How to Find an Executive Assistant: Step-By-Step Hiring Guide

This article is adapted from The 29-Hour Work Day.

In the early 2000s, Ethan worked for one of the largest, most high-profile advertising agencies in the United States. Their offices were located in Manhattan and were run by a celebrity in the field. He had a brash personality—a “true New Yorker”—was opinionated and not afraid to yell. Consequently, at that time, many on his leadership team ruled their departments in a similar style.

Ethan entered the company as the assistant to the man leading the digital and direct/print production portion of the agency. He was a man who yelled—a lot! To say he was demanding would be an understatement. So perhaps it’s no surprise that, prior to Ethan’s arrival, he had gone through thirteen assistants in the previous twelve months.

That last line is not a series of typos—the man literally had thirteen assistants in twelve months. Yes, you could say he was a bit of a tyrant. However, in the end, Ethan got the last laugh; he stayed with the company longer than his principal did. You could also say that if Ethan’s principal had been a little pickier and taken the time to find the right EA for him from the beginning, he would not have spent so much time looking for others—time he could have spent on activities that would positively impact the company’s bottom line.

Granted, it can be difficult to find the right EA. Everyone looks almost too perfect on their resume. So, here are some key considerations to keep top of mind when recruiting an EA.

What Does an Executive Assistant Do?

Today’s executive assistants do far more than answer phones and schedule meetings. 

At the most fundamental level, EAs provide time arbitrage for their executives. The true value of a great EA isn’t measured in percentages on a spreadsheet but in how much time they give back to their principal.

According to “The 29-Hour Work Day” by Ethan and Stephanie Bull, founders of ProAssisting, top executive assistants serve as performance multipliers who enable leaders to accomplish more than they could alone. 

They function as:

• Business Partners: They represent you in meetings, provide input on decisions, and act as your “mini-me” when needed.
• Chiefs of Staff: They become the single point of contact between you and everyone else, filtering information and handling communications.
• Project Managers: They take ownership of projects from start to finish, coordinating all aspects and players involved.
• Assistant/Schedulers: They master your calendar like Tetris pros, ensuring you’re always in the right place at the right time.
• Personal Assistants: They handle tasks in your personal life that save you time and mental energy.

On a practical level, an EA serves as the conduit for information flow. This allows the principal and assistant to have an 8-minute conversation on Wednesday morning that transforms the principal’s to-do list from 12 items down to 2. 

The EA handles the rest, representing the executive, their office, and the company in the best possible light.

A day in the life of an EA might involve:

• Managing complex calendars and prioritizing meeting requests
• Serving as the first point of contact for clients and team members
• Triaging emails and responding on your behalf
• Preparing briefing materials for upcoming meetings
• Coordinating travel arrangements
• Creating presentations and reports
• Handling personal tasks like booking reservations or researching gift ideas
• Managing short, medium, and long-term projects

The overarching goal of an executive assistant remains constant: giving back time to the executive!

Executive Assistant Skills and Qualifications

When searching for an EA, you’re looking for a unique blend of technical abilities and interpersonal skills. 

It’s important to note that the barrier to entry for the executive assistant title is low to non-existent—anyone can call themselves an executive assistant. 

This makes it crucial to distinguish between someone who’s truly an executive assistant vs an administrative assistant or just a task-based person.

The most effective EAs possess what we call “superpowers“:

• ESP (Executive Support Perception): This isn’t mind reading, but the ability to anticipate your needs and have solutions ready before you even ask. A good EA will learn your preferences, habits, and priorities to stay two steps ahead.
• Synchronization: Great EAs understand your productivity cycles and energy patterns. They know when you’re most alert and schedule important meetings accordingly. They protect your time and ensure your day flows smoothly.
• Omniscience: Top EAs develop systems and processes that ensure nothing falls through the cracks. They create workflows that keep everything running efficiently.
• Translation: The best EAs can effectively communicate with everyone from mailroom staff to board members. They master the “velvet no”—the ability to decline requests in such a gracious way that people still feel valued.

Beyond these superpowers, look for these tangible executive assistant skills and qualifications:

Hard Skills:

• Excellent written communication
• Proficiency with productivity tools (Microsoft Office, Google Workspace, etc.)
• Calendar management expertise
• Basic bookkeeping and expense tracking capabilities
• Typing speed and accuracy
• Research skills

Soft Skills:

• Exceptional verbal communication
• Discretion and confidentiality
• Problem-solving abilities
• Adaptability and flexibility
• Emotional intelligence
• Proactivity
• Attention to detail
• High-touch hospitality mindset

When evaluating qualifications, experience is paramount. 

Look for candidates who have actually performed in the role and can articulate how their support has helped previous principals. 

