Frequently asked questions
About the Chief of Staff role, the career path, and the Aperture workspace.
What does a Chief of Staff do?
A Chief of Staff extends an executive's capacity. The work typically spans four areas: running the operating cadence (leadership meetings, business reviews, planning), driving cross-functional special projects, preparing communications such as board updates, and supporting decisions by gathering context and tracking follow-through.
How is a Chief of Staff different from an Executive Assistant?
An Executive Assistant owns logistics: calendar, travel, and meeting mechanics. A Chief of Staff owns substance: agendas, decision memos, projects, and follow-through. The two roles are complementary and often work closely together.
How is a Chief of Staff different from a COO?
A COO is a line executive with direct reports and accountability for business outcomes. A Chief of Staff has no standing team or P&L; they coordinate, synthesize, and drive execution on the principal's behalf. In some companies a strong CoS eventually grows into a COO role.
What background do you need to become a Chief of Staff?
There is no single pipeline. Common feeders include consulting, banking, strategy and operations teams, product management, and internal high performers. The consistent requirements are strong writing, fast synthesis, sound judgment under ambiguity, and low ego with high standards.
How long do people stay in a Chief of Staff role?
Most healthy tenures run 18 to 36 months. The role is usually a chapter rather than a destination, commonly leading to operating roles, general management, founding a company, or a larger CoS seat.
Does every executive need a Chief of Staff?
No. The role pays off when an executive's coordination load exceeds what they can handle without losing focus, which typically happens during rapid scaling, a turnaround, or a heavily cross-functional agenda. Before that point, a strong EA and disciplined meeting habits are often enough.
How can AI help a Chief of Staff?
AI is well suited to the mechanical parts of the job: summarizing meetings, extracting action items and decisions from notes and threads, generating a daily brief, drafting updates, and answering questions across everything captured. The CoS stays responsible for curation, judgment, and anything politically sensitive.
What is Aperture?
Aperture is an AI Chief of Staff workspace. You capture meeting notes, emails, and documents in one place; it extracts action items, decisions, people, and open questions automatically, generates a daily brief, and lets you ask questions across everything with an assistant. It is evolving toward a full agent: one that connects to your work systems directly, gathers context on its own, and delivers the brief before you ask.
Is the Aperture workspace free to use?
The workspace is currently a private, passcode-protected tool. You can join the email list on this site to hear about access and updates.
What makes a Chief of Staff fail?
The most common failure modes are set up at the start: accountability without authority, unclear scope, being perceived as a gatekeeper or spy by the leadership team, and the role silently collapsing into administrative work. Explicit scope, access, and success criteria agreed with the principal up front prevent most of them.