Freelancer: Why You Weren’t Hired

In the time I’ve been doing the freelance/solopreneur/consulting thing as a content strategist, I have had the opportunity to develop strategy and oversee the production of visual identities, pitch videos, blog posts, sales sheets, pitch decks, website content, and the like.

I have hired and managed copywriters, graphic designers, videographers, animators, and virtual assistants to help see these projects get completed.

From going through the process of advertising for labor to hiring that labor, let me tell you, many freelancers blow it immediately. Well, I set them up to blow it early if they’re going to blow it, because I’m deadline driven and cannot suffer fools who bring drama.

I don’t waste my client’s time, and I won’t hire anyone who looks like they’re going to waste my time, and by extension, my client’s time.

Here is my super simple freelance hiring process, and real-life examples of how freelancers have taken themselves out of the applicant pool.

Step One: Ask Applicants to Email Something Specific that Shows Their Value

One particular project I was developing required sales copy development. I instructed the applicants to email me copy selling themselves: just three reasons why you’re great at sales copy. Some freelancers emailed me their portfolio and didn’t write the sales copy. Some freelancers posted their portfolio to one of the threads where I advertised the gig.

One freelancer followed directions. ONE. Okay, that’s easy. One freelancer to interview from this round. Thanks for making my job easier, applicants! This writer was actually great. I recommend him all the time to others.

Step Two: 15 Minute Phone Call Demonstrating Your People Skills

Another project required a market interviewer. This time 3 applicants passed the email test, so I scheduled three interviews where they interviewed me. One applicant was able to own and direct the conversation the way a good interviewer should. I hired her, and, again, sang her praises to everyone who needed to know, and then some who didn’t.

Step Three: Look at the Portfolio

I never look at the portfolio before I conduct these two tests. The truth of the matter is, if you can’t follow simple directions, or cannot communicate clearly in a business environment, I’m not going to hire you. If you cannot do these two things, odds are, you will make me look bad, and that’s bad for my business.

Honestly, It Ain’t Rocket Science to Make a Good Impression

All the talent in the world won’t make you successful. Understanding directives, knowing how to present your value, and NOT adding drama to the process is what will make you successful. A mediocre creative with strong communication skills will always do better in business than a more talented creative who derails the process.

Just for Fun, Other Examples of Behavior from People I Didn’t Hire

  • Come one hour late to the planning meeting, then fill the room with the story of the drama that you chose to focus on (it was not a legitimate emergency), instead of the business we are hiring for (if you make me miss yoga, and you did, you’re out)
  • Tell me you will have your portfolio to me Tuesday, then deliver it Wednesday with the explanation that you just got busy (it’s just a link in an email, puhlease)
  • Tell me the skills of the gig are below your expertise, but not to worry, you won’t poach my client with your greatness
  • Tell me you only talk to the decision maker (i.e. the client – who is paying me to make the decision)
  • Complain that the client “mansplains” too much when they are sharing their experience

So, there you have it, freelance creatives, and those who hire them. Easy ways to screen, easy ways to blow it.

Dawn Weathersbee


  1. Thanks for this, Dawn! It’s always good to know what goes through a potential client’s mind when they’re hiring. I know the opposite behavior of what you’ve described could be reasons a freelance would get the job, but can you give a few others? What really impresses you when you’re interviewing?

  2. Hi Cindy,

    You’re welcome, and great question!

    Freelancers need to realize, they are in sales, no matter their service or product offering.

    Sales 101: Show you understand the customer’s problems and have the solution.

    What impresses me the most? Showing respect for what I need to solve my problems. Yes, I may be advertising for a copywriter and am asking for copy written for a blog, but my real problems are keeping the client happy and being able to fulfill my timeline and scope of work promises.

    In short, listen more than you talk, identify the true need, then speak to that need.

    A specific example from a conversation I just had today with a client about getting their pitch deck together (paraphrased, of course).

    Me: “…and you need it yesterday.”
    Client laughs: “Yes.”
    Me: “I figured, like most startups, you don’t know what you want, but you want it now.”
    Client, laughing some more: “Guilty.”
    Me: “That’s what I’m here for, to ask you questions to help you figure out what you need and help you get there faster.”

    This client’s needs are not really a pitch deck. Their needs are guidance, looking professional, and getting it done quickly because they scheduled meetings before the deck was done. My solutions are to tell them the best path to looking professional and getting it done as quickly as possible.

    The job of all sales people is to minimize pain and maximize wellbeing. Want to be impressive? Speak to the need.

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