Is Your Security or Engineering Team ready for a Chief of Staff?
Advice from a CISO Chief of Staff on how to know when the time is right and how to find the right one.
By Jessica Walters, Discernible Advisory Board Member and former Chief of Staff to the CISO of Cisco’s Security Business Group
Image by @austinchan.
Bringing on a Chief of Staff to help supercharge your team’s cross-organizational impact and influence is a trend that has picked up momentum in the last few years and isn’t slowing down anytime soon. And while I love the excitement surrounding the Chief of Staff role, there’s more to the decision of when to bring on an individual with these superpowers. It’s a decision that leaders often neglect until they can no longer ignore the symptoms of a dysfunctional working environment or their organization reaches what they think is the ideal size. To get the most out of this role, it should be a proactive decision rather than a reactive one.
First and foremost, you can’t just throw anyone into the mix and have the magic work! Chiefs of Staff have different areas of expertise, strengths, and expectations of the leaders they work with. They should be someone you feel comfortable giving the reins of your most strategic programs and confident in covering for you in a pinch. Getting the right match for you and your organization is key, so take the time to understand what you need ahead of hiring! When the fit is right, the magic works, and I call this “well-matched.”
Here are a few key indicators that your Security or Engineering organization might be ready for this critical investment:
You are getting ready to navigate a period of significant change or growth
With periods of significant change or hypergrowth come great amounts of ambiguity and uncertainty. A well-matched Chief of Staff can serve as a powerful stabilizer for your team through the waves of uncertainty that technical teams experience under these circumstances. Why, you ask? Chiefs of Staff should be catalysts for trust within your organization, building strong relationships with your individual contributors over time and opening up the door for transparency in communication. Sure, C-level leaders and strong first and second-line managers should also be a source of trusted support. But it’s the Chief of Staff role that is able to keep a pulse across the breadth of your entire organization from multiple angles if positioned correctly, including how those leaders you’re also relying on are really doing. It’s common for teams to realize a need for this stabilization only after significant changes or growth has started, making it a more challenging situation for a Chief of Staff to join and navigate (if there’s even any budget left for such a role in the team’s growth plan!).
Your team identity is unclear and needs attention
Creating a team culture that people are proud to be a part of should be at the top of the priority list for technical leaders, but quite often the roles critical to nurturing team cohesion are deprioritized to make way for technical talent. While that’s understandable, hiring great engineers and knowledgeable infosec team members is not enough. Building a cohesive and sustainable team identity requires a great deal of investment and time that only “glue roles” can provide to your organization (IE: Chiefs of Staff, Program Managers, Technical Program Managers, etc). Investing in a well-matched Chief of Staff can quite literally ‘glue’ your teams together by helping translate your vision into a powerful, motivating, and consistent message that is reflected throughout all facets of your organizational operations. How you talk about that vision, how you celebrate your work towards that vision, and how your team thinks about that vision when they’re doing their daily work are all influenced by the programs your Chief of Staff can build and lead for you.
You need to break down working silos within or across teams
The dreaded enemy of all teams…. information silos. All organizations experience some level of siloing, whether within a team or across teams. While there are hundreds of tactical ways to break down such silos, at the root of all effective approaches is the importance of intentional and strategic communications. Leveraging a Chief of Staff as your trusted air traffic controller for all things communication within your leadership team and across your organization can drive clarity and consistency. A well-matched Chief of Staff can ensure you build the most effective communication infrastructure by taking into account the many perspectives within your organization, where those most frequently intersect, and how to systematically unblock information in critical areas. Additionally, a strong Chief of Staff can leverage their relationship-building superpowers to unlock communication gaps with key partners across the business. When your critical partners have high confidence in your Chief of Staff they also develop trust in you as a leader and the guess work in how to engage with your organization effectively is removed.
You are building a team in an already-established organization
If your team is in startup mode, building from the ground up trying to catch up with the rest of your organization, bringing on a well-matched Chief of Staff can significantly multiply your ability to grow quickly and start making a meaningful impact. Your Chief of Staff should serve as an extension of you as an executive leader, allowing you to divide and conquer quickly as you set up new working patterns within your organization and develop and refine your priorities during information gathering. They can also ensure others fully understand your team vision and charter while just generally accelerating trust in the team you’re building through their intersection with other leaders and individuals. Bringing on this partner early to co-pilot this journey will allow them to be part of the strategy-building process where they can predict challenges, identify risks for you, and provide different perspectives based on their cross-organizational insight and relationships.
In most of these scenarios, the decision to bring on a Chief of Staff earlier rather than later is the best way to set yourself and your team up for success. Their relationship-building superpowers are the ultimate key to building a smooth path for your team and your vision to grow. But, the stars don’t always align. Here’s what I would recommend if you’re not quite ready for a Chief of Staff or if there are immovable blockers in your way:
Consider other ways to bring aboard pieces of the Chief of Staff superpower until you are ready! Teams like the one at Discernible can work with you to build purposeful communication strategies and programs that enable trustworthiness within your organization and with key partners.
Be curious about what your peers have learned in their team-building journeys! The reality is that there are hundreds of approaches to building out successful teams and likely many others who have walked the path before you. Tap your trusted CISO or CTO communities and ask how they have personally navigated introducing a Chief of Staff role. What are the greatest lifts they have personally felt after bringing on a Chief of Staff? Do they have any learnings from the process that would have made it better? How have they gained buy-in from the rest of the organization to bring on the role? Understanding these different experiences will help you build the case to add this important role when the time is right.
Connect with real-life Chiefs of Staff in your area of expertise and take steps to understand their philosophies. There is a vibrant Chief of Staff presence on LinkedIn where many in-seat or advising Chiefs of Staff are actively sharing their perspectives. Seek them out and look for any contributors who may have experience working alongside roles similar to yours. It’s likely they will have some really valuable learnings to share that will set you up well to work with your future Chief of Staff!
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