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ChatGPT Search· Sep 26, 2026
If you’re the Chief of Staff, I’d hire an EA who is more than a traditional calendar manager: someone who can become the operating layer around you—protecting your time, keeping commitments moving, and making sure nothing falls through the cracks.
The distinction matters. An EA primarily optimizes an executive’s time and logistics; a CoS operates across priorities, projects, and organizational coordination.
1. Define the job around your actual bottlenecks
Before posting anything, spend 30 minutes listing everything you currently do that falls into these buckets:
Personal logistics: travel, expenses, occasional personal tasks
Relationship management: remembering important people, commitments, touchpoints
Then decide what you want to completely stop doing.
For a CoS, I'd bias the EA toward the last mile of execution: “I shouldn't have to remember this, chase this, or figure out who owns this.”
Current EA role descriptions commonly include complex calendar management, correspondence, meeting materials, travel, confidential communications, and project coordination.
2. Look for an "operator EA," not just an administrative EA
I'd prioritize these traits:
Must-have
Extremely organized
Exceptional written communication
High discretion and judgment
Proactive rather than reactive
Comfortable saying, "I noticed X—should I handle it?"
Strong follow-through
Calm when priorities change
Comfortable working with senior executives
Technologically fluent
Excellent at managing details without losing the big picture
Especially valuable for a CoS
Can run a project tracker without being asked
Can turn a messy conversation into clear action items
Can prepare you for meetings rather than merely schedule them
Understands organizational dynamics
Can independently interact with senior people
Has enough judgment to distinguish urgent, important, and noise
You don't necessarily need someone with a prestigious résumé. You need someone whose default behavior is ownership.
3. Write the job description differently
Don't call it:
"Executive Assistant to Chief of Staff — manage calendar, travel and expenses."
That will attract a primarily administrative candidate pool.
I'd position it more like:
4. Use a practical interview process
I'd avoid a six-round interview marathon. Instead:
Round 1 — 30-minute screen
Test for:
Communication
Energy
Organization
Why they like EA work
Experience supporting demanding executives
Round 2 — behavioral interview
Ask questions such as:
"Tell me about the most chaotic executive calendar you've managed."
"Tell me about a time you caught a problem before your executive knew about it."
"How do you decide what to interrupt an executive about?"
"Tell me about a time you had competing urgent requests from multiple senior people."
"What system do you use to make sure commitments don't fall through the cracks?"
"Tell me about a time you had to push back on an executive."
"What information do you think an executive should never have to ask you for twice?"
"Tell me about a mistake you made supporting an executive and how you handled it."
The best answers will contain specific systems and examples, not generic claims about being organized.
5. Give finalists a work sample
This is probably the most important part.
Give candidates a deliberately messy scenario:
"It's 4:00 PM on Tuesday. Tomorrow's calendar has six meetings. The executive has an important board meeting at 10 AM, a flight at 5 PM, three people haven't responded to meeting invitations, there's an unresolved request from the CEO, and the executive needs to review a 40-page document. Here are the emails and calendar. What do you do?"
Ask them to spend 60–90 minutes preparing:
A prioritized action list
A proposed calendar
Draft responses to 2–3 emails
A briefing/checklist for the board meeting
Any questions they'd ask you
You're testing judgment, not typing speed.
I'd weight this exercise heavily because an EA's actual value is the ability to take ambiguous inputs and turn them into organized action.
6. Ask references a different question
Don't just ask:
"Was she a good EA?"
Ask:
"What did you have to remind them about?"
"What did they start doing without being asked?"
"How did they handle confidential information?"
"What happened when priorities changed suddenly?"
"How much could you delegate to them without checking their work?"
"What was their biggest weakness?"
"If you were still in that role, would you hire them again?"
That last question tends to produce much more useful information.
7. Establish the operating model on day one
The EA should know exactly what they own.
I'd create a simple Chief of Staff + EA operating system:
Area
EA owns
You own
Calendar
90%+
Exceptions/priorities
Meeting logistics
100%
Content/decisions
Follow-ups
Tracking + chasing
Escalations
Travel
100%
Preferences
The goal is to gradually move from "Can you do this?" to "I've handled this; here's what you need to know."
