How to Outsource on Upwork

How to Outsource on Upwork

 Welcome to the ultimate guide on outsourcing and hiring virtual assistants to make your life easier.

In this post, you will learn:

1. How to outsource on Upwork for virtually any task and hire virtual assistants.

2. How to take advantage of incredible, overseas labor for as little as $4 per hour.

3. My protocol for hiring, training, and managing virtual assistants.

4. My first experience with outsourcing and using virtual assistants.

My First Experience with Outsourcing on Upwork and Hiring

I began experimenting with outsourcing when I was 14. I started my second company, Doormat Delivery, which delivered flyers (pre-internet boom), on behalf of companies, directly to the doors of prospective clients. (My first company was a dessert baking operation for a local coffee shop, but the food inspection agency closed it down, claiming my home kitchen had not passed inspection.)

I began delivering flyers for my parents’ real estate company and charged $0.10 per door. The average track of houses consisted of 300 homes and took six hours on foot to complete. $5 per hour, in the year 2,000, wasn’t bad for an unemployed kid.

To expedite delivery, I started using roller blades, which cut down my time by two hours, thereby increasing my hourly rate to $7.50. For the first time my company grew bigger.

A few months later, I had my first genius idea: If I could add other businesses with my service, I could deliver multiple flyers simultaneously—doubling or tripling the money—without increasing the workload.

I came up with a simple script, pulled out the yellow pages, and cold-called painters, roof designers, home remodelers, and any business that would benefit from having their service seen by hundreds of potential clients.

At my peak, I had four clients going at once (the most amount of flyers I could carry by hand while roller blading) and was making $0.40 per house, or $30 per hour!

Again, my company grew bigger.

However, I soon realized that while all my friends were out playing and chasing girls, I was still sweating balls in the sun on my Saturdays.

Consequently, I learned my first real lesson in lifestyle design: it didn’t matter how much money I made if I couldn’t enjoy it.

That’s when I had my second genius idea.

I had a commodity many of my friends wanted, a fun, easy business that paid well. If I could hire someone else to deliver the flyers at $10 – $15 per hour (plenty of cash for a fellow 15-year-old), I could pocket the difference without doing any work.

Of course, that’s what I did. I had Mike, Kevin, Rick, and Scott working for $15 per hour, sweating balls in the Saturday sun, while I did more of whatever 15-year-olds do.

They were thrilled, and so was I.

It was the first time I grew better but not bigger, and it changed my life.

I ran that business for two years, until I found poker, which I bankrolled from the money I saved.

What I Learned from Outsourcing on Upwork and Hiring Virtual Assistants

When I started my online marketing company, Spinther, in 2008, I used the lessons I learned as a young adolescent in outsourcing and lifestyle design to turn my modest company into a well-oiled machine with 12 employees from 5 countries.

It grew quickly; mostly, because I didn’t waste time doing unnecessary, busy work. My system was simple yet effective: as soon as I learned a task I would immediately hire, delegate, and train someone who was more specialized than I was.

My accountant, for example, is essentially a virtual assistant (he works remotely from the Middle East) and does everything I need for less than $100 per month. It’s important to stress that we created systems which automate much of his workload, as well as mine.

Instead of wasting 10 hours, or $500 a week on accounting, I reinvested my time and money back into my business.

Keep in mind that outsourcing and hiring virtual assistants on Upwork doesn’t mean you have to compromise an ounce on quality. In fact, to the contrary, by using outsourcing services such as UpWork (which we’ll discuss later in this post), I can choose from a global player pool, thereby increasing the number of prospects and the likely quality of employees I have to choose from.

While Muhammad crushes my accounting needs, I’m focused on creating systems to grow better.

How to Outsource Virtually Any Task

Too many people focus exclusively on bigger, which is when they get overwhelmed and overworked and things collapse.

Don’t make that mistake.

Typically, there’s a limit to how much one can grow on one’s own, but with the right systems in place, there is no limit.

My goal: Outsource everything to virtual assistants, except the highest productivity item (HPI), to overseas, virtual labor. If done correctly, one can find excellent labor for as little as $4 per hour. (I usually pay $10-$15 and choose more premium services, because it often requires less filtering, and I save precious time in the hiring process.)

The implementation of outsourcing with virtual employees made my company grow exponentially; moreover, after spending 3 months training and hiring a full-time manager to run the day-to-day operations (the final piece of the puzzle), I was working an average 5 hours per week to maintain my lead generation business.

