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How to Hire an Executive Assistant or Chief of Staff

By James Ketteringham · Founder

8 October 2026

An Executive Assistant and a Chief of Staff are hired for different reasons, from different markets, and against different scopes. Here is how to get each one right.

Knowing how to hire an Executive Assistant or a Chief of Staff starts with knowing which of the two you need. The seats relieve different constraints, draw from different talent markets, and fail in different ways, so the scope and the search have to be built for the seat in front of you.

Decide which seat you are hiring

An Executive Assistant (EA) multiplies the principal’s time. A Chief of Staff multiplies their reach, carrying the principal’s authority into rooms the principal cannot be in. The first scoping question is which of five constraints the seat is meant to relieve, using the leverage model.

Leverage The problem the principal has Seat
Time Coordination, preparation, and logistics consume the day Executive Assistant
Authority Decisions get made and stall; cross-functional work has no owner Chief of Staff
Information Raw information arrives faster than the principal can digest it Analyst, or a technical Chief of Staff
Narrative Others are shaping the principal’s voice and reputation Communications lead
Execution Projects, transactions, and initiatives need senior ownership close to the principal Chief of Staff, with analysts on technical work

A principal who asks for a Chief of Staff but describes a calendar problem needs an EA. A principal who asks for an EA but describes unowned cross-functional projects needs a Chief of Staff. In smaller firms one person can cover both, provided the principal accepts they are getting half of each and prices the role accordingly.

How to hire an Executive Assistant: scope the readiness layer

For an EA, the scope defines the recurring outputs the role owns: calendar, access, travel, inbox, and the readiness of the principal for every meeting. It sets the decisions the EA can make without asking, who they deal with on the principal’s behalf, and what is out of scope, with a named owner for each excluded item.

The scope also has to say how far the role reaches into the principal’s life. For an EA supporting an ultra-high-net-worth principal, this is where personal and family support is defined or excluded. At a public company, it is where the EA’s lane ends and the Chief of Staff’s begins, because two people who both believe they own board preparation will duplicate it or drop it.

How to hire a Chief of Staff: decide the version of the role

The Chief of Staff title covers several distinct jobs, and the scope is where a principal chooses one:

  • The owner of specific outcomes: special projects, integrations, planning cycles, and board preparation that need a senior owner and have none.
  • The keeper of secondary responsibilities: operating cadence, follow-through on decisions, and holding the leadership team to its commitments.
  • The talent accelerant: a high-potential operator placed beside the principal for two to three years, then moved into a line role.

The version decides the profile and the price. Strategic, technical work suits a technical Chief of Staff from banking, consulting, private equity, or corporate strategy, with a tight scope and higher pay. Operational work with an open scope suits an organizational Chief of Staff, often from an EA or operations background. Firms get into trouble when they want one and hire the other.

A Chief of Staff scope needs protecting from day one. Every leader in the firm will try to hand the seat their unowned problems, and without a defended scope it becomes an expensive dumping ground. The principal also has to back the role visibly: a Chief of Staff has no formal power, and the borrowed authority disappears the moment the principal undermines them.

Scope tight or open, and revisit it

For either seat, tight scope and open scope are both viable, and the choice should be deliberate. Tight scope gives precision, clear accountability, and an easier search. Its risk is a capable person waiting for instruction. Open scope gives initiative and a person who grows with the principal, and suits work that cannot be predicted. Its risks are scope creep, burnout, and collision with other seats.

If an Office of the CEO already exists, the scope has to set the boundaries with every other seat in it, because the usual failure is overlap. Revisit the scope annually and whenever the business changes shape.

Each seat draws from a different market

Most firms post the role, collect two hundred applications, and assume the search is covered. A résumé cannot separate a good candidate from a great one, because the traits that matter sit beneath the title. For an EA, it is judgment under pressure and discretion. For a Chief of Staff, it is carrying borrowed authority and delivering outcomes without formal power. That is why assessment has to go beyond the interview.

The candidates are also in different places. Senior EAs who can operate at public company CEO altitude are few, and almost none are looking. Technical Chiefs of Staff come from banking, consulting, private equity, and corporate strategy, so the hiring firm is competing with those industries for the same person. Both move through referral and discreet approach, and reaching them takes a market map built for the seat and a confidential first conversation.

These people move only for something compelling. A hiring firm has three levers: compensation, chemistry with the principal, and a genuine step up in scope. A bigger title on the same work moves nobody.

Frequently asked questions

What should a CEO define before hiring an executive assistant?

Define the recurring outputs the EA will own, such as calendar, access, travel, inbox, and meeting readiness. Then set the decisions the EA can make without asking, who they deal with on the principal’s behalf, how far the role reaches into personal and family matters, and what is out of scope, with a named owner for each.

How do you know whether you need a Chief of Staff or an Executive Assistant?

Look at the problem you describe. A calendar, coordination, or preparation problem calls for an Executive Assistant. Decisions that stall, cross-functional projects with no owner, or initiatives that need a senior lead call for a Chief of Staff. In smaller firms one person can cover both, priced as half of each.

Where do you find a strong Chief of Staff?

Technical Chiefs of Staff usually come from banking, consulting, private equity, and corporate strategy, so firms compete with those industries for them. Organizational Chiefs of Staff often come from EA or operations backgrounds. The strongest candidates in both groups are already employed and move through referral and discreet approach, rarely through a job posting.

From The Blackbook Report 2026

Section 7 of The Blackbook Report 2026 covers the full hiring process for every seat in the Office of the CEO, from scoping and sourcing through assessment, references, and chemistry.

Read the full report: The Blackbook Report 2026

If you are scoping an Executive Assistant or Chief of Staff seat, we would be glad to talk it through.

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