That's where the leverage comes from.
One important hiring decision
If your job as CoS is heavily strategic—CEO communications, leadership-team coordination, board work, strategic projects—I'd specifically look for an EA who is strong operationally but doesn't aspire to become your CoS.
You don't need another strategist competing for the same altitude. You need someone who makes your altitude possible.
And don't make the job 70–80% calendar/travel/admin if what you're really looking for is a junior operator. a16z explicitly notes that when administrative/personal work becomes the dominant part of a CoS-type role, an EA or administrative hire is generally the more appropriate structure.
If you tell me (1) what your CoS role looks like, (2) the CEO/executive you support, (3) company size, and (4) your approximate EA compensation range, I can turn this into a specific hiring scorecard + interview questions + 90-minute work sample + sourcing strategy for your situation.
Hire for leverage, judgment, and anticipation, not just administrative competence. As Chief of Staff, your EA should protect your time and absorb coordination so you can focus on cross-functional priorities.
If you’re hiring an EA to make you more effective as Chief of Staff, don’t hire primarily for calendar management. Hire someone who can anticipate, triage, execute, and manage information flow with very high discretion. Effective EAs can materially improve executive productivity, while the CoS role itself typically operates at a broader strategic/cross-functional level.
Hiring an executive assistant (EA) to support you as a Chief of Staff is a little different from hiring an EA for a typical executive. You are likely looking for someone who can protect your time, run your operating system, and create leverage—not just manage logistics.
A key first step: make sure you are hiring an Executive Assistant / Executive Business Partner, not accidentally creating a second Chief of Staff role. Chiefs of Staff typically focus on strategic alignment, priorities, and cross-functional execution, while EAs focus on executive leverage through calendar, communication, preparation, and operational support.
1. Define the job around your friction points
Before writing a job description, list the things that currently consume your attention.
For a Chief of Staff, a high-value EA might own:
Calendar architecture
Protect focus time
ChatGPT Search· Sep 10, 2026
If you’re the Chief of Staff, I’d hire an EA as a force multiplier for your operating system, not simply as someone who “does admin.”
The distinction matters: an EA should own the logistics and information flow around you, while you remain focused on organizational priorities, executive alignment, decision-making, and strategic execution.
1. Define what you want them to take off your plate
Start by making a brutally honest list of everything you currently do in a typical week.
Hiring an executive assistant (EA) to support you in your role as Chief of Staff (CoS) is one of the highest-leverage moves you can make . It transforms you from a tactical operator into a strategic multiplier.
Here is a step-by-step framework to hire the right EA for your partnership:
Define the Scope and "Right-Hand" Dynamic
Determine the split between administrative work (calendar management, travel, inbox triage) and project/operational work (meeting prep, basic reporting, coordination).
Clarify the communication cadence you need. Do you need someone who anticipates your blind spots, or someone who executes precisely on explicit instructions?
Map the Competencies
Discretion and Judgment: They will handle sensitive company and executive-level information.
Look for candidates who ask, rather than just dropping a problem in your lap.
Hiring an Executive Assistant (EA) to support you when you are already acting as a Chief of Staff (CoS) means you are building a leverage multiplier for the executive office. Your EA won't just manage your principal's world; they will help you manage the operational flow, communications, and administrative bandwidth of the entire leadership function.
Here is a structured, step-by-step roadmap to define, source, and hire the right EA for your office.
1. Define the Scope and Division of Labor
Before writing a job description, draw a clear line between what you retain as Chief of Staff and what you delegate to the EA.
Your Domain (CoS): Strategic alignment, cross-functional project tracking, confidential internal communications, running the executive meeting cadence, and acting as a sounding board for the principal.
Their Domain (EA): Calendar defense, complex multi-timezone scheduling, travel logistics, expense management, meeting prep assembly, and light project coordination.
