How to land a cyber security mentor

8 tactics to find a mentor in 2024

January 09, 2024

👋 Good morning!

Each week I provide an in-depth response to your questions about careers, building security teams, AI security, cloud security, and anything else you need support with. Send me your questions and I’ll do my best to provide actionable advice.

Let’s dive in!

Q: How do I find a mentor for my cyber security career?

What is mentorship really all about? Simon Sinek thinks that mentorship is more like a friendship. You can’t just walk up to someone and ask them to be your friend, that would be weird. That’s not how it works.

Mentor relationships evolve because they see something in you and are willing to make time for you. The best relationships are when the mentor can still learn as much as they teach. Perhaps we should reframe this dynamic from Mentor-Mentee, to Mentor-Mentor.

For this type of relationship to come into existence, you need to find someone you get along with, share values and beliefs with, build trust and discover that you become friends. This is what the best mentorship relationships look like.

You don’t need to be mentored by an industry leader or someone with a huge following. You only need guidance from someone a few steps ahead of you. The goal is to save you some time and avoid common pitfalls on your journey.

Coaching vs Mentoring

Many people use mentoring and coaching interchangeably, but they are very different. It’s important you know what you’re looking for.

  • Coaching is when someone engages with you, assesses where you are at and makes suggestions on how to improve. A coach would identify a problem or skill shortfall and suggest a course of action. A coach is much more involved than a mentor.

  • Mentorship is where you seek help with specific problems you’re experiencing. A mentor will propose a solution to specific problems based on their experiences. Mentoring is best for goal setting, behaviour changes and skills development.

Goal setting examples:

  • Should I become a manager or a high level technical person?

  • Should I work for a big enterprise or startup?

  • Should I be a specialist or a generalist?

Behavioural examples:

  • How should I deal with a difficult coworker or manager?

  • How do I know when to speak up during a meeting?

  • I’ve got a big deadline looming and I’m not getting the support I need. What should I do?

Skills examples:

  • How do I get better at coding?

  • How do I improve my cloud security knowledge?

  • What security controls framework is best to use for this client?

  • How do I get better at writing?

What does good mentoring look like?

For mentoring to be successful, you need to know what you want to work on. It’s important that you complete a self-assessment to figure out where you are at in your journey.

You need to be willing to expose yourself and your shortcomings, which can be hard. But you need to be honest with yourself if you want to get the most out of your relationship with your mentor.

A good mentor should deliver hard truths and radical candour in a non-harmful way. If you ask for something and you’re going to ignore or deny their guidance, you are not ready for mentorship.

How to do it well:

  1. Ask specific questions. Don’t use open ended questions like: ‘what should I do?’, or ‘tell me what I need to know to do this’. It’s lazy and they may not have the time.

  2. Do what a mentor tells you and report back. This keeps the dialogue going and shows you’re serious.

  3. Start professional. Stick to talking primarily about work topics in the beginning. Avoid oversharing. As your relationship develops, bring in more of your personality and background, and ask them about theirs.

  4. Be useful. Ask your mentor what you can do to help them.

  5. Give it time! Quality relationships don’t form overnight.

How to find a mentor

Security can be a flat structure and it’s hard to find the right person. Despite this, it’s important you don’t skip levels. If you’re an analyst, find someone who is a senior analyst or a manager. Not a senior manager. You may accidentally miss important steps that will impact you later on.

You need the right mentor for your position (this will change over time).

  • Pro tip: the cold reach out never works - it has a 0% success rate. People have limited time and they can only mentor a finite number of people. Therefore they have to pick and choose. That’s why you need to build a relationship first, share value, help them in some way, something they’ll take away from knowing you.

  1. Don’t lead with your ask. Don’t straight-up ask someone to be your mentor without further context. Your message will be ignored or deleted.

  2. Connect with courage. You need to be an expert at introducing yourself. If in person, smile, clearly communicate, and match their tempo. If virtually, keep it short and sweet - no life back stories.

  3. Start close to home. Start with looking at where you work, intern, or go to school - this is where you will have the most success. If you’re asking someone online with thousands of followers, they’ve likely got an inbox with dozens of requests.

  4. Be specific. Define a specific set of things you want to work on - this shows self awareness. Avoid asking broad questions like ‘What should I do?’ or ‘Can you help me, I want to get into security?’. Ask a specific question based on two options, it will make it easier for them to respond and you’ll have successfully opened dialogue.

  5. Limit the formality. When you reach out, call it a chat, coffee, or one-on-one.

  6. Reduce the intensity. Start small! You don’t need a 1-hour session to discuss your goals, ask for 10 minutes. If it’s someone you work with and you’re both in the office thinking about grabbing a coffee, you can ask a couple questions on the way. You don’t need to make it more than it needs to be. This will allow the relationship to develop organically.

  7. Provide value to them first. Be there to go-to-person for something. They’ll be more inclined to help you. Work for free, impress them and take extreme ownership.

  8. Get creative. You could write a blog on cyber security and try to interview them as part of it - this builds the foundations of your relationship. Essentially, create your own openings.

Weekly Roundup - X Posts:

That’s a wrap!