Best Questions to Ask a Cyber Security Mentor in 2024

Questions to Ask a Cyber Security Mentor

Active participation as a mentee is crucial for unlocking the full potential of your mentorship, ensuring that both your time and your mentor's are well spent. 

Yet, the burning question remains: how do you extract the maximum amount of benefit from this mentorship? How do you ensure that your mentor's guidance is practical and fits your situation? 

Rest assured: we've got you covered! We’ll help you prepare clear and targeted questions to ask your cyber security mentor beforehand.

In this article, we'll dive into the importance of questioning when seeking guidance from a mentor for cyber security. We'll explore what makes a question truly impactful, discuss the elements of a valuable answer, and pinpoint some areas where mentorship support can truly elevate your career journey with confidence.

Let's get started!

The Value of Cyber Security Mentorship

It's widely acknowledged that success and fulfillment in cyber security are cultivated through collaboration, networking, mentorship, and continuous learning. 

A cyber security mentor is a powerful ally who can help you expand your knowledge, refine your leadership skills, enhance your networking abilities, foster personal development, and manage stress.

Mentors provide insights that go beyond traditional resources like books and courses. From avoiding common pitfalls to gaining an "unfair" advantage over your peers, mentorship offers a pathway to success that's unparalleled. 

In a field as competitive and challenging as cyber security, embracing mentorship isn't just smart—it's essential for thriving in this dynamic industry.

Knowing What Questions to Ask a Cyber Security Mentor

Knowing which questions to ask your mentor can significantly impact your mentoring relationship and journey. Rather than settling for generic advice, strategic and contextualized questioning empowers you to receive personalized insights tailored to your needs and aspirations. 

By asking thoughtful and targeted questions, you demonstrate your curiosity and drive and pave the way for enriching discussions with your mentor.

Whether you need advice on overcoming imposter syndrome or navigating workplace challenges, knowing what questions to ask your mentor will equip you with tangible solutions to improve your situation. 

However, what distinguishes a good question from a bad one?

Weak questions tend to be vague and lack specificity. In contrast, good questions are clear, insightful, relevant, and directly inspired by your mentor's experience and the industry's demands. 

For instance, instead of asking about the prevalence of imposter syndrome in the industry, a more effective approach would be to seek guidance on differentiating between genuine areas for improvement and feelings of inadequacy.

Bad Question: How prevalent is imposter syndrome among cyber security professionals?

  • This question encompasses all cyber security professionals and calls for a generic answer that can easily be found through a Google search. Therefore, your mentor’s reply might limit itself to mere statistics and not be helpful for your unique circumstances.

Good Question: How can I differentiate between legitimate areas for improvement and feelings of inadequacy caused by imposter syndrome? Can you share stories from your experiences dealing with imposter syndrome and the lessons learned from overcoming it?

  • Why it’s a good question: These questions are specific and provide a clear focus rather than seeking general information. They are actionable as they seek practical advice or strategies for addressing the issue. By asking for personal anecdotes, the second question makes the topic relatable and allows for an exploration of imposter syndrome through firsthand experiences.

Now, let’s explore some good questions you might consider asking during your mentorship session.

It's crucial to note that the questions outlined in this article are not an exclusive or complete list. They may not apply to every situation. Instead, we intend to emphasize the value of questioning, highlight your mentor's role, and discuss what constitutes effective questions and actionable answers. We encourage you to customize your questions according to your needs and circumstances.

Career Development and Pathways Questions

Advancing your career is a primary objective, and seeking guidance from your mentor ensures that you receive personalized support, insights, and encouragement tailored to your journey in cyber security. 

You can ask numerous questions within this category. Let's delve into a few of them.

Q. What's a big career move you made in your cyber security journey? Looking back, would you do anything differently if you were in that same situation today?

  • Why it's a good question: This question prompts your mentor to provide concrete examples from their own professional experience, making the advice tangible and relatable to you. By focusing on a specific decision and potential alternatives, you can gain practical insight applicable to your career path.