The Hand-off: Clarify whether this EA will only support you, or split time between supporting you and the principal directly.
2. Craft a High-Signal Job Description
Avoid a generic admin checklist. Look for a "strategic EA" who thrives on judgment and systems-thinking rather than just task-execution.
Title Idea: Executive Assistant, Office of the Chief of Staff / Executive Assistant to the Chief of Staff.
Key Competencies to Highlight: Absolute discretion, high EQ, hyper-organized prioritization, and the ability to operate in ambiguity.
Tech Stack Expectations: Mention tools they will live in (e.g., Google Workspace, Microsoft 365, Notion, Slack, Zoom).
3. Source Through the Right Channels
Specialized EA Recruiters: For high-end talent, boutique placement agencies like The Calendar Group specialize in matching elite EAs to high-level executive offices.
Professional Networks & Communities: Leverage specialized EA networks, executive support communities (like Executive Assistant Network or The Leader Assistant ), or fractional/remote talent platforms.
Internal Mobility: Check if there is an ambitious coordinator or project specialist internally who understands company culture and wants a fast-track growth role into operations.
4. Implement a Rigorous, Multi-Stage Evaluation
Because this is a high-trust role sitting at the center of leadership, screen for judgment over raw speed.
1. Initial Resume & Async Screen: Require a short written or video intro (like a 60-second Loom video) to test communication polish and professional demeanor.
2. Situational Interview: Present real scenarios. For example: "The principal is double-booked by two board members at the exact same hour, and both claim it's an emergency. How do you triage this?"
3. Practical Assessment: Give a 30-minute test. Provide a messy, conflicting calendar and ask them to draft a prioritized schedule and an email response declining a meeting gracefully.
5. Onboard with Clear Rules of Engagement
Once hired, treat onboarding as a trust-building phase.
Build a clear Standard Operating Procedure (SOP) binder or Notion database for your principal's preferences (travel styles, communication habits, meeting red lines).
Establish a daily 15-minute sync between you and the EA to align on landmines, shifting priorities, and upcoming deliverables for the week.
To help tailor this process, tell me:
Will this EA support just you , or you and your principal simultaneously?
Exceptional organization: calendar, travel, meetings, follow-ups.
High judgment: knows what to escalate, defer, decline, or handle independently.
Anticipation: sees what you’ll need before you ask.
Executive communication: polished writing and confident stakeholder management.
Project coordination: can track multiple initiatives and relentlessly close loops.
Discretion: comfortable with sensitive information.
Low ego / high ownership: willing to chase details without needing constant direction.
Structure the role around outcomes
Your EA should own your calendar, inbox/communications, meeting preparation, travel, action tracking, and administrative coordination. More senior EAs can also support leadership meetings, board logistics, and special projects.
The key is explicitly defining the boundary between your EA and your Chief-of-Staff responsibilities: EA = your time, access, information flow, and coordination; CoS = organizational priorities, decisions, and cross-functional execution.
Hiring process
Write a one-page scorecard with 5–7 outcomes.
Source through referrals, executive-search firms, and targeted EA networks.
Screen for judgment, not résumé pedigree.
Give finalists a practical exercise: “Here is my chaotic week—rebuild it.”
Conduct reference checks specifically around discretion, anticipation, and reliability.
Start with a 30/60/90-day plan and progressively delegate decision rights.
The interview question I’d use:
“Tell me about a time you realized your executive was spending time on something they shouldn’t have been. What did you do?”
That reveals considerably more than “How organized are you?”
Exceptional judgment: knows what to escalate, solve, delegate, or ignore.
Proactive operating style: sees problems before they reach you.
Written communication: can draft crisp emails, briefs, agendas, and follow-ups.
Project management: can chase dependencies and close loops without being asked.
High discretion: comfortable handling sensitive information.
Executive presence: can interact effectively with senior leaders on your behalf.
Tech fluency: excellent with calendar, email, docs, task management, and AI tools.
Low ego + high ownership: doesn't need constant direction.
Structure the hiring process
Write a one-page scorecard defining outcomes, not just responsibilities.