Some companies consider a college degree essential for an EA position. A degree does show someone can pursue long-term goals and achieve a certain level of accomplishment. 

However, this educational qualification alone doesn’t guarantee they’ll excel as an executive assistant.

The ideal EA has administrative experience and a service-oriented personality. They should take pride in making others successful and find fulfillment in supporting leadership. 

How to Find an Executive Assistant

Finding the right EA requires a thoughtful approach. Here’s a step-by-step process:

1. Define Your Needs

Before you start searching, get clear on what you actually need:

• How many hours of support do you need weekly?
• Do you need in-person assistance, or would remote work be sufficient?
• What are your must-have skills versus nice-to-haves?
• What budget can you allocate to this position?

Create a detailed job description outlining responsibilities, qualifications, and expectations. Be specific about the role you envision.

2. Determine the Type of Assistant

You have several options when hiring an assistant:

Type	Description	Best For
In-house, Full-time EA	Works exclusively for you in your office	Executives who need constant support and face-to-face interaction
Remote Executive Assistant	Dedicated support, but they work virtually	Leaders who need high-level assistance but not physical presence
Virtual Assistant	Typically handles more administrative tasks, often part-time	Small business owners with basic administrative needs
Fractional/Shared Assistant	Works for multiple executives within a company (or different companies)	Organizations (or entrepreneurs) looking to maximize their budget

The costs associated with these options vary widely:

• A full-time, in-house EA in major metropolitan areas can cost $80,000-$120,000+ annually ($8.5K+ per month), plus benefits 
• A remote executive assistant from a premium service provider like ProAssisting typically starts around $3,300 monthly
• Virtual assistants typically charge $5+ per hour

You might find you don’t need a full-time assistant. That’s where a fractional executive assistant could be ideal. 

Or perhaps you need even less support, in which case a virtual assistant might be sufficient.

3. Source Candidates

There are multiple ways to find qualified candidates:

Traditional Recruiting Methods:

• Post job ads on Indeed.com, LinkedIn, or other job boards
• Hire an executive assistant staffing agency
• Get referrals from your network
• Consider internal promotions from administrative roles

Specialized Services:

• Premium remote EA providers like ProAssisting
• Virtual assistant companies
• Freelance platforms (Upwork, Fiverr)

Networking Approaches:

• Assistant professional organizations
• LinkedIn searches and outreach
• Industry conferences and events

If you’re serious about finding a full-time executive assistant, consider hiring a recruiter who can filter candidates based on your specific requirements. 

They can narrow down prospects based on industry experience, compensation level, tenure, and how long they’ve worked as an assistant.

4. Screen Resumes

When reviewing resumes, look for:

• Career progression showing increased responsibilities
• Longevity in positions (at least 1-2 years)
• Experience supporting executives at your level or higher
• Industry knowledge (helpful but not always necessary)
• Evidence of professional development and learning

Red flags might include:

• Frequent job changes without explanation
• Gaps in employment without context
• Vague descriptions of responsibilities
• Poor formatting or errors (attention to detail is crucial)

5. Interview Process

A thorough interview process is essential. 

Consider using these stages:

Initial Screening:

• Brief phone or video call to assess communication skills
• Basic questions about experience and availability
• Technical assessment if relevant (typing test, software proficiency)

In-depth Interview:

• Situational questions about handling specific scenarios
• Deeper dive into past experience and achievements
• Discussion of your working style and what support you need

Skills Assessment:

• Practical tasks that simulate real responsibilities
• Writing sample to evaluate communication
• Calendar exercise to test organizational skills

Casual Meeting:

• Coffee or lunch to assess personality fit
• Observation of how they interact with others (restaurant staff, etc.)
• Conversation about interests and working styles

Sample interview questions might include:

• “Tell me about a time you had to manage a challenging situation for an executive.”
• “How would you handle conflicting priorities from multiple stakeholders?”
• “What systems do you use to ensure nothing falls through the cracks?”
• “How would you manage my calendar if I tend to overbook myself?”

6. Check References

Always contact the references that the potential EAs provide directly. 

Ask specific questions about:

• Reliability and punctuality
• Problem-solving abilities
• Communication style
• Discretion and confidentiality
• Areas for improvement

7. Onboarding

Once you’ve selected, properly onboarding an executive assistant into your world is crucial. 

Share:

• Your communication preferences
• Decision-making authority limits
• Access to necessary accounts and information
• Introduction to key contacts
• Clear expectations and feedback mechanisms

Looking to skip the time-consuming search process?

ProAssisting offers a simpler solution. Our rigorous vetting process accepts less than 5% of applicants, ensuring you’re matched with a highly qualified remote executive assistant. 

With plans starting at $3,300 per month, you get dedicated support from an experienced professional without the overhead costs of a full-time hire. 

