Get Exactly What you Want From Outsourcing

Law school trained your mind to think a certain way. You think about issue-spotting and causation.  You think about precedents. But mostly, you learned to worry about risk.

So many lawyers resist using an outsourcing marketplace like Upwork, Guru or People by the Hour because they believe that the platforms are risky and filled with scammers.

Hey, I admit that I felt the very same way.  I couldn’t believe that you could get administrative work for $5 when I first heard about Fiverr.  In fact, I was so skeptical that I joined as a Seller just to spy on the platform. Here’s what I learned.

Most of the people who offer their services on outsourcing platforms are small business owners or freelancers with excess capacity they want to put to good use.  They are well-intentioned and care about doing a thorough job for you.

Of course, there are exceptions. Recently, I stopped recommending Fiverr because I noticed that the quality of their work pool had gone down dramatically. It’s very difficult to find someone experienced anymore unless you use the Pro feature.  I guess that’s what happens when you take 60 million dollars in VC money. Your model changes significantly.

All that to say that I was very skeptical about asking a stranger to help me do work for my business.  I understand your hesitation. However, there is a way to get exactly what you expect without a lot of hassle.

Complete the Pre-Go Phase

What is that?  The Pre-Go Phase. I know it sounds like part of a NASA launch sequence. The Pre-Go phase happens prior to ordering any work online.  It is your first line of defense against poor work and your last chance to control all aspects of your project.

What is the Pre-Go Phase?

I developed this process when I noticed that I was consistently spending more time than I wanted either hand-holding the freelancer or asking for revisions to their work.  Once I took a step back to reflect, I realized that how I presented the job had a huge impact on how the freelancer performed. The more thorough I was during Pre-Go, the better outcome I received and the more satisfied I became.

Steps to the Pre-Go

Whenever I meet a lawyer who says that outsourcing doesn’t work, nine times out of ten, that person had a bad experience.  A little questioning quickly reveals the issue. No planning.

I get it. I’ve been there.  You’re working so hard for so long you just need a lifeline…now!  So you hop online, find the first VA who fits your budget and order. The results come back. Very disappointing.  It happens to everyone who fails to plan, even me after a decade using the platforms.

Doing the Pre-Go allows you to be organized and be crystal clear about your:

  • Goals
  • Needs
  • Level of expertise needed
  • Timeline
  • what is a suitable outcome
  • what is an ideal outcome

You aim is to create a concise yet informative document that you can share with your freelancer on the platform.  Sites like Upwork ask you to provide a ‘job posting’ that explains the project and what you want to the freelancer to do.  I call that document your Project Legend.

The Story of your Project

Anyone who spent any time in corporate American knows what a standard operating procedure is and how utterly boring they are to read.

Your Project Legend has the power to inform like an SOP but is way more fun to write and read. ( In fact, it’s so much like storytelling that you can even use Quicktime to record an audio file of your Project Legend then have it transcribed on

Think of it as writing a news story where you are reporting the who, what, why, how, as well as the restrictions. The information you gathered for Pre-Go become part of your Project Legend.

For example, suppose you decided to launch a podcast. That would be a wise marketing move and easy to do since much of the work can be outsourced.

You reach out to an artist on Upwork to do your cover art.  The Project Legend would read as follows:

Hi Freelancer Name,

I’m Dina. I own High Law Firm which serves cannabis dispensary owners.  I plan to launch my podcast, 420 News shortly. Can you help me create cover art that is :

3000×3000 in pixels

Uses hex color #008080 and# 000000

Features a font combination similar to Oswald and Century School Book

Is compliant with iTunes and Stitcher

Uses only licensed photos

Uses the copy provided

Has a serious news vibe

(please see uploaded example)

How many revisions are available? Does the quote include the commercial license? Can I have this completed no later than 4 days from today?

I selected you because I appreciated # 24 in your portfolio.  I’ll be available via Upwork messaging if you have any questions.


The artist has the information they need to get started and do a great job.  Pro tip: Be sure to purchase the source files for any graphics project you do so you have the ability to update them later if needed.

Get Exactly What You Want

It’s not hard to get exactly what you want when you outsource. You get the best outcome when you invest a bit of time in completing the Pre-Go and Project Legend.

You can relax because you’ve given the freelancer directions on how to proceed and what not to do.  Best of all, you have documentation for the next time you create cover art and a process for the next time you outsource.

What is the first project legend you intend to write?

About Dina Eisenberg, Esq.

Dina is a lawyer/Ombuds turned award-winning entrepreneur. She is the CEO of, a consulting & training firm dedicated to helping solo and small firm lawyers delegate, automate and grow to $500k without burnout. She loves seeing lawyers stand in their truth and own their power.

« »

Practice Management Tips You’ll Actually Use

Proven strategies from legal experts, delivered straight to your inbox

No thanks, not right now

Get the Latest Firm Management & Growth Strategies

Best practices from REAL legal experts

How-to guides and articles

Webinars with thought leaders