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Outsourcing to Entrepreneurial Service Providers

It’s another Expert Briefs, where I ask really smart business owners to answer your burning questions.

If you've missed past Expert Briefs, you can click on the undies to see them all –>

The question for this week is about outsourcing. I got this from a friend on Instant Messenger. I'll have to reword it a bit, but the gist is…

The questions in my head is about frickin' “entrepreneurs” masquerading as service providers – how do you find people that stick? Basically, I hire people who'd rather putter around in their own business than to actually work in a job as a service provider – which they were hired to do. I pay well and I'm easy to work for. What's the deal? How do you find people who WANT to work?

I think you'll find the answers this week interesting and hopefully motivating.

Rachel Rofe of says:

I totally understand your frustrations and have been there many times before.

I like testing people with small tasks first, seeing if they perform, and then giving them bigger ones.

I will never EVER entrust anybody with a big project until they've proven themselves. (I used to have a company with 120+ contracted employees so I've been burned a lot!)

I know this approach takes a little more time but it's well worth it in the end (and you can outsource the process to a virtual assistant so you don't have to worry).

You could also look for word of mouth referrals, check internet marketing forums, or do internet searches to gauge for reviews of specific providers.

Also, if you need a specific service provider, feel free to leave a comment at – I know a TON of people and would be happy to help!

Note from Nicole:
Rachel knows outsourcing. Her Outsourcing Report is very good (and affordable). I bought it and recommend it.

Check it out here: Happy Outsourcing

Connie Ragen Green of says:

I have excellent experiences with outsourcing because I look for people who have fun doing the things I can't do or don't like to do. This makes a lot of sense, if you think about it.

In the beginning I tried to do everything myself, as many new entrepreneurs do. When it came to graphic design, I was beyond terrible. I even took a PhotoShop class at my local community college, but it did not help me at all. Then I found someone who had been playing around with graphics and web design since she was about 12 years old, and who was now doing it for others. She creates beautiful designs for me, including the cover of my first book, as well as my soon to be released next book.

Each day I take a look at what needs to be done in my business to see which activities I would rather not do myself. Then I turn that task over to someone who enjoys doing it. Usually the work is done more efficiently and with better quality than if I were to do it myself.

Ask others you know who they would recommend, and attend live events to meet people in person. In a group of two hundred attendees, there is more than likely someone who can help you do most anything you need help with in your business. This will free up your time to do the things you love to do, and to focus on your next steps as you build your online business.

Alice Seba of Contentrix says:

Just like with a brick and mortar business, it's not always easy getting good help, but when you find someone you hang onto them. The reverse is also true, if they aren't working out and don't seem to priorities in check, let them go.

Some ways to keep your good people:

* Communicate regularly. Make sure they are happy with the work and find out if they have any concerns.

* Communicate efficiently and be specific in your requests. There's nothing worse than a lack if clear direction and repeated revisions needed due to lack of communication.

* Help them excel in their best areas. If you hire a VA, for example, and they do certain tasks better then others, let them work in those areas. Find someone else who is good at the other stuff.

* Give them pay raises regularly, even if they don't ask. Make them feel appreciated and valued and realize someone who knows your business and is proactive in helping you with it is manifold more valuable than someone off the street.

The more you value you good work, the more good work you get.

Shannon Cherry of The Business Building Live Intensive says:

Gosh! I remember when I was going through help for my business like water. That was years ago – and it was extremely frustrating.

Today I have a great team who have stuck with me for some time. What's the secret to finding good help? It's you.

Seriously, I see many entrepreneurs blame their ‘helpers' for their ills. But the fact of the matter is, you, as the business owner, are not doing your job managing your team.

Do you have in place things like:

  • job descriptions?
  • policies and procedures, including a ‘trial period?'
  • contracts for service providers?
  • systems to get things done the way YOU want them done?
  • a plan for your business and marketing?

If not, then it's your fault you can't find good help.

Many entrepreneurs hire help to be a ‘catch-all' instead of looking at the persons skills and strengths, as well as their personality. Imagine trying to get someone who is shy to try to cold call reporters. Not only will the person be unsuccessful at the task, but they will get frustrated – and often, simply disappear. (And if you are wondering, that happened to me a while back.)

The key to having a good working relationship is to have your ducks in order BEFORE you go hiring.