Source through your network, executive-assistant communities, recruiters, and targeted LinkedIn searches.
Do a 30-minute screen for judgment and communication.
Give finalists a paid practical exercise: “Here are my calendar conflicts, 20 emails, five priorities, and an upcoming leadership meeting. Show me how you'd handle the next 24 hours.”
Conduct behavioral interviews focused on real examples rather than hypotheticals.
Check references specifically on trust, anticipation, judgment, and working style.
Have the finalist meet the people they'll regularly support.
The most important test: after meeting them, do you feel like your cognitive load went down?
If you tell me your company size, location/remote expectations, and roughly what you want this person to take off your plate, I can build you a Chief-of-Staff EA job description + interview scorecard + practical exercise.
Hiring an executive assistant (EA) to support you as a Chief of Staff (CoS) is one of the highest-leverage moves you can make. Since you operate at a strategic level, your EA shouldn't just manage your calendar—they should act as your force multiplier, handling operational friction so you can focus on high-impact initiatives.
Here is a step-by-step framework to hire the right partner:
Define the Scope and Leverage Points
Audit your week: Track your time for a week and highlight everything that falls into the $20/hour, $50/hour, or $100+/hour buckets.
Identify the gaps: Determine what you need off your plate first—is it heavy calendar management for the executive team, project tracking, travel logistics, or gatekeeping?
Set the reporting structure: Clarify whether this person will report directly to you, support your executive as well, or sit within a broader administrative team.
Draft a High-Signal Job Description
Avoid generic lists: Skip standard duties and focus on outcomes (e.g., "Keep executive priorities aligned by ruthlessly protecting calendar capacity and anticipating schedule conflicts 48 hours in advance").
Highlight the CoS dynamic: Explicitly state that they will be partnering with a Chief of Staff to support a senior executive or fast-paced organization.
Emphasize soft skills: Look for traits like radical discretion, hyper-communication, emotional intelligence, and proactive problem-solving.
Source High-Caliber Talent
Leverage specialized agencies: Use networks that vet executive assistants specifically for tech, startups, or corporate environments, such as eaHELP or Athena Executive Assistant.
Tap into professional communities: Post in specialized operations or assistant networks like Executive Assistant Network or local administrative groups.
Direct sourcing: Search LinkedIn for former executive assistants, operations generalists, or high-performing hospitality/project coordinators looking to pivot.
Design a Rigorous Interview Process
The initial screen: Check for meticulous communication, punctuality, and baseline organizational intuition.
The competency interview: Ask behavioral questions focused on prioritization under pressure (e.g., "Tell me about a time a schedule collapsed at the last hour—how did you triage it?").
The practical assessment: Give them a realistic work sample test, such as drafting a complex travel itinerary with conflicting constraints or triaging a messy inbox scenario.
Onboard for Partnership
Share your operating manual: Give them a cheat sheet on your communication styles, pet peeves, and decision-making frameworks.
Establish a feedback loop: Schedule daily 10-minute alignment huddles during the first month to calibrate on expectations.
Grant gradual autonomy: Start with task delegation and move quickly toward trusting their judgment on executive communication and gatekeeping.
If you'd like, let me know:
What industry or company size you are in
Whether you are looking for remote, hybrid, or in-person support
I can help you draft a custom job description or design a practical test for candidates.
Hiring an executive assistant (EA) to support you in your role as a Chief of Staff (CoS) is a major force multiplier. When done right, you build a powerhouse partnership that scales your impact across the organization.
Here is a step-by-step framework to hire the right EA for your partnership:
Define the Scope and Leverage Points
Role breakdown: Map out your current responsibilities. Identify what you must own as CoS (strategic alignment, high-level project management) versus what you can delegate (calendar orchestration, meeting prep coordination, travel, inbox triage).
Capability level: Decide whether you need an entry-to-mid-level coordinator to execute tasks or a strategic "Chief of Staff to the CoS" (a high-octane senior EA) who can anticipate problems, manage upwards, and gatekeep effectively.
