Outsourcing for Beginners – Outsourcing Remote Staff

“I know that in some countries saying words like sh** and fu** are something that is kinda normal, but in our country it’s offending.”

No, this isn’t our Filipino Administration Coordinator telling me off for swearing; it’s the first thing she mentions when I ask her for some outsourcing tips for an article I’m writing. It brings a smile to my face, as I breathe a sigh of relief knowing worst thing I’ve ever said is “bugger” in our daily Slack conversations!

With 3 full-time staff in the Philippines, plus numerous contractors for bigger jobs, we have assembled a solid team with good skills and a positive work environment. Sure, part of this may be down to luck, but the processes we had in place from the very beginning have played a major role in this success. If you’re at the stage in your business where you’re thinking of outsourcing, I want to give you the best chance of success by sharing some useful tips that we’ve learned through our hiring experiences.

When is the best time to outsource remote staff?

If the following things are happening in your business, it is probably time to take the plunge:

  • You’re spending too much time working in areas that you either dislike or aren’t good at. For me, book-keeping was my nemesis. I hated book-keeping and I was no good at it. Hiring a bookkeeper was therefore a no-brainer.  It freed my time to concentrate on the things I was good at, therefore saving me money and stress.
  • Your workload has been steadily increasing and although it may not be constant, by hiring someone, you’ll be able to use the extra time bringing in new clients, improving your business systems or getting on top of your huge workload.
  • You’ve sat down and done the figures. You’ve looked at your current incomings and outgoings and estimated the amount of time and money you’re spending doing the job you want to outsource. The figures tell you that the cost of hiring someone looks viable.

Even if you tick all the above boxes, you may still have doubts about where to start, the pressure of having to cover wages and letting go of sole control. That is totally understandable and normal. The key is not to let these thoughts paralyze your progress. Hopefully, the following steps will put your mind at ease.

Where to Start

Step 1: Procedures

Develop clear processes for the tasks that you’ll be allocating your new side-kick. By documenting checklists, resources, files, contacts and the step-by-step tasks associated with the specific job, you’ll save yourself hours in questions, training or job re-do time. We find that making short videos explaining tasks or procedures are useful and well received.

Step 2: Hiring

There are a plethora of hiring options out there. It may take some trial and error to find your best match, but I've listed some popular and respected places to start your journey here (BTW these aren't affiliate links, I just want to share what we’ve found works for us)…

Contract / Short term work

If you’re looking to test the waters and hire someone for a short-term contract, or a specific web or design job, a good place to start is one of these well-known freelancer marketplaces:



Outsourcely (NB. I like the fact that remote workers get to keep 100% of their wage through this company)


Each of these companies have a huge number of freelancers to choose from, for almost any job that you can think of. The sites are popular and user-friendly. They take care of the search, contracts, and payment in one neat place. Simply search from a list,  or post an ad in the site. Your decision is made easier with ratings, resumes and work samples which are provided for all freelancers. Just remember that you get what you pay for. Often the cheapest freelancer may not be the best.

We found a reliable video editor for our podcasts in UpWork and continue to use him on a regular basis.

Virtual Assistant

Agency Mavericks began expanding a couple of years ago, but before putting on full-time staff (like yours truly), we outsourced VA work through Zirtual

Virtual Coworker  is a similar company. These sites offer experienced US or Australian based Virtual Assistants, who may be just what you need to get on top of your workload. We found an efficient and pro-active VA who helped us immensely in documenting and implementing processes, but we’ve spoken with others who have used the above sites with less luck. As I mentioned before, it may take a few trials and errors before you find an exact match.

PRO TIP: Test outsourcers with small, low-risk jobs to begin with. Eg. Writing a blog piece; a small design job, or as we did when hiring admin help, make some videos, then ask them to turn the videos into processes. This solidifies the process in their mind, gives your business the documentation it needs and gives you a clearer idea of their capabilities.

