Adventures in Outsourcing

JillProductivity8 Comments

It's no secret that we have been a little hesitant to loosen the reins on our business and hand over some of the responsibility to someone we have only ever met on a computer screen.

We hmm'd and hawed, wrote out a list of pros and cons and came up with worst case scenarios until we finally decided to stop being pussies and just take the plunge.

It's been quite the ride so far—full of ups and downs, sighs of relief and feelings of disappointment.

The good news is however, we are making progress (slowly but surely) in finding and creating the perfect team for us—thank tha lawd!

So in the interest of helping someone else make the transition from working ON their business instead of working IN their business, we've put together a few things we've learned along the way…

Our Adventures in Outsourcing

Have Systems in Place

When we first began outsourcing our business, we started with content and social media. We hired our girl Sabrina to not only manage the social media for our affiliate sites but create most of the content, week to week.

Did we give her any guidelines or formatting tips?


Should we have?


Fortunately, she is a savvy chick and has learned the ropes, developed and grown alongside us, and is easily our best business decision to date.

So, you think we would have learned our lesson from there, right?


Our next move was to hire an SEO manager.

Since Josh loves his SEO you would probably expect us to have a clear vision on what we were wanting to achieve with our backlinking. Instead, we told him to solely backlink our money pages.


So we moved onto another SEO manager who was amazing and whose focus was more on building high-quality links and tools that readers would want to interact with and share, and other sites would want to link to.

This time we had a better idea of what we wanted but we only saw marginal success. So we parted ways once more.

We couldn't figure out for the life of us what was going wrong. I mean, what the hell were we missing?

Procedures, baby!

Once we realized that we needed to get clear on exactly how our business runs, what works and what doesn't we started the process of writing out step-by-step procedures (complete with screenshots and templates, if needed) for each and every task required for our business to run.

It was a fucking mission, but it allowed us to have documents in place that could be assigned to a new team member and allow them to hit the ground running—without too steep of a learning curve.

I can't even describe the difference this made. Actually maybe I can: It was like the heavens parted, angels sang and cherubs played glorious music on harps while unicorns frolicked in green pastures and candy rained from the sky.

It was a game-changer, to say the least.

But then we assigned our newest team member 7 procedures to start off with.


Which brings us to our next point…

One by One

Now that we have found Joel—our Filipino saving grace—we have altered our approach.

We started out by giving Joel one procedure at a time (locating high PR domains—a topic we'll be talking about in the near future); he crushed it.

So we started handing off other tasks, one by one. He crushed those too and within a few short weeks Joel was singlehandedly saving us about 15 hours a week of menial tasks—allowing us to focus on tasks that would help to build our business, not just maintain it.

We then realized when you allow your new team members to get accustomed to your business, how you run it and the level of quality you expect, they rise to the occasion.

From there you can start adding to their list of tasks, slowly easing them into the process of taking over the majority of your everyday tasks.

Just remember…

Don't Get Discouraged

When you first start dipping your toes into the world of outsourcing you may find your first few choices don't pan out or really drop the ball:

Like the girl we first hired to format The Art of Authority who told us (a day before launching) that she didn't “work after regular hours”, irregardless of the fact that she promised us she would have it done on time.

Or the guy we hired to handle a few daily tasks and told us he was “too sick” to work for 3 days right after accepting the job from us.

It will happen, and it's probably best you expect to have a few let downs—and maybe a disappointment here and there—before you really figure out what you are looking for, and who fits that mold best.

You just have to stick with it, brush off the setbacks and try again.

I assure you, you will find someone who fits into exactly what you want, will work hard to complete the tasks you delegate to them and surpass your expectations.

And once that happens, hold onto that person. Treat them well, surprise them with a bonus out of the blue and solidify that relationship with them.

Because those team members? They can be the missing link between you making four figures a month and five.


  • Joel Carr

    Good post, +1 for the processes. You really start questioning what things mean – when you have to explain them to someone. I’ve finally found some great workers in Phillipines. I’ve probably had 10 so far, finally found some keepers.

    I found a great way to weed out the slackers is to track their time with timedoctor(or something similar). The honest workers don’t object one bit. The lazy bastards have a million excuses why they cant install it. Easy way to weed them out.

    • Jill

      Oh I love that idea Joel! Thank you for the tip 🙂

      So far Joel has been awesome and we haven’t had too many problems with him yet *crosses fingers*

      We also just found a dude out of Mauritius to build our upcoming digital product site who also seems quite good. I just hope this lucky streak doesn’t end with outsourcers! lol 😉

      Are you doing anything specific to make sure your “keepers” don’t drop the ball on you? Do you use incentives or anything?

  • Exactly. In a way you are wasting your expertise if you spend time doing things you could more effectively outsource. It’s not even limited to menial tasks, things such as web design or development issues.. trying to figure everything out by yourself can be a giant time vacuum.

    • Jill

      Oh absolutely! I just figured most people do outsource that sort of stuff if they don’t know how to do it, but I should’ve thrown that in there as we’ve started dabbling in outsourcing tech work – we just outsourced a Optimize Press 2 site because we didn’t want to waste months trying to figure it out ourselves and get sucked into the vacuum 🙂

  • Having a system in place in essential to a successful working arangement! My first hire was to a guy in India. I wanted a niche site built. But honestly didn;t know what I wanted!

    So many back and forth, wasted time, bad work..

    Now when I am hiring. I know exactly what I want, have it pre-written and have a few regulars that I hire.

    It takes time to get the ropes down, but once you do it is great. I could not be bothered with learning Photoshop!..

    • Jill

      We could not agree more. The systems and procedures we have created have been our saving grace!

      Still trying to sort out who our go-to’s are as they seem to change all the damn time but I guess that’s part of the process. We currently have someone building an OP2 site for us because we just do not have the time to learn yet another platform right now! 😉

  • Hey Jill, great post. It seems like outsourcing is always an adventure, but totally agree that starting someone off with ONE well-defined process is a recipe for success. Once they master that, add another to the mix, and on and on until they’re running like a pro! Just discovered your site today and look forward to seeing your future posts — love the domain btw!



    • Jill

      Yeah that was something we had to learn the hard way! lol

      Luckily, we realized before we burned through too many VAs 😉

      And thanks for the kind words…I’m diggin’ your site as well! Just about to listen your podcast 🙂