Draft a High-Context Job Description
Core competencies: Emphasize ruthless prioritization, emotional intelligence, absolute discretion, and proactive problem-solving over just "proficient in Microsoft Office."
Culture fit: Note that they will be an extension of your brand and the executive office. They need high resilience and grace under pressure.
Transparency: Explicitly state that they will report to/partner with the Chief of Staff to support a broader executive function.
Source Through Specialized Channels
Executive assistant networks: Look where top-tier EAs congregate, such as EAtoCO or specialized boutique administrative recruitment agencies.
Professional platforms: Post targeted listings on LinkedIn using keywords like "Strategic Executive Assistant" or "Chief of Staff Support."
Referral networks: Tap into local or virtual Chief of Staff peer groups and communities where former EAs or rising coordinators are recommended.
Design a Rigorous, Multistage Interview Process
Screening call: Assess baseline communication, polish, and enthusiasm for supporting a fast-paced office.
Competency interview: Dig into behavioral questions. Ask for a specific time they had to manage an executive's changing priorities or fix a logistical disaster last minute.
Practical work test: Give them a scenario-based exercise (e.g., “Here are 10 conflicting meeting requests and an email thread where an executive is frustrated. How do you triage this?” or “Draft an agenda and briefing doc for this raw input data”).
Onboard for Partnership, Not Just Tasks
Shadowing & immersion: Spend the first week or two doing a brain dump of your preferences, communication styles, executive quirks, and organizational landmines.
Establish a feedback loop: Set up a daily 15-minute sync to align on the day ahead and a weekly retro to calibrate what is working and what isn't.
Would you like help with:
Drafting the exact job description?
Designing a practical work test/assessment for the interview?
Creating an onboarding and preference-mapping template?
Prioritize meetings
Resolve scheduling conflicts
Ensure preparation happens before important conversations
Executive communications
Draft and polish emails
Manage inbox triage
Track commitments you make
Prepare briefing notes
Operating rhythm
Maintain your weekly priorities
Capture action items
Follow up with stakeholders
Keep recurring meetings running smoothly
Travel and logistics
Complex itineraries
Executive travel preferences
On-the-ground problem solving
Personal productivity
Improve systems
Manage tools and workflows
Reduce context switching
Light Chief-of-Staff leverage
Build meeting prep documents
Coordinate projects
Research topics
Prepare first drafts of presentations
Avoid making the role “everything you don’t want to do.” Great EAs need a clear operating model and decision rights.
2. Hire for judgment, not just experience
The strongest candidates often have:
5–10+ years supporting senior leaders
Experience with confidential information
Excellent written communication
Strong prioritization instincts
Comfort pushing back respectfully
Ability to anticipate needs before being asked
Calmness under pressure
The biggest differentiator is usually judgment: “What should happen next?” rather than “What task was assigned?”
3. Consider the profiles you want to attract
Good backgrounds include:
Senior Executive Assistants supporting CEOs, founders, or presidents
Executive Business Partners
Operations managers who enjoy executive support
Chiefs of Staff earlier in their career who prefer an execution-focused role
High-performing assistants from demanding environments (finance, consulting, technology, government, entertainment)
Do not over-index on famous companies or titles. A person who supported a less-famous executive exceptionally well may outperform someone from a prestigious company.
4. Write a compelling job description
Your posting should answer:
Who will I support?
“You will be the operational partner to the Chief of Staff, helping manage priorities, communications, and execution across a fast-moving organization.”
What authority will they have?
“You will independently make decisions about scheduling, prioritization, and follow-through.”
What does success look like after 6 months?
Examples:
My calendar reflects my priorities
Important meetings are consistently prepared
Follow-ups do not fall through the cracks
I spend less time coordinating and more time leading
5. Use a practical interview process
A strong process:
Round 1: Background and judgment
Ask:
“Tell me about the executive you supported. What did you own without being asked?”
“Describe a time you had to push back on an executive.”
“How do you decide what gets escalated?”