Q. As someone without an IT background, what are three actionable steps you recommend for successfully transitioning into the field?

  • Why it's a good question: By asking for implementable steps, you'll receive clear guidance for transitioning into cyber security. Drawing from your mentor's experience ensures the advice is realistic and proven effective in real-world scenarios.

Q. What strategies have you found effective for long-term career planning, and what advice would you give for setting and achieving career milestones?

  • Why it's a good question: This question aims to uncover detailed strategies and practical tactics for crafting a successful long-term career plan and achieving significant milestones. Your mentor's response will likely include insights readily applicable to your professional journey, empowering you to take concrete steps toward your career goals without delay.

Skill Development and Technical Expertise Questions

Acquiring the right skills is essential for your progression. Having danced through the intricate pathways of cyber security, your mentor understands which competencies are crucial for your development. 

Based on your goals, they’re also well-positioned to recommend hands-on projects to hone your abilities effectively. Let's review a few key questions to help you obtain precise and relevant answers in this context.

Q. What are the top three crucial skills aspiring GRC professionals should focus on? How can I effectively build proficiency in these areas?

  • Why it's a good question: Inquiring about essential skills and effective development methods opens the door to practical and insightful guidance. Your mentor can then provide advice tailored to highly valued skills relevant to the specific cyber security role you aspire to. This personalized approach ensures you receive assistance that aligns with your professional goals and equips you with the tools needed to excel in your chosen field.

Q. What practical tips do you have for getting hands-on with cyber security, like recommended labs, projects, or community contributions?

  • Why it's a good question: Seeking specific recommendations for hands-on practice ensures executable advice. By doing so, you can discover practical activities that may not have crossed your mind but can directly enhance your skills and proficiency. This approach allows you to direct your efforts and focus on tasks that yield tangible results and can accelerate your learning journey.

Q. How do you keep your technical skills sharp? Any advice for staying up-to-date and adaptable with technical expertise?

  • Why it's a good question: By exploring your mentor's strategies, you can access tried-and-tested methods that have consistently produced tangible results. This enables you to approach technical domains with increased confidence and resilience.

Education and Certifications Questions

When it comes to selecting the right training or certification, a mentor's guidance can be invaluable. Mentors can help identify certifications that align with your goals and offer valuable advice on navigating the choice between self-study and formal training.

By actively seeking your mentor's guidance and asking relevant questions, you empower yourself to make informed decisions, thus enabling you to achieve success in your chosen field.

Q. I'm really keen on becoming a cyber security analyst. Any idea on which three certifications would give me a good head start? Also, any study tips or resources you'd suggest?

  • Why it's a good question: This question directs your mentor to provide personalized recommendations that align with your goals, skills, and experience. It's a good question because it demonstrates initiative, focus, and a genuine interest in pursuing a career in cyber.

Q. Which skills do you think I could pick up on my own, and which ones do you believe would require formal training to land a junior penetration tester role within the next two to three years?

  • Why it's a good question: Your inquiry demonstrates your proactive approach to learning. This trait is particularly vital in cyber security, where continuous learning and self-improvement are indispensable. By specifying a time frame of two to three years, you demonstrate a defined objective and a dedicated commitment to your career path. This question allows your mentor to offer personalized counsel, providing a valuable roadmap for your career stage and aspirations.

Q. In your opinion, what are the top two certifications for cyber security managers? Also, what specific career advancement benefits do they offer?

  • Why it's a good question: This query looks for precise recommendations and allows for a focused discussion on highly valued certifications. Those endorsed by your mentor hold particular significance, as they’re more likely to align closely with your career aspirations and are made to address the evolving complexities of cyber security management.

Industry Insights and Trends Questions

Your mentor’s insights into industry thought leaders, trends, and challenges offer invaluable perspectives for informed decision-making. Understanding the evolving landscape equips you with the knowledge and foresight to effectively navigate emerging threats and technologies.

