Hiring Freelancers? Here’s a 3 Step Checklist for a Successful Project

As a digital consultant handling marketing strategy and development for several clients and juggling multiple projects simultaneously, I speak to dozens of freelance writers, graphic designers, strategists and web developers every week. The support they provide is essential for the success of my various projects and clients. And for my own sanity.

What I have found is this. By creating a checklist that I can go through during the interview with any freelancer, I am able to create a higher job success rate than ever before.

Illustration: Lital Bar Noy

To find the right freelancer for any specific project, I have identified three distinct actions plans that I need to take before deciding to sign them up or not.

1. Review and Agree on the Project Brief — in Detail.

Offer the freelancer to look over the project and decide if they have the necessary skills needed to complete the work. I create briefs with three things in mind: project description, deliverables and timeline.

  • Project description. Here is the where I explain not only what the project is about but also who it is for. I share my expectations for each task and give the freelancer the chance to clarify any questions they may have. I usually ask them how they would go about this as well to check that we are on the same page.
  • Deliverables. I have found it to be extremely helpful to write out exactly what I expect, such as a 500 word essay on economics with a source list in a separate document or if I expect a report on the hours spent completing the project. It has also been a huge asset to me to place file formats and image sizes for my deliverables to avoid any delays. Knowing exactly what is expected of them and in what format ensures that there is less ‘Do I need to send you this, in this way?’ kind of questions from the freelancer. You don’t want to be holding their hand when they work.
  • Timeline. For small projects this can be easy but for larger projects I recommend creating milestones that can be used as a guideline for how to complete the project. Milestones can be a valuable tactic in creating a realistic timeline and being able to check in on the work and make sure it’s on schedule. It also raises a red flag whenever your freelancer is falling behind schedule and alerts you to possible delay in final delivery time.

★★★★★ Great client — very communicative w/ detailed project briefs. Responsive and paid on time. Would definitely work with again!

2. Reach a consensus about communications.

One of the more valuable I lessons learned was to never assume consensus when not otherwise specifically clarified. This applies to the simplest things, like communication standards that can easily cause delays and discomfort in the project. Before starting to work together I like to reach a clear consensus about communications.

I like to point out my availability to answer questions ahead of time and my expectation of the work delivery whether I’m available or not. Some projects are fit to say “just figure it out without me” and others are strictly “do not move forward without checking in.

  • For example, will I be available for questions or do I expect the work delivered based on brief (here’s where a great brief will save you time/hassle)?
  • For design concept tasks I focus on creating an open line of communication between myself and my freelancer as I see a higher project success rate with this kind of live communication.

Having a freelance creative work directly from a brief has resulted in them finding interesting and creative solutions that I would have never considered. It has been a great way for me to see how different projects can be completed and allowed me to take these ideas and initiatives into my other projects/clients as well. A win-win all around.

3. Probe for questions.

Is the deadline reasonable? Do they have any suggestions as to how to increase the success of the project? Answers to these questions will help you determine if you are choosing the right freelancer for the job.

From experience I have learned that the freelancers who reply to my detailed brief with an, “OK! Will do!” tend to have the lowest success rate. On the other hand, those who ask for clarifications or have specific questions of the project send me impressive completed projects.

I once had a teacher ask the class if they had any questions regarding a project and when nobody asked a question she said, “Okay, then that must mean you understood everything…or nothing at all!”. She knew exactly what she was talking about.

★★★★★ She is a repeat client of mine, we worked on two projects together and I am really happy. She always knows what she needs to be done, her requirements are clear and she will answer to every question that you might have. If you had the chance to work with her “JUST DO IT”! :)

With this 3 step checklist I have been able to provide successful projects to my clients across varying industries while simultaneously keeping my own peace of mind. I have experienced both sides, hiring freelancers and hoping for the best and hiring freelancers and showing them exactly what you expect from them.

This checklist has escalated my reputation with my clients as they come to confidently see me as their go to consultant for their most important projects. Can it do the same for you? Don’t know unless you try :)



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Crypto Gili

Crypto Gili


Digital nomad who delights in the meta. Priorities are optimize my skills, grow my fortune, make the world a place I like. Favorite emoji: ❤ 🎈🤗🤷🏻‍