Round 2: Work simulation
Give them realistic exercises:
Calendar test
“You have a week with investor meetings, leadership meetings, travel, and urgent requests. How would you restructure it?”
Writing test
“Draft a response to this difficult email in my voice.”
Prioritization test
“Here are 15 tasks. What do you do first and why?”
Round 3: References
Ask former executives:
“Would you hire this person again?”
“What did they notice before you did?”
“What situations did you trust them to handle independently?”
6. Establish the relationship correctly from day one
The best EA–Chief of Staff relationships have:
Daily or near-daily alignment
Shared visibility into priorities
Clear escalation rules
Permission to challenge each other
Trust with sensitive information
Create a “user manual” for yourself:
How you like information presented
How you make decisions
What annoys you
What requires immediate escalation
Your preferences around meetings, travel, and communication
7. A possible first-90-day plan
First 30 days
Learn your calendar, stakeholders, preferences
Shadow meetings
Build systems
Document recurring processes
Days 31–60
Take ownership of scheduling and preparation
Improve meeting workflows
Create proactive reminders and follow-up systems
Days 61–90
Anticipate needs
Recommend process improvements
Operate independently
8. Decide whether you need full-time or fractional
Consider:
Full-time EA if your calendar, communications, and execution load are daily.
Fractional EA if you need structure but have less than ~20 hours/week of support needs.
Executive Business Partner if you need someone who can manage projects and operate with more autonomy.
If you are already a Chief of Staff, I would generally bias toward a senior EA / Executive Business Partner profile rather than a traditional administrative assistant. The right person becomes a force multiplier for your role.
If helpful, I can also provide:
a Chief of Staff–specific EA job description,
an interview scorecard, or
a list of sourcing channels and compensation ranges.
Personal/admin logistics: travel, expenses, vendors, events, occasional personal tasks
Then add a fifth category: “Things I wish someone would notice without me asking.”
That last category is where an exceptional EA separates themselves from a competent administrator.
For example:
“If I have three meetings about the same initiative, I want my EA to notice the pattern, pull the relevant documents together, identify missing information, and make sure I'm prepared.”
2. Hire for judgment, not typing speed
For a Chief of Staff, I would prioritize:
Exceptional judgment
Proactive follow-through
Discretion and confidentiality
Extreme organization
Written communication
Ability to manage ambiguity
Comfort with senior executives
Technical fluency with your tools
Calm under pressure
Low ego
You want someone who thinks:
“I see a problem coming. Here's what I did about it.”
rather than:
“You didn't tell me what to do.”
A senior EA is making continual judgment calls about priorities, access, scheduling and escalation, so this is substantially more important than administrative experience alone.
3. Consider an “Executive Business Partner” title
If the job is genuinely sophisticated, I'd consider titles such as:
Executive Assistant to the Chief of Staff
or
Executive Business Partner, Office of the Chief of Staff
The second can help signal that you're looking for someone who operates with judgment and ownership rather than a traditional administrative role.
I would not call them a Chief of Staff unless you actually want them owning strategic/cross-functional work. The two roles can overlap, but a CoS generally operates at a broader strategic level than an EA.
4. Write the job description around outcomes
Here's the structure I'd use:
Mission
Make the Chief of Staff dramatically more effective by owning the systems, logistics, information flow, and follow-through that allow the Chief of Staff to focus on the highest-leverage organizational priorities.
What they will own
Own and continuously optimize the Chief of Staff's calendar
Prepare the Chief of Staff for important meetings and decisions
Manage scheduling and stakeholder coordination
Triage incoming requests and determine what requires escalation
Maintain action-item and follow-up systems
Ensure commitments don't fall through the cracks
Coordinate travel, events, expenses, and logistics
Build briefing documents and meeting materials
Maintain key organizational documents and information
Anticipate needs and proactively solve problems
Develop repeatable systems and processes for the Office of the Chief of Staff
What success looks like after 90 days
My calendar reflects my actual priorities.
I rarely have to chase people for follow-up.
I walk into important meetings fully prepared.
