How To Know When It’s Time To Hire An Assistant

Feel like there is too much to do and not enough time to get it all done? Consider these factors before looking for an assistant.

How To Know When It’s Time To Hire An Assistant
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If there aren’t enough hours in the day to get everything done and administrative tasks like expense reports and invoicing are falling through the cracks, you may have considered getting an assistant. But before you hire someone, make sure you’re really ready, or you could be wasting time and money.


How will this help your business? “You need to understand why this hire will move your business forward,” says hiring consultant Rikka Brandon. “If you can’t articulate the business result you expect to see–an actual benefit to you or your business–you shouldn’t hire just yet.”

Can you afford it? You should also have enough cash in the bank to pay for the person for at least 60 days without dipping into your own paycheck, says Brandon. “Many entrepreneurs hire help, assuming it will immediately turn into more cash flow, but it simply doesn’t turn that fast,” she says. “Your business needs to be doing well enough to support itself, you, and the cost of this new overhead without you taking a pay cut.”

What are your expectations? Additionally, make sure you have clear activity expectations before the person shows up. “This step is often skipped by people who are excited their business is doing well enough to hire and they are feeling overwhelmed,” says Brandon. “But this is the key to success. If you aren’t clear in your own mind about exactly what you are paying them for and what you expect as a result, you will end up disappointed.”

Nick Loper, author of Virtual Assistant Assistant: The Ultimate Guide to Finding, Hiring, and Working with Virtual Assistants, recommends taking at least two weeks to log your activities. “This will give you a detailed picture of where your hours are actually going, and you’ll be able to itemize delegation opportunities from that list,” he says. “It will also give you an idea of the approximate number of hours a week you’ll initially be hiring for.”

What’s worth delegating? Outsource and delegate the tasks that are not making you money or growing your business, such as screening emails, scheduling meetings, and travel planning, suggests Jennifer Maffei, founder and president of VEA Services, a consulting firm specializing in helping CEOs get the most out of their executive assistants.

“The best way to hire a qualified assistant is to treat it like an investment,” she says. “This person will be your business partner.”


The Hiring Process

When you’re clear on what you need, you should also be able to gauge how many hours you’ll need from someone. If you want to hire someone on a part-time or virtual basis, Loper recommends a site such as Upwork or Zirtual.

“In my job description, I’ll include the projected tasks from my time-tracking study, and note that this is a long-term position for the right candidate,” he says. “In the world of the weekly freelance hustle, having at least a few hours a week spoken for is an attractive proposition.”

For an assistant who will work with you in person, get the word out, says Brandon. “It is hard to hire amazing people if you only have three mediocre applicants,” she says. Post ads on job boards, and tell your personal network that you’re looking.

After you identify potential candidates, Loper suggests giving each a test that could provide clues about their work style. For example, he asks them to copy three blog posts from his site into Microsoft Word, with a page break between each post, making sure the formatting matches the format online. From this exercise, he learns how detail-oriented they are.

Another way to find the right person is to know yourself, says Brandon. “Are you a great manager? Or are you more wired to be an individual contributor?” she asks. “Both are okay, but they should get different types of help.”

An individual contributor who doesn’t want to “hand-hold” employees would be better served with a more expensive but experienced virtual assistant. A person who enjoys and excels at managing people can spend less money on payroll but more time on training and getting the new assistant up to speed.


What To Expect

Once you find the right person, make sure you provide adequate training. Reframe this time spent as an investment, says Loper. “If you can spend four hours training an assistant and not have to deal with it again for weeks or months, that’s a huge win,” he says. “The same goes for higher-level tasks.”

A six- to nine-month learning curve is the standard to get to the point where it feels like your assistant has always been with you, says Maffei. And once you find your flow, an assistant should save you a minimum of two hours per day.

“That equates to one whole quarter per year of regained productivity for you to work on building and growing your business,” says Maffei. “Depending on the level of involvement you want your assistant to have, it will only go up from there.”