10 Tips I Learned from 10 Years of Outsourcing My Internet Businesses

Outsourcing Tips

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If you have a lot on your plate and don’t know where to start, one of the best ways to free up some time is to outsource some of your workflow.

Outsourcing isn’t easy, though. It can go south quickly if you aren’t careful.

This leads to …

  • Lost money
  • Wasted time (even worse)
  • Massive frustration

But fear not! I’ve compiled my 10 biggest outsourcing tips to help ensure that doesn’t happen to you.

These aren’t in random order either. The first 2 tips might make the other tips obsolete!

You’ll see what I mean... Let’s get into them.

Tip #1 Don’t Outsource Things That Don’t Need to Be Done

Peter Drucker said it best...

Drucker portrait bkt

“There is nothing so useless as doing efficiently that which should not be done at all.”

Peter Drucker  // "The Man Who Invented Mangagement"

It doesn’t matter if you’re doing it or paying someone to do it. Tasks that don’t get meaningful results should not receive our time, money, and energy.

Typically, we outsource things that are of lower value to us. “It’s definitely not worth MY time to do this…”

Go a step further and ask, “Is this actually worth ANYONE’S time?”

Sometimes, it takes trying to outsource a task to realize that it really isn’t something we should do at all.

Tip #2  See If a Software Can Do It First

Some people aren’t going to like this one.

Indeed, robots have taken lots of online jobs. 

Especially ones that require massive unskilled labor, like scanning through large documents or repeating a single process over and over. 

Tools replace manual work ---

It is bittersweet. It’s great if you are hiring people to do the tasks but not so great if you’re the person who does them as a service. 

Don’t worry though, many of the people who perform these unskilled jobs STILL get paid to do them. They just use these tools, too!


Much of Fiverr.com, for example, is simply people selling the end-result of a software solution that other people aren’t aware of...

Tip #3 Consider a Subscription Service or Agency

Over the past decade, many companies have taken services and bundled them into products. 

These are essentially agencies, but many are much less personal and require little input from you and have flat rate prices. 

Some examples include...

These services make most of their money in the same way that gyms do...off the fact that most people won’t use them. If everyone used them, most would go out of business.

In most cases, using one of these services will be far less expensive IF (and this is a big if) you use the service to the maximum degree possible.

Pros and Cons of Agencies/Subscription Service Solutions

  • [Usually] no need to hire and train. 
  • No firing of single clients.
  • [Usually] Large companies protect their reputations better and have better refund policies (less risk). Your risk of being scammed is much lower.
  • [Usually] Flat rate and easy to budget.
  • [Usually] have great dashboards and communication portals.
  • [Sometimes] can be cheaper.
  • [Usually] can be more expensive than hiring yourself IF you don't use all your allotted credits/hours/tasks.
  • [Sometimes] quality of work can be “so-so” since they typically hire low wage workers to protect their margins.
  • [Sometimes] less “personalization” for your brand.
Outsourcing without Hiring

Tip #4 Don’t Be Cheap

It can be tempting to hire the cheapest labor possible for each task. Trust me when I tell you that going cheap isn’t wise in the long run. 

Many unskilled administrative tasks can be outsourced at very low rates, but other tasks deserve better wages. 

For instance, you can pay $4/hour for data entry work, but you shouldn’t pay $8/hour for web development. Use common sense, and don’t let yourself get burnt trying to save a few bucks. 

If the task is worth outsourcing, it is worth outsourcing right. Understand what the financial value of a task will be to you if it’s done properly and pay accordingly. 

Tip #5 Be Extremely Clear and Give Examples

Outsourcing is an art. Some people can do it well, and others can’t. 

As a blogger and former warehouse manager, I’m used to explaining things in easy-to-understand ways. (See my post about how to speed up or slow down a GIF.) 

I’m able to delegate tasks well because I am very clear, and I don’t leave much room for interpretation. 

Make your tasks as clear as possible. Some ways to do that include... 

