The 1 simple question you must ask every new freelance client

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new freelance client questionAfter all these years, I like to believe I’m pretty skilled at avoiding red-flag clients.

Alas, I’m writing today to confess an unforced error, because I recently neglected to ask the 1 simple question you must ask every new freelance client:

What’s your past experience working with freelancers?

The whole tale is a bit too sordid to tell in full detail, but here’s the quick take: I received an inquiry about copywriting services for a local business that was adding a retail line to its wholesale products. It’s a successful company, located on the top floor of a fancy downtown building, and I thought it sounded like a great opportunity. I met in person for about an hour with the owner and his marketing manager, and we had instant rapport. They needed three pieces: a consumer-facing brochure, an educational guide for retail shops, and a basic website.

It seemed straightforward, and I hate wasting time in meetings, so I dove right into asking about branding, timelines, page counts, and other details, and told them I’d get back to them with an estimate, which I did the next day.

Here’s Why Past Experience with Freelancers Matters

By focusing on their needs, expectations, and the technical aspects of the process, I failed to glean the most important details of all: Did they understand the creative process? How easy were they going to be to work with?

I knew that they had created their existing materials in-house, and had worked with ad agencies in the past. But by missing that critical qualifying question, I didn’t uncover the fact that they were far less experienced than I assumed them to be. That only became clear as they…

  • changed their minds multiple times on creative approach, format, length, and other parameters
  • ignored my polite requests to not make revisions to old documents
  • provided conflicting edits that they expected me to reconcile
  • drove my designer crazy by requesting endless minuscule changes to the logo

My guess is that if I’d asked them up front about past experience with creative freelancers, it was either minimal or confrontational, or both. In any case, it would have been revealing, and allowed me to incorporate the answer into my pricing fudge factors, or just plain turn down the project.

What Would I Do Differently?

In retrospect, it was a strange enough circumstance that I’d like to let myself off the hook. I got paid in full, so I was fine on that count. When I informed them that costs were going up from expanded scope, they said, “OK, that’s fine, just add it to the invoice.” I finished the brochure, but declined to pursue the other two pieces.

The reality is, they did a very good job of cloaking how inexperienced they were, and how crazy the process was going to be. As the project went on, I arguably could have done a better job of managing and controlling the process. In the final analysis, however, my conclusion is that I sowed the seeds of disaster in the first meeting. The red flags were there, I just didn’t give them a chance to raise ’em.

Oh, and by the way: I just checked, and six months later, the company still doesn’t have a website. In fact, I wonder if they even managed to produce the brochure.

In the comments: In your opinion, what’s the 1 question you must ask every new freelance client?

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  1. says

    That’s a great suggestion, Jake, and I admit it’s not one I’ve thought to ask. Recently, I did ask a new contact at a long-time client if she had worked with freelancers. She assured me she had – in fact a team of 12! To be honest, I was surprised because we struggled to get off the mark.

  2. Jake Poinier says

    Interesting, Cathy. I am reading between the lines on “struggled to get off the mark,” ha. As I think about it, the question probably works better to ferret out problems with less-experienced clients than those with more experience.

    For example, a client with ample background working with freelancers would surely know better than to confess to having had issues, and potentially scaring you off! In that case–if you were suspicious–you might do a little more vetting, almost like an interview. “Tell me about a recent project with a freelancer, so I can get a better understanding of your process and work style, and how I can work most effectively with you. What were the things that went well, and what didn’t go so well?”