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You’re outsourcing wrong: 7 experts explain how to delegate the right way

The idea of virtual assistants was made extremely popular by Tim Ferriss and The Four Hour Workweek and while I have yet to outsource any blog activities here, I hired freelance writers on Bargaineering. Even with such limited experiencing with outsourcing, I made a lot of mistakes, mistakes that are easy to correct and avoid before you outsource.

And I had a discrete job that was relatively easy to evaluate and obvious work products.

Rather than try to share these ideas based on my own limited experience, I asked a few of my fellow entrepreneurs how they use virtual assistants. I then followed up with individual conversations and learned a lot about how to do things the right way.

The answers below were edited for flow and readability but are otherwise left unedited:

Andrea Deckard,

Andrea Deckard of Savings Lifestyle

Andrea Deckard of Savings Lifestyle

Lots! Compile content into ebook a, write content, organize email, socialize content. Basically whatever I can delegate I try to.

What don’t you outsource? I don’t delegate post optimization or creating my editorial calendar. I actually enjoy testing and doing this type of work so I keep it. I also answer all of my email but I know others outsource that as well.

I chose to keep the tasks that I enjoy because I enjoy them, but also because I’m particularly strong within this area. I also have my VA’s set up to be specialists and keep them doing what they are good at. I’ve changed the responsibilities over the years to refine the exact tasks they own. Some may not be strong in one area but they excel in another. Their lack of competency in one area doesn’t mean they are bad it just means they need to be doing something else.

When you find the “sweet” spot, it’s rewarding.

How did you find your VAs? One person who works with me was someone I hired in one of my last companies. Two of the others were blogger in the same niche as me that wanted to make a more stable income ( they then stopped blogging since they were making more $$ with me). I then found a few writers in a VA’s for hire group (if you need someone to write content for you, I can recommend someone).

Asking others if they know of people seeking that type of work is another way to find someone good. Depending on what you need help with, Erin and Toni’s VA may be taking on additional clients. I can ask her if she has time and could make an introduction if that would help.

Carrie Smith, Careful Cents

Carrie Smith of Careful Cents

Carrie Smith of Careful Cents

I have multiple VA’s that help with different projects. One in particular runs my private community group, the weekly community newsletter and book club. It’s nice to have multiple voices too!

My “Club Coordinator” VA helps run our private community, which includes the weekly newsletters and book club. She welcomes new members, posts updates, gathers blog posts and content that members have produced and inputs it into the template for the newsletter. She also researches info on any jobs and gigs that come our way, and lists them in the newsletter.

My other VA is an Assistant Editor/Research Writer who organizes content for my blog, edits the copy, researches experts for interviews and lists out any contact info. She also writes reviews and blog posts, as well as keeps them updated for changes (like the health insurance stuff for the self-employed).

I create simple instructions for each task, that includes screenshots and step-by-step actions. I’m pretty much a control freak so I want things done a certain way. I layout exactly what needs to be done, step 1, step 2, etc., then go over it with them the first time. Normally there aren’t any problems since they can just refer to the doc. I also use ASANA to track all the tasks, deadlines and comment threads. Less emails!

Melanie Nelson, Blogging Basics 101

Melanie Nelson of Blogging Basic 101

Melanie Nelson of Blogging Basic 101

I’m hiring one to go through and flag content that needs to be updated, group content for ebook(s) and Pinterest page hubs, create newsletters, and much more. My biggest challenge has been finding someone reliable that knows the space and is still affordable.

I’ve also hired VA’s to help me with editing and organizing content and designing ebook covers when I haven’t had the time to do it myself.

How do you find VAs? Word of mouth from friends. So far, the best one I ever had was my friend Jenny. And then she went and got a job with Apple customer service. I’m currently using someone I met at Disney and has worked with other friends of mine, but her hours are thin. She can do most of the work, but not the technical things I need done. But I can guide her on that. There also a guy named Chris Ducker who lives in the Philippines and has a VA service he runs out of there. He has a large clientele.