Felicia Slattery of Credibility and Cash Flow says:

Here's my take on finding people who want to work. It's simple, really– you go to places where those who want to work are hanging out, paying attention, and looking for work.

Places I like to go to find useful service providers:

  • — for $5 you can find people to do all sorts of quick, one-off types of things
  • — This site is for Moms who have stepped away from the corporate world, who want to keep their skills sharp, and make some money while they are home raising their kids. You'll find highly qualified people here at very reasonable prices. Fill out an RFP and wait for the resumes.
  • — Be specific in what you're looking for, check out the feedback they received, and look for those who bid on your job to be personal in their response. Then Google them to see what you can find before hiring.

One place I'd be careful of is looking to folks on social media. While you can definitely find excellent talent and people willing to work, carefully look at how much time they seem to spend on the various social sites. If they seem to spend/waste a good portion of their days on social media chatting, they may not be doing much work in the background or they may be on social media to promote themselves — and we all know how addictive that can be. It could be difficult for some to get out of that rut and get to actual work. Not that you shouldn't look to network with people on social media, it's just not necessarily the first place I'd look when I want someone willing to roll up her sleeves and dig in.

Finally, be clear in what you are looking for and with everyone you hire draw up a simple contract or letter of agreement so you can communicate your expectations, deadlines, and other requirements. Oftentimes we get into trouble because of a lack of communication of expectations up front. Be clear about what you need, want and expect and you should easily find someone willing to meet the challenge and make some money!

Susanne Myers of says:

I hear ya … been there, done that and it can get pretty frustrating. You're all excited to have someone take care of some crucial business tasks and then it just doesn't get done, they quit etc. Unfortunately we do sometimes have to go through quite a few assistants, VAs, service providers until we find the one that's a perfect fit. (I had to go through about 10 before I found the right one).

Let's talk about service providers for a minute. There are those that just want some tasks and a weekly or monthly paycheck in return. They are very reliable and work exclusively on this kind of stuff. The problem is you have to provide every single step of the process. They don't think outside the box, they don't see the bigger picture of where you're going with your business.

Service providers who are also entrepreneurs on the other hand will come to you with ideas and suggestions for improvement. They are the types of people you can hand an entire segment of your business to and have them run with it.

The thing to keep in mind to make this work is that these different types of assistants are motivated by different “things”. While paying well and being easy to work with is great for the first group of VAs, it won't quite cut it when you're dealing with an entrepreneurial minded person. They want more than just a paycheck for the hours they worked. One way to keep them focused on and interested in your business is to give them a cut of your profits. Another option may be to help them grow their business by referring sales, clients etc. Encourage them to work on their own products on the site and promote those if your target markets match.

One last tip and this is something I'm still working on. Document everything you have them do. Instead of just showing or emailing them about a task, take a few extra minutes to make a video or write the instructions in a word document. Save all this so you don't have to do it over if you need to train someone else.

NicoleNicole Dean of .. here! .. says:

Oooh. I was so tempted not to answer this question and instead just defer to the others. But, I think the question wasn't quite clear. It was about outsourcing to other entrepreneurs rather than outsourcing in general. So, let me see if I can tackle it without offending anyone… Wish me luck.

As you may know, I go through a lot of helpers.

Wait. That sounded bad. eek! I mean, running 3 PLR sites, plus my niche sites, customer support, graphics, and even managing my household — it takes a village some times. 😉

Although this question was submitted by a friend, it's one that I've struggled with over the years.  “How do you find people who want to work? Especially if they are entrepreneurs?”

This is a frequent scenario for us…

My Content Acquisition Manager: Would you like consistent writing work for Nicole Dean?

Writer: Really? OMG. YES! I'd love that. That would be awesome. I really need the money because (insert expense here ie. my husband lost his job, we have a leaky roof, our pet needs surgery, kid just got into private school, we're moving, etc.  ).

(They discuss price and topic of articles.)

My Content Acquisition Manager:  ok. Nicole pays weekly every Friday via Mass Pay. If you'd like to get into the current week's Mass Pay (and have Nicole pay the paypal fees instead of it coming out of the payment like normal) then I need this back by (date).  Can you do that?

Writer: YES!

Looks promising, right?

Here's what happens as the deadline approaches.

My Content Acquisition Manager: Checking in. The deadline is this afternoon. How's the article pack coming?

Writer: Well… (insert story – which is likely true – here). I need an extension.

My Content Acquisition Manager: When can you have it to us?

