ICYMI: Same newsletter, fresh look. Here’s the full story.

Note from Jill

After my right hand, Paige Sparkman, wrote about how to delegate to a virtual assistant, several of you asked how to find and hire virtual support. Paige is back this week with her tips on how to find and hire a VA for yourself. 

On another note, we’re gathering all of the recent delegation how-tos into a single document that will be published soon! In the meantime, you can find the individual articles on my blog.

If you’re ready to hire a virtual assistant, this is where you start

A good VA can take a lot off your plate, especially if you’re at the point where you really do need the help. But before you start asking around, posting in groups, or scanning Upwork, let’s talk about what needs to happen first.

Because if you think a VA will walk through your front door of your business and already magically know what needs to happen, you’re going to be disappointed.

A virtual assistant can be incredibly helpful, but how helpful they’ll actually be starts with you. Because the process of hiring a VA is as much in the preparation, as it is in the actual hiring itself.

First, know what kind of help you actually need

Most of the time, when people say they need a virtual assistant, they’re looking for a generalist in running a business. It’s usually some mix of executive assistant work, admin, operations, and marketing. 

In reality, a lot of the highest-value VAs (or online business managers / OBMs) aren’t doing more admin, thanks to AI. They’re doing less execution and more decision support: managing other contractors, owning a launch, or building the systems that a business runs on. Yes, some VAs are hands-on-the-keyboard support, but there are exceptions.

Some VAs specialize by industry. If you run a medical practice, consultancy, photography studio, or business where client experience or compliance matters, it can be helpful to find someone who already understands that world.

But before you worry about finding someone in your exact niche, you need to have some idea of what you want to offload. It doesn’t have to be a perfect list, it will undoubtedly change over time.

But if someone comes in and you’re basically asking them to tell you what you need help with, that’s not a great place to start.

Be honest about your processes

Before you hire, you also need to know where your business stands with processes.

There are basically three versions of this:

  • You have no SOPs or documented processes, and the VA’s first job will be helping create them.

  • You have some processes, but they’re incomplete, outdated, or living in five different places.

  • You have clear SOPs and the VA can come in and execute them.

All of these starting points are okay, as long as you communicate where you’re at and set expectations. If you have no processes and you expect someone to come in and start executing immediately, that is probably going to be frustrating for both of you. 

If you know the first few months are going to involve documenting, organizing, and building the way things get done, that’s fine. Just be clear about it, and make sure you hire someone who’s up for the project.

A good VA doesn’t just execute on your SOPs, they are helpful in building your operational judgment. They notice what’s missing, ask the right questions, and often see the gaps you don’t know to look for.

Start with referrals

The most reliable way to find a VA is through referrals.

Ask people you know. Ask other business owners. Ask people in your industry. If someone mentions their VA in content, in a mastermind, in a coaching group, or in passing, ask about it.

This is like finding a good babysitter. You have to go hunting.

Referrals work because someone has already seen that person do the job. And even if the VA they recommend is not available, that VA may know someone else. A lot of great VAs build their business this way. I didn’t market my business for years. It was almost entirely referrals.

Agencies are another option. They can be helpful because they do some of the matching work for you, and if someone leaves, they can usually replace them. An agency might get matched and running in as little as a week. But you’re also hiring the agency, not just the VA. That means you need to vet the agency, too, and understand their contract. Your dollar also may not go as far because there’s an intermediary taking a cut.

Platforms like Upwork or Fiverr can work, especially for project-based work or if you’re open to international options. Just treat them like marketplaces. You’ll need to do more sorting, more vetting, and more proof-checking.

Ask the right interview questions

A lot of your questions will depend on what you need, but I would always start with capacity. Ask how many hours they actually have available and how many clients they already have.

It's incredibly easy to overbook as a VA. Small contracts and fluctuating work are hard to schedule around, and I've watched it happen to almost everyone in this line of work, myself included. If someone has more than 10 clients, that’s a red flag, because managing that many relationships is a job by itself. Better yet, find a VA with 5 long-term clients. 

Discussing working hours, how often they meet with clients, and preferred methods of communication will make a huge impact on choosing the right person for you. 

The tech your business uses is also important, and an experienced VA will lead this portion of the conversation. Come prepared to answer questions about your systems, your processes, how you like to communicate, and what kind of support you actually need. 

But the most important question isn't logistical at all. 

One of my favorite discussions to have with a potential new client is how they would like to manage and be managed. I prefer to operate with autonomy, so I want to know that my own judgment and ability to make decisions without handholding is a benefit. Neither style is wrong, but mismatched expectations here cause more friction than almost anything else.

The real work starts before the hire

A VA can relieve pressure. They can't save your business.

