How to Outsource Web Projects

Over the years as a software developer, I’ve worked with people from all countries and cultures. I’m grateful for my experiences and many conversations. I want to share my experience with how I outsource web projects.

After the Dot Com bust and my separation from in 2001, I started consulting. Soon I found a couple of entrepreneur course creators who wanted website work.

I put out a lot of work over three years for these clients. We built custom web applications like:

  • Customer portals

  • Website building apps with built Content Management, CMS

  • Project management PM systems

  • Email autoresponder systems

  • And more

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I couldn’t do all that requirement gathering, specification writing, and coding myself. Outsourcing was the solution.

I started outsourcing on, which has become From 2004 through 2022, I’ve outsourced many projects.

At first, I used the PM lessons from my early career. It all helped up to a point, but one key ingredient was missing.

Humanity. In short, I was an asshole sometimes.

It took me about two years to get over myself and realize things were not getting done because I sucked at managing freelancers and outsourcing web projects.

I needed to change who I was and how I behaved in web projects.

Here’s how outsourcing web projects works.

  • Your project will get done, and you’ll achieve the outcome if you’re pleasant.

  • If you like and respect the client, things will go better than planned. What are you doing working with people you don’t like?

  • If you and the client have a relationship built on trust and respect, your possibilities are endless.

Where do you find a freelancer?

You can search for freelancers or an agency on Google or LinkedIn or use a job board like Upwork, Fiverr, or The escrow model of the job boards work for low-end projects under 5K or 10K. You should create a Request for Proposal RFP for any project over 10K. It’s best practice to chunk larger projects into smaller phases, though.

Follow these steps to find quality freelancers.

If you’re using a Job Board, you need a system to evaluate freelancers who bid on your projects. The system looks like

  • You look over their profile and ensure it matches the work you posted.

  • Read into their past projects and, most importantly, look at reviews.

  • Your evaluation will combine their work history, reviews, and

  • the total amount of money earned. This information gives you the picture you need.

If you’re posting a project to RFP, you need a different system but one you’ve probably used your whole adult life. You’ll research them on the interwebs and social media. Whatever you can find.

Creating an RFP is another article, but they’re essential tools.

The next step applies to both methods, job board, and RFP. You write a few criteria questions that you’ll ask all the freelancers, and you’ll rate their responses from 1 to 5. What do you get from this? A lovely table and simple math help you decide who gets the work.

What do I mean by criteria questions?

  • Have you done this work before, and can I see it?

  • How long have you been doing this?

  • How soon are you available?

  • Are you doing the work yourself, or do you have staff?

You can come up with questions of your own.


Here are some tips for creating a project request on a job board.

  • Begin with the reason why you’re doing the project.

  • Don’t reveal your cards, but give enough of a business reason to give this project some purpose—just a few sentences or paragraphs.

  • Then describe in your words what the project outcome looks like to you. Even use those words, “…to me the end of the project looks like…”.

Outsource web projects of any type

You can get anything within reason built, designed, written, produced, or created, and the possibilities end in what you know. You reach out and post projects, whether by RFP, job board, or direct search.

Does the content in this post provide you value? Please let me know if you have questions.