Moreover, tapping into your mentor's knowledge of evolving roles and specializations in cyber security enables you to align your career aspirations with industry demands, paving the way for long-term success and advancement.

Q. Beyond AI, what other trends do you think might impact cyber security? Any advice on how to prepare for them?

  • Why it's a good question: When inquiring about emerging trends beyond AI, you leverage your mentor’s expertise to grasp potential future challenges and opportunities in the field. Your mentor can then provide concrete steps to ensure you remain ahead of the curve.

Q. How do you stay current with cyber security trends without getting overwhelmed by information?

  • Why it's a good question: This is an excellent question for several reasons. Firstly, it offers insights into effective learning strategies and access to relevant information. Secondly, it aids in prioritization by learning how to filter through data efficiently. Moreover, it strengthens the mentorship relationship by demonstrating a commitment to learning and respect for the mentor's expertise. 

Networking and Professional Growth Questions

Connecting with peers, mentors, and experts enables access to diverse perspectives, best practices, and invaluable resources, which can lead to new career opportunities and skill enhancement. 

A mentor is pivotal in providing guidance on effective networking strategies, such as engaging with professional communities, attending industry events, and nurturing meaningful relationships.

Here are some networking questions you might find helpful:

Q. What action plan do you have for building and maintaining relationships with industry experts?

  • Why it's a good question: Your mentor’s answer is likely to be concrete and grounded in experience, aimed at supporting you in cultivating meaningful relationships that enhance your career development and success.

Q. Which online forums or communities do you recommend for cyber security pros, and how can I effectively engage to maximize learning and networking opportunities?

  • Why it's a good question: Online forums and communities serve as invaluable resources and hubs for networking, yet the abundance of options can be overwhelming. Guidance from your mentor aids in discerning which platforms truly enhance learning and networking. Adopting proven engagement strategies from your mentor allows you to navigate these communities effectively, elevate your personal brand, and establish yourself within the industry.

Work-Life Balance and Stress Management Questions

Maintaining a healthy work-life balance and managing stress are paramount in cyber security, where the "right to disconnect" is sometimes non-existent. 

In that regard, a mentor can offer useful strategies for prioritizing tasks, setting boundaries, managing stress, preventing burnout in a high-pressure environment, and allocating time for self-care. 

By drawing on your mentor’s wisdom and support, you can develop sustainable habits to achieve a healthy work-life balance while excelling in your career.

Here are some related questions you might find helpful:

Q. Over your career, what's been your secret weapon for dealing with stress and avoiding burnout? Any tips on how I could apply those tricks in my own professional path?

  • Why it's a good question: Your mentor has likely faced their fair share of stressful situations and even experienced burnout at times. But remember, you're not alone in this journey. Seeking guidance demonstrates your commitment to improving, and by asking your mentor questions based on their experience, you're more likely to discover tactics to manage stress efficiently. Together, you can find the quickest and most effective ways to navigate difficult times and thrive in your career.

Q. What's your personal hack for maintaining a healthy work-life balance in cyber security's high-pressure environment? And how do you incorporate it into your daily grind?

  • Why it's a good question: Your well-being is paramount. When it comes to setting goals, maintaining optimal mental health and a balanced work-life dynamic should top the list.

    Therefore, by asking this question you demonstrate a commendable awareness of the challenges inherent in cyber security and a proactive commitment to self-care. It invites practical responses that highlight the importance of setting clear boundaries between work and personal life, effective time management strategies, prioritizing self-care activities, nurturing social connections outside of work, and incorporating mindfulness techniques to manage stress effectively.

Practical Work Experience and Projects Questions

When it comes to practical work experience and cyber security projects that catch the attention of potential employers, a mentor is your go-to guide. 

With their extensive industry expertise and real-world insights, mentors can assist you in strategically selecting projects that emphasize skills and experiences valued by employers. 

Moreover, they offer personalized tips on effectively showcasing your projects to highlight your strengths and differentiate yourself from the competition.

