Security Leadership: Moving On

How to Know When It’s Time To Go

This week, after spending more than seven years as CISO, I resigned. It was lovely to get an avalanche of good wishes from colleagues and teammates. I’m excited about my future opportunities. I was asked “why now?” and my response was “because I knew it was time”. And a number of folks asked,

“How do you know when it’s time?”

The simplest answer is that it just felt like the right time to go — but that’s too easy an answer, ignores a lot of soul searching that took place and is not helpful!

As a leader of an organization, the decision to stay or leave isn’t one made lightly, there are too many people relying on you for the decision to be made in a vacuum. It’s not just about me, and what I want — I have a responsibility to my team and my family and my organization, to deliver on commitments, and to make sure the trust others placed in me was not undermined.

It’s also true that the more senior you are, the longer it takes you to find the next role (usually, anyway), so it’s a rare thing that something just arrives out of the blue to whisk you away. There’s a lot involved in changing senior jobs — networking and research and networking and updating branding and networking. And did I mention networking?

So, if leaders can’t (or at least, shouldn’t) move on a whim, how do they know when it’s time to move on?

They’ve Completed What They’ve Started

When you start in a new role, you usually know why you’re there, and what you’re there to do.

From the company perspective, you may have been brought in to build a new team or resurrect a failing team, or just maintain a top-performing team for a period of time.

From a personal perspective, perhaps you wanted to work with someone in particular, to learn new skills, or to get experience in a new industry.

Well, did you? Did you do what you set out to do? Have you achieved your goals, and the goals the organization set for you?

If so, then maybe it’s time to move on. Or maybe it’s time to set some new goals and stay where you are. Only you can know.

If you haven’t met your original objectives, why not? Perhaps you need more time, and if that’s the case, stay where you are. Or perhaps conditions are such that you won’t be able to achieve those goals, and maybe it’s time to move.

In Security and leadership roles in general, there will always be more work to be done. It’s not a sprint, or a marathon, or a 100-mile endurance race. The work never, ever finished. That doesn’t mean that YOUR participation in the work needs to be neverending.

They’ve Maxed Out Their Growth

For some leaders, they’ve completed their original goals, and they look around the existing company and realize there is no other place for them. Maybe the upper decks are stacked with people who won’t leave. Maybe the leader has a passion for something that exists nowhere else in the organization. Maybe the company and the industry is in contraction mode, and the growth opportunities just aren’t available.

In this case, you could certainly choose to stay in your current position. But most leaders are leaders because they don’t stay still, and they continue to seek growth opportunities for themselves and others. It’s not that you’d never learn anything new if you stayed — it’s that the rate of growth has slowed to a point where you’re starting to get bored, or impatient.

They Make Way For Talent

The best leaders aren’t about their own growth, but about growing the team they lead. Sometimes, leaders leave their roles to make way for the careers of the people they’ve developed.

You can see this in action when the leader has purposefully spent time giving team members opportunities to demonstrate their own leadership capabilities. The leader has a documented and intentional succession plan, that has been shared with the broader organization. The team members are ready and willing to step up to a vacant role when the opportunity arises, and the rest of the team can adjust around that succession.

If you’ve prepared your team so that they will successfully step in when you move on, perhaps it’s time to leave.

Their Strengths Are No Longer Needed

Most leaders are brought into a role because they have strengths that the organization needs at that time. Maybe they are great at startups and building teams and programs, but once the program is up and running, their operational management skills are weak. Maybe they were brought in to bring operational rigor to the culture, but now the organizational leadership wants the culture to change to be more innovative and ad hoc and the leader doesn’t have that strength.

Organizations change, and sometimes what brought the leader to the role in the first place is no longer what the organization wants or needs. When this happens, it’s time to go.

Their Support Community Is Ready

Most leaders have people around them — family, friends, children — who are impacted by the changes in a leader’s role. As our work and personal lives have blended, so has the impact of our decisions. So a leader considering a work move is not only concerned about their work team but the impact of their decision on their personal community.

Leaving one role for another takes energy, and it is usually the family who has to bear the burden of energy drain while the leader adjusts to a new role. So when considering when it’s time to move, consider if it’s a good time for the family — a spouse’s job, a child’s schooling, a parent’s care. This is particularly true if the new role involves a relocation, but even if it doesn’t the impact on the non-work community is real.

It’s super unusual for a CISO to be in a role for more than four (or three, or two) years, so I can say that I’ve given this role my full attention. I thought I’d be maybe three years in the role, and I’ve more than doubled that.

Some of it was because it took me longer to achieve my initial goals than I originally planned. Some of it was because I grew the role into more and more areas of responsibility. Some of it was because I learned a lot.

Mostly I stayed in my role for a long time because I loved the people around me. Don’t get me wrong, some of them drove me NUTS — but the community in and around the team, and the broader organization, are extraordinary. I learned so much and was given the grace to try things and fail. I made life-long friends and mentored a bevy of younger workers who have wonderful careers ahead.

I wasn’t ready to leave until I was convinced that the work I had done, that we had done, would continue into the future. The team that is there now will make different choices than I would, and take the programs in new, creative directions that I would never have imagined. But their work will be based on the work I did with them, and I will be able to come back and visit and see that the time I spent was well worth it.

If you’re wondering if it’s time to move on, check your gut. It will be your first indicator of readiness. But also think about the other things, and make sure you’re truly ready to go. The decision is a big one, so take the time to make it right.

May it be so.

Cyber Security, Technology Ethics, and Humanity. What else? I can be found on Twitter @CisoHelen