Your ProAssistant can handle everything from calendar management and email triage to project coordination and personal tasks—all aimed at giving you back valuable time. 

Schedule a free consultation to learn how a ProAssistant can simplify your work life!

Common Mistakes to Avoid When Hiring an Executive Assistant

Even experienced executives make these common mistakes when hiring EAs:

• Focusing Too Much on One Dimension: Some executives hire based strictly on resume qualifications while overlooking personality fit, while others prioritize personality at the expense of experience. You need alignment on both fronts. Look for someone who has the experience you need, combined with a personality that enables a true business partnership.
• Making Educational Requirements Too Rigid: Don’t overlook great candidates just because they lack a college degree if they have exceptional experience. When companies like Apple and Google removed college degree requirements from their hiring processes, they recognized there’s outstanding talent available through non-traditional paths.
• Limiting Your Search to Industry Experience: A common mistake is believing you need an assistant who already works in your specific industry. Great executive assistants are industry and principal-agnostic. Don’t overlook exceptional talent just because they haven’t worked in your field before.
• Not Being Clear About Expectations: Vague job descriptions lead to misunderstandings. Be specific about responsibilities, working hours, communication expectations, and how performance will be measured.
• Rushing the Hiring Process: Finding the right EA takes time. Rushing can lead to a poor fit that costs more in the long run. Be patient and thorough in your search.
• Micromanaging After Hiring: Once you hire an EA, you need to trust them to do their job. Micromanaging defeats the purpose of having an assistant in the first place and wastes both your time and energy.
• Not Providing Feedback: Regular, constructive feedback helps your EA improve and better support you. Schedule check-ins and performance reviews.
• Undervaluing the Position: If you treat the EA role as “just an assistant,” you’ll never get the full benefit of what a great EA can provide. View them as a strategic partner, not just support staff.

Tips for Hiring the Right Executive Assistant

When searching for the perfect executive assistant, consider that different positions require different types of assistants. 

An EA supporting vice presidents may primarily manage calendars and expense reports. On the other hand, an executive assistant to the CEO often serves as the face of the company and requires different qualities.

The right executive assistant for a high-level position combines personality, seasoned experience, and alignment with your specific job requirements.

Look for someone with poise, presence, and emotional intelligence who can translate those qualities into effective soft skills when representing you and your office.

Here are some practical tips:

Look Beyond First Impressions

As with a resume, that first handshake and the first conversation you have may not give you an accurate portrayal of your candidate. Their speaking voice and the way they make eye contact and hold their posture during the initial interview will be done with utmost care to present to you the person you want to hire—not necessarily the person they really are.

Gruff people can pull off polished and charming for an interview. So, go beyond that first impression and ask questions aimed toward revealing what may be behind the veneer.

1. How did they manage their previous principal’s time? Can they give an example of when it was more tricky than usual?

2. What about an example from when they had to play the role fo gatekeeper? How did they deal with the senior leadership team wanting to see the executive without an appointment of checking with them first?

3. How did they handle a crisis or problematic situation?

Listen to the answers and look for clues that tell you whether this person used EA superpowers to achieve the best results for everyone. And, if not, were the results they achieved accomplished with panache and confidence? Or with abrasive assertiveness? Based on their answers, you should ultimately ask yourself: is this the kind of person I want representing me and my company?

Something to keep in mind as you are interviewing is that a pause before answering is not a negative. EAs often perform so many functions and have been through so many different scenarios that they may need to stop and think about specific examples to pull from a vast array of experiences.

So, instead of asking them, “What did you do at Company X?” instead ask, “Tell me what your responsibilities were when you first started.” Then, when they have answered that, ask them what their responsibilities were when they left (or are currently fulfilling). Compare and contrast the two, and you will be able to fill in the blanks for a full scope of their capabilities.

Additionally, pay attention to the way a candidate answers your questions. If you have to continue to pull a thread to get them to tell you their story in a succinct way, realize that is probably how they will interact with your clients and staff members. Such a communication style makes it difficult to create personal connections and partner with others.

Be Casual

We always suggest that principals try to have at least one interview that is more casual than an in-office meet-and-greet. Meeting over breakfast or lunch can be ideal because it will give the principal a better idea of what the person is really like. Your office, with a desk between you, will set up a psychological barrier that may prevent the candidate from giving you a full picture of who they are and what kind of character they possess. Whereas breakfast or lunch meetings tend to remove that barrier so you get a fuller, more real picture of them on which to base your hiring decisions.

At these meetings, consider their tone of voice—are they at ease having a general conversation? Do they easily make eye contact? How do they treat the staff at the restaurant? Are they pleasant to them? Does it seem as if this person will be congenial to work with? Being able to communicate clearly and effectively, to carry on a free-flowing conversation that doesn’t feel forced or stilted is so very important—especially in today’s world where so much interaction is done via phone or video conference.

