Freelancers Outsourcing Website Development To Freelancers

I once treated my hiring of freelancers as a monumental task to be used in cases of extreme emergency.

I’d over-promise something, and I’d be in danger of under-delivering: “Hire the freelancer!” I’d yell out the window onto Franklin Ave.

Or I’d realize that I didn’t know how to do whatever it was I just promised to a customer.  “Hire the freelancer!”

Hiring Freelancers is Empowering

I’ve since learned that other freelancers can help me in ways that go way way beyond emergency support & filling gaps in my knowledge.

Outsourcing work to freelancers is now a core business function of my WordPress development company.

Not only do I outsource important work to freelancers…I outsource ALL the work to freelancers!

And my customers and I have never been happier.

I am empowered, not limited by hiring freelancers to do the work of my company.  

In fact, hiring freelancers has been a critical component to building calm company practices.

Common Misunderstandings of Hiring Freelancers

Thoughts I’ve experienced when hiring freelancers include:

  • Freelancers’ll be too expensive.
  • My customers won’t approve of me hiring others
  • Freelancers will be a pain to manage.
  • I’m ashamed to have someone else do my work.
  • They’ll mess it all up, and I’ll have to do the work anyway.
  • They’ll hate me for demanding they deliver, and I’ll lose them as friends.
  • Hiring, paying, & managing a freelancer will be a HUGE headache I’d rather avoid.

These thoughts are not truths.  

The reality is that with a little intention, you can create an amazing, empowering experience for you and your freelancers, alike!  

You Need To Hire Freelancers

You are a freelancer who is curious about outsourcing website development to another freelancer.

Don’t be scared.  You can do this – And I’ll teach you how.

Maybe you’ve had bad experiences outsourcing website development in the past or have heard horror stories from friends.

Ignore them.  You can do better.

Over the last decade, I’ve personally experienced the full spectrum of feelings about outsourcing — pure joy, satisfaction, disappointment, anger, surprise, and sadness.

Today, I outsource WordPress development daily, and almost every single project I’ve worked on over the last 5 years has had components developed by an outsourced freelancer.

But of course, even with all that experience, I still have good days and bad days with my outsourced team.

For example, today, I had to re-teach to a freelancer, for the 100th time, my core value of “owning your work”.

I do think it helps to have a rudder.

Outsourcing Class

Here are the things I’m gonna teach you about:

This article is a primer on outsourcing website development projects.

Therefore, before we start, I really really feel like I need to share some high-level business concepts to get you thinking about why you’d want to outsource website development in the first place (and why not).

Smart Businesses Outsource the Stuff That Is Least Important

The most important thing I can teach other freelance web developers is: “Web development isn’t your most-important product!”  It should be outsourced.

As a freelancer, you are a business owner.  And your primary business function is getting, retaining, & up-selling customers.

IMPORTANT: Your customers don’t care how the work gets done nor by whom.

Job #1 Is to Meet or Exceed Expectations

What expectations have you set?

  • Timeline
  • Deliverables
  • Communication frequency
  • Cost

And which single expectation is most important to the customer.  Please don’t say, “All”, because  I’ll die if you do.

Your job as a business owner is to figure out the most important expectation and over-deliver on that.

Customers don’t actually care about website development.  They care about other things: feeling good about the project, pleasing their boss, looking good in front of their peers, setting themselves up for a raise next year, getting it done so they can take a vacation, etc. etc. etc.

Very rarely is “website development” a core concern to a small business owner on planet Earth.  It’s a means to an end.  (the “end” being, perhaps, attending their son’s wedding next Saturday)

99% of the time, the up-front work of planning and expectation-setting I did is vastly more valuable to my customers than the actual website thing I’ve produced.

And remember this: Buyers hire you to do something. But they re-hire you if you satisfied whatever their “most-important-thing-to-them” is.

A Quick Story From My Life

I was recently fired by a company, because I failed to make the buyer happy.

The CEO and all the people I touched on the project were happy with my work.  But there was an internal battle brewing that had nothing to do with my work.

The money person (i.e. the buyer) didn’t feel good about how they were spending his money.

So, he went out and hired a different agency to do the work.

It should be noted that this new agency sucks at website development and marketing (the main job functions they were hired to complete).  But I know the owner of this agency, and he’s the best at making buyers feel amazing about the product.