My Step by Step Process for Outsourcing Any Task and Hiring Virtual Assistants using UpWork

Your objective: Systemize. Do. Hire. Train. Repeat. Here’s a step-by-step breakdown of the program I follow to outsource virtually any task, including finding and training virtual assistants.

Once you have determined what jobs in your life need outsourcing (link post here), you should aim to find the best labor possible for the lowest price. In that order.

In my personal experience, I have found that while it’s possible to get tasks done extremely cheap, it often makes sense to pay more for better labor. It saves me hours of time, stress, and heartache later.

Here are some rules and observations:

  • Do not compromise on quality.
  • Always hire someone better than yourself at the given task.
  • After the initial training process, employees should be able to add creative input to their job to improve your current system.
  • You know you have hired the right employees when you trust their opinions, when you don’t feel the urge to micromanage their jobs, and when they contribute improvements to your current system.
  • Hire slow and fire fast.
  • The right person for the job costs less than you think it does.
  • When recruiting labor, lead with your vision.
  • Almost every task requires an extensive training period via Skype and often times in-person training is worth the company time and expense.
  • Almost every task can be outsourced digitally, even the most difficult jobs.

Here’s the actual process I use to hire workers, broken down step by step. While there are many platforms for finding great virtual labor, I use UpWork, formerly Odesk.

  1. Determine your highest productivity item (HPI). Only you can do this task in your business. Everything else can and should be outsourced using virtual assistants.
  2. Find the one thing you want to offload from your plate and create a system for it. If you don’t have an immediate answer, try working backward.

Use the 80/20 rule to determine where your time is best spent. What one or two things in your business or life give you the most return on your investment?

Let’s take a further look at how to outsource and hire virtual assistants using the following example.

In Jim’s business, his HPI was finding new clients for his law practice. In Jim’s personal life, his HPI was spending more time with his dog, Whiskey.

 Great. For his business, he should aim to outsource everything that’s not specifically related to finding new clients.

He starts with the one task that bleeds most of his time and produces the least results.

If he can, he will eliminate the problem all together (for example, he can closeout the accounts of those one or two clients who suck all his energy but don’t pay him well).

He can then outsource his remaining tasks—writing contractual paperwork, doing menial research, and so on.

  1. Once you have your task, it’s time to find the right labor. While you have plenty of places to choose from when it comes to hiring virtual labor, my go-to place has always been UpWork.

It’s online, safe, 100% virtual, and has a database of candidates for literally every conceivable job. Indeed, I’ve found everything from video editors, to web designers, to accountants online.

I managed a marketing company with 12 employees from anywhere in the world. Eleven of those twelve employees came from UpWork.

How to Outsource Virtually Any Task

Here’s how I found them.

    1. Make a video of the specific task you need your virtual assistant to do. The value of this cannot be overstated:

a. Time: You can use this video to hire workers and virtual assistants in the future (In one case, I used the same video for four years).

b. Clarity: Putting everything you need into one, easy to follow, video forces you to be concise and specific when it comes to delegating. As a result, your future virtual assistant employee knows exactly what she needs to do.

c. Efficiency: Your employee can now watch and re-watch the training video at her leisure. Should she have questions, she can bring them to you later and discuss the deeper workings of the business. This saves you hours of repeatedly answering the same questions.

d. Vetting: Use this video (and a related questionnaire) as a pre-requisite to applying for any job that you post online. This helps you navigate a sea of prospective employees, selecting only the most qualified prospects.

    1. Post the Job on UpWork

Be careful to select the best category for your work. This way you can give yourself the best chance of finding someone who actually matches your criteria. Fortunately, UpWork has countless hyper-specific niches, so you can easily find the right person for every possible task.

2b. Before posting the job, setup customized questions that each applicant must fill out. Having them jump through a few simple hoops (send you an email with a subject line of your choosing, for example) will eliminate 70% of the applicants. It shows who actually read the job description and who can follow instructions (many people simply apply to every available job in hopes that someone responds).

2c. Once you post the job, seek out the recommended workers that fit your criteria. Otherwise, click on Freelancers > Find a Freelancer, choose your desired category, and then filter by success rate.

Potential employers should beware that freelancer ratings are easy to manipulate, as prospective employees know that high ratings attract employers. That’s why it’s imperative to have a system that vets them even further.