Writer: Tomorrow afternoon.

My Content Acquisition Manager: ok. Of course, you won't be paid until next Friday since you missed the cut-off. But that's fine. It has to be to us by that time.

Still looks promising, right?

Well, the next afternoon…

My Content Acquisition Manager: Do you have the articles ready?

Writer: No, I …

My Content Acquisition Manager: We're sorry, but we won't be able to work with you.

On to the next writer.

We probably go through 3-5 writers for every one that sticks (either for actually completing the project or for the high quality standards we have). When we find a writer that sticks, that person gets consistent work.

What's my point?

There are a few lessons that I've learned about outsourcing to entrepreneurs who are freelancers.

1. Many entrepreneurs are not good motivated freelancers, because they *really* want to be focusing on building their own businesses and getting passive income.

It's an ongoing battle for the freelancer. And, I can relate because I've been BOTH, myself. Feeling “stuck” working for an hourly rate, while really wanting to have a passive income. This is fine as long as the people on both sides of the fence recognize that. Just don't let resentment build between you.  As the business owner (the one doing the hiring), you're the one taking all the risk, bringing in the leads, and the one who is ultimately responsible for the success of your business. You're responsible for having the money to pay them at the end of each month, too. That's a lot of pressure. Where there's risk, there is reward.

2. If you hire an entrepreneur-freelancer to do work for you — recognize what's important to them, and try to acknowledge that.

This normally, in my experience, is not just about money. Not that money doesn't matter, too, of course, but you can give in additional ways that are meaningful. I always talk about the “The 5 Love Languages: The Secret to Love That Lasts” and how it applies to outsourcing. (If you haven't read that book, please do.)  Motivation comes from different things in different people.

It may be one or all of the following…

  • Flexibility. Perhaps it's a college student or mom who needs a flexible schedule. Just knowing they can work at 9pm or 9am is enough to really keep them going.
  • Doing something that matters. Hence the number of people who work for non-profit organizations.
  • Feeling Appreciated. I've worked for bosses who could get me to do anything by appreciating me. Work long hours? Sure! No problem.
  • Kind Words and Recognition. Similar to being appreciated, this can be huge. When I worked for Jimmy D. Brown, all he had to do was mention my name in an email that he sent to his list and I would hop around for a week, like it was my birthday.
  • Doing what they Love. For some people, they want to be able to focus on their talents. So, if you find a Virtual Assistant who says that she's a customer support rep, but you find out that she plays with Search Engine Optimization in her free time for fun — then you might want to see if that's really what she'd prefer to be doing.
  • Gifts. Some people like small gifts. Sending a surprise token of appreciation can be all that it takes.

And, for the entrepreneurs that I hire — oftentimes they want ME. My time. Which is fine if we've arranged that. But, of course, I can't coach every person who I work with all day long – so there is normally additional bartering that goes along with that. Even my mom expects and gets coaching time with me when she needs it.  That's part of our arrangement for her working for/with me.

Others trade work (sweat equity) for coaching time with me. I've had coaching clients for months and months — and they work for me in trade. For them, that's a better arrangement than having me pay them for their time spent working.  Each of us has profited much more from the bartering arrangement than we would have otherwise.

So what's my advice? Well… good question. 🙂 Of course any outsourcing really comes down to the people on both sides of the relationship.  I've had some really great experiences and two where I had to consult my lawyer about starting litigation. (Don't ask.)

My advice is going to be a summary of what has already been said:

  • Take it slowly with anyone new. Start small. Test the waters before making any commitments.
  • Set up Standard Operating Procedures. This will ensure that expectations are clear from the start.
  • Place people correctly. Find out what they love to do, instead of what they say they do.
  • Continually look for new people. Make sure you have access to new people on a continual basis – if you need more than a few people working for you at a time.
  • Understand what motivates your new hire. Praise publicly. Critique privately.
  • Reassess often. The person you hire today to do a job may not be the same person who should be doing that job a year from now. (Either because they've bubbled up the ladder or down it.)
  • Expect excellence, but plan for disaster. There's a saying I love – “Hope for the best, but plan for the worst.” That's the case in any area of business.

Go ahead and share your thoughts. I would love to hear your experiences on both sides of the outsourcing coin.

