The Chief of Staff role is one of the most powerful and least standardized roles in modern organizations.
This guide gives language to what is often felt but rarely articulated. It helps executives design the role intentionally and helps Chiefs of Staff understand how to operate strategically, sustainably, and with clarity.
Whether you are hiring your first CoS, leveling an existing one, or stepping into the role yourself, this guide breaks down what the role actually is, what it is not, and how to make it work.
The Executive’s Guide to the Chief of Staff Role
What’s included in the guide
A clear definition of the Chief of Staff role and how it differs from EA, BizOps, COO, and other executive support roles
The non negotiable skills, operating behaviors, and leveling framework including scope and compensation
When and why to hire a Chief of Staff, plus the signs it is time
How to design the role intentionally, including scope clarity and internal vs external hiring tradeoffs
A structured performance evaluation framework focused on impact, leverage, and strategic influence
This guide is for you if…
You are a CEO or Principal
who feels stretched thin and needs leverage at the highest level.
You are hiring or redefining
a Chief of Staff and want clarity before you commit.
You are a Chief of Staff
who wants language, structure, and strategic grounding for the role
About Pretty Operational
Pretty Operational is a place of belonging and understanding. A space to ask the messy questions, vent without a filter, and celebrate the wins that too often go unnoticed. A place to feel seen, supported, and a little less alone.
Get the Guide
When designed well, the Chief of Staff role creates leverage, clarity, and momentum across the business.
When designed poorly, it becomes isolating, exhausting, and unsustainable.
This guide helps you design it right.