My name is Scott King, and I am the Senior Director of Advisory Services at Rapid7. But before that, I was a CISO and have held many different roles in the infosec profession.

Today, I am excited to announce the release of “Confessions of a Former CISO,” a video series that highlights some of the mistakes, challenges, and successes I have learned from throughout my career, with the hope that others can learn from them as well.

In our first episode, I will share some lessons I learned the hard way about myself, leadership, and promoting new leaders. Please watch the video below, or read on for a recap of what was covered.

1. The DIY Disaster

Really early in my leadership career, I was given the opportunity to work for an organization and put together a project that would interconnect a lot of aspects of this organization into a central spot. It was a really important project, and I was given a team of people to work with. This was one of the first true leadership opportunities I had, and the boss I was working for at the time let me execute this project and gave me a lot of runway.

One of the members of the team was really struggling with an aspect of the project. This person went on and on for several days working on the same aspect, and just couldn’t get it. This was actually an element I knew really well—I had done it before and knew exactly what needed to happen. So, one night after they went home, I logged in to the systems and made the changes that were necessary to bring the whole environment up in our lab.

The next day, this person came into work and was astonished. They were amazed that everything was working, and that’s when I had to tell them what I’d done. I’ll never forget the look on this person’s face. I felt horrible, because instead of teaching them and showing them what I knew how to do and helping them through it, I set them up for failure from the very beginning. I knew they didn’t know how to do it, and despite me trying to coach them with documentation and literature, it wasn’t having an effect.

Instead, I should have gone in and shown them how to do it. They would have been better off and would have learned from it. Ultimately, that person ended up leaving the organization, in large part because of my own impatience and immaturity as a leader. This was a really important lesson learned for me that I’ve carried forward to this day.

2. The Reluctant Leader

In this second situation, I had someone who was an amazing individual contributor and absolutely kicked butt at everything they did. I had a need for someone like that who could lead a team of people focused on a really important function for our organization.

I had known the person I had in mind for this job for a long time. I had worked with them in a couple environments, and they were absolutely top-notch. And I pushed this person. I said, “Look, I need you to lead this team. I need you to take a leap of faith. I need you to jump in front of this one, handle this team, and make them function as well as you do as an individual.”

This person was really reluctant to do it, but ultimately agreed. They were doing a great job and really putting a lot of effort into it, but several months later, they came to me and said, “Listen, this is not going to work. I don’t want to do this job. It’s not for me, I don’t want to lead people, and I just want to go back to what I was doing.”

I was shocked. I couldn’t believe it. This person had been doing an excellent job and their team liked them, but they just didn’t want to do it anymore. Fortunately, we were able to put that person back in an individual contributor role, but the lesson learned from that is that if someone isn’t ready and tells you they aren’t ready, you need to trust them and respect that, and figure out another way to solve your problems.

3. The Premature Promotion

This situation was similar to my second example in that I had an outstanding individual contributor who applied for an open leadership role. They had demonstrated a lot of qualities we were looking for in someone to lead this team, so they got the job, and did an excellent job with it.

However, about six months down the line, this person came in and said, “Look, I just don’t want to lead people anymore. I don’t want to solve their problems, and I don’t want their problems to be my problems. I want to go back to being an individual contributor again.”

Again, we were fortunate to be able to move that person back into a role they were really going to excel at. But the lesson I learned from this was that sometimes, even though you’re so excited to see that someone wants a leadership position and has demonstrated the necessary qualities to succeed, you need to challenge them up front about why that leadership position makes sense for them, why the role will help them in their career, and how it plays into their longer career strategy. If you don’t, it’s likely you could get six or 12 months down the road and have to go back to the search.

4. The Successful Superior

For my last scenario, I will share a success story! In this case, the person was a fantastic performer and individual contributor who had past experience in leadership positions. When they applied for a leadership position at my organization, they really excelled in their interviews and got the job. This person did exceptionally well, and wound up getting promoted twice to ultimately run the entire organization.

It’s such a great success story because this person wanted to lead an organization, had the aptitude to do it, and had the track record to do it. Because we talked to them about where that leadership position fell within their career track and how it’s ultimately going to get them to the point they want to be, you can help them celebrate when they actually achieve those ultimate goals.

Key takeaways

There are a couple things you can take away from my experience. First, if someone bolts at the idea of being a leader, don’t force them down that path. Second, if someone applies for a job as a leader but you know they aren’t ready or the leadership position doesn’t coincide with any aspect of the career track, really challenge why that job makes sense for them before you make that decision.

Last, don’t be like me and make mistakes because of your own impatience. Keep your emotions out of the equation and focus on the heart of the matter by ensuring the people you move into leadership roles are ready for them, are emotionally intelligent enough to drive toward your organization’s goals, and are going to be successful in their role.

Thanks for reading! We will be releasing new videos once a month, so keep an eye out for our next one!