How to Hire a Virtual Assistant for Busy Executives

When I first considered hiring a virtual assistant (VA) to help manage my growing to-do list, I thought the process would be straightforward. After all, I just needed someone to handle my emails, calendar, and a few administrative tasks, right? But after a few attempts, I quickly realized that hiring the right VA for a busy executive is a lot more than just outsourcing admin work. It’s about finding someone who can take things off your plate and help you scale your productivity while understanding your needs and working style.

Here’s the process I use now to hire the right VA for my role as a busy executive.

Step 1: Clarify What You Need Help With

Before posting the job or reaching out to candidates, take a step back and define exactly what you need help with. I quickly learned that being vague or trying to outsource “everything” doesn’t work. I had to be specific about which tasks would make the most impact on my day-to-day life.

Some common tasks for a VA that can help a busy executive:

• Email Management: Sorting, responding to, and flagging important emails while filtering out spam.
• Calendar Management: Scheduling meetings, sending reminders, and keeping your calendar organized.
• Travel Coordination: Booking flights, accommodations, and managing travel itineraries.
• Task Management: Helping track projects, deadlines, and keeping things on schedule.
• Document Preparation: Writing reports, presentations, and other business documents.
• Social Media Management: Managing and scheduling posts, responding to messages or comments.
• Research: Conducting market or industry research to provide you with insights.

Practical takeaways:

• Don’t outsource everything: Focus on tasks that free up your time for high-priority responsibilities.
• Be specific about which aspects of your role are draining your energy and time.

Step 2: Look for the Right Skills and Experience

I initially hired a VA based on general administrative skills, only to realize that not all virtual assistants have the expertise I needed for my high-paced, detail-oriented schedule. The ideal VA for a busy executive should be experienced in the following:

• Advanced organizational skills: A VA should be great at managing complex calendars and juggling multiple priorities without getting overwhelmed.
• Strong communication skills: They need to be able to filter through emails, handle client communications, and send professional replies in your tone.
• Tech-savvy: Your VA should be proficient in tools like Google Workspace, Microsoft Office, project management tools (Asana, Trello), communication platforms (Slack, Zoom), and whatever industry-specific software you use.
• Confidentiality and discretion: As an executive, you deal with sensitive information. Ensure that the VA understands confidentiality and is trustworthy when it comes to handling proprietary or personal data.
• Problem-solving ability: You’ll need someone who can anticipate your needs and handle issues without needing constant direction.

Practical takeaways:

• Look for a VA with experience in high-level executive support.
• Prioritize skills in organization, communication, and tech.
• Ensure they understand the importance of confidentiality.

Step 3: Write a Clear and Detailed Job Description

The first time I posted a job description for a VA, it was a bit too broad, which led to a flood of applications from candidates who weren’t a good fit. A well-written job description is key to attracting the right talent. Here’s what I include in mine now:

• Role Responsibilities: Be clear about what the VA will be expected to do. Break it down into daily, weekly, and monthly tasks (e.g., “Manage executive’s calendar,” “Organize travel plans,” “Handle email communications,” etc.).
• Required Skills: Mention the tools they need to be proficient in (Google Suite, Microsoft Office, project management tools, etc.). Also, include any specific knowledge or skills relevant to your industry.
• Working Hours: Specify if they need to be available during certain hours or time zones. Some VAs work flexible hours, but it's essential to set expectations.
• Confidentiality Expectations: Make it clear that the VA will be handling confidential information and may need to sign an NDA (non-disclosure agreement).

Practical takeaways:

• Be specific about daily tasks, tools, and confidentiality needs.
• Include working hours to ensure they align with your schedule.

Step 4: Use a Scorecard to Evaluate Candidates

After receiving applications, I now use a scorecard to evaluate candidates based on their responses, skills, and past experiences. This allows me to objectively assess each candidate’s suitability without getting distracted by fluff or vague claims.

Here’s an example of a scorecard for evaluating a VA for a busy executive:

Role: Executive Virtual Assistant

Hours: 9 am–5 pm (or your preferred hours)

30-day outcomes:

• Calendar is organized and optimized; no scheduling conflicts.
• 90% of emails are filtered or answered on your behalf, prioritizing urgent responses.
• Travel arrangements (flights, hotels, itineraries) are booked 1 week ahead of time.
• Task management system updated daily, with no overdue tasks.

Red Flags:

• Slow response time or failure to meet deadlines.
• Lack of initiative to proactively resolve issues or improve processes.
• Unprofessional communication or misunderstanding of priorities.

Practical takeaways:

• Use a scorecard to evaluate candidates and ensure they align with your goals.
• Define clear outcomes for the first 30 days to measure their success.

Step 5: Assign a Paid Test Task to Evaluate Their Skills

To avoid wasting time with candidates who don’t fit the role, assign a small paid test task to assess their capabilities. A paid test shows that you’re serious, and it gives you a real-world preview of how they will perform. For example:

• Email Management: Ask them to sort through a sample inbox and create a prioritized response list.
• Calendar Organization: Provide them with a sample calendar and ask them to schedule meetings, making sure there are no conflicts.
• Research Task: Have them research a specific topic or industry trend and summarize key insights in a brief report.

Practical takeaways:

• Give them real tasks to gauge their performance in practical scenarios.
• Pay for the test task to ensure they invest time and effort into their work.

Step 6: Set Up a Smooth Onboarding Process

Once you’ve hired the right VA, ensure you set them up for success with a structured onboarding process. This includes:

• Providing access to necessary tools: Share access to calendars, email accounts, communication platforms, and any other tools you use.
• Clarifying processes: Provide clear instructions on how to handle specific tasks like email triaging, meeting scheduling, or booking travel.
• Setting clear expectations for communication: Let your VA know how often you expect check-ins, updates, or progress reports. You’ll also want to establish how they should communicate with you when issues arise.

Practical takeaways:

• Ensure they have access to the tools they need from day one.
• Set communication expectations to prevent misunderstandings.

Summary: How to Hire a Virtual Assistant for Busy Executives

Hiring the right virtual assistant for a busy executive can make all the difference in your productivity and well-being. To find the best fit, you need to be clear about what tasks you want help with, look for someone with the right skills and experience, and use structured methods like scorecards and test tasks to evaluate candidates.

My non-negotiables for hiring a VA:

• Clear job description with detailed tasks and confidentiality expectations.
• Skills in organization, communication, and tech.
• A scorecard and paid test task to evaluate their performance.
• Structured onboarding process with clear communication expectations.

By following this process, you’ll have a VA who not only frees up your time but also becomes an essential part of your executive team.