  • Making video recordings of what you need done. I recommend Scribe (scribehow.com) and Loom (loom.com) for this.
  • Creating annotated screenshots when appropriate. I recommend Snagit (techsmith.com/snagit) for this.
  • Encouraging the contractor to ask questions. 
  • Providing examples of what you want completed.

Clarity is king. You can never give too many examples, either.

Examples are extra valuable if you’re hiring someone in the design space. 

  • Need a logo made? Send them 10 logos that you like. Even better, write notes on each explaining what you like or don’t like about them.
  • Want to have someone build a software? Show them examples of the closest current options. Focus on specifics like “I like how this program has a search bar in the top right”... etc. Do this for multiple programs and you’ll make it much easier on your developer. 
  • Hiring a video editor? Send them examples of video styles you like. Make specific notes on them. I recommend a tool like Frame.Io if you have the budget for it.

Get the idea?

Again, no one ever complains that you gave too many examples (as long as you organize them well and share in a way that makes sense). 

Tip #6 Always Document Your Process

You should always be growing a library of repeating tasks you perform. By doing this, you make it much easier to step away from them and outsource them later. 

If you hire someone and explain a task to them, be sure to document it and save the instructions for later in case they fail to perform, leave the industry, aren’t available, or you need to hire more people to complete the same task. 

I recommend tools like Scribe (ScribeHow.com) and Loom (loom.com) for recording and storing processes.  

I now use a combination of Scribe, Loom, Google Drive, and Notion.so for my own SOPs (standard operating procedures). 

There are also services (too many to mention) that allow you to store your processes in an employee portal. Most aren’t cheap, and I don’t find them to be better than cheaper options like Google Drive.

Tip #7 Ask for Referrals

Ask people you trust for referrals to people that they’ve worked with. This is like a cheat code that lets you bypass searching through hundreds of job candidates

45% of referral hires stay longer than four years, compared to only 25% of job board hires. [Source

Of course, you still need to perform your own due diligence and ensure that each candidate meets your own criteria, but this is wildly helpful. 

Tip #8 Reward and Acknowledge Great Work

People do better work when we acknowledge them for a job well done. 

Are you a scrooge who doesn’t really care about this sort of thing? 

“They got paid, that’s enough,” or “they did the job exactly as described, so I should pay exactly as described!”

You’re not wrong there (although I don’t want to adopt that sort of mindset myself), but this isn’t as simple as that.

Giving more isn’t just an altruistic move; it’s strategic and good for your business. It really is one of those, unfortunately, somewhat rare “win-wins” that we love as business owners.

It will help you get consistent work in the future if you follow the next tip....

Tip #9 Rehire Top Performers

If it’s not broken, don’t fix it!

The hardest part of outsourcing is creating the posting and reviewing candidates. 

Once you do this once and the person performs well, don’t overcomplicate things, just hire them again. Build rapport with them. Let them learn what your business is about, and you’ll get better, faster, and more consistent results.

If you're interested in retaining top performers or finding other quality candidates, survey your top performers using a metric called an Employee Net Promotor Score or (eNPS). This will tell you all you need to know about what your top performers think of your business.

Tip #10 Hire Slow and Fire Fast

Don’t rush to hire someone. Do your due diligence and reduce the risks of things not working out.

No matter how much due diligence you put in upfront, things can still go poorly, and you may need to end projects or fire people.

Don’t let this drag out, though. Once you feel someone isn’t working out, stop the contract, pay them whatever you owed them (if anything), and move on.

Keeping them around will not make firing them easier. It will be harder, and you will only waste more time and money waiting.

Now, don't confuse "fire fast" with giving up too soon on someone. It will almost always take longer for a freelancer to get up to speed than you expect. Be patient with them, but do be ready to fire if they do things that show they are never going to be a good fit. 


Outsourcing is hard, but it's worth it. Follow the tips above, and put in the effort to make it work. 

It will be hard at first, and it might take awhile to see an ROI, but I promise you, it is so worth it. 

This is not a comprehensive guide on virtual outsourcing. I highly recommend reading and learning more about the topic of outsourcing. I've put together another blog post that you'll enjoy that covers the best books on outsourcing. They are all winners.

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