What to Look for in an Executive Assistant

If you’re thinking about getting executive assistant services but are unsure about what to look for in a virtual executive assistant, this article is for you. The relationship between an executive and their EA is so profound and their priorities are so intertwined, that hiring someone who simply has an impressive resume might not be enough. 

You need to make sure the candidates you’re interviewing are in sync with the way you work. Don’t just look for someone who has impeccable communication skills. Instead, screen candidates so you end up hiring someone who can read you so well, that they can use the same words you use on a daily basis. If they can write emails on your behalf without anybody noticing, you made the right call. 

Look for qualities relevant to the role, of course, but pay extra attention to how the candidate would tailor them to your working preferences and your specific needs. 

Where should you start? Here are five essential qualities you should look for in your next executive assistant. 

What to Look for in an Executive Assistant

Wondering what to look for in an executive assistant? These five essential qualities are the perfect starting point. 

Table of contents

• Communication skills
• Organizational skills
• Problem-solving abilities
• Attention to detail
• Adaptability skills

Communication Skills

Executive assistants provide support to one or maybe two executives, but that doesn’t mean they will exclusively interact with them. On the contrary, one of the areas in which an EA can provide highly impactful support is communicating with others. 

EAs are capable of communicating with you as their executive, your team members, other executives within the company, and even external stakeholders: from vendors to prospects to board members. That’s why you need to make sure your new EA’s communication skills are exceptional, so much so that they can facilitate meetings and speak with stakeholders without creating risk.

• How can you test your EA’s communication skills?

Role-play scenario: You are an executive assistant tasked with relaying important information to both your CEO and the marketing team regarding a change in the company’s branding strategy. In this scenario, the CEO wants a brief overview, while the marketing team requires detailed documentation. Role-play a conversation where you effectively communicate the necessary information to both parties.

Organizational Skills

Are you often invited to meetings you don’t really need to attend? Is your calendar packed with overlapping meetings? Well, you’re not the only one. This is actually one of the most common pain points we’ve seen among startup executives. 

That’s why your executive assistant’s organizational skills need to be top-of-class. Your EA should be able to act as a gatekeeper and prevent team members from simply putting time in your calendar. They will evaluate the importance of a meeting, and decide if it’s the best use of your time or if you’re better off doing something else. 

Your EA can manage your calendar so there’s no overlap. They can also perform a total calendar overhaul to ensure you’re spending time on the most impactful work and that you meet deadlines. They can also organize any sort of meeting or event you or your team might need, from all-hands meetings to company offsites. 

• How can you test your EA’s organizational skills?

Practical test: Provide the candidate with a sample project brief containing multiple tasks, deadlines, and resources. Ask them to create an organized project plan outlining the steps they would take to complete the project within the given timeline. Then, introduce a change in the project scope or a new urgent task and observe how they adjust their plan accordingly.

Problem-solving Abilities

How can you get any strategic work done if you’re constantly busy putting out fires? That’s a big part of your EA’s new role: finding a solution without even texting you about it. 

One of our EAs (based in Latin America) found out that her customer’s headquarters in NYC didn’t have an office manager. As a result, basic supplies like paper, water, or coffee ran out regularly. Since office management didn’t fall under anyone’s scope, it was just not being done.

She decided to take care of it and started ordering everything the office needed. She was so on top of it, she was able to determine how long things lasted and how often she needed to place a new order. Eventually, she automated the whole process without her executive even having to ask.

• How can you test your EA’s problem-solving abilities?

Role-Play Scenario: You are the executive assistant for a busy executive who suddenly needs to travel overseas for an urgent meeting. However, their passport has expired, and the renewal process will take several days. Role-play the conversation where you devise a plan to expedite the passport renewal process or find an alternative solution to ensure the executive can attend the meeting on time.

Attention to Detail

If all that comes to mind is grammar when you think about attention to detail, you’ll need to expand your thinking a bit. An exceptional EA isn’t just paying attention to what it takes to make you look good on paper or in digital communications. Instead, the kind of EA you want is someone who can identify gaps in internal processes, and improve them for the benefit of all stakeholders. 

