Hire Slow, Onboard Slower: The Entrepreneur’s Guide to Hiring Your First VA
- Louisa Thiessen
- 15 hours ago
- 6 min read
When you started your business, it took grit. You were operating lean, serving clients and learning on the fly about things like tax structures and marketing.
Your business grew. More customers. More revenue. Referrals started flowing in. You set your sights on scale: making more money while doing less work.
Except you haven’t quite gotten the hang of the “less work” part. It’s starting to feel like the company is growing so fast you can barely hang on. You’re drowning in your to-do list, and most of it isn’t even client work.
This is the point where most business owners decide it’s time to hire their first virtual assistant. The problem is, they’re already late.
When Should You Hire Your First VA?
Entrepreneurs should hire a virtual assistant when administrative work starts pulling them away from things that build revenue. Most wait too long.
I help growing businesses scale sustainably. In my work, I’ve met founders who don’t want to hire a VA until business picks up. “Oh, I don’t have enough work right now to keep one busy,” they say. “It’s not that bad right now, I can manage until the busy season hits.”
This is like waiting for a rainstorm before patching the hole in your roof.
When you’re already drowning, you can’t muster up the time and the energy to do a proper search and onboarding. You’ll hire your first VA in panic mode and just dump a bunch of work in their lap, hoping they’ll make it disappear.
The time to patch the roof is when the sun is shining. The time to hire a VA is when you can still keep your head above water while you find one and get them up to speed.
What to Delegate to Your First Virtual Assistant
Myth: It’s too early to hire a VA because you don’t have enough work to keep them busy.
Fact: You don’t have to bring someone on to work with you 20-plus hours a week. When I’m onboarding a new VA, I start with five hours a week.
I hire hourly contractors instead of people on retainer because it gives me flexibility to ramp their hours up when I get busy and ramp them down during slow times.
As we go through onboarding, I have them handle one or two tasks to see how they do. As they get comfortable and earn my trust, I give them more.
The first tasks are administrative: things that are required to keep the business running, but are repetitive and don’t need your personal judgement. Hand off things that eat up your time without adding revenue. Like following up leads, sending proposals, and tracking business metrics.
The second set of tasks to delegate are the things you have the skills to do yourself, but you really hate doing them.
For me, that was bookkeeping. I started out keeping my own books. It wasn’t hard. But I absolutely hated it. Every time I opened QuickBooks, I felt my energy drain.
Plus, it put me in a foul mood. I wasn’t in the right space mentally to come out of
bookkeeping and be productive doing client work.
If there is a part of your business that has to be done but it sucks the life out of you, delegate it as soon as you can afford to.
Take Your Time Hiring
When you hire a VA before you’re desperate for help, you give yourself time to be choosy. This is a person who, ideally, will be working with you daily or almost daily.
Skills and work experience are important, but so is attention to detail, personality match, and whether you feel like you can trust them.
I use detailed applications designed to catch AI or copy-paste answers. I also ask fun questions that give me a sense of the applicant’s personality, because I want to hire people I like working with.
Most first-time VA hires fail. Not because entrepreneurs hire the wrong person, but because they rush the process.
They bring in the first skilled person they find and hand over a task list without first setting expectations or explaining processes. And they don’t create any feedback loops to clarify confusion and help the VA perform.
Give Yourself at Least 90 Days to Onboard Your VA
If you look closely at businesses with high turnover rates, you will usually find an awful onboarding process.
Onboarding lays the foundation for the employer-contractor relationship. Business owners who skip it or rush it end up frustrated and constantly hiring new people. Studies show that a good onboarding process can cut new-hire questions by 25% and improve retention by 50%.
A successful relationship between an employer and a VA has shared expectations, shared understanding, transparency, and trust. Onboarding is where it all starts.
If you want a virtual assistant fully onboarded and ready to support you when your busy season starts, hire one at least 90 days before the busy season.
Ninety days feels like a lot. But taking a shortcut will cost you.
Even though you hired a professional with skills and work history, you are still throwing them into a business with established processes and expectations. They can’t just instinctively know what you want and how you want it.
How to Onboard Your Virtual Assistant: Step by Step
Document your SOPs
For a lot of entrepreneurs, an assistant is their first hire. Up until now, you might have been doing everything yourself, with processes you just keep in your head. If they stay in your head, you become the bottleneck.
It has never been easier to create standard operating procedures, or SOPs. Here’s what you do:
Record yourself while you perform a routine task. While you work, explain out loud what you’re doing and why.
Remove any sensitive or confidential information, then drop the transcript into your favorite AI tool and tell it to turn that transcript into an SOP.
If the output is correct, use it to train your VA. You now have a reference for the way that task is done in your business.
SOPs are living documents. They’re not set in stone. When I give my VA SOPs, I tell them I expect them to update the document as the way we do things changes.
Set milestones and KPIs
At the start of your relationship with your new VA, you need to set clear expectations. Within those expectations, set milestones.
For example, in 30 days, I expect you to be able to answer an email using the appropriate company tone.
In 60 days, I expect you to fully understand how to use the CRM.
By 90 days, I expect you to be able to complete your tasks independently.
Within each of those milestones are key performance indicators (KPIs) that tell you and the assistant if they’re on the right track.
By 60 days, you’ll start to have a pretty good idea if this person is a good fit for your business. If they aren’t working out at 90 days, cut the cord and start over.
Meet with your new hire regularly
For the first 30 days, you should meet with your new VA every week. After 30 days, you can start spacing out the meetings to every two weeks.
This is your chance to offer feedback on their performance. Tell them where they’re doing well and where you’d like to see a different approach.
It’s also your chance to get feedback. A relationship flows two ways, and you can’t expect great performance from someone getting zero support. Answer their questions and give clarification where they need it. Ask them what they need and if there’s anything you can do differently that would make things easier for them.
Building Trust With a VA Takes Time
For a lot of us, our business is like our baby. It’s scary to hand over your baby for the first time and not hover around to make sure no one drops it.
Trust is earned over time. Be transparent: “I know you’re the expert, but this is my baby and letting go is hard for me. I need to go slow and build up trust in you.”
Start by giving your assistant small tasks that won’t do much damage if they mess up. Explain the outcome you expect and give them SOPs for the process you want followed.
Then step back and let them do it.
Increase responsibility gradually. Maintain final approval of their projects before anything is sent out or finalized.
As trust builds, make sure clear boundaries remain about what they can manage independently and what needs to come to you.
You Don’t Just Need to Hire – You Need to Lead
When you hire your first virtual assistant, your role in your company changes, too. In addition to being an entrepreneur, you become a leader. Stepping into that leadership role can mean a shift in the way you understand your business.
Before any of my clients hire a VA, I always conduct an operations audit. When you’re in the thick of running your business, especially during a high-growth phase, you can start missing the forest for the trees.
I examine the entire operation from an outside perspective. An audit makes it clear where to automate, where to delegate, what role to hire for, and what systems to fix first. This prevents Band-Aid solutions and the cost of hiring for the wrong thing.
With a clear view of your operation, documented operating procedures, and the right person or people supporting you, you can finally step into that vision of scale like it’s supposed to be: more money, less stress.
Book your operations audit now and get a roadmap to growing your business while getting your life back.