Important commitments don't get lost.
I spend substantially less time on logistics and coordination.
You know what needs my attention before I do.
We have a reliable operating rhythm for the Office of the Chief of Staff.
That last section is particularly important. For senior support roles, defining concrete outcomes up front makes hiring and performance management much easier.
5. Use a practical interview process
I'd avoid a traditional interview-heavy process. Instead:
Round 1 — 30-minute screen
Look for:
Communication
Energy
Organization
Career trajectory
Why this role?
Examples of anticipating an executive's needs
Round 2 — behavioral interview
Ask questions like:
“Tell me about a time your executive made a commitment and you realized it was going to be missed. What did you do?”
“Tell me about a time you disagreed with how your executive wanted to use their time.”
“How do you decide what's important enough to interrupt an executive about?”
“Tell me about something you noticed that nobody asked you to do.”
“What would your previous executive say you were unusually good at?”
“Tell me about a mistake you made while supporting an executive.”
The answers will tell you much more than “How do you manage calendars?”
Round 3 — paid working exercise
This is the most important part.
Give them a deliberately messy scenario:
“Here is my calendar for next week, 40 unread emails, five meeting requests, two upcoming trips, three outstanding commitments and a list of priorities. Show me how you'd organize my week.”
Don't expect them to know your preferences. You're evaluating how they think.
Then ask them to explain their choices.
You're looking for someone who says:
“I'd first clarify these three priorities. Then I'd move these meetings because they're lower-value. I'd protect Tuesday afternoon because you have a major deliverable. I'd handle these four requests without bothering you, and I'd escalate these two.”
That's your person.
6. Give them decision rights from day one
This is where many EA hires fail.
Create three buckets:
“Decide without me”
Examples:
Routine scheduling
Moving meetings
Travel arrangements
Declining low-value invitations
Following up with people
Formatting/preparing materials
“Recommend, then act”
Examples:
Rearranging a major executive meeting
Prioritizing competing stakeholders
Changing recurring meetings
Handling sensitive requests
“Always escalate”
Examples:
Personnel issues
Major external commitments
Financial commitments above X
Anything politically sensitive
Anything involving confidential strategic information
Your goal is to progressively move items from “ask me” → “use your judgment.”
7. Make the first 30 days unusually structured
I'd give them a ramp like this:
Week 1: Observe
Calendar, meetings, workflows, tools, stakeholders, preferences.
Week 2: Take over logistics
Calendar, scheduling, travel, meeting preparation.
Week 3: Take over information flow
Inbox triage, follow-ups, action tracking.
Given that you're supporting a Chief of Staff, I'd target someone who is 2–7 years into a high-performance professional career, rather than necessarily someone with 15 years of traditional EA experience.
Good backgrounds can include:
Executive Assistant at a startup or high-growth company
Executive Business Partner
Operations coordinator
Project/program manager
Management consulting analyst/associate
Investment banking analyst
Startup operations
High-end hospitality/event operations
The common denominator is high agency + excellent organization + excellent judgment.
And don't over-index on the resume. Some of the strongest EAs won't have had the exact title before. Even a16z's CoS hiring guidance emphasizes evaluating transferable competencies rather than requiring candidates to have held the precise title previously.
One important warning
Don't hire an EA and then gradually turn them into a junior Chief of Staff.
If you're expecting them to run strategic initiatives, manage executives, own organizational priorities, and make cross-functional decisions, you've probably created a CoS/Business Operations role instead. Conversely, you don't want your actual CoS spending half their week booking flights and chasing calendars. The cleanest setups often have the EA owning the daily operating layer while the CoS owns strategic execution.
If you tell me (1) your company size, (2) whether you're remote/in-person, (3) roughly how many hours/week you're currently spending on admin, and (4) your approximate compensation budget, I can build you a specific EA scorecard, job description, interview rubric, practical exercise, and 30/60/90-day plan for your Chief of Staff role.
"Here is the problem and three solutions, which do you prefer?"
Project Management: Experience keeping cross-functional tracks moving without micromanagement.
