Interview: Debra Danielson, CTO and SVP of Engineering, Digital Guardian

Mentorship is proven to have various positive impacts on both the professional and personal development of individuals in a wide range of industries and disciplines. By engaging in mentorship processes, mentees are able to learn and gain insight from more experienced, skilled or knowledgeable peers, whilst mentors themselves can also expect to develop their own skillset as a result of helping others to achieve their potential.

In an industry as fast-moving and complex as information security, what role can (and does) mentoring play, and is it currently being utilized within the sector to its maximum effect?

To find out, Infosecurity spoke to Debra Danielson, CTO and SVP of engineering at Digital Guardian, an industry professional who is a strong advocate for and supporter of mentoring in the information security community.

Why is effective mentoring important in the information security industry?

There are two aspects to mentoring that are important to consider. The first is mentoring around technology and skills; the second centers around personal development and career growth. In the security industry, being able to nurture both of these areas is critical. The former, because a skill and talent shortage exists in the industry and the latter, because many people can have an affinity for information security but struggle with leadership, organizational or communication skills.

According to a recent study, half of the cybersecurity workforce doesn’t have a good idea what desired career paths. For workers who do know what their path is, it usually ends with a leadership role. Only about half of those in the security profession intended to be there in the first place. Many were drawn to the opportunity and the dynamic nature of the field. While having relevant experience is a key to success, it’s also important to have strong professional mentorship. This field is all about learning and navigating the explosion of new technologies.

Providing effective mentoring is more critical now than ever. We’re in the middle of a talent shortage, with the gap projected to be approximately 3.5 million workers, according to Cybersecurity Ventures.

Is there enough mentoring going on in the industry currently?

I think to answer that question we need to ask if we’re where we want to be as an industry, and if not, where do we need to get to?

While we’ve made progress over the past few years when it comes to increasing diversity in the industry, it’s still largely male and white. Women and minorities are either not choosing the field or are not staying in the field. Why should we care about the balance? If we look at the projected 3.5 million job gap, we should ask whether we can afford not to recruit and hire the best talent from all backgrounds.

Some might say that over the years, the security industry has gained a reputation as a haven for antisocial, introverted, misfits. This is not an appropriate characterization of the professionals I know but it is a stereotype that a number of us get labelled with. In my experience, much of this reputation comes from a lack of experience (and skill) in communicating security issues to leaders in business terms. Working to address these communication barriers is an area where mentorship can be very effective.

“The two biggest roadblocks to executing an effective mentoring program are matching mentors with mentees and appropriately setting expectations”

What are the greatest challenges around mentoring schemes, for both mentees and mentors?

The two biggest roadblocks to executing an effective mentoring program are matching mentors with mentees and appropriately setting expectations.

Finding the right match between mentor and mentee is the key. It’s rare to have third parties (a program administrator, for example) that know enough about the skills and talents of the candidate mentors and the gaps and objectives of the mentees to be able to successfully match the two.

The best programs I’ve seen to facilitate mentor-matching involve a hybrid approach. A facilitator that provides a set of ‘possibles’ to be selected from by both sides. One of my favorites is Springboard Enterprises Boot Camp Coaching assignments. The Springboard team has a robust set of experts on their councils (for disclosure, I’m a member of the Tech & Media Council) that they’ve curated over years. I have been a mentor for 10 different CEOs over more than eight years of participation.

Another program that I found successful with brokered matching was the CA Council for Technical Excellence mentoring program.

What is true of both programs is that they cannot and will not scale beyond dozens of mentors/mentee matches. Any program that is larger is not going to work well with a curated matching process, but don’t despair – I have had equal success with pairing that isn’t curated. Sometimes, one just needs to circumvent the programs and make a request directly. Sometimes the relationship just evolves from a single question posed out of the blue. Some of my most valuable mentors have emerged that way. I just called them up to ask a question and they quickly became speed dial numbers.

Anyone interested in being mentored must be willing to respect their mentor’s time. To make best use of that time requires advanced planning and structure. New mentees often don’t understand what their role is and just expect the mentor to drop gems of knowledge in their lap. It’s important that the mentee understands that this time should be split equally and used effectively and wisely. Never show up to a mentoring session without an agenda and objectives and never show up to a mentoring session without preparing first. This doesn’t mean that the mentee should be talking the whole time; mentoring isn’t therapy. Often, the mentor can provide structure to a challenge.

What advice would you give to anyone who is a) looking for mentorship and b) looking to become a mentor?

In my experience, the biggest mistake people make in looking for a mentor is assuming that someone won’t do it for them. You won’t know if you don’t ask. I have been pleasantly surprised over my career by the people who’ve been willing to mentor me. At one point in my career, I asked our CFO to mentor me (I was an individual contributor at the time) and she said yes. Don’t take it personally if you get turned down. The best mentors are people with successful careers, and they are usually busy people. Just move to the next name on your list.

As a mentor, one of the hardest things is to stop yourself from solving your mentees problem. For a mentor, it can often be so clear to us what needs to be done in a specific situation. Sometimes this can just turn your mentee’s confusion into dependence. I’m a huge fan of having a good methodology for doing things. For a mentor, helping a mentee develop their own methodology for problem solving while enriching their personal and professional development is one of life’s greatest achievements.

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