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TCD #005: How To Discover Mentorship

If you're looking for practical tips on building successful mentor-mentee relationships in the cybersecurity field, this blog post is a must-read.

Daniel Kelley
Daniel Kelley
4 min read
TCD #005: How To Discover Mentorship

Table of Contents

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Throughout my time in cybersecurity, I've had the privilege of working with two incredible mentors. While my experience with them was unique, as one has since retired and the other is facing a life sentence for hacking and espionage-related charges, I've learned a lot about what makes a mentor-mentee relationship successful.

For me, a mentor is someone who invests time and energy into helping you grow and achieve your goals. In the field of cybersecurity, there are various ways to find mentorship, including group meetings and paid sessions. However, in this post, I'll be focusing on the friendship-first approach to finding a mentor.

Here's The Main Points

  • Focus on developing a friendship before seeking out mentorship.
  • Show interest through research by asking specific questions.
  • Give more support than you receive, at first.
  • Make yourself available for the mentor when appropriate.
  • Consider expanding your support network, not just seeking one-on-one time.

Focus On Developing A Friendship

To form a successful mentorship relationship, it's important to first establish a connection and friendship with the person you hope to learn from. Social media can be a useful tool in this process. To build a connection, you can show your support for the person by:

  • Sharing their content.
  • Engaging with their content regularly.
  • Becoming a customer of theirs.
  • Recommending their work to others.
  • Joining any groups they’re a part of.

By becoming a familiar face, you'll form a positive impression while reaching out to them in the future, setting the foundation for a successful mentorship relationship.

Show Interest Through Research

One way to capture the attention of a potential mentor is to demonstrate your genuine interest in their work and a desire to learn and improve. This can be done by asking specific and thoughtful questions related to their specific niche. Here's an example message that I sent to a security researcher a few weeks ago, asking for advice on some research:

"Hi there, I recently came across your work on VLOOKUP() and XLSX research. It was really fascinating. I'm currently trying to extract a silent HTTP request from the same file format. Have you come across anything worth further exploration during your research? I've already fuzzed most of the parameters in the XML hierarchy."

Although this didn't lead to a mentor-type relationship, it still opened up the avenue for potential collaboration. This message worked because it demonstrated that I had done my research and was specific with my request. A few days later, I received a response.

Here's an example of this gone wrong:

Ben makes valid points in this thread. If you don't demonstrate that you've done any research and simply ask a generic question, you won't get the desired outcome.

Try To Give More Than You Receive

To form a strong mentorship relationship, it's important to give more than you receive. For example, a few months ago, I heard someone that I admired, on a podcast talking about not knowing how to schedule social media posts, so I created a Loom video showing them how to do it with a tool. This act of kindness, which was completely unrelated to their niche, gave them a positive impression of me and presumably increased the likelihood that they would be willing to help me in the future.

Here’s a summary what I said in the video:

“I was watching a podcast and I heard you mention that you're having trouble publishing social media posts on a daily basis. I just wanted to let you know that there are actually tools out there that make it really easy to do. I've put together a quick video to show you how it works. I'm not affiliated with the company behind the tool; I just wanted to help you.”

I use Loom all of the time to create short and direct videos for people. In this instance, I received a positive response, thanking me for my help. Loom videos are just one example of how to be a little different and provide value to someone based on their individual needs. There are countless other ways to do this as well.

Make Yourself Available For Them

Finally, if someone is offering to help you, it's important to make yourself available to receive it. You can't expect them to fit your criteria while you're the one looking for assistance. If a mentor offers to help, be respectful of their time and work with their schedule. Don't send messages telling them when you're available, as this puts the burden on them to fit your schedule. Instead, be flexible and work around their schedule to make the most of their time and expertise.

This point may seem obvious, but I have seen instances of people reaching out for help, only to then tell the person they are asking for help when they should make themselves available and to accommodate their schedule. Unfortunately, this is not how these relationships work initially.

Quote Of The Week

"A mentor is someone who gives you the tools you need to succeed, and then steps back to watch you soar." - Unknown

Daniel Kelley Twitter

I'm a reformed black hat computer hacker that has contributed to over 100 bug bounty programs.