Ya know what?  I’m not even sour about the experience.

Because I know that my strength isn’t making buyers feel great about the products I build.  People love me, because I increase the intrinsic value of their products.  And, frankly, customers and my team, alike, all have a good time doing the work!

Things that might be more important to the success of your web development project than web development:

  • Customer communication. (How often you call, the quality of the information you give, your trustworthiness in delivering on your promises, response times, do you answer the phone, do you set & meet expectations, etc.)
  • Scope management/Scope creep.
  • Other projects with the customer.
  • Your relationship with the buyer (i.e. the buyer might be a different person than the person you are regularly in touch with).

Some of the Things You Value Have No Business Value

Ever see a customer’s eyes glaze over when you talk about your code deployment workflow? Me too.

Code workflow is important to me and my team, but my customers don’t care one lick about it.

99% of the people I’ve completed paid website development projects with over the last decade+ don’t care one lick about things like “code quality”, “code is poetry”, SASS, LESS, and plugins. They just care that expectations are met.

In fact, I can only think of one project where the customer cared about the ambiguous and subjective topic of code quality.  He fired me.

Even things I think are important to any good sales process (good design, usability, e-commerce flow, page speed) are oftentimes totally not valuable to the buyer.

More Common Misunderstandings About Outsourcing Website Development

  1. It’s cheaper.
  2. It’s easier.
  3. It’s faster.

All of these can be true, and all can be false.

Should I Outsource Locally, Regionally, or Abroad?

As you get started outsourcing website development, don’t worry about where you outsource. Just follow the detailed outsourcing process below — It’s location-agnostic.

There are advantages and disadvantages to hiring everywhere in the world. I’ve had full-time employees in the U.S.A., Colombia, and Philippines. I’ve also hired contractors for lots of website development jobs in other parts of the world (Pakistan, India, Mexico, Australia, Brazil, Colombia). They are all great for different reasons!

Each locality has its own customs, culture, timezone, vacation expectations, etc. that you’ll learn about as you move forward.

But also everyone is a human being with her own eccentricities, experiences, likes, dislikes, biases, etc.  Ultimately, how you handle human communication will make or break your success.

IMPORTANT: If you are someone who is curious about the uniqueness of people and interpersonal relationships, you will love outsourcing your website development work.  If you are not curious about people and what drives them, you will have a rough go of it.

How Is Outsourcing Website Development Different Than Having a Full-Time Employee?

What is the difference between a full-time employee and a contractor?

I’ve given this question a lot of thought, and you might be surprised to hear that, from a practical standpoint, they are basically the same thing.  (Legal and IRS definitions, notwithstanding)

At the end of the day, you are managing humans. Humans, for the most part, are tough to manage when their work output is as nuanced as it will be for your website development project.

There is, however, a difference in methodology between managing a human on-site vs. off-site. Many books have been written about this difference. I recommend reading The Year Without Pants if you are curious about how big companies manage remote teams.

But for the most part, if you are managing off-site, the problems that you’ll run into are consistent — communication.

How Do I Communicate With My Off-Site Contractor?

Communication is the hardest work of any business (and some businesses ignore communication issues to their detriment).

At the end of the day, you need a process that works for you. Choose the option you prefer and stick to it: Facebook, Slack, email, phone, Skype, Google Docs. The tool doesn’t matter. What matters is that the expectations are follow-up are clear to both you and your hired contractors.

My Communication Workflow

This is how I communicate with my off-site contractors.  (If you need a place to start, just do this.  If you have strong opinions on a different workflow, then do that.)

  1. I add to-dos to a shared Google Doc, commenting, editing, clarifying in the doc where appropriate. My contractors and I do most of our communication in the comments inside the Google Doc.
  2. I require a daily email update from my contractor that answers 3 simple questions: 1) What did you do yesterday? 2) What will you do today? 3) Is anything going to stop you from getting that stuff done today?
  3. In the case that a phone call is needed, I pay for the contractor to call my cellphone via Skype. (Why not use Skype directly you ask? Because I prefer the phone!)
  4. I keep Slack open for emergency and blocker communication. I instruct my contractors to only use Slack when there is an issue that is stopping them from getting their work done (usually this is when I forget to give them a required password [Background Reading on This Concept]).
  5. For some projects, I have my contractor communicate directly with my customers via phone and email (preferably phone). It saves everyone time and headaches. I’m very intentional about this, and the pros outweigh the cons.

