Failproof Questions to Ask When Hiring a Freelancer

Written by on September 12, 2010 in General, Internet Marketing - 1 Comment

Picture this: A brand new ecommerce company had just lined up a Web developer, SEO company and copywriter to get the company off the ground. The team was in place and site development seemed off to a good start. Projected launch for the new site was 6 months. Actual launch: 1 year later!

During that time, the client’s budget was depleted. The developer was dismissed. And the company ran out of resources needed to promote the new website after launch. All troubles that could have been avoided had the team been more carefully selected.

little girl wearing big hat

If you are marketing your company on the web, you've most likely had occasion to hire a freelancer or other service vendor. But working together over the Web brings potential pitfalls that can be minimized with attention to a few details at the start of the relationship.

This scenario, or some other version of it, is more common than we’d all like to think. It’s no secret that the majority of small businesses are doomed. But we’re all optimistic starting out. Even when minor things start to crop up, we do what we can and pray that issues will iron themselves out in the end.

As marketing director at an Internet marketing company, I’ve hired vendors and managed projects we’ve outsourced. As a freelance copywriter, I’ve been on the other side many times, too. In fact, many of the businesses who approach me about writing their online materials are licking their wounds from a failed relationship with another copywriter.

I can tell you, finding the right vendor is tough. Try looking for these top 5 traits that I think are key to a successful relationship with a freelancer or other vendor:

1. Dependability

Dependability is my number one criteria. Why? Because all the talent and experience in the world won’t do you any good if the copywriter, designer, or SEO company can’t be counted on to follow through as promised.

Signs of dependability: Prompt responses to your communications, involvement in ongoing projects that might require a high level of reliability. (If they are contributing to a blog, do they write regularly or sporadically? Are they involved in activities like writing or producing a monthly newsletter—and how long have they been doing it consistently?)

2. Engagement

Does the vendor or freelancer really care about their work for you? Or are they just going through the motions looking for the paycheck? Enthusiasm for your project will pay off in additional effort that can show up in the form of innovative ideas and higher quality work. A willingness to go above and beyond can trump experience at times.

Signs of engagement: Do they take the time to offer suggestions and explain why they approach things in a certain way? Or do you get lazy one-line responses to your emails? The vendor or freelancer should do a bit of research before they talk to you so they can ask meaningful questions.

3. Flexibility

Do you prefer phone contact? What if your designer or copywriter is more an email person? You may find this causes snags in the process and can lead to unnecessary delays. Make sure your freelancer or the account executive you’ll be working with at a vendor company is flexible enough to match your communication style.

Also consider time zones. If you prefer to do calls in the morning but you’re on the east coast and your copywriter is in California and prefers afternoon chats, you’ll have a tough time scheduling calls.

Flexibility is also important when it comes to deadlines. Even though you want to give long lead times, there will be situations where you need things done fast. You’ll want to make sure your designer, copywriter or other vendor can step up at those critical times.

Ina addition, you’ll find some freelancers and providers can be stick in the muds when it comes to how they approach their work. If you have a style guide for your written communications that specifies how certain words and phrases should be used, make sure the writer is on board with that. You don’t want to have to edit their work for technicalities or debate things that have already been decided. You shouldn’t hear complaints from the designer when you ask them to make changes to their work (although their rationale and suggestions should be welcomed).

Signs of flexibility: Ease of scheduling times to talk, past projects completed on tight deadlines, experience with different styles and brands that would require a flexible approach to their work, confirm any fees for rush work.

4. Experience

Certain efficiencies arise from working with providers already experienced in your industry. There’s a smaller learning curve. They can offer wisdom and guidance. Talk at length with the potential vendor to get a true sense of their knowledge and experience.

Signs of experience: Samples of work for others in your industry, previous projects dealing with the same technologies you require, a grasp on the basic issues and language of your target audience, elements in their portfolio you can identify with your business.

5. Talent

Of course you want to hire a great copywriter, a talented designer, and an SEO company that really rocks Google. But just be aware that their talent must match your needs. You should ask some tough questions to make sure they can fit your style and vision.

Signs of talent: Check out their existing work and ask yourself if that’s how you want yours to look. Examine their most recent work to understand the direction the copywriter or designer may be moving in, even if it’s not directly in your industry.

What about you? Have you had any issues with freelancers that you’ve learned from?

Photo credits:  Kevin Spencer,

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One Comment on "Failproof Questions to Ask When Hiring a Freelancer"

  1. Kurt Gross September 13, 2010 at 1:35 pm · Reply

    Timely for me and informative as I am about to journey down the road of searching for some help with upcoming websites I’m developing, like the one I’ve listed here.

    I’ll have your post printed out and use it as a guide along with some ideas of my own.

    Thanks, again,

    Kurt Gross

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