How to Hire an Executive Assistant
Finding the right executive assistant can change everything about how you work. A great EA doesn't just manage your calendar or answer emails. They anticipate needs, solve problems before they escalate, and become a trusted partner in achieving your organizational goals. But hiring executive assistants isn't as simple as posting a job and picking a resume. You need someone who fits your workflow, understands confidentiality, and has the skills and traits to keep pace with a demanding executive role.
Whether you're a C-suite leader at a growing company or running a small business that's scaling fast, this guide will walk you through how to hire an executive assistant who delivers real value.
Why You Need an Executive Assistant
Before you start the hiring process, get clear on why you need an EA. Top executives often spend hours on administrative tasks that pull them away from strategic work. An executive assistant can offload scheduling, correspondence, travel arrangements, and even some personal tasks, freeing you to focus on what moves the business forward.
The best executive assistant does more than follow instructions. They think ahead, manage sensitive information with discretion, and adapt to your unique needs. They supplement your strengths and cover your blind spots. If you're drowning in operational details or missing important deadlines because you're stretched too thin, it's time to hire someone who can help.
Executive Assistant vs Administrative Assistant
People sometimes confuse an executive assistant with an administrative assistant or even a secretary, but there's a big difference. While administrative assistants typically support teams or departments with general office duties, an executive assistant works directly with senior leadership. They need stronger problem-solving abilities, better communication skills, and a deeper working knowledge of the business. An EA operates with more autonomy and handles higher-stakes responsibilities.
Define What Your Executive Assistant Role Looks Like
Every executive has different needs, so cookie-cutter job descriptions rarely work. Start by listing what you need to delegate. Do you want someone to manage complex travel logistics? Coordinate with other administrative professionals across departments? Handle both professional and personal tasks?
Think about whether you need someone in-person or if a remote executive assistant would work. Remote work has opened up access to top talent outside your immediate area, though some executives prefer having their EA physically present for spontaneous collaboration and quick problem-solving.
Your job posting should be specific. Instead of vague phrases like "organized and detail-oriented," describe actual scenarios: "You'll manage a calendar with 40+ meetings per week across three time zones" or "You'll prepare briefing documents for board meetings and maintain strict confidentiality around financial data." This helps you attract the right candidates and filter out people who aren't a fit.
Should You Use an Executive Assistant Staffing Agency?
Finding someone who checks all the boxes takes time you probably don't have. That's where staffing agencies come in. An executive assistant staffing agency specializes in matching companies with pre-vetted, qualified candidates. They understand what makes a great EA and can tailor their search to your requirements.
At Oceans Talent, we focus on connecting businesses with executive assistant talent that fits their specific culture and needs. Unlike generalist recruiters who might throw any administrative position your way, a boutique executive search firm digs deeper. We assess technical skills, emotional intelligence, time management abilities, and cultural fit before introducing you to candidates.
Working with a search firm or recruiter saves you from sorting through hundreds of unqualified applications. You get access to vetted candidates, often including passive job seekers who aren't actively looking but would be perfect for your role. Many agencies also offer direct placement services and help with onboarding, making the transition smoother.
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What Skills Should Your Executive Assistant Have?
The right executive assistant brings both hard and soft skills. On the technical side, they should be comfortable with common business software, have strong organizational systems, and know how to prioritize when everything feels urgent. They should understand your industry well enough to communicate intelligently with partners, clients, and staff.
But the intangibles matter just as much. Look for someone who's proactive rather than reactive. The best executive assistants spot potential issues and solve them quietly. They're discreet, especially when handling sensitive information. They communicate clearly, whether they're drafting an email on your behalf or explaining why a meeting needs to be rescheduled.
Time management is non-negotiable. Your EA will juggle competing priorities daily, and they need to stay calm under pressure. Problem-solving skills separate good EAs from great ones. When plans fall apart, can they find solutions quickly?
Interview Questions That Actually Matter
Generic interview questions won't tell you much. Instead, ask about specific situations:
"Tell me about a time you had to completely rearrange an executive's schedule last-minute. How did you handle it?"
"How do you prioritize when everything is marked urgent?"
"Describe how you've maintained confidentiality in a previous role."
"What systems do you use to stay organized, and how would you adapt them to my workflow?"
