Leader Over Company? The Importance of Choosing the Right Principal in the Chief of Staff Role
June 25, 2021

The Chief of Staff role is so unique compared to any other position at a company. The different dynamics of where they sit within the hierarchy of the company, the need to work across every department, and even the level of trust that’s required to be successful in the role. So for anyone stepping into a new Chief of Staff position, whether it’s your first time in the role or you have past experience, understanding what’s needed of the role and your fit is critical. 

However, when evaluating possible fit in the Chief of Staff role there is one important question that might not be as relevant for other positions at a company, and that is ‘How do I complement the leader I will be working alongside in the COS role?’ 

As Scott Amenta, Founder of the Chief of Staff Network, shared with us on Aspiring Ops, ‘In a Chief of Staff role, you’re often choosing the principal even before you’re choosing the company.’ In the clip below he goes on to share more on what this looks like in practicality when evaluating the position. 


As Scott and others would tell you, overlooking the company entirely and basing your decision solely on the principal, probably isn’t recommended. But the importance of establishing a great rapport with the principal you will be working with is crucial. To put it more simply, Scott goes on to say, ‘You have to really trust your gut instinct on that relationship.' 

We’ve heard similar advice from past guests like Zeke Fraint (Chief of Staff at Clearcover), Steph Shaw (Chief of Staff at Agio), and Ben Battaglia (Chief of Staff at Lessonly), who have all shared that their relationships with the leaders they served was just as important as the position at the company. 

And it makes sense why this would be so important. Unlike any other position at a company, in the Chief of Staff role, you aren’t only acting or speaking your own thoughts, oftentimes you’re representing the office of the CEO or other members of leadership. 

For example, an account executive often isn’t being asked to sit in on multiple team meetings and represent the thoughts or direction of the CRO at the company. However, the Chief of Staff has to be able to flex between providing their own thoughts and opinions, while still being able to effectively communicate and align other team members with the principal's vision and direction for the company. 

So while it’s certainly important to pick the right principal that you will be working closely with in your role of Chief of Staff, it isn’t an either/or situation. You have to buy into the long term vision and direction of the company, as well as trust the relationship you have with the principal you will be reporting to at the company. 



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