How to Hire a Great Executive Assistant

Making the in-office vs. remote decision

When you likely need an in-office executive assistant:

If you work primarily from the office and most of your team is on-site, you’ll probably want someone physically present.

The reality is that many senior executives still prefer the immediacy and rapport that comes from having their assistant steps away. If you frequently host clients, need someone to manage physical files, or value the ability to have quick in-person check-ins throughout the day, local hiring makes sense.

When remote executive assistants work perfectly:

If you have a hybrid setup or your company operates as a distributed team, remote executive assistants can be just as effective—and often more cost-efficient.

The key requirement is time zone compatibility. Most executive assistant tasks—calendar management, email screening, travel coordination, project tracking, and stakeholder communication—work seamlessly through digital tools.

Remote executive assistants often bring additional advantages: they’re typically more self-directed (having to work independently) and often have experience with multiple digital collaboration tools.

The practical reality: If you can work effectively with remote team members in other roles, you can almost certainly work effectively with a remote executive assistant. The relationship is built on clear communication, systematic processes, and mutual trust—none of which require physical presence.

Once you’ve made this decision, your sourcing strategy becomes much clearer.

Sourcing channels for executive assistants

Why working with a recruiting partner makes a difference

Specialized recruitment partners bring three critical advantages to executive assistant hiring: access to pre-vetted talent pools, deep understanding of the role’s nuances, and expertise in evaluating the soft skills that determine long-term success.

• Access to passive candidates: The strongest executive assistants often aren’t actively job searching—they’re typically happy in their current roles but open to the right opportunity. Recruitment partners maintain relationships with high-performing executive assistants and can present opportunities that might not otherwise come to market.
• Expertise in cultural fit assessment: Beyond technical skills, executive assistant success depends heavily on personality alignment, communication style, and working preferences. Experienced recruiters understand these dynamics and can identify candidates likely to thrive in your specific environment.
• International hiring expertise: Specialized staffing and recruitment partners handle the complexities of international hiring, English proficiency screening, and ongoing support that ensure successful remote working relationships.

The investment in specialized recruitment often pays for itself through reduced time to hire, lower turnover rates, and access to candidates who wouldn’t be available through traditional job posting methods.

For example, Kordis, a fractional CFO services provider, initially struggled with offshore hiring from the Philippines due to time zone challenges and communication barriers. When they partnered with Near to hire an executive assistant in Latin America, they hired a candidate with two degrees (Business Administration and Psychology) and over 10 years of experience in similar roles.

The result? They cut their normal hiring timeline in half while getting better time zone alignment and no longer dealing with communication difficulties.

Stage 1: Before and during sourcing

Define the role and your true priorities beyond generic requirements

Rather than creating a wish list of every possible skill, start by outlining the key responsibilities and expectations for your specific executive assistant position.

Are you looking for someone who can manage complex project coordination, or do you need someone who excels at stakeholder communication and relationship management?

Craft job descriptions that attract proactive candidates

Use your role definition to craft a comprehensive job description that includes specific examples of the types of problems your executive assistant will solve, the decision-making authority they’ll have, and the impact they can make on your productivity.

According to our recruiters, you should ask for “at least 2 years of experience in the same position, assisting a CEO or VP” as a baseline requirement.

Include required soft skills, experience, and any particular software proficiencies needed, but be clear about what are nice-to-haves versus must-haves.

Skills-based hiring approaches expand candidate pools by 6.1x globally, so focus on relevant capabilities rather than rigid degree requirements.

For detailed guidance on writing job descriptions that will attract the right talent, check out our executive assistant job description guide and template.

Determine salary range and choose the right sourcing platforms

Research and establish a competitive salary range based on industry standards, the candidate’s experience level, and their geographical location.

Then choose one or more of the sourcing strategies we covered earlier.

Stage 2: Screening and evaluation

Screen resumes and look beyond credentials for systematic thinking

Review applications to shortlist candidates who meet the job requirements and demonstrate potential cultural fit. The best executive assistants demonstrate organized approaches to complex challenges, so during initial conversations, ask candidates to walk through their current organizational systems and how they handle competing priorities.

