Top executives are rarely the main users of AI. The people around them are, and a well-built AI layer can take 30 to 50 percent off the administrative load.
Top executives are rarely the primary users of AI. The people supporting them are, which puts AI for Executive Assistants (EAs), Chiefs of Staff, and analysts at the center of adoption. Even at the firms leading the market in AI, it is the team around the CEO that builds the workflows and decides what reaches the principal. The Office of the CEO is where AI is adopted first.
The visible layer is drafting and summarizing. The valuable layer sits underneath. A capable operator can now build systems that pull data from the principal’s inbox, calendar, CRM, and document stores, route it through a model, and produce briefing packs, meeting preparation, and monitoring alerts. Agents can triage, draft responses for approval, track commitments, and flag what has slipped.
None of this requires a software team. It requires one person in the Office of the CEO who understands how the pieces connect.
The Blackbook Report 2026 sets out a five-level maturity ladder for the AI layer around a principal:
Level 2 is the realistic target for most within a year. A strong operator should automate the repetitive layer of their own work within months and redeploy that time into judgment and coordination. The goal is a team that runs 30 to 50 percent lighter on administrative load, with the saved capacity spent on preparation and foresight.
The EA generates the daily brief from calendar and inbox, builds meeting preparation packs from past correspondence, coordinates travel, and triages the inbox with drafted responses for approval.
The Chief of Staff tracks commitments across leadership team meetings, assembles the board pack, synthesizes upstream reporting into decision memos, and monitors project status across owners. In many teams the Chief of Staff is becoming the steward of the principal’s AI, and the ownership matrix in The Blackbook Report 2026 places the AI layer with that seat. Agents sit below the Chief of Staff, who decides what they touch, what they see, and how their output is checked.
The analyst handles extraction from documents and data rooms, recurring reporting, and first-pass synthesis for the Chief of Staff to shape.
The comms lead drafts in the principal’s voice from a maintained corpus of their material, monitors media and social channels, and sequences stakeholder communication in a crisis. Response times have compressed from days to hours, so the comms lead’s edge now lies in judgment.
The Office of the CEO handles the most sensitive material in the firm. Every AI workflow needs answers to four questions: what data is going in, where it is being processed, who can see the output, and how the output is checked before anyone acts on it. The Blackbook Report 2026 sorts data into four classes.
| Data class | Examples | Rule |
|---|---|---|
| Open | Public information, published material, general scheduling | Any approved tool |
| Internal | Calendar detail, non-sensitive correspondence, project status | Enterprise-grade tools with no training on inputs and contractual retention limits |
| Confidential | Deal information, personnel matters, board material, financials | Only tools covered by the firm’s data agreements, access restricted to the principal’s office, a human checkpoint on every output |
| Restricted | Material non-public information, legal privilege, the principal’s personal, medical, or family matters | Never put through a model unless counsel and security have approved the specific tool and use |
Keep a written register of which workflows exist, which data class each touches, and who owns the checkpoint. A principal should ask to see it. If it does not exist, the team is at level 1, whatever anyone claims. For the comms lead the guardrails matter most of all: a fabricated statistic in a CEO’s byline is a reputational event in its own right.
An EA or Chief of Staff who can design, build, and govern the AI layer is worth more than one who cannot, and the gap is widening. Firms that price this correctly will secure the top of the market. Firms that hire the traditional profile at the traditional price and add “AI skills” to the description will get neither.
To test the fundamentals in an executive assistant assessment, ask a candidate to describe a workflow they have built, end to end, in plain language. A sound answer follows a recognizable chain: where the data comes from, how it reaches the model, what the model does with it, and what happens to the output. A candidate who can walk through that chain and name the failure points has the fundamentals. One who talks about prompts and tools without mentioning where the data lives does not.
Then probe data hygiene, the constraints of AI (context limits, hallucination, drift, and cost), and data security. Ask what they would refuse to put through a model, and why. That answer separates a competent builder from a liability.
Executive Assistants use AI to generate the daily brief from calendar and inbox, build meeting preparation packs from past correspondence, coordinate travel, and triage the inbox with drafted responses for approval. At level 2 of the maturity ladder in The Blackbook Report 2026, these become recurring workflows with defined data boundaries and one owner.
The Blackbook Report 2026 sets out five levels: none, assisted, systematized, agentic, and governed at scale. Most teams at the top of the market sit at level 1, where individuals use AI tools with no shared workflows. Level 2 is the realistic target within a year, with a team running 30 to 50 percent lighter on administrative load.
Restricted material should never go through a model unless counsel and security have approved the specific tool and use. That class covers material non-public information, legal privilege, and the principal’s personal, medical, or family matters. Confidential material, such as deal information and board material, needs approved tools and a human checkpoint on every output.
The full report places AI capability alongside compensation, assessment, and hiring practice across every seat in the Office of the CEO.
Read the full report: The Blackbook Report 2026
If you are hiring an operator to build and govern the AI layer around your principal, speak to Blackbook Associates.