This talk explores the benefits of mentoring, how to form / maintain successful mentorships and how organizations can spin up formal mentoring programs.

1. Mentoring: the biggest problem we
don't know we have
Niru Ragupathy (@itsc0rg1)

2. ● Senior Security Engineer at Google
○ Assessments - code reviews, design
reviews, black box testing
○ Offensive security
● Trainer
○ Web Application Security
● CTF Organizer
○ Bsides SF
● Serial doodler
● Most importantly a mentor and mentee
Bio

3. Do we have enough people in security?

4. Shortage of cybersecurity professionals is close to 3 million globally.
(ISC)2
Cybersecurity workforce study 2018

5. Not enough people, but why?
● Organizations
○ Require prior experience and expertise
○ Sometimes unwilling to hire and nurture junior talent
● Education / Resources
○ Not many formal security programs or degrees
○ Overabundant resources, finding the right one is hard
● People
○ According to h1’s 2019 Hacker report, of the security researchers
surveyed only 9.9% were involved in mentoring

6. How does mentoring fit into this?
Mentoring provides:
● Encouragement and motivation for
newcomers
● Advice for personal and career
development
● Professional connections and networking
OG Mentor from Homer's Odyssey
Source: Wikimedia

7. Why should I mentor?
● Satisfaction of helping someone and
seeing them grow
● Improve leadership skills
● Exposure to new perspectives
● Long lasting relationship
● Increase knowledge through teaching
Mentors can use mentorships as a mechanism to force introspection of their strengths and
weaknesses, allowing them to make the journey from self-awareness to self-actualization.

8. How can we make mentoring successful?

9. Good mentors
As far as mentors go, there are three types,
those who:
● Are already good mentors
● Can be trained to be one
● Don't want to be mentors
○ At this time
Good
Mentors
Can be
trained to
be good
mentors
Don't
want to
be
mentors*
The main characteristics that need to be cultivated are active listening, good interpersonal skills,
flexibility and ability to give constructive feedback.

10. Successful Pairing
● Match mentees with mentors who can
help achieve their goals
● Similarity in attitude matters more than
race/gender [1]
Mentors who see themselves in their mentee are more likely to form a connection.

11. Productive Sessions
● Discuss goals
● Needs / Support
● Develop a roadmap
● Periodic feedback
Both mentors and mentees need to set clear expectations to avoid disappointments and
disagreements.

12. How can organizations help?

13. Organizations and Mentoring
● Mentoring junior engineers scales!
● Increases career commitment, job satisfaction, workplace diversity[2]
and reduces turnover intentions[3]
● Identifies and fosters new leaders
● Improves culture and morale
According to a survey by American Society for Training and Development, 75% of executives said
that mentoring has been critical to their career development.

14. Formal mentoring programs
● Clear program objective
● Good matchmaking
● Defined roles for mentor / mentee
● Periodic oversight and feedback
If there is pushback from the organization, consider running a small pilot to prove value and
identify gaps.

15. The secret sauce
The key factor which determines the
success of the program is the
matching process, which requires[4]
,
● Having a large, diverse pool of
mentors
● Comprehensive information on
the mentor’s strengths and
mentee’s needs

16. Increasing the mentor pool
● Nominate potential mentors
● Provide training
○ Shadow experienced mentors
○ Initiate, build, and maintain the
relationship
● Recognition and rewards
Involvement needs to be voluntary, since it requires commitment and interest. Forcing people to
participate will only introduce negativity and cynicism.

17. Mentor / Mentee Matching
● Detailed mentor / mentee profiles
● First few sessions focus on ensuring that
the pair is comfortable with each other
● Option to try a different mentor
Remember attitudinal similarities are critical for a successful pairing!

18. Feedback and Support
● Direct channel to raise concerns,
particularly behavioral ones
● Feedback surveys at start,
midpoint, and end of the program
Negative experiences can stem from mismatch of mentor-mentee, lack of mentor expertise,
distancing behavior, manipulative behavior and general dysfunctionality [5]

19. Any advice for mentees?

20. For mentees
● Have multiple mentors
● Seek mentors from multiple sources
○ More sources = more success [6]
● If you can’t find a mentor within your company, try:
○ Local meetups, conferences or online forums
○ Tanya Janca’s (@shehackspurple) hashtag #mentoringmonday
Mentorship will organically develop or decay with time, changing mentors isn’t “breaking up” with
the mentor, the bond will still remain.

21. Closing thoughts

22. And.. that's a wrap!
● Support and encouragement helps reduce
stress and sets up people for success
● We all appreciate guidance when we receive
it, now it’s our turn to provide it
● If you are a manager in an organization, help
set up a formal mentoring program
Remember, good mentors are the real 10x engineers - they spin up 10 new engineers!

23. Acknowledgments
A big shout-out to Phil Ames (@philames), David Tomaschik (@matir), Conan
Dooley (@conandooley) and Matthew Bryant (@iammandatory) for their valuable
input and feedback.

24. References
[1] Ensher, Ellen A., Elisa J. Grant‐Vallone, and William D. Marelich. “Effects of perceived attitudinal and demographic similarity on
protégés’ support and satisfaction gained from their mentoring relationships.” Journal of Applied Social Psychology 32.7 (2002):
1407–1430.
[2] Dobbin, Frank, and Alexandra Kalev. "DIVERSITY why diversity programs fail and what works better." Harvard Business Review
94.7-8 (2016): 52-60.
[3] Allen, Tammy D., et al. "Career benefits associated with mentoring for protégés: A meta-analysis." Journal of applied
psychology 89.1 (2004): 127.
[4] Chao, Georgia T. “Formal mentoring: Lessons learned from past practice.” Professional Psychology: Research and Practice 40.3
(2009): 314.
[5] Eby, Lillian T., and Tammy D. Allen. “Further investigation of protégés’ negative mentoring experiences: Patterns and
outcomes.” Group & Organization Management 27.4 (2002): 456–479.
[6] van Eck Peluchette, Joy, and Sandy Jeanquart. "Professionals' use of different mentor sources at various career stages:
Implications for career success." The Journal of Social Psychology 140.5 (2000): 549-564.

25. Thank you!