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How to Hire an Executive Assistant: Skills, Fit & What to Look For

By August 14, 2025October 9th, 2025No Comments

Are you considering hiring an Executive Assistant?

Well… what’s stopping you? Not sure how to best utilize the support? Nervous about trusting the wrong person?

Hiring an Executive Assistant is a critical decision for a leader or organization. An effective EA serves as a gatekeeper, strategic partner, and operational backbone, enabling executives to function at their highest level. Hiring the right EA can significantly improve your productivity and focus. However, hiring the wrong person can cost you. Let’s discuss what to consider so you make the right hiring decision!

Define and Understand the Position

We recommend you start by understanding what an Executive Assistant is capable of. A common misconception is that an Executive Assistant’s role consists of only administrative tasks such as answering incoming calls, making coffee, ordering lunch, scheduling, etc. While these responsibilities may be a piece of the job, this mentality immensely underestimates the value of an Executive Assistant. In reality, a great EA is an extension of their executive.

With that in mind, assess your needs.

  • What responsibilities take up the majority of your time?
  • What can you hand off immediately and what might take time/training?
  • Do you need support in your personal life?
  • Will you require support outside of normal working hours?
  • What are tasks you currently do that you shouldn’t be doing?

Then consider personality fit and work style compatibility.

  • Common personality traits of an Executive Assistant include being detail oriented, proactive, trustworthy, adaptable, and confident.
  • You should seek these traits but think deeper and consider whether you prefer someone who is introverted or extroverted, patient or impatient, old fashioned or innovative?
  • Consider working pace, communication preferences, decision making style, autonomy vs. collaboration.

Finally, determine what level of experience and skills are required for this person to successfully support your needs.

For some leaders, it is necessary to hire an EA with prior experience that closely matches the specific demands of the role, lessening the need for extensive training. For others, direct experience may be less important than identifying someone with the appropriate attitude, potential, and adaptability to grow into the position and meet evolving needs.

An elderly woman with long white hair sits at a desk, focused on reviewing documents. She's writing with a pen, conveying a sense of concentration.The Search

Beginning the search to find an Executive Assistant can be intimidating and the reason many executives drag their feet. Here are some things to consider when beginning your search to hire an Executive Assistant:

1. Tap Into Specialized Recruiting Channels

  • Using a local staffing firm, such as Chief of Staff KC, to hire an Executive Assistant offers a number of strategic advantages, especially when you’re looking for someone who not only fits the role, but your company culture and working style. Some of these advantages include:
    • An extensive network of pre-vetted, local talent
    • Deep knowledge of the talent and job market
    • Quicker, more efficient hiring
    • Personalized service and cultural alignment
    • Lower risk through a contingency model
    • Ongoing partnership and support
    • Stronger candidate commitment

2. Leverage Your Personal Network

  • Ask your network who they know! Requesting referrals is an excellent way to find trustworthy, talented, and qualified candidates.

3. Use Thoughtful Job Postings

  • Posting a generic job description rarely attracts top talent. Stand out through your job posting by being specific, engaging, and genuine. Express what is unique and exciting about this opportunity and your organization.

4. Screen Thoroughly

  • Take the time to thoroughly review resumes
  • Establish a multi-stage interview process and follow it. During these stages:
    • Assess communication skills, professionalism, and basic alignment
    • Ask behavioral and situational questions
    • Consider if any skill related assessments are necessary
    • Be curious and dig deeper as you get to know the candidate(s)
    • Pay close attention to personality and work style compatibility
  • Complete background and quality reference checks

5. Prioritize Chemistry

  • You will work closely with your executive assistant, therefore, don’t underestimate the importance of personal compatibility.

 

Three professionals walking on a tree-lined sidewalk, discussing with folders and coffee in hand, conveying a collaborative and focused mood.Onboarding and Retention

Once you’ve hired your Executive Assistant, set them up for long-term success by onboarding properly.

      1. Set clear expectations from the beginning
      2. Introduce them to others in the organization and ensure people understand your Executive Assistant’s role
      3. Encourage regular check-ins to stay aligned
      4. Provide and seek feedback, empower your Executive Assistant and show appreciation

 

Conclusion

Hiring an Executive Assistant is one of the most impactful decisions a leader can make. A strong EA doesn’t just make your life easier; they make you better at your job. By taking the time to define your needs, identify the right qualities, and conduct a thoughtful search, you can find a partner who helps you stay focused, strategic, and supported.

Whether you use an outsourced recruiting partner, your personal network, or internal search process, remember the best Executive Assistants are not just “task-doers,” they are force-multipliers. Choose wisely, and you’ll gain a trusted partner who helps to move both you and your organization forward.

Need help finding your next Executive Assistant? Contact our admin team today and get matched with top-tier talent who align with your values and goals.

 

FAQs

1. What should I look for when hiring an Executive Assistant?

    • When hiring an Executive Assistant, look for someone who is proactive, trustworthy, and adaptable. This is a person who can act as an extension of you, not just complete tasks. Define your needs clearly and include what responsibilities can be delegated and your preferred work style. Strongly consider prioritizing personality fit and communication style, not just experience. The right EA should enhance your focus, productivity, and  leadership.

2. How much experience should an Executive Assistant Have?

    • The level of experience needed depends on your specific needs. If your role is fast-paced or complex, prior EA experience can reduce training time and increase impact rather quickly. However, some leaders prioritize attitude, adaptability, and potential over direct experience. It’s all about finding the right balance between skillset and growth capability to meet your needs!

3. Where can I find qualified Executive Assistants?

    • You can find qualified Executive Assistants through specialized staffing firms like Chief of Staff KC, which offer access to pre-vetted, culturally aligned talent. Your personal and professional networks are also great resources as referrals often lead to strong candidates. Use thoughtful, specific job postings to attract the right person and stray away from generic listings that overlook the strategic nature of the role. The more you can highlight unique aspects of the role, the better!

 

timbre leeks

Written by Timbre Leeks

Division Manager Chief of Staff KC

 

Currently hiring and need a helping hand? Haven’t had a smooth job search?

Reach out to Chief of Staff KC with any questions you may have, and we’ll pair you with a dedicated recruiter that is motivated to find the right fit for you. Let’s get started.