know what services unknown methods require)

By mapping these relationships, you've identified exactly what you're missing: the services Windows must offer to enable unknown remote access methods.

This insight guides your next research: investigate all Windows services that support remote access. Unknown methods likely exploit these services in ways you haven't yet encountered.

The Stackable Nature of ROQ

ROQ's special feature: it's stackable. When you discover that unknown method, it becomes known, and the model evolves. The "Unknown" field becomes "Known," and you can build another layer of questions on top.

This allows for deep investigation. Each iteration of the model refines your understanding and reveals new questions.

Practicing ROQ

The model feels unusual initially. But here's the remarkable part: after 5-10 practice sessions, you'll use it subconsciously.

You won't need to consciously think through each component. You'll internalize it. You'll start using it automatically in conversations and problem-solving.

This is like learning a recipe. The instructions seem complex. But with practice, cooking becomes intuitive.

Start with the 3-5 situations you identified at the chapter's beginning. Apply ROQ to the questions from those situations. Notice how the model reveals what information you were missing.

Important: If ROQ doesn't apply cleanly to a question, that's a feature, not a failure. The model forces you to rephrase and clarify. This constraint prevents you from asking questions that lack clear answers.

What Is the Right Question?

Finally, we can answer the essential question:

It's not about being "good" or "bad." It's about precision, clarity, and usefulness. A right question reveals structure. It shows you exactly what you know, what you don't know, and what connections exist between them.

The right question is your map. It shows where you are and where you need to go next.

Exercise 1 — Rewrite a low-signal question into a high-signal one

Take a vague question like:

• “Why doesn’t this work?”

Rewrite it with:

1. Goal
2. Context (system/app/lab)
3. What you tried
4. Exact error/output
5. What you suspect

Question 1 — What makes a question “high leverage” in security learning?

Next Lesson

With questioning mastered, the final lesson teaches how to transform frustration into fuel for growth and self-confidence.

Next: Managing Frustration