Conduct structured interviews that assess ownership and proactive problem-solving

Arrange in-person or virtual interviews to assess each candidate’s communication and interpersonal skills, problem-solving abilities, and overall compatibility with the executive and company.

Look for specific examples where candidates identified inefficiencies and implemented improvements without being asked. This reveals the entrepreneurial mindset that separates excellent executive assistants from task-focused administrative support.

When interviewing executive assistant candidates, consider that 86% of HR professionals find behavioral interviewing effective, according to the US Chamber of Commerce, and Google’s research shows structured interviews result in 35% higher candidate satisfaction among rejected candidates, improving your employer brand even among those not selected.

Evaluate communication style and cultural fit

Since executive assistants often represent you in communications with internal teams and external stakeholders, pay close attention to how they articulate ideas, ask clarifying questions, and adapt their communication style to different audiences.

Check references and administer practical tests

For shortlisted candidates, contact references to verify the candidates’ past job performance and reliability.

If applicable, provide practical tests to evaluate the candidates’ proficiency with daily tasks they’ll be handling, such as scheduling or drafting correspondence.

Our recruiters note that companies can “create a case study based on their needs, for example building an email classification system or investigating how a tool would impact their team.”

Stage 3: Making the offer and closing

Move quickly with competitive packages

Top executive assistant candidates often have multiple opportunities. Once you’ve identified the right person, be prepared to make a compelling offer that includes not just salary but also professional development opportunities and clear growth trajectories.

Our recruiters note that “PTO and flexibility to have local holidays off make the difference for this role” when it comes to benefits that matter beyond base compensation.

Set clear expectations for the first 90 days

Provide a thorough onboarding process to familiarize the executive assistant with your company’s operations, culture, and expectations.

This structured onboarding plan helps your new executive assistant understand your preferences, priorities, and communication style while giving them quick wins to build confidence and momentum.

By following this systematic approach, you can streamline the hiring process and significantly increase the likelihood of finding an executive assistant who becomes a valuable strategic partner to your team.

“How do you stay organized on a daily basis?”

As our recruiters explain, “As an EA, it’s essential to be organized and stay one step ahead of your executive’s needs.” This is their go-to question to reveal candidates’ underlying systems and whether they think strategically about organization rather than just reactively managing tasks.

What to listen for: Specific tools, methodologies, and thought processes. Strong candidates describe systematic approaches that include both digital tools and mental frameworks for prioritization.

“Can you share an example of a project you implemented to optimize your executive’s day-to-day operations?”

This gets directly at the proactive mindset that separates excellent executive assistants from reactive support staff. You want to hear about initiatives they took independently to solve problems.

What to listen for: Examples that show business thinking, measurement of results, and consideration of broader team impact—not just task completion.

“Tell me about a time you had to manage conflicting priorities from multiple stakeholders. How did you handle it?”

Executive assistants regularly navigate competing demands while maintaining relationships with different personality types and communication styles.

What to listen for: Evidence of diplomatic communication, systematic prioritization frameworks, and the ability to make judgment calls when you’re not available for guidance.

“Describe how you would handle a sensitive situation where someone important is demanding access to me, but I’ve indicated I’m not available.”

This reveals communication skills, judgment under pressure, and understanding of professional boundaries—all critical for someone who serves as your gatekeeper.

What to listen for: Responses that balance firmness with professionalism, show understanding of relationship dynamics, and demonstrate creative problem-solving.

“How do you anticipate needs before they become urgent requests?”

The strongest executive assistants develop intuitive understanding of patterns, seasonal business cycles, and your personal preferences to stay ahead of requirements.

What to listen for: Specific examples of pattern recognition, systematic approaches to learning preferences, and proactive communication about potential issues.

1. Obsessing over industry experience instead of core capabilities

Many companies create unnecessarily narrow requirements like “must have 5+ years in SaaS” or “experience in financial services required,” which eliminates candidates with stronger organizational skills and business judgment.

According to our recruiters, industry-specific experience rarely impacts performance. What matters is whether someone can learn your business quickly and think strategically about priorities.

The fix: Focus your requirements on transferable skills like systematic thinking, stakeholder management, and proactive problem-solving. A talented executive assistant who’s supported a CEO in retail can absolutely excel supporting a CEO in tech—they understand executive needs, not just industry jargon.