Pay attention to how candidates answer. Do they provide concrete examples? Do they take ownership of mistakes? Can they articulate their process? The best executive assistant candidates will ask you questions too, showing they're thinking about how to add value from day one.
Don't Skip Checking References
Checking references sounds obvious, but many hiring managers rush through this step. For an EA role, references are critical. Ask former employers about reliability, discretion, and how the candidate handled high-pressure situations. Did they anticipate needs or just respond to requests? How did they handle mistakes?
If you're hiring through an executive assistant staffing agency like Oceans, much of this vetting happens before you ever meet the candidate. That's part of what makes working with talent solutions providers valuable. You're not starting from zero.
Consider the Logistics: Remote, Hybrid, or In-Person
The rise of remote work has changed how companies think about administrative positions. A remote executive assistant can be just as effective as someone in local offices, especially if your work involves lots of virtual meetings anyway. Remote options also give you access to US-based talent across the country, not just people who live near your headquarters.
That said, some executives prefer having their EA nearby for in-person collaboration. Think about your working style. Do you tend to think out loud and prefer someone you can turn to immediately? Or do you work primarily through digital channels anyway?
Making the Final Decision
When you're down to your final candidates, trust your instincts but verify with data. Which candidate demonstrated the best understanding of your unique needs? Who asked the smartest questions? Who seemed most aligned with your company culture?
If you're working with a recruiter, lean on their expertise. They've seen hundreds of placements and can offer insights you might miss. Hiring the right executive assistant is too important to rush. A dedicated executive assistant who's the right fit will make your professional life significantly easier. The wrong hire creates more work than doing it yourself.
Setting Your New Assistant Up for Success
Once you hire a top EA, invest time in proper onboarding. Share your preferences, pet peeves, and priorities. Give them access to the systems and people they need. Introduce them to key staff members and external contacts. The better you set expectations upfront, the faster they'll start adding value.
Remember, even highly experienced administrative professionals need time to learn your specific style. Be patient but clear about what success looks like. At Oceans, we've seen that client success often comes down to how well executives communicate with their new hires during those first few weeks.
Hiring an executive assistant is an investment in your productivity and peace of mind. When you find the right EA, you'll wonder how you ever managed without them.
Frequently Asked Questions
How much does it cost to hire an executive assistant?
Executive assistant salaries vary based on experience, location, and whether the role is remote or in-person. Entry-level EAs might earn $50,000 to $65,000 annually, while top executive assistant professionals with extensive experience can command $90,000 to $150,000 or more, especially in major markets. Using an executive assistant staffing agency typically involves a placement fee, but it saves significant time and often results in better long-term matches.
What's the difference between hiring through an agency versus posting a job myself?
When you post a job yourself, you'll spend considerable time reviewing applications, conducting initial screenings, and checking references. Agencies present only vetted candidates who match your specific requirements, saving you weeks of work. They also have access to passive candidates who aren't actively job hunting but might be perfect for your role. The right people aren't always the ones browsing job boards.
Should I hire a virtual assistant instead of an executive assistant?
Virtual assistants and executive assistants (link to Executive Assistant vs. Virtual Assistant blog post) serve different purposes. Virtual assistants typically handle discrete tasks (link to Tasks to Outsource to a Virtual Assistant blog post) on a project or hourly basis and often work with multiple clients. An executive assistant is dedicated to supporting you full-time, developing deep knowledge of your business, and taking on increasingly complex responsibilities. If you need strategic partnership and someone who can anticipate your needs, hire an executive assistant.
How long does it take to hire a great executive assistant?
If you're handling the search yourself, expect 6 to 12 weeks from posting to start date. Working with a search firm or executive assistant staffing agency can cut this to 3 to 6 weeks since they maintain networks of pre-vetted, qualified candidates. However, don't rush. Hiring the right executive assistant is worth taking the time to find the perfect match rather than settling for someone who's merely adequate.
What should I look for when you're hiring an EA for the first time?
Focus on finding someone with proven organizational skills, excellent communication abilities, and experience supporting senior leaders. Look for candidates who demonstrate initiative, discretion, and adaptability. An assistant who's worked with executives in similar industries will have a shorter learning curve. Most importantly, find the right cultural fit. Your EA will be your closest professional partner, so chemistry and trust matter enormously.
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