Invite only the best-matched prospects to your new job by sending them a personal message. Change only their name and copy/paste to save time.

Here’s a simple example of a message you can send to a potential virtual assistant:

Hey (copy/paste Name),

Your application looks awesome, and I think we’d be a great fit. Please apply to the job and we can setup a time to chat.

Look forward to connecting.

I’ve used this exact template to find the best freelancers for my existing positions.

  1. Wait 24 hours and check your inbox. Send a follow-up response to the first round of applications with a link to your video, which you uploaded to a website or Dropbox. Ask them to watch it and respond when finished, answering three short questions about the video.
  2. Select the best five applicants and schedule Skype interviews with them on a designated day. Schedule them all during a one-hour stretch, with each interview lasting 10-15 minutes. I use Google Calendar to send invites with any notes or necessary prep work for the meeting.

During the interview, get a feel for them, assessing their English skills and assessing how well they absorb and comprehend the required task. You can observe firsthand their creative input and timeliness (two important traits to look for when hiring great employees).

I always send each applicant the same prep questions for the interview, so they can come prepared with answers. I might even create a short video explaining the company’s visions and expectations.

When appropriate, I may ask them to bring a mockup exercise to the interview, so I can gauge their attentiveness to quality. Most of our discussion is spent on the creative aspect of their work, as I’m always looking to assess what higher level value they can bring to the company.

  1. Select the best candidate and offer them a job. Negotiate with them directly on Skype or via email and ensure that the details of the project are clear. It helps to have a one page contract written up and signed, which outlines the basic tasks, deadlines, and any other relevant information. This ensures you’re both on the same page and accountable in the event of any discrepancy.
How to Outsource Virtually Any Task

How to Effectively Manage Virtual Assistants and Employees Digitally

 Once you find your dream employee, effective training is essential.

Here’s the five-step protocol I follow to effectively manage virtual assistants and employees digitally from anywhere in the world.

  1. Meet daily (until they no longer need supervision) for 15 minutes to discuss objectives and questions from previous assignments.
  2. Add one new task per meeting, with a follow-up assignment that is due by the next day.
  3. Use screen sharing (via TeamViewer or Skype) to walk your employee through the project or task with systematic guidance.
  4. Record the training session, upload it to the Internet, and send them the link for future reference. (I have a website dedicated just for training workers where I upload all videos; however, a dedicated Dropbox folder will work just fine. I recommend saving these recordings, as you may need them for future employees.)
  5. Maintain good standing by complimenting good work: quick to praise and slow to criticize. I always preface constructive criticism with a compliment. I reward good work with bonuses and aim to align their interests with the growth of my business, making them part of my team.

Once hired, build your UpWork profile together by setting short and specific projects; provide high ratings and positive feedback for tasks completed correctly and on time. Building your UpWork profile helps with credibility when attracting talented workers. Remember, excellent employees have their choice of employer just as employers.

When it comes to paying your virtual assistant or employee, you may want to use an external service like PayPal or Bank Wire—once trust is established to avoid hefty UpWork fees.

How to Effectively Run an Online Business from Anywhere in the World

You’ve found your new employee, and you’re ready to move on to the HPI.

Make sure that you are continually optimizing your systems. You don’t want to fall into the deadly mistake of working for the sake of working or occupying free time with useless busy work just to feel productive.

Do things that count and remember that your job as an entrepreneur and CEO is to focus on the bigger picture.

Outsourcing allows you to focus on things that matter: doubling revenue, implementing better procedures, and automating your systems.

With all that extra free time, you, my friend, are free to enjoy simple pleasures, as Jim does walking his dog, Whiskey.

You’ll also want to check out the free download available on my blog (on the right side bar) to optimize your finances, to clarify your company’s vision, and to prioritize your lifestyle goals.

With the above skills and a newfound vision, you’re ready to effectively run your online business from anywhere in the world!

I hope you enjoyed this definitive guide on How to Outsource on Upwork. If you found value in it, please share it with someone who would benefit.

Happy Outsourcing!

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1 Comment

  • Caroline Tamaki November 2, 2020 3:12 am

    Hi im looking for outsource assistance to:1. upload designs to a POD company 2. Create an account for a selling platform 3. Create listings for my designs to sell in Etsy and Amazon and Ebay

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