Nicole Dean

PS. Let me just say that I do encourage service providers to work on getting an alternate source of income, preferably passive income. But, not at the expense of meeting deadlines for clients or getting a bad reputation.  Schedule at least 1/2 hour every day on your own business, but keep all client obligations met. That's what I taught my mama. 🙂

Check out these Recommended Resources:

I appreciate shares and I adore comments! Please share your thoughts.

  • Tracy Roberts

    Seems to me the real question is as an admitted entrepreneurial service provider is: Am I giving the person I agreed to work with quality work in a timely manner?

    There is nothing wrong with creating passive income and in fact, it’s a smart thing to do. However, if I want payment for services provided, it’s probably a good thing to actually provide the service. Quality Work. On Time.

    The fact of the matter is that most entrepreneurs aren’t making a passive income yet and need quick cash. They contract for work and then life gets in the way. Life happens to everyone….it’s how you manage things that matters.

    If someone tells me they really need money and I give them a job to do and then when the deadline looms and still nothing….there’s a disconnect in what is truly important to that person. I’m guessing it really isn’t coming up with money to pay the mortgage, car, college, etc.

    The tough thing to learn (and which Nicole does so well – she’s one that will take the time) is what will motivate the people you outsource to.

    So, a question to my fellow service providers: Are you doing what you say you’ll do when you say you’ll do it?

    • The Mom

      Hi Tracy! It’s so nice to see your smilin’ face here. Good input, too. I hear ya and agree.

      Providing quality work ON TIME is a challenge for sure, but is so crucial. And for VA’s and other freelancers it’s all about reputation. If someone continuously says “Yes, I can do that” then keeps missing the deadline, or provides shoddy work, there’s a disconnect going on.

      And, yes, it’s also about motivation. We all need our ‘atta girls/boys’ don’t we. Beyond the kudos, it really is important to find out what drives someone to work hard.

      And, yes, I agree with you Tracy. When a business owner is understanding and patient when ‘life happens’ to disrupt a VA’s schedule, it’s nice for sure. Most business owners are kind caring people who really feel for their workers. Heck, many business owners started out as freelancers themselves. So, when things happen, they really do understand and care.

      I also agree that this can get a bit tedious for the business owner who keeps hearing how desperate their VA’s or freelancers are for money, but then how unable they are to meet a deadline. hmmm… I feel for those poor business owners who are left trying to juggle their own life and their own business now with a missed deadline.

      Anyway, I just wanted to chime in to your comment, Tracy. It was fun to see you here. 😀

  • Becki Maxson

    I’ll second the recommendation for I own a busy transcription service for internet marketers and have a team of transcriptionists that’s varied from 6 to 15 to 9 etc, depending on the need. Some of my best workers have come from that site and I LOVE being able to help moms work flexible hours from home.

    One thing I unfortunately don’t recommend anymore is trying to hire people you know UNLESS they have a proven track record in what you need done. We’ve all had the frustrating experience of trying to help someone by giving them work and getting that dialogue pretty much as Nicole spelled out – YES they want the work, YES they can do it, YES they just need a chance – and then it’s nothing but excuses or disappearing.

    I learned to actually put a time on the deadline, as ‘afternoon’ to you may mean ‘early evening’ to someone else. If your work is time sensitive, be specific. That way there’s no debating whether it’s on time or not. Include your time zone 🙂

    Also watch for undiscovered talents as you work with people. Some of my team have been able to move into editing, project management etc as I see they can do more than what I hired them to do. It’s so much easier than starting from scratch with someone unknown.


  • The Mom

    … and, of course I couldn’t stop there.

    (as you might have read here on NOTN, I tend to be quite verbose)

    I just wanted to add…

    I love what all the experts had to say. This is a great topic. AND, I know for a fact that Nik encourages freelancers to get going on their own stuff. Yes, it’s okay to work hard for someone else (instant money talks) but it won’t get you where you want to be in the future. That doesn’t give you the freedom that you long for. You are still tied to your computer if all you’re doing is writing or working for someone else. (Yes ma’am.)

    It’s a difficult juggling act for us freelancer/VA types. Money now v. Money later. hmmm… I know I go through this dilemma EVERY SINGLE DAY! I wake up thinking about my own projects, look at the clock, and realize how many hours I have to work for ‘instant money’ and see the day slipping by without working on my own stuff.

