When Is the Right Time to Hire a Virtual Executive Assistant?
Most of the time, when I'm talking to prospective clients, they tell me that they know they should have hired a VA a long time ago. I often joke that by the time you realize you need a virtual executive assistant, you should have had one months ago. But how do you make sure you aren't missing that window? But how do you make sure you aren't missing that window?
I see this pattern constantly. Business owners call me when they're drowning, not when they're just starting to feel the water rise. They're already working 60-hour weeks, things are falling through the cracks, and they haven't taken a real day off in six months. They know they need help. What they don't know is how much easier life could have been if they'd made the call earlier.
I understand because I lived it. I was telling everyone the power of hiring a remote executive assistant but I was doing everything myself. It wasn't until a fateful family vacation, where I spent the entire time responding to a client emergency while at the zoo with my in-laws and small kids, that I realized something had to change. I needed to stop working IN my business and start working ON it. If you're reading this and wondering whether it's time to hire a virtual assistant at the executive level, I'm going to walk you through the actual signs so you don't wait as long as I did.
What Makes an Executive Assistant Different?
Before we dive into timing, let's clear something up. A virtual executive assistant isn't just someone who handles your inbox. They're a strategic partner who anticipates your needs, manages high-level tasks, and keeps your entire operation running smoothly. Think of them as your right hand, not just an extra pair of hands.
Regular virtual assistants are phenomenal for tactical tasks like data entry, scheduling basic appointments, or posting on social media. But virtual executive assistants are managing your calendar like a chess game, preparing you for board meetings, handling sensitive communications, coordinating with your leadership team, managing operations, automating, thinking ahead, and making decisions on your behalf when appropriate.
Here’s an example: One of our Denver clients, a CEO of a growing SaaS company, came to me very frustrated. She'd hired an oversees general VA who was great at checking boxes but couldn't think three steps ahead. When her VA scheduled back-to-back meetings all day without buffer time, lunch breaks, or travel considerations, she ended up exhausted and behind. An executive assistant would have seen the bigger picture and structured her day for maximum effectiveness, not just maximum bookings.
Sign #1: You're Making Money But Losing Time
Here's a test: Look at your calendar from last week. How many hours did you spend on tasks that didn't directly generate revenue or move your business forward? If the answer is more than 10 hours, you're ready for an executive assistant.
I see this constantly with founders and executives. They're closing deals, building strategies, and leading teams, but they're also:
Booking their own travel and comparing flight prices for an hour
Rescheduling meetings when conflicts pop up
Formatting presentations at midnight
Managing their own expense reports
Following up on action items from meetings
Researching vendors for office supplies or software
None of these tasks are worth your hourly rate. Let's do the math. If you bill at $200 an hour (or your time is worth that to your company), and you spend 15 hours a week on admin tasks, that's $3,000 in lost value every week. That's $156,000 annually. A virtual executive assistant costs a fraction of that. Then there’s opportunity cost. All of the time you spend doing those tasks, you aren’t spending on growing your business and finding new clients. I was just talking to one of our clients who came to us, spending 20 hours a week on administrative tasks. After hiring a virtual executive assistant through Alpine Virtual, she reclaimed that time and took on three new clients in the first month. Those clients brought in an additional $15,000 in revenue. The VA paid for herself five times over, immediately.
Sign #2: Your Inbox Controls Your Day & Things Are Falling Through The Cracks
I'll be honest, inbox zero for inbox zero's sake alone is worthless. The end goal isn't having a clean inbox (although it is an amazing feeling), the goal is to save time and to have things stop slipping through the cracks. A messy inbox often means missed opportunities or not great customer service.
Email management sounds simple until you're an executive. It's not just about responding, it's about prioritizing, delegating, flagging urgent items, drafting responses that match your voice, and protecting your time from unnecessary meetings disguised as "quick questions."
Here's what executive-level email management actually looks like:
Morning Review: Your EA reviews your inbox before you wake up, flags the five emails that actually need your attention, drafts responses for the rest, and archives or delegates anything that doesn't require your input.
Priority Filtering: They create a system where emails are categorized by urgency and importance. You see "needs decision today" separately from "FYI only" and "EA can handle."
Response Templates: For recurring questions or requests, they develop templates in your voice so you're not rewriting the same email 50 times.
Meeting Defense: When someone emails asking for "just 15 minutes," your EA evaluates whether it's necessary, suggests alternatives like async communication, or schedules it strategically.
I spent years being completely overwhelmed by my inbox before I finally handed it off. The first week, my EA flagged that 60% of my emails that she was able to respond on her own. She created a FAQ document and template responses. My "urgent" email pile dropped by half.
Sign #3: You're Missing Strategic Opportunities
This one's sneaky because you might not even realize it's happening. You're so busy managing day-to-day operations that you're missing the forest for the trees.
Ask yourself:
When's the last time you had a morning to think strategically without interruptions?
Are you reading industry news and staying ahead of trends?
Have you pushed off that big partnership conversation or business development opportunity?
Is there a project you've been "meaning to start" for six months?
If you answered "I can't remember," "no," "yes," and "yes," you're ready for an executive assistant.
Executive assistants create space for strategic thinking. They protect your calendar, build in thinking time, prep you for important conversations with research and briefs, and handle the operational details so you can focus on vision and growth.
A client of ours who runs a marketing agency told me she'd been trying to launch a podcast for a year. Between client work and managing her team, it never happened. Her virtual executive assistant took over the logistics: researching equipment, booking guests, scheduling recording sessions, coordinating with editors, managing the publishing calendar, and even editing the podcast. The podcast launched in six weeks and brought in two major clients within three months.
