Question-Asking Guide

Questions are the most powerful learning tool in Malware & Monsters sessions. Great questions drive discovery, clarify understanding, and help teams solve problems collaboratively. This guide provides practical techniques for asking questions that enhance learning for everyone.

The Power of Strategic Questions

Why Questions Matter More Than Answers

Questions Drive Discovery:

  • They uncover information that might otherwise stay hidden
  • They help teams explore different perspectives and approaches
  • They reveal assumptions that need to be examined
  • They guide investigation toward important insights

Questions Create Learning Opportunities:

  • They show what you’re genuinely curious about
  • They help others clarify and deepen their own thinking
  • They demonstrate engagement and active participation
  • They model how to approach complex problems

Questions Build Team Dynamics:

  • They invite others to share their expertise
  • They create space for different perspectives
  • They help quiet teammates find ways to contribute
  • They foster collaborative problem-solving

Types of Questions That Enhance Learning

Clarifying Questions:

  • Help you understand concepts or information better
  • Show respect for others’ expertise
  • Create opportunities for peer teaching
  • Prevent misunderstandings that could derail progress

Connecting Questions:

  • Link different pieces of information together
  • Help teams see patterns and relationships
  • Build on previous discoveries and insights
  • Synthesize knowledge from multiple sources

Exploring Questions:

  • Open up new avenues of investigation
  • Challenge assumptions and conventional thinking
  • Encourage creative problem-solving approaches
  • Deepen understanding of complex issues

Application Questions:

  • Connect learning to real-world situations
  • Help teams think through practical implications
  • Bridge theory and practice
  • Plan how insights might be implemented

Question Frameworks for Different Situations

When You Don’t Understand Something

Direct Clarification:

  • “I’m not familiar with [term] - can you explain what that means?”
  • “Can you help me understand the difference between [A] and [B]?”
  • “I’m lost on this technical part - can you walk me through it?”
  • “What’s the most important thing I should understand about this?”

Context-Seeking:

  • “Why is this concept important in cybersecurity?”
  • “How does this relate to what we discussed earlier?”
  • “What would this look like in a real organization?”
  • “Can you give me an example of when this would happen?”

Analogy Requests:

  • “How is this like something I might be more familiar with?”
  • “Can you explain this using a non-technical analogy?”
  • “What’s a good way to think about this concept?”
  • “How would you explain this to someone outside IT?”

When You Want to Learn More

Depth Questions:

  • “What else should we know about this approach?”
  • “What are the implications of what we just discovered?”
  • “How does this change our understanding of the situation?”
  • “What questions does this raise for you?”

Process Questions:

  • “How did you figure that out?”
  • “What made you think to check that?”
  • “What would be the next logical step?”
  • “How would someone typically investigate this?”

Alternative Exploration:

  • “What other approaches could we consider?”
  • “What if we tried a different strategy?”
  • “Are there other ways to interpret this evidence?”
  • “What would happen if our assumption is wrong?”

When You Want to Help Others Learn

Socratic Questions:

  • “What do you think might be causing this pattern?”
  • “How would you approach this type of problem?”
  • “What concerns you most about what we’re seeing?”
  • “What would you want to investigate next?”

Perspective-Gathering:

  • “How does this look from your role’s perspective?”
  • “What would [specific role] be most worried about here?”
  • “How might different stakeholders view this situation?”
  • “What would this mean for your organization?”

Knowledge-Sharing Invitations:

  • “Have you encountered something like this before?”
  • “What’s been your experience with this type of threat?”
  • “What would you recommend based on your background?”
  • “How does this compare to cases you’ve seen?”

Role-Specific Question Strategies

Detective Questions

Pattern Recognition:

  • “What patterns are we seeing across these incidents?”
  • “What doesn’t fit with the rest of the evidence?”
  • “What timeline can we establish for these events?”
  • “What evidence are we missing that would help confirm this?”

Investigation Focus:

  • “Where should we look for additional clues?”
  • “What would prove or disprove our current theory?”
  • “What forensic evidence would be most valuable?”
  • “How can we verify the accuracy of this information?”

Protector Questions

Threat Assessment:

  • “How immediate is this threat to our systems?”
  • “What’s the worst-case scenario if this continues?”
  • “Which systems are most vulnerable right now?”
  • “What can we do to stop this from spreading?”

Defense Planning:

  • “What security measures should we deploy immediately?”
  • “How do we balance protection with operational needs?”
  • “What resources do we need to mount an effective defense?”
  • “How do we prevent this type of attack in the future?”

