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Scaling Up! How to Expand your Chief of Staff Role

Scaling Up! How to Expand your Chief of Staff Role

Scaling up! How to expand your Chief of Staff role panel at the Chief of Staff Summit!

Note: please see the following summary of the core ideas from this conversation at the Summit. We did our best to clarify the ideas for you. Please refer to the video for specific details, ideas, and context.

Moderated by: Laurie Benezra - Arron Trusted Advisor & Executive Coach to senior leaders, entrepreneurs and Chiefs of Staff

Panelists include:

- Shanaz Chowdhery Revenue Operations at Emeritus & former Chief of Staff at Vemo Education

- Andrea Geroldi Chief of Staff at Rising Tide Capital

- Eleazar Orellana Operations Leader, Global Accounts at AWS & former Chief of Staff at Visa

How do you scale yourself as a Chief of Staff:

Andrea: proceed with caution. Don’t take on too much. Be strategic. Know where you want to scale into.

Shanaz: as a Chief of Staff, you can lean-in to any direction and you can learn a lot. Being a Chief of Staff can be like getting a MBA. 

Eleazar:  aim to go from doing X for other people to empowering other people. I personally believe that's where the journey to leadership starts. Develop the body of work that you will deliver on, and for everything else, empower other people to do it.

Transitioning as a Chief of Staff:

Eleazar: 5 steps:

  1. remove invisible roadblocks. 
  2. embrace a day one culture, which was popularized by Amazon
  3. know what your endgame is (i.e. company size, product size, what levels of responsibilities)
  4. ruthlessly prioritize to achieve your endgame
  5. you can always choose again, if steps 1-4 do not result in what you expected

Andrea: some Chief of Staff roles are rotational and some can be more long-term. If you love the Chief of Staff role, it doesn't need to be something that you leave. 

Shanaz: know that as a Chief of Staff the role is not always perfect because you can get thrown into projects that may not work out. 

How to amplify the team performance as a Chief of Staff:

Shanaz: try to understand the pain points in the dynamics of the executive leadership team (i.e. which orgs are working really well together and which ones aren’t). From which, you can be an empathetic leader, as well as a partner-in-crime or problem solver to get really in the trenches with them. And sometimes I would also do deep dives into individual functions and find that the pain points (i.e. lack of cultural building, lack of delegation, lack of clear direction and strategy, etc). 

Zar: Beyond fixing problems and removing things on a to-do-list, aim to operationalize them. That way, that problem remains solved. 

Andrea: At bigger companies, it is important to get buy-in and how that can be a key part of your role. 


Eleazar: When you start that first role, you need to set the tone with your boss. Aim to have one or two ideas of where you role could be in the next in the next 12 to 18 months. It doesn't have to be concrete. It’s important to ask but you also have to tell in terms of where you want to go in your role.  

Shanaz: empower others when you have no direct reports is the job of a Chief of Staff. Focus on empowering the folks around you to do their best work. 

Laurie: Chief of Staff are not just problem solvers, but problem preventers. They can also serve as “Coaches of Staff.” 

Most common CoS transitions:

Shanaz: VP of Operations

Andrea: VP of Operations or in the People department

Eleazar: Head of Operations

Favorite part about being a Chief of Staff:

Shanaz: exposure to all of the different parts of the business

Andrea: the people and seeing people grow together

Eleazar: seeing how lego blocks of the company fit all together

What learning will you takeaway most from your role:

Shanaz: you can learn anything. Roll with the punches and opportunities. 

Andrea: grace. Learning when to ask for it and when to give it. 

Eleazar: managing ambiguity.