Linsey Knerl, Knerl Family Media

Linsey Knerl of Knerl Family Media

Linsey Knerl of Knerl Family Media

We have 3-6 freelancers on our payroll at any given time. Some are VERY part-time, others are project-based. Write evergreen content. Contact and respond to giveaway winners. Put together my newsletter and roundup posts. Promote giveaways. Participate in linkies and carnivals. Post generic social media updates (like winner announcements.) Refer new sponsors to me via a commission structure.

How do you find VAs? I look for bloggers that are savvy and are looking for freelance work. They usually give away what their rates are when they announce how much they charge for a post. I ask if they would like to perform some of the tasks that they already do well on their own blogs as a service for me.

If they have the time and patience to pick up extra writing, they usually are open to this. We work out an hourly rate that we’re happy with (it ranges from $15 – 25 per hour) and I pay weekly if they choose to be paid via PayPal (I use my PayPal card and gets points every time I pay them) or monthly if they want to be paid by check.

How do you handle payroll and taxes? Everyone is an independent contractor, so they get paid their full amount and are responsible for their own taxes. I have them do a tax form before they start, and I issue the 1099’s at the end of the year with my TurboTax software that I use.

It’s super simple now that we’ve had people working for us for the past 3 years. When we have new projects come up, I always ask my existing crew first before I pick up someone new. I also have a pool of writers that write in spurts. I save the evergreen content to use when we are short on content on the blogs. I try to always hire U.S. bloggers before I go international.

I know that some people think it’s cheaper to hire VA’s outside of the country, but if you pick a good U.S. blogger as your VA, you can usually get by with not having to proofread their posts, they can communicate directly with readers on your behalf, etc. You get what you pay for. 🙂

Heather Stephens,

Heather Stephens of

Heather Stephens of

If you’re a personal finance blogger, you may know Heather from her work with Fatwallet.

I’ve been a VA for years for an Arbonne team and I have done whatever was needed that I could do off-site. Some of the things included creating newsletters, helping to write/edit content, creating power points, editing videos or audios, recording back-ups of webinars, scheduling social media updates, organizing events, creating invitations, designing business cards, etc.

Since you’re the only VA on this list, what do you think clients can do to make the relationship work better? I think clear communication, detailed instructions, and making sure the VA’s have all the resources they need to do the project ahead of time. A lot of time can be wasted with back and forth emails, trying to clarify the project. That’s also part of the VA’s job too, as far as asking lots of questions to help make sure that expectations on both sides can be met.

Most VA’s specialize in certain areas of business. Depending on what you need help with in your business, you may have different VA’s for analytical tasks, administrative jobs, or creative projects. Let them do their job, if you know them and trust the quality of their work. Don’t micromanage. Giving them some artistic leeway in a the creation of project can help you get better results than what you would have gotten on your own. If you’re working with a new VA ask to see samples of their previous work and references from past clients.

Set clear deadlines and price. Expect your VA to keep you up to date on the progress of the projects he/she is handling. Offer suggestions/tweaks along the way to make sure you get the results you’re looking for in the first or second edit.

Paula Pant, Afford Anything

Paula Pant of Afford Anything

Paula Pant of Afford Anything

I have multiple VA’s, depending on their skill set and pay scale. One of them adds fancy graphics and text to my photos. Another one then posts those photos on Pinterest. I write my own articles, but I have one VA that edits and formats some of these. I even use a VA to make sure my Flickr photos have the proper attribution.

My biggest challenge with hiring/managing VA’s has always been finding someone with a strong skill set who also works cheaply. Hence the use of multiple VA’s, each trained for a very specific purpose.

Where does she find VAs? Odesk and Fiverr, all of them. I know there are many other services (eLance, GetFriday, EA) but I’ve found that it’s easiest to consolidate my hiring into one or two web sources.

Any lessons learned? First, be incredibly detailed when you’re giving them instructions. I initially refrained from giving too much detail because I worried that being overbearing with my instructions would make me un-likeable.

Examples include: “Make sure every point within a list post begins with a present-tense verb.”