Tracker Questions

Data Flow Analysis:

  • “Where is this data coming from and going to?”
  • “What connections look suspicious or out of place?”
  • “How is information moving through our network?”
  • “What patterns do we see in the communication attempts?”

Technical Investigation:

  • “What does the network traffic tell us about this threat?”
  • “How can we trace the source of these connections?”
  • “What monitoring data would help us understand this better?”
  • “How do we track the spread of this threat?”

Communicator Questions

Stakeholder Impact:

  • “Who needs to know about this situation and when?”
  • “How do we explain this technical issue to business stakeholders?”
  • “What are the communication priorities during this incident?”
  • “How do we manage stakeholder expectations during response?”

Business Context:

  • “What’s the business impact of what we’re seeing?”
  • “How does this affect our operational priorities?”
  • “What compliance or regulatory concerns does this raise?”
  • “How do we balance transparency with security during communication?”

Crisis Manager Questions

Coordination Focus:

  • “How do we prioritize our response efforts?”
  • “What resources do we need to coordinate this response?”
  • “How do we ensure all team efforts are aligned?”
  • “What’s our timeline for resolving this situation?”

Strategic Planning:

  • “What’s our overall strategy for handling this incident?”
  • “How do we balance immediate response with long-term considerations?”
  • “What contingency plans should we prepare?”
  • “How do we coordinate with external partners or authorities?”

Threat Hunter Questions

Proactive Investigation:

  • “What else might be hidden that we haven’t found yet?”
  • “Where would an attacker likely try to establish persistence?”
  • “What other attack vectors should we investigate?”
  • “How sophisticated is this threat, and what capabilities might it have?”

Adversary Thinking:

  • “If I were the attacker, what would I do next?”
  • “What would make this attack more effective?”
  • “How might this be part of a larger campaign?”
  • “What other organizations might be targeted similarly?”

Advanced Question Techniques

Building on Others’ Responses

Ladder Questions:
Start with their answer and build upward:

  • “That’s interesting - what led you to that conclusion?”
  • “Building on that idea, what would happen if…?”
  • “That makes sense - how does it connect to…?”
  • “Following that logic, what should we investigate next?”

Bridge Questions:
Connect different perspectives:

  • “How does what Sarah found relate to what Marcus discovered?”
  • “Can we combine Alex’s network analysis with Jamie’s business concerns?”
  • “What’s the connection between the technical evidence and the user reports?”

Questions for Synthesis and Integration

Pattern Recognition:

  • “What themes are emerging from all these discoveries?”
  • “How do these different pieces of evidence fit together?”
  • “What story is the data telling us?”
  • “What’s the simplest explanation that accounts for everything we’ve found?”

Strategic Thinking:

  • “Given everything we know, what’s our best course of action?”
  • “How do we address the technical issues while managing business needs?”
  • “What’s the most important thing to focus on right now?”
  • “How do we prevent this from happening again?”

Questions for Real-World Application

Transfer Questions:

  • “How would this apply in your actual work environment?”
  • “What would you do differently if this happened at your organization?”
  • “How does this change how you think about security in your role?”
  • “What would you want to implement based on what we’ve learned?”

Learning Questions:

  • “What’s the most important insight you’re taking from this?”
  • “What skills or knowledge do you want to develop further?”
  • “How does this connect to other cybersecurity concepts you know?”
  • “What questions do you still have that we should explore?”

Question Timing and Flow

When to Ask Questions

During Explanations:

  • Ask clarifying questions immediately when confused
  • Request examples to make abstract concepts concrete
  • Seek connections to concepts you already understand
  • Check your understanding before the conversation moves on

During Discussions:

  • Ask perspective questions to include quiet teammates
  • Use building questions to deepen good insights
  • Ask exploring questions when discussions become narrow
  • Use connecting questions to synthesize different viewpoints

During Problem-Solving:

  • Ask process questions to understand reasoning
  • Use alternative questions to explore different approaches
  • Ask implication questions to think through consequences
  • Use application questions to connect to real-world situations

Reading the Room

Signs You Should Ask Questions:

  • Someone looks confused but hasn’t spoken up
  • The discussion is getting too technical for some participants
  • The team seems stuck or going in circles
  • Important perspectives aren’t being heard
  • Assumptions are being made without examination

Signs to Hold Back:

  • Someone is in the middle of explaining a complex concept
  • The team is making good progress and you’d interrupt the flow
  • Your question would derail an important discussion
  • Others are asking similar questions and getting good answers