Why Do You Want to Outsource Your Website Development?

Your specific “Why?” is important.

But it is important that you have a why.

So go ahead — write it down on paper. Define it. Answer these questions:

  1. What is your biggest goal with outsourcing. It could be saving money, scaling, or maybe just curiosity. Whatever it is, define it clearly.
  2. How will you measure success? (free time, fewer headaches, extra money in your bank account, etc.)  Make it a concrete something that you can measure.

You Are Making Assumptions About Outsourcing Website Development. Own Them.

You are making assumptions about website outsourcing — some true, some false. This is normal.

Lay your assumptions out on the table – write them down.

For example, you might assume that outsourcing website development is cheaper, gives you access to a broad pool of skilled people, is faster than doing it yourself, allows you to scale quicker, etc.

Write down your assumptions on a piece of paper.  You’ll disprove and prove them as you go along, and it’s good to keep track and do an inventory of these assumptions periodically.

Start Here — Your First Website Outsourcing Job How To Guide.

  1. Choose a well-defined project that can be completed in a day (or ideally in a few hours).
  2. How much you want to pay for the project completion? Divide that number by 3. This new number is your project budget (you’ll see why below).
  3. Go to and post the project and budget, clearly-demanding a 24-hour turnaround in the project description.
    You’ll start getting applications immediately. As soon as you have 20 or so applications, close the application process down. Review the applications quickly and hire 3 contractors that fit both your required skillset and your budget.
    Q: Is this fair?
    A: So long as you clearly define the project expectations it is fair.
    Q: Why be so demanding with both budget and timeline?
    A: Because the goal is to get you experience outsourcing your website development.
    Q: Is this a nice way to do things?
    A: Yes. So long as the expectations are clearly-communicated and you are extremely-respectful of your contractors, it is okay to be demanding on timeline.
  4. RULES
    – If a contractor does not meet your deadline, cancel the contract and pay the contractor if their effort is visible, even if their work sucks. Some people work really really hard and just aren’t up to the task. This is on us as employers to filter out, and we have an obligation to pay contractors for their efforts, even if they don’t do the job correctly. (i.e. Workers who show up for the first day of work and never return again still get paid for the first day of work.  This is fair.)
    – Of the contractors who do complete the job (or something close to completing the job), choose 1 to move forward with.
    Q: Why 1 contractor?
    A: Keep it simple and protect your time. Communication is costly. Just choose the best contractor of the bunch. There are a million others out there if the 1 does not work out later.
  5. Save the 1’s contact info for future work.
  6. Rinse & repeat.

What Should I Outsource?

We only outsource the things that aren’t important to our freelance biz.

The problem is that you don’t know what’s not important to your freelance biz.

You think that your customers will only buy from you if:

  • You are the one answering the phone, replying to emails, doing the work, asking for money, designing the deliverable, writing the code, managing the project, dealing with scope creep, etc. etc. etc.
  • You are available at their whim.
  • You say, “yes”, to whatever stupid thing they say.
  • Your prices are low.
  • You join their Slack/Basecamp/Trello/etc. 
  • etc. etc. etc.

Stop it.

This is my first attempt at getting all this down on paper here, and I’m sure I said some stupid things.  Please email or call me to correct any mistakes I’ve made.  🙂

Toby Cryns
[email protected]


  • Signal v. Noise blog (general business best-practices)
  • 4-Hour Workweek (A ridiculous primer on outsourcing…yet the best one I’ve found to get the concepts down.)
  • Moneyball [film & book are both great!](A corporate version of 4-Hour Workweek)
  • Uncommon Service (An academically-oriented and insightful look at 80/20’ing the customer experience. This book blew my mind and forever changed the way I do business.)
  • Antifragile (Thoughts on building a resilient business & life.)
  • Is Group Chat Making You Sweat? (How Calm Companies use Slack, Skype, Email, etc.)

Originally published on Oct. 19, 2017 as my notes from an MSPWP conversation I led.

Significant updates made on Aug. 17, 2018.

Added Email Marketing Automation & another link on Oct. 8, 2018


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