Sign #4: You're the Bottleneck in Your Own Business
Nothing moves forward without you. Your team is waiting on your approval, your signature, your feedback, or your decision. Emails sit in your inbox for days. Projects stall because you haven't had time to review the proposal.
This is where executive assistants save the day. They don't just take tasks off your plate, they keep the wheels turning. They can:
Review documents and flag only the sections needing your input
Make judgment calls on smaller decisions within parameters you set
Follow up on your behalf so things don't slip through the cracks
Prepare decision memos so you can approve quickly
Coordinate between team members so you're not the middleman
I realized this was a problem for me when my core team said they felt like projects went to a "black hole" when they needed my review. My EA implemented a system where she pre-reviews everything, summarizes key points, and presents me with clear decision options. What used to take me three hours of reading and reviewing now takes 20 minutes.
Sign #5: You're Scaling Fast and It's Chaotic
Growth is exciting until it's overwhelming. You're hiring, onboarding, managing new clients, possibly opening new locations or launching new services, and everything feels like controlled chaos (or uncontrolled chaos).
This is exactly when you need someone managing the operational details so you can lead the growth. An executive assistant can:
Coordinate onboarding for new hires
Manage your investor or board communications
Keep track of multiple projects and deadlines
Prepare you for important meetings with briefings and context
Handle the logistics of expansion
Create systems so it’s done well
Sign #6: You Are Always Working
Remember actual weekends? Remember having dinner without checking your phone every five minutes? Remember what it felt like to actually disconnect on vacation?
If you're working 50+ hour weeks, or if your family has started scheduling time with you through your work calendar, you need help. Not because you're weak or failing, but because you're trying to do a job that's actually meant for two people.
Executive assistants don't just handle work tasks, they protect your personal life. They can:
Block off personal time and defend it from encroaching meetings
Handle logistics for your personal life (booking family travel, managing household vendors, coordinating with kids' schools)
Create boundaries so work emails don't invade your evenings
Manage your schedule to ensure you're not burning out
After hiring my first executive-level support, I took my first real vacation in three years. My EA handled everything, made decisions when needed, and there weren’t any truly urgent items. I came back refreshed instead of returning to a dumpster fire. I also learned that there’s a lot my EA can handle without me; I’m not as critical as I thought.
The Financial Timing Question
Let's talk money because I know that's the question in your head. When can you afford an executive assistant?
Here's my rule of thumb: If you're personally generating $150,000+ in revenue or running a business with $250,000+ in annual revenue, you can't afford NOT to have executive support.
Virtual executive assistants typically cost between $35-$45 per hour depending on experience and expertise. If you hire one for 20 hours a week at $45/hour, that's $3,600 a month. Now compare that to:
The revenue you're not generating because you're buried in admin work
The opportunities you're missing because you're too reactive
The cost of hiring a full-time executive assistant (salary, benefits, office space, etc.)
The mental health cost of burnout
When you run the numbers, the question isn't "Can I afford this?" It's "How much is not hiring one costing me?"
How to Know You're Actually Ready
Here's a simple evaluation. You're ready to hire a virtual executive assistant if you check three or more of these boxes:
You're spending 10+ hours weekly on administrative tasks. Time is money, and yours is too valuable for inbox management.
You have clear processes or are willing to create them. Executive assistants thrive when there are systems to follow or improve.
You're comfortable delegating meaningful work. If you need to control every tiny detail, start with a regular VA and work your way up.
You have recurring tasks that follow patterns. The more predictable your work, the easier it is for an EA to anticipate needs.
You're ready to invest in communication upfront. The first month requires training and adjustment. If you can commit to that, the payoff is enormous.
You value your time enough to protect it. Some people wear busy-ness as a badge of honor. If you're ready to work smarter instead of harder, you're ready.
What Actually Happens When You Hire
Let me paint a picture of what life looks like after hiring a virtual executive assistant, based on real clients:
Week 1-2: You spend time documenting processes, sharing passwords, and explaining your preferences. Yes, this feels like extra work. Do it anyway.
Week 3-4: Your EA starts taking tasks off your plate. You're still involved but less so. You might feel weird about it. That's normal.
Month 2: You stop thinking about logistics. Your calendar makes sense. Your inbox is manageable. You attend meetings actually prepared.
Month 3+: You wonder how you ever functioned without support. You're working on projects you'd shelved for years. You're making strategic decisions instead of fighting fires. You might even take a weekend off.
One client told me, "I didn't realize how much mental energy I was spending just remembering everything I needed to do. Now I show up, do the work, and trust that everything else is handled. It's life-changing."
Making the Decision
If you're still on the fence, here's my advice: Track your time for one week. Everything. Every email, every scheduling conflict, every task you do. At the end of the week, highlight everything that didn't require your specific expertise or decision-making authority. That highlighted pile is what an executive assistant handles.
The right time to hire a virtual executive assistant isn't when you've achieved some arbitrary milestone or when you're perfectly organized. It's when the cost of NOT hiring one, in lost revenue, missed opportunities, and personal wellbeing, exceeds the investment.
For most executives and founders, that moment arrived six months ago. The second-best time? Right now.
Ready to reclaim your time and focus on what actually grows your business? Let's talk about finding you the perfect virtual executive assistant who'll become your secret weapon for scaling smarter, not harder. Book a free consultation and let's figure out exactly what kind of support will transform your day-to-day.