Then I stopped worried about being likeable, and got much better results. 🙂

Another pointer: tell them how much maximum time to spend on a project, e.g. “Spend no more than 2 hours on this, and then send me your progress so I can evaluate it.”

Jaime Tardy, Eventual Millionaire

Jaime Tardy of Eventual Millionaire

Jaime Tardy of Eventual Millionaire

I met Jaime Tardy of Eventual Millionaire at FINCON13 and she uses a virtual assistant (who happens to be a client too) for quite a few tasks. What does she outsource to her assistant?

  • Podcast editing and uploading
  • Putting all videos on YouTube
  • Facebook Twitter and social media updates
  • Research articles
  • Prepping posts
  • Gathering data for book
  • Email
  • Scheduling interviews
  • Calendar appointments

And that’s just the list off the top of her head!

What don’t you see on the list? Interviewing the guests on her show. It’s her strength, her differentiator, and, honestly, the Eventual Millionaire would be something completely different without her. She doesn’t have to be the one editing and uploading podcasts, scheduling interviews and managing the calendar. Instead of doing those tasks, she can focus on what separates her from the rest.


Thank you to the seven entrepreneurs who were willing to share with me (and you!) how they outsource some of their work. One common theme through all the responses was that no one outsourced the essence of their blog or their business. The thing that makes their site special, they held onto that.

What did you learn from these experts? Was anything surprising? Not surprising? Please let us know!

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In 2005, I founded a personal finance blog ( that became successful enough that I quit my career as a software developer in the defense industry. It is my goal to share everything I learned so that you can do the same - build an online business that let's you pursue your passion.

12 responses to “You’re outsourcing wrong: 7 experts explain how to delegate the right way”

  1. Linsey Knerl says:

    Thanks so much for including me, Jim! I love this article, in that I can see how others are using VA’s and can possibly add even more services that they can assist with. While it was really hard to let things go in the beginning, once my VA’s earned my trust, it was such a blessing to have them on board. I couldn’t have a small business, 6 kids, a marriage, and a homeschool if it weren’t for my great team! I appreciate you highlighting how outsourcing can be a smart business move and a lifesaver for busy families!

  2. Thanks for including me in your list, Jim! I like Andrea’s comment of hiring bloggers in her niche to be VA’s since they know the topic well and are more likely to be networked with other bloggers in their niche.

    The tax and payroll question you asked Lindsey is an important one. As a VA, like a blogger, it is important to make sure you’re setting aside enough money for income tax. There are some tax write offs you can take as well, so save receipts. Invoicing people through PayPal has been the easiest way for me to get paid.

    • Jim says:

      Andrea is great at managing her team so it was fantastic to have her share her experiences.

      Being a VA is a job with income and an income needs to be taxed (unfortunately). 🙂

  3. Thanks for the wealth of information everyone. I definitely need to start outsourcing some of the more mundane and repetitive tasks that take a lot of time because honestly I just don’t do them sometimes and that hurts my business. I’ll definitely be bookmarking this!

  4. Ryan says:

    Outsourcing has always been a weakness of mine. I have tried a few times, but didn’t have great results. I’m sure part of that is on my end, for not being explicit enough in my requests. I think outsourcing and running a team of VA’s is a skill unto itself.

    • Jim says:

      It’s definitely a skill and it’s one where you really need to be clear exactly what you need to be done and how it’s to be done, rarely does someone else’s thinking and approach mirror yours. Like the saying goes, if you want something done right you have to do it yourself – there’s merit to that.

  5. This is all great information, thanks so much for putting it together Jim! I hired two VAs several months ago and they’ve been a lifesaver for me as I can hand off more of the mundane work and focus on higher level things related to the blog and our business. I thought I’d feel like I was losing ownership of the blog at first, but it actually has gone the other way in freeing me up to do other things to help my site grow.

  6. Jim,
    This is a great article. We are looking at what we will hire virtual assistants and what we will do in house. My husband and I work together on two sites. This was a great round up to see what others hire out. Great list for the beginner bloggers.

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