2. Dismissing startup experience in favor of “prestigious” corporate backgrounds

Large companies often overlook candidates with startup or small company experience, assuming corporate experience equals higher quality. But according to our recruiters, startup experience actually develops the proactive mindset and sense of urgency that makes executive assistants truly exceptional.

The fix: Value adaptability and initiative over brand names on resumes. Someone who’s been the sole administrative support for a 50-person startup likely has broader skills and more resourcefulness than someone who handled one specific function at a Fortune 500 company.

3. Trying to evaluate relationship potential in a single interview

The executive assistant relationship is deeply personal—you’re trusting someone with your schedule, communications, and often confidential information. Yet many companies make hiring decisions after just one conversation, missing critical chemistry and trust factors.

The fix: Build multiple touchpoints into your process. Consider a working interview where candidates handle real tasks, schedule separate conversations with different team members they’d interact with, and, when possible, speak with previous executives they’ve supported, not just HR references.

4. Ignoring communication red flags because other qualifications look good

Since executive assistants represent you in emails, calls, and meetings, communication quality directly affects your professional reputation. Yet hiring managers often overlook unclear explanations, rambling responses, or difficulty expressing ideas during interviews.

The fix: Pay close attention to how candidates structure their thoughts, ask clarifying questions, and adapt their communication style during your conversation. If they struggle to communicate clearly under the low pressure of an interview, they’ll likely struggle when representing you to important stakeholders.

Is an executive assistant the same as a secretary?

No, an executive assistant is not the same as a secretary. Executive assistants handle a broader range of responsibilities, including managing executive schedules, strategic planning, and dealing with confidential information. They often require advanced communication and problem-solving skills.

Secretaries typically focus more on routine clerical duties, such as typing, filing, and handling phone calls.

What is the difference between an executive assistant and an administrative assistant?

While both executive assistants and administrative assistants provide high-level administrative support, their roles differ in scope and level of responsibility.

Executive assistants typically support top-level executives and may have decision-making authority, handle confidential information, and are involved in strategic planning.

Administrative assistants, on the other hand, generally provide broader support to an entire team or department, focusing on clerical tasks, such as filing, scheduling, and basic correspondence.

Executive assistants often require more experience and may command higher salaries due to their specialized roles and closer work with executive leadership.

Should I hire an in-office or remote executive assistant?

The choice between an in-office or remote executive assistant hinges on your business’s needs. In-office assistants offer direct, on-site support that is ideal for hands-on tasks, while remote assistants can reduce overhead costs and provide flexibility. Assess your operational requirements and cost considerations to make the best decision.

What’s the difference between a virtual assistant and an executive assistant?

The term “virtual assistant” usually refers to someone who provides basic administrative support remotely, handling tasks like data entry, inbox cleanup, research, or simple scheduling.

Many VAs work part-time or support multiple clients at once, and they’re often focused on task completion rather than strategic support. Having said that, many businesses hire full-time virtual assistants.

An executive assistant (EA) might also work remotely, but the role is very different. Executive assistants typically support one executive or leadership team full-time and take on a much higher level of responsibility. They manage complex calendars, coordinate communications, anticipate needs, and often serve as a gatekeeper and strategic sounding board.

In short: all executive assistants can be virtual, but not all virtual assistants operate at the level of an EA. If you’re looking for a high-trust partner who can protect your time and help you operate more efficiently, you’re looking for an executive assistant—not a general VA.

Should I hire a full-time executive assistant or outsource executive assistant tasks to an agency?

It depends on the level of support you need and how important continuity, discretion, and strategic thinking are to the role.

Outsourcing EA tasks to an agency can work if your needs are limited to repeatable, transactional work like booking travel or responding to simple emails.

But if you’re looking for someone who can step into a more proactive role—managing stakeholder relationships, coordinating complex projects, or acting as a gatekeeper to your time—a full-time executive assistant is the better path.

Executive support is a high-trust relationship. That’s why many growing companies choose to hire a dedicated EA (either in-office or remote) who can learn the business, adapt quickly, and become a long-term asset to the leadership team.