Here are some experience-oriented questions that might be helpful:

Q. What's the best way to secure internships, freelance gigs, or volunteer roles to gain hands-on experience and advance in cyber security?

  • Why it's a good question: This question invites your mentor to provide invaluable support in tailoring a compelling resume that aligns with your desired role, effectively showcasing your relevant skills, experiences, and projects to capture the interest of potential employers. Moreover, your mentor can facilitate connections with companies seeking freelancers or volunteers. They can also provide personalized advice and practice scenarios to help you ace your cyber security job interview and secure coveted opportunities like internships.

Q. What are the top three factors employers prioritize when evaluating cyber security projects or work experience? Any tips for making my projects or job applications stand out?

  • Why it's a good question: Mentors have firsthand insights into the industry's demands and expectations. They’re best suited to assist you in strategically tailoring your project portfolio and resume to effectively showcase your relevant skills and experiences. This enhances your competitiveness in job applications and demonstrates your ability to effectively meet industry demands.

Q. Can you share a project or experience that significantly boosted your skills and marketability in cyber security? What key factors led to its success?

  • Why it's a good question: Asking this question allows you to learn from your mentor's experiences, understand key success factors, and find inspiration for your own journey. Hearing about your mentor's successful project is a powerful motivator, showing you what’s possible and encouraging you to strive for similar accomplishments in your career.

Additional Questions

  • How have you seen cyber security roles evolve over time, and what tips would you give to folks like me in cloud security looking to keep up?
  • What's a recent cyber security challenge you've faced? How did you handle it, and what did you learn that could help others in similar situations?
  • Do you have any favorite professional associations or events that have really made a difference in your career?
  • What are two strategies you've found super effective for boosting career growth using social media?
  • Can you tell me about a networking connection from your journey that really paid off? What did you do to nurture and make the most of that connection?
  • How do you best showcase your projects to catch the eye of employers?
  • For someone aiming to land a SOC analyst role, what's your advice for gaining hands-on experience?

Recognizing a Valuable Answer From Your Cyber Security Mentor

Knowing what constitutes a valuable answer is essential when consulting your mentor. Here's a breakdown of what you should be looking for:

  • Actionable Guidance: A valuable answer should provide practical steps that you can take to address your question or problem. Look for usable and specific advice, giving you a clear direction on how to proceed. Your mentor should be able to detail how they would approach your specific situation.
  • Personal Insights: Valuable answers often include personal anecdotes or experiences shared by your mentor. These stories illustrate key concepts and provide precious insight and perspectives that can deepen your understanding. By drawing from their own experiences, mentors can offer practical wisdom and lessons learned from real-world situations, making the advice more relatable and impactful.
  • Additional Resources: A good answer should also point to additional resources or materials for further learning. Whether it's recommending relevant articles, podcasts, books, online courses, conferences, or ways to get cyber security experiences, providing additional resources expands your knowledge beyond the scope of the mentorship session.


Getting the most out of your mentorship hinges on your ability to ask good questions and to recognize valuable answers. This will impress your mentor and, most importantly, allow you to grow and succeed in this constantly evolving field.

Don't waste time reinventing the wheel or stumbling through unnecessary mistakes. Your mentor has walked the path before you, overcome fears, and found ingenious solutions to obstacles similar to those you face. Use your mentor’s expertise wisely, confidently, and with acumen.

Remember, specific questions lead to actionable answers and deeper understanding, while bad ones can lead to confusion or missed opportunities.

A valuable response from your mentor offers practical solutions, incorporates personal insights, and provides additional resources for continued learning. By recognizing these elements, you can make the most out of every interaction with your mentor. 

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  • Michel-Ange Dagrain

    Michel-Ange is an experienced IT auditor driven by a passion for cyber security governance, threat intelligence, data privacy, and emerging technologies. She enjoys volunteering, writing, reading, learning new tools, and staying updated on cyber security news. She aims to share her expertise and insights through her engaging blog articles. Want to explore the intricate world of IT auditing and cyber security? Connect with her on LinkedIn.