    What I LOVE about the gals I write for is that they really do KICK MY BUTT! That is such a good feeling. I don’t think they would be kicking my butt if I was letting THEIR work go, missing deadlines, or providing shoddy work. I’m guessing if these gals were frustrated with my work, they would be leaving me alone. 😉

    So, my question to freelancers/VAs is:

    Are the people you’re providing services for kicking your butt?
    If not, maybe you aren’t providing the kind of quality work that you should be.

    And yes, Susanne, having a successful entrepreneur lend her name, time, website, reputation, and even content to a fledgling wannabe entrepreneur is absolutely PRICELESS! Thank you!

    And yes, Nicole, being The Mom and receiving shout-outs here and elsewhere definitely feels good and produces wonderful results, too. Of course, having your ear doesn’t hurt, either! kiss kiss

    Like I said earlier, business owners are typically warm fuzzy caring people. They understand the mindset of freelancers because they often came from the same place in life – wanting to provide a better life for themselves and their family. Everyone can respect that.

    So, on that note, we should all be after the same thing – a good relationship.

    Business owners want their work done well and on time.
    Freelancers want to work on things they like with people they like, while learning how to make their own business grow.

    Thanks Nik for this great topic as well as your honest appraisal. Thanks, too, to all the experts. As a freelancer/VA, it’s so good to hear the business owner’s side of the story.

  • A. David Beaman

    I get some of the PLR for my membership site from Nicole, Alice and her partner, and occasionally from a couple of other who are top shelf in the PLR article-world. I also found a very good lady through Elance who does exclusive stuff for me.

    I am fed up with the hype-masters, upsellers and video mongers. Currently, I am revising my site, rewriting the pitch page and courting customers who appreciate honest professional with quality, evergreen products.

    I have learned much from, and have great respect for Nicole, Alice and the other associated ladies. Why is it that it is mostly male marketers with whom I am fed up, while the female marketers get my respect? Because that’s where I see the honesty, quality and professionalism. I hope one day to see myself and other like-minded men join the ranks of these women whom I greatly admire.

  • Alice Seba

    Thanks for the vote of confidence, David! 🙂

    I think I understood the question because it doesn’t really matter who you’re outsourcing to, the advice is the same. If you want good work out of people, you have to provide the right environment for them. Of course, nothing is guaranteed and there will be good apples and bad apples, but such is life.

    There are 3 people on my team who have been with me for a very long time (betwee 6-8 years). 2 of them are freelancers who focus on freelancer…although one has a couple of side projects. The other is very much an entrepreneurial freelancer, but I think we have the type of relationship where there is so much benefit between us that it just works and have worked for 8 years!

    The working relationship is what you make it. If you do your part and it still doesn’t work, don’t sweat it and move on. 🙂

  • Emily

    Those are some great tips/cautions for those of us who have not reached the outsourcing level. Will definitely keep them in mind.

  • Bronwyn

    This is a great article. I will put much of this into action as someone who has just started outsourcing as a little income is starting to come in:-) Also, I can highly recommend Rachael’s products. I have taken everything on board, it is a great investment.

  • blue flamingo productions

    As a full-time writer for the past 20+ years, I have found a few things that have helped me to provide exceptional service to my clients.

    1) I state or request a specific “due date” for the writing project. Even if the client is not in a hurry, my ususal turnaround time is 7 business days; projects can be completed sooner, of course, but an extra fee is incurred.

    2) I have my own set fees for my professional services and do not depend on someone else (the person who hires me) to tell me what he/she thinks my education, experience, skills, and creativity are worth; that weeds out some potential projects, but leaves quality time for quality work. If I am “earning” what I asked for, it completely eliminates any “procrastination problems” because, as all professional writers have experienced at some point in their careers, there is little worse than accepting a big project for pocket change just to get the job. I respect YOUR fees and your professional insight, and simply expect and ask for the same in return. While I would love to take on every project offered to me, if the client can’t afford my fees (that have been established over decades of professional work), he/she won’t appreciate the authenticity, creativity, and professionalism of the magnum opus I would create for him.

    3) I value my time; as a result, I choose not to waste it in idle chatter over the phone, reading what someone had for lunch at the seminar via their FB postings, or spending the day surfing the net or the tube.

    4) I do every single project as if it were for my own business, project, needs.

    5) I start every project the day I am hired; this way, I’ve got a huge portion done by the time it gets closer to the established deadline.

    6) I absolutely love what God has blessed me with the ability to do – bring brainstormed ideas to fruition via the written word. As a result, referrals are the best form of advertisement any business owner or service provider can’t buy!

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