Design a Rigorous, Multi-Stage Hiring Process
Resume Screening: Look for longevity in previous EA roles supporting high-capacity leaders (C-suite or VP level).
Initial Screen (30 mins): Test for communication style, emotional intelligence, and cultural alignment.
Skill Assessment: Give them a practical test. For example, a messy calendar-reconciliation scenario or drafting an executive briefing email from rough notes.
Behavioral/Partnership Interview: Assess how they handle stress, competing priorities, and pushback.
Onboard Them as an Extension of Yourself
Set up a daily 15-minute sync in the beginning to align on priorities and feedback.
Grant them gradual authority (e.g., letting them decline meetings on your behalf or speak for you in scheduling loops).
Clarify how they interact with your principal (the CEO/executive) and the rest of the leadership team.
If you want to tailor this process further, tell me:
What is your primary pain point right now (e.g., calendar chaos, project overload, or inbox management)?
Are you looking for a remote, hybrid, or in-office EA?
I can help you draft a job description or design a take-home assessment test.
Hiring an Executive Assistant (EA) when you are a Chief of Staff (CoS) is a massive leverage play. As a CoS, your plate is full of cross-functional projects, strategic alignment, and stakeholder management. Your EA won't just be helping you—they will be multiplying the impact of the entire executive office.
A structured, step-by-step approach ensures you find the right operational partner:
Audit Your Time and Map the Division of Labor
Track your hours for a week and categorize tasks. Separate what requires your strategic CoS brain from what is tactical or administrative.
Keep for yourself: High-level stakeholder comms, sensitive organizational planning, strategic projects, and driving executive initiatives.
Delegate to the EA: Complex calendar management, inbox triage, meeting prep/follow-up tracking, travel logistics, and internal cadence coordination (e.g., tracking team updates or agenda building).
Define the Scope and Write the Job Description
Position this not just as a standard administrative job, but as an Operations/Executive Partner to the Chief of Staff office.
Highlight the core competencies required: hyper-organization, absolute discretion with confidential information, proactive problem-solving, and emotional intelligence.
Clarify the tool stack they will need to master (e.g., Slack, Google Workspace or Microsoft 365, Notion, Asana/Jira, and advanced calendar tools).
Source Through Specialized Channels
Avoid posting blindly on generic boards where you'll get overwhelmed by unqualified resumes.
Tap into specialized EA networks, executive search micro-agencies, or communities like Chief of Staff Network or specialized EA forums and newsletters (like EA Leadership or Baseline).
Reach out to executive recruiters who specifically place high-level administrative talent.
Design a Rigorous, Multi-Stage Interview Process
Screening Call: Focus on communication style, poise, and baseline competence.
Competency Interview: Dive into how they handle chaos. Ask situational questions: "If the CEO's schedule completely implodes 10 minutes before a board meeting, and two department heads are demanding your attention at the same time, what is your triage protocol?"
Practical Assessment: Give them a realistic test. Send a messy, conflicting calendar and ask them to draft an optimized schedule and a polite pushback email to a stakeholder. Test their attention to detail and prioritization speed.
Test for the "CoS-EA Dynamic" (Cultural & Working Fit)
As a CoS, you act as a proxy and a filter for the executive. Your EA acts as a filter and anchor for you.
Look for someone who is proactive rather than reactive —someone who looks around corners to fix a problem before you even notice it.
Ensure your communication styles mesh (do you prefer quick Slack bullets or detailed briefs?) and that they have the confidence to push back on you when necessary.
Onboard with Radical Clarity
Treat their first 30 days as a dedicated integration period.
Document your preferences explicitly (how you like briefs formatted, what constitutes an "interrupt-level" emergency vs. a Slack message).
Give them early, low-risk autonomy so they can build confidence in representing your office across the broader organization.
If you'd like to dive deeper, let me know:
What are the top 3 tasks eating up your time right now?
Do you need this EA to handle any personal support or strictly business operations?
I can help you draft a custom job description or design a practical skills assessment test for the interview loop.