Here are some other companies that offer similar services (we haven’t used any of these, but some of our members have and like them):







We have an office in Manila and we recruit through the recruitment firm Manila Recruitment. Once we find a potential candidate, we put them through a testing processes before hiring them. Tests for Geeks has online tests that you can give to your programmers to assess their level of competency. You don’t need to have any knowledge in programming – the test and results do the work for you!

Once hired we then train the developers in any areas they need extra help with using TeamTreehouse as the primary training tool.

PRO TIP: Employ remote staff and work with them long-term. It’s the only way to really understand each other and move together towards a common goal.

Step 3: Communication

I can’t stress enough how important communication with your team is. Establish your expectations clearly from the very beginning and make sure they are fully understood.

If it’s a short contract job, email may be your main choice of collaboration. However, if you’re looking at a longer project or building a team, you may prefer a tool like Asana or Basecamp. Asana is the tool we use for all of our projects and procedures. Our procedures are documented in a step by step process so that if anyone is sick or on leave, any staff member could effectively complete the task.

For daily communications with the team, we moved from Skype to Slack. We found Slack much more conducive to group discussions and specific project talk. To streamline discussions, we've set up different topic channels such as: Attendance (where we all greet each other and say we’ve arrived for the day); Programming; General;  Members; and Wins. It’s great for building a strong team environment and efficient communication.

Step 4: Ongoing Collaboration

Once you’ve onboarded your staff, the most important piece of advice I can give you is to keep communicating. I check in with our Administration Coordinator each morning either via Slack or a quick Skype chat. We discuss the jobs she has been designated for that day, the timelines and any help she requires. This is also done with our Developer and Designer each morning. In addition, we also have a Skype team meeting once a week to ensure that everyone knows exactly what is going on in the different areas of the business.

You’ll soon find the best way to communicate. We find that some of our Filipino staff aren’t confident in speaking English and so prefer to chat via text. Although we can’t always do this, I try to accommodate that as much as possible to make sure they don't feel too pressured or put on the spot.

PRO TIP: Use lots of screenshots to explain tasks. Visuals are fantastic when there is a language barrier.

If you find you’re not happy with an aspect of the employee/freelancer’s work, address it sooner rather than later. Be clear about what you need – even make a short video or use screenshots to explain if you need to. And remember, if you've tried all of these things and it's still not working out, it's fine to let them go and find someone else. Sure, it's annoying to have to start again, but once you've found the right person, it's definitely worth the initial trials and mishaps.

A Bonus Tip on Cultural Awareness

Finally, if you are working with staff from another country, take some time to learn a bit about their culture; it will help you and also show them that you respect their heritage. When I asked our Administration Coordinator for a few cultural tips for working with Filipinos, as well as the ‘mind your language’ instruction, she also mentioned that staff appreciate being treated fairly and acknowledged when they do a good job. “In the Philippines we call it “utang na loob” – debt of gratitude. Once you win that you will get more than what you want.”

I started up my own spreadsheet of common Filipino phrases and found that our team really appreciate it when I use them in our daily conversations. Little things like saying ‘thank-you’ or ‘you’re welcome’ make a big difference. There are many dialects in the Phillipines; our staff speak Tagalog, so here are a few of the Tagalog phrases I use regularly. Give them a try!

Gandang umaga – Good morning

Salamat – Thank-you

Walang anuman – You’re welcome

Ang galing – Good job!


These Steps should get you started on your outsourcing journey. Once you take the leap, you won’t look back. You owe it to yourself to make your business as successful as it can be and this is the first step in taking it to the next level. Go for it!

I'd love to know about the successes you've had with different outsourcing companies, or how you set up processes in your business for your working with your remote staff. Drop me a comment below!

BTW Another useful article that goes into more depth about outsourcing remote staff (with some that I had never even thought of) is Mario Peshev's Outsourcing and Hiring Remote Talent. Well worth a read.

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Gin McInneny

Gin McInneny is head of Customer Happiness at WP Elevation. She has experience in website development, digital marketing, videography, and education. Gin brings these skills plus her unique enthusiasm to the wonderful world of WP Elevation.

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