The Way We Work

Try as you might, you can’t do everything yourself if you want to grow your business. “If you’re a one-person shop, eventually your availability will max out. Trust me, I’ve been there,” Matt Keener, the Executive in Sweatpants, wrote recently when explaining key signs it’s time to get help.

It’s one thing to accept that you can’t do it all on your own; it’s another to actually welcome someone new into your business. When you’ve relied on a team of one, how can you feel confident that someone else will understand your priorities, motivations, or rationale?

“I think trust is the biggest factor,” confirmed Lee Drozak, a virtual assistant (VA) who specializes in web marketing and WordPress. But trust isn’t the only challenge; bringing a new team member on board can be a lot of work — especially if you don’t find the right person.

The secret to success? Drozak and two professionals who’ve used VAs to support their work, Nick Loper and Jenna Weiner, explain their experience and advice for those preparing to take the next step.

Yes, it takes time to train a virtual assistant

“We can come up with a lot of excuses when it comes to hiring someone to support our businesses,” said Nick Loper, the entrepreneur behind Side Hustle Nation, who has been working with VAs for nearly 10 years.

“When you’re already up to your neck, it can be hard to believe it’s worth the extra time to bring someone on board,” he said. “You have to invest time up front; the benefit is the long-term payoff. Even if it takes an hour to prepare — even if it takes one or two days — consider the break-even point of never having to do that activity again.”

Loper notes that documentation became important when he started working with a VA. “All my processes were in my head,” he recalled. “I created some training materials, then we spent time reviewing things together and sharing the information.”

You also need to learn to let go. “My VA is free to edit my processes and procedures if she finds a better way,” he said. “My way isn’t necessarily the single best way to do it.”

Be specific about what you want a virtual assistant to do

What can a virtual assistant help with? Jenna Weiner, content strategist at Dropbox and former editor-in-chief of the oDesk blog, says it’s not just what someone else can do. You also need to decide what you actually want to hand off.

“There are some things you simply won’t be comfortable having someone else do,” she explained. “But — depending on your relationship — a VA can help with everything from research, to data entry, to tasks that involve making judgment calls.”

Loper agrees. “Do what’s right for your business, so you can focus on strategic stuff. But don’t get rid of all the fun stuff; you’ll lose the things you enjoy in your business.”

Drozak adds that you shouldn’t be afraid to ask for advice. “Asking how an assistant can help you is a realistic conversation to have; there may be things you’re not thinking about,” she said. “But it’s an open-ended question; you need to listen to what they tell you.”

Find the right match for you — and for them

Drozak says you must be prepared to bring a VA into your business. “When you have the budget, the mindset, and the goals in place, it will more often be a successful relationship than not.”

Budget matters more than some people think. “If you’re penny pinching, it makes the relationship tough because you want all this stuff done but don’t have the money.”

You also need to think beyond hard skills. “Where do you see yourself in a few years with the person you’re going to hire?” Drozak asked. “If your needs are short term, it doesn’t matter as much. But if you want to hire someone who will grow with your business, your long-term goals need to be aligned.”

For example, how do they feel about being a business owner — do your business philosophies match up? Are your business practices a good fit for their routine? Are your personality styles complementary?

The best way to get these answers is to connect in person — whether physically, on the phone, or via video conference. “Always have a conversation as part of the hiring process, and trust your gut instinct,” Drozak said. “Your instincts will tell you a lot more than an email or an RFP.”

Confirm your choice with a test project

Weiner had a VA to support her work at oDesk. To ensure she was getting the information she needed, she used test projects as part of the hiring process.

“Effective use of a VA depends on your ability to trust that they will deliver what you need,” Weiner said. “Test projects are a great way to confirm whether your work styles are a good fit, too.”

She suggests a small assignment (1-5 hours) that’s comparable to the work they’ll be doing for you. “I found it helpful to assign small projects I’d already done, because I could then compare results. Sometimes, I found that VAs did an even better job because they had more expertise in a particular area or industry.”

Loper also relies on test projects, and emphasizes that it’s not just whether a candidate does the project, but how they do the work.

“Yes, you need to find someone who can follow instructions without a lot of help,” he said. “But if I’ve made myself available to answer questions or otherwise help, and someone who’s new to me and my business doesn’t take time to ask anything, the lack of initiative is an easy way for me to screen people out.”

Depending on your needs, it’s not unusual for someone to hire a team of VAs, each with different areas of specialization. With thoughtful planning and preparation, expanding beyond your team of one can give you the time you need to focus on the activities that matter most!

Whether you’re a virtual assistant or an entrepreneur, what advice do you have for people who want to hire a VA? Share your advice in the comments section below!

Amy Sept

Managing Editor

As the managing editor of the Upwork blog, Amy Sept works with regular and guest writers to share information that helps freelancers and businesses navigate the future of work. She owns Nimbyist Communications and helps non-profits, startups, and small business owners get their content marketing on track.