The right VA will help a business with momentum get organized, execute, and get things off your plate. But they can't walk into a business with no clarity, no money plan, and no process, and fix it. Your business strategy is not a VA problem, that's a founder problem. (Luckily, you know someone you can call to help you with founder problems.) 

You don't need everything perfect before you hire. You need realistic expectations, and you need to release some control.

Start-stop-keep: virtual assistant edition

Ready to get started? Great, here’s what you do:

  • START defining what you want to hand off before you begin the search.

  • STOP expecting a VA to walk in and figure out your business for you.

  • KEEP documenting and improving your processes as the role evolves.

Need a sounding board for rethinking your delegation strategy? Book a free 20-minute strategy session.

Important Dates

  • September 7: Labor Day federal holiday

  • September 15: Multimember LLC and S-corp extension filing deadline

  • October 15: personal and C-corp extension filing deadline

Things I’m Monitoring

Memory chip costs. The tech press is gleefully calling it “RAMaggeddon.” But as much as I want to force an EBN Affleck quip, it’s no joke -- new data center demand has tripled the cost of the most common memory chips. Lenovo says higher costs are here to stay, and Apple and Dell have recently announced substantial price increases. If you’re hiring, allow an extra 20-30% to purchase desktop tech. If you’re on a budget, flex your Costco card or consider refurbishing what you already have.

Always-on recording. By now, you’ve been enthusiastically welcomed to a virtual meeting by zero humans and six punctual AI note takers. You can block the assistants, but the human attendee may be recording it anyway. Wearables like Plaud and app-based note takers like Granola are ever more present. Before you fire up your lavaliere, remember that twelve US states require two-way or all-party consent for recording, and California has explicit privacy requirements. Even if it’s not required, any seasoned Love Island fan will tell you that it’s better to assume everything is being recorded and the right thing to do is to disclose proactively. At the very least, revisit your privacy policy and Ts and Cs to clearly disclose what tools you’re using and state your retention policies. If you’re not sure how to do that, check out this affordable DIY site compliance package from our friends at The Legal Website WarriorⓇ.  And for yourself, just like email is forever, you may want to consider your in-person statements more carefully. I’ll reserve commentary on people who use recordings to optimize their dating.

Tariffs. The greatest hits are back! While $85 billion in IEEPA refunds are flowing, the 10% uniform tariff set in January expires on July 24. The Trump administration has used a never-before-applied tariff provision from the 1930s to levy new 50% tariffs on Canadian cars, alcohol, and dairy products, and will be rolling out more “anti-competitive” tariffs on trading partners in the coming weeks. In a bit of good news, it looks like many companies used last few months to restock

Inflation measurement. The first thing you learn in financial statement analysis is that the good stuff is buried in the footnotes. So while this is wonky, it matters. The Bureau of Labor Statistics is changing how the US measures inflation. This matters because the Fed sets interest rates relative to annual target inflation of 2%, and Chair Warsh recently told Congress that getting back to target is a priority. He also opened several task forces, one of which will evaluate whether the US is using the right inputs to measure contemporary inflation. With somebody spiking oil prices every other week and puking new tariffs everywhere, yet insisting on lower interest rates…yeah, I’m watching the asterisks and footnotes.

Your questions answered

ICYMI, here are resources you should know about:

  • Can you afford to pay yourself as a founder? Yes, and here’s how. Your business has to account for the cost of your labor. Otherwise, you run the risk of building a business that looks “profitable,” but only because you’re working as an unpaid volunteer. If the math only works if you don’t get paid, you won’t have the capital you need to grow.

  • What happens to your business if you can’t show up? Most of the time when people tell stories about a major life event derailing their best laid plans, the ending is pithy and tidy. Everything’s wrapped up in a nice bow, everyone’s healed, and the learnings could be published as case studies. That’s not how life works, particularly when you run a business that depends on you.

Media Kit

Scammers are emailing small business owners with fake offers to buy their companies. You’ve spent years building a company, and then someone shows up claiming a private equity firm has noticed your brilliance and would like to hand you a large check. It’s a real thing that could happen.  Unfortunately, if the next step is a request for financial access, a prepaid “independent valuation,” or a click-to-sign NDA, take a pause and validate the opportunity. Financial conversations are still surprisingly low-tech. A real buyer won’t charge you to find out the name of their firm, and will have a verifiable email address and company website. And that NDA click might deliver a payday, but for a cybersecurity company that spends the next few weeks cleaning up malware.

Thank you for reading! If you have feedback or suggestions, hit reply or email me at [email protected]. If you’d like some help with growth planning amidst waves hand all of this, book a free 20-minute Strategy Session with me.

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