One of our EAs identified a crucial gap in her company’s operations: there were 228 contractors, but no centralized repository containing essential vendor information.

Vital details such as contract start and end dates, background checks, and payment terms were scattered across various sources. This EA took the initiative to develop a comprehensive database consolidating all vendor details, providing easy access for all company leaders. Additionally, she implemented reminder systems to prompt leaders to review and make decisions regarding vendor contract renewals.

• How can you test your EA’s attention to detail?

Practical test: Provide the candidate with a set of documents containing intentional errors, such as misspellings, formatting inconsistencies, or incorrect information. Ask them to review the documents and make corrections. Observe how meticulously they identify and rectify each error, noting their attention to detail and accuracy in addressing the issues.

Adaptability Skills

Startups are known for moving fast, which means that you, as a startup executive, might also have to shift gears and suddenly focus on something new. For this reason, adaptability is not just a nice-to-have quality in a potential EA; it’s a must-have skill. If you need to move fast, your EA should be moving even faster. 

When looking for a new executive assistant, make sure the candidate is flexible and can shift their priorities at a moment’s notice. One of our executive assistants was busy working on a project her executive delegated when she suddenly received a Slack message from him. “The board meeting is running long and I might lose my train. Can you help out?” Her executive was traveling and if he lost his train, he would also lose his flight and connection. 

She immediately went online and booked new trains and flights. She was so fast that even before the board meeting was over, her executive had all the boarding passes on his phone. When you hire an EA who can adapt, your life unfolds almost seamlessly.

• How can you test your EA’s adaptability skills?

Role-play scenario: You have been managing the calendar and scheduling for your executive, but due to unforeseen circumstances, they have decided to switch to a new calendar app/software immediately. Role-play the scenario where you quickly familiarize yourself with the new tool, transfer all existing appointments and reminders, and ensure a seamless transition without any disruption to the executive’s schedule.

Additional Considerations

The qualities mentioned above are truly critical when looking for a new executive assistant, especially if you’re hiring an EA for the first time. But if you want to truly make the perfect hire, here are some additional considerations. Adding them to your must-have checklist can be the cherry on top for finding the best EA to suit your needs.

Experience and Qualifications
People who start looking for an EA for the first time often make the same mistake. They think that several years of previous EA experience should be mandatory and dismiss any candidate who doesn’t tick that box. If this is something important for you, just hear the candidates out and see if their experience in other fields would come in handy for you, regardless of their lack of EA experience.

When it comes to certifications, don’t expect a candidate to hold the exact titles you need. If you meet a promising candidate, make sure they enroll in those courses and get those certifications. After all, supporting your EA through their professional journey will be beneficial for both parties: they will get to grow in their role and you get a business partner with even stronger skills.

Cultural Fit
To know if a candidate is a good fit for your company, take a look at your company’s values and determine if this candidate lives by the same principles. Some people think the personality of an EA doesn’t matter as long as they deliver, but the truth is that the relationship between an executive and their EA is so deep, that you’d feel much better if the person involved in your calendar, email, and meetings is someone you personally like and trust.

Many EAs are paired with an executive, and they develop such a strong bond, that when the executive changes jobs they take their EAs with them, or if they grow in the company, they’ll make sure to bring their EAs along.

Technology Proficiency
Most of our customers are tech startups spread around many industries; that’s why we understand the importance of an EA being proficient in an array of tools. Our EAs have mastered the most popular tools for startups (Slack, Notion, Hubspot Superhuman, etc.) and, if their customer needs them to learn a highly specific software, we make sure they learn it as fast as possible.

When looking for an EA, make sure they know how to operate the basic systems you use to run your company and give them time to learn the ones they might not know yet.

Hiring a critical role can be lengthy and draining, but following these steps can make it a lot easier. If after learning everything it takes to hire an executive assistant, you realize it’s too much hassle, consider doing it through a specialized company. 

At Viva, we train some of the best executive assistants in the industry and pair them up with executives like you. If this sounds like an option you’d like to explore, chat with our team. They would love to guide you through the process.