In such a casual situation, you can also see how open someone is to criticism. A technique we use to check on that is to challenge people about how their resumes differ from their LinkedIn profile. Watching how they react to such a question in a relaxed atmosphere will reveal just how they will handle mistakes or corrections.

Of course, the danger in such meetings is that the person may feel too comfortable and overshare personal information. That is yet another red flag. If they do not have the discretion to maintain a sense of privacy and confidentiality with their personal business, then you know they will not have it to maintain yours.

Your Gut Will Know

Often, you’ll know you have found the right EA because you will feel it in your gut. There have been times when we have found assistants that seemed perfect on paper—they had the skills, they had the experience, but our gut told us something was off.

Every time we ignored our gut because a candidate’s on-paper information was just so very good, we regretted it. So listen to your gut. If your first instinct is to say “yes,” then it is probably right. Likewise, listen if your gut tells you “no.” In the long run, you will save time and aggravation if you have the wherewithal to sit and touch base with your instincts—and follow through on what they say.

It’s often better to take your time when hiring an EA. A sense of urgency may cause you to discount any potential negatives in a candidate that could wind up causing you to let them go in just a couple of months and start the hunt anew (as with Ethan’s principal, who had to go through the search thirteen times).

As Dr. Stephen Covey says, “What is important is seldom urgent, and what is urgent is seldom important.” It is more important you find the right person than it is that you find the first one to fill a vacancy.

For more advice on finding the right EA, you can find The 29-Hour Work Day on Amazon.

Frequently Asked Questions (FAQs)

Here are answers to common questions about hiring an executive assistant:

What’s the Difference Between an Executive Assistant and a Personal Assistant?

The main difference between having an executive assistant or a personal assistant is in focus and scope:

Executive Assistant:

• Primarily supports professional responsibilities
• Manages business communications and scheduling
• Represents the executive in professional contexts
• Often works with multiple stakeholders

Personal Assistant:

• Focuses more on personal tasks and lifestyle management
• Handles personal scheduling, errands, and home management
• Typically doesn’t represent the executive professionally
• May handle family responsibilities

However, in practice, many high-level EAs handle both professional and personal responsibilities. The Bulls note that “by making your EA part of both worlds, you optimize their ability to save you time.“

How Much Does it Cost to Hire an Executive Assistant?

Costs vary widely based on location, experience level, and employment type:

• In-house, Full-time EA: $60,000-$300,000+ annually plus benefits (20-30% additional cost)
• Remote Executive Assistant: $3,000-$7,000 monthly from premium service providers
• Fractional EA: Typically 1/3 to 1/2 the cost of a full-time EA, depending on time allocation

Remember that the right EA should provide a positive ROI by freeing you to focus on higher-value activities.

What Certifications Should an Executive Assistant Have?

While certifications aren’t essential, they can indicate that a candidate truly respects the craft of being an executive assistant. We don’t place much merit on certifications compared to seasoned work experience combined with the right personality. 

However, certifications can demonstrate that someone takes their role seriously and is committed to continuous improvement.

Valuable pursuits might include:

• Certified Administrative Professional (CAP)
• Microsoft Office Specialist (MOS)
• Project Management certifications (CAPM, PMP)
• Social media management certifications
• Event planning certifications
• Chief of staff programs
• Emotional intelligence training

Conclusion

Finding the right executive assistant requires understanding both what you need and what skills to prioritize in your search. 

The process takes time, but with clear expectations and a focus on both technical abilities and interpersonal skills, you’ll find someone who can truly transform your productivity.

For those seeking a simpler solution, ProAssisting offers elite executive assistants with 5+ years of experience who can handle 95% of what an in-house EA would manage. 

Our unique 1:3 ratio ensures your assistant isn’t spread too thin, costing 50-80% less than a full-time hire!

The best part is that 75% of your monthly retainer goes directly to your ProAssistant. That means we attract and retain the highest-caliber talent for long-term partnerships, creating continuity and more profound knowledge of your business.

Schedule your free consultation today and discover how quickly you can reclaim your time!

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Ethan Bull is a co-founder of ProAssisting, a next-generation remote executive assistance firm for business owners and C-suite executives. With a background in hospitality and expertise in the EA space, Ethan has held a variety of senior positions, including Director of Administrative Services and senior EA to the president and CEO at Rochester Regional Health.

Stephanie Bull is ProAssisting’s co-founder and the former EA for J. Crew’s CEO and the CEOs of two multibillion-dollar hedge funds. Before developing ProAssisting, Stephanie proved herself an expert in the field and a vital addition to the C-suite by fulfilling a variety of roles, including chief of staff, estate manager, and investment liaison.