When To Know You're Ready for a Chief of Staff

A #ChiefofStaff is many things. Through my 15 interviews with different Chiefs of Staff (CoS), in industries from tech to banking to petroleum, in startups and publicly listed companies, I heard them describe themselves as therapist, truth-teller, confidante, counselor, thought partner, recorder, organizer, and ringmaster.?

The CoS must be independently strategic and have an unprecedented level of discipline because from the very beginning they deal with a high level of uncertainty. Prime Chief of Staff does an excellent job of breaking down the six main functions, but every role is its own unique mix, which needs to be initially explicitly defined and then organically settled on. For the CoS’s I interviewed, they sat down with their Principals to identify some agreed upon principles and then they used test cases to leverage the scale and speed with which each function could be carried out.?

As the ultimate purpose of this project was to help me hire a Chief of Staff, and help my friends find better CoS’s, I realized that CoS’s are really only the most effective when you get to a certain level of executive functioning. Anything before that, the CoS does not serve the true and real purpose of a CoS, but their efficacy goes down and they become glorified operations managers or worse PA’s. The cases are as follows:?

• At a group level: where the Principal does not have time to gain the necessary visibility and context, and needs someone to gather information in order to make the informed decisions.?
• When the company is at a stage when a lot of time-sensitive decisions need to be made.?These decisions may have inter-complexity and lead to matrix impact. The Chief of Staff can then be the driver that helps timely and comprehensive decision making.?
• Once a company is more established, change and transformation become the essence of business competitiveness, which is extremely difficult to execute on, especially when the very leaders who had brought it to the success are the ones who have to make the changes. Chunking and tackling of execution needs to be done, which typically happens through new strategy, which is where the CoS can offer the unique blended role of structure, resources, and execution.?

Never Hire A CoS out of through a traditional interview process?

The one resounding trait and most important factor that nearly every single principal and CoS mentioned was the chemistry between the two. This is a blend of similar values, goals, communication factors, as well mutual investment in the growth of the CoS. Successful CoS’s always saw their role as an apprenticeship, a way to level up in the company. In terms of power dynamics, there wasn’t a huge power discrepancy-- certainly the principal is senior, but they also see the CoS as necessary and creating enormous value.???

Out of those, communication style seemed to be the least important, as it seems possible for the CoS to quickly learn the style of the principal, and adjust as needed. Although this is foundational groundwork that needs to be done before further work, and will be a constant adjustment as time goes on.?

Balancing Efficiency and Trust

On one hand, in the company of the Principal, the CoS must be a sounding board and thought partner, so they must have informed opinions that are separate and different from that of the Principal. On the other hand, in front of others, the CoS must communicate and make decisions completely and absolutely aligned with the Principal, so that they can be a proxy for the Principal. In order to be able to separate clearly these two roles, the CoS must have a very strong sense of self.?

Be Clear about Steps after CoS

All of the Chiefs of Staff I interviewed were very ambitious and career-driven in their own right, and they emphasized the necessity of having a candid conversation in the interviewing process regarding their futures and clarification of expectations. Many leaders see the CoS within the Tour of Duty concept, so they may only stay 2-3 years. However, there are also circumstances where the Principal feels the CoS is so high-performing that they become reluctant to let them ascend. In such cases the Principal needs to consider the bigger picture and let go, or often the motivation of CoS diminishes. In such cases, the CoS can be instrumental in finding an effective replacement, someone with a similar profile to them.?

The Principal as an Ally?

Because the role of CoS is new for a lot of companies, it is very easily misunderstood by others, especially senior team members who have worked very closely with the Principal previously. They may view the CoS as an unnecessary gatekeeper, or even as competition. Very rarely does a CoS have their own team, so they spend a lot of time building rapport with others to gain resources and leverage. Therefore, it is paramount the Principal not only vocalize the power they are bestowing upon the CoS, but actively exhibit it, such as indicating that the CoS will be making a certain business decision rather than them.?

Overall, the role of the CoS is very strategic and offers incredible opportunities to young and even mid-career rockstars to understand and grow underneath a principal. In some companies, it’s a very political role and actually garners a lot of power. However, fit matters more for this role than most others, and not being intentional about values and communication mix can lead to dissatisfaction on both sides.?