Overcoming Question-Asking Barriers

“I Don’t Want to Look Stupid”

Reframe Your Thinking:

  • Questions show engagement, not ignorance
  • If you’re confused, others probably are too
  • Smart people ask questions to learn more
  • Everyone was new to these concepts once

Start Small:

  • Begin with simple clarification requests
  • Ask about terms or concepts that are genuinely new
  • Build confidence with questions you know are reasonable
  • Gradually work up to more complex inquiry

“I Don’t Want to Slow Things Down”

Remember:

  • Good questions often save time by preventing misunderstandings
  • Clarification now prevents bigger confusion later
  • Learning is the purpose - speed isn’t the primary goal
  • Your questions help others who are also confused

Strategic Questioning:

  • Ask questions that benefit the whole team
  • Request clarification that will help everyone understand
  • Focus on questions that advance team learning
  • Time questions for natural conversation breaks

“I Don’t Know What to Ask”

Default Question Categories:

  • Clarification: “Can you explain what [term] means?”
  • Context: “Why is this important?”
  • Connection: “How does this relate to [previous topic]?”
  • Application: “What would this look like in practice?”
  • Process: “How would someone typically handle this?”

Listen for Question Opportunities:

  • New terms or concepts you haven’t heard
  • Statements that assume knowledge you don’t have
  • Conclusions that aren’t clearly explained
  • Technical details without context

Practice Exercises

Daily Question Practice

In Meetings:

  • Ask one clarifying question per meeting
  • Practice building on others’ comments with questions
  • Experiment with different types of questions
  • Notice how questions change discussion dynamics

In Conversations:

  • Practice asking follow-up questions instead of immediately sharing your thoughts
  • Try asking “how” and “why” questions to understand reasoning
  • Use questions to show genuine interest in others’ expertise
  • Notice how questions deepen relationships and understanding

Session-Specific Preparation

Before Your Session:

  • Prepare 2-3 general questions about cybersecurity topics
  • Think about questions your role might typically ask
  • Practice asking questions about your own area of expertise
  • Prepare questions that invite others to share their knowledge

During Character Development:

  • What questions would your character ask in this situation?
  • How does your character’s background influence their curiosity?
  • What would your character be most concerned about?
  • How does your character help others feel comfortable sharing?

The Impact of Great Questions

On Your Learning

  • Deeper Understanding: Questions help you grasp concepts more thoroughly
  • Better Retention: Engaging with material through questions improves memory
  • Broader Perspective: Questions expose you to different viewpoints and approaches
  • Enhanced Curiosity: Asking questions develops your natural curiosity about cybersecurity

On Team Dynamics

  • Increased Participation: Good questions draw out quiet teammates
  • Better Communication: Questions clarify misunderstandings before they compound
  • Shared Learning: Questions create opportunities for peer teaching
  • Stronger Relationships: Thoughtful questions show respect and genuine interest

On Session Quality

  • Richer Discussions: Questions lead to deeper, more meaningful conversations
  • Better Problem-Solving: Questions help teams explore issues more thoroughly
  • More Inclusive Environment: Questions ensure all perspectives are heard
  • Enhanced Discovery: Questions guide teams toward important insights

Question Bank for Emergency Use

When You’re Lost

  • “Can someone help me understand the big picture here?”
  • “What’s the most important thing I should focus on?”
  • “Can you explain this in simpler terms?”
  • “How does this connect to what we discussed earlier?”

When You Want to Contribute

  • “What would happen if we approached this differently?”
  • “How does this compare to your previous experience?”
  • “What concerns you most about this situation?”
  • “What should we investigate next?”

When You Want to Help Others

  • “What do you think about this approach?”
  • “How would you handle this in your organization?”
  • “What questions do you have about what we’ve discussed?”
  • “What perspective would [role] bring to this?”

When Discussions Stall

  • “What are we assuming that we should question?”
  • “What information would help us make progress?”
  • “What would an attacker do in this situation?”
  • “How do we balance these competing priorities?”
The Question Multiplier Effect

One great question often leads to three more insights. Questions don’t just get you answers - they create momentum for deeper learning and discovery. The best participants aren’t those who know the most answers; they’re those who ask the questions that help everyone learn together.

Remember: In Malware & Monsters, your questions are contributions. Every time you ask a thoughtful question, you’re helping your team learn more effectively and solve problems more thoroughly. Great questions are one of the most valuable skills you can develop, both in sessions and in your professional life.