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15 Must-Ask Questions When Hiring A Creative Freelancer

When your team needs to bring in specialized outside help, the first (and sometimes only) questions that usually spring to mind are “How much will this cost?” and “Is this person any good?”

While dollar figures are (relatively) easy to negotiate and portfolios provide a solid starting point for assessing a potential freelancer’s creativity and skill set, if your aim is to set up a mutually beneficial relationship, your pre-hiring due diligence should extend beyond talking money and talent. Below are 15 questions to ask your team, your prospective hire and their references to ensure you’re doing business with the someone who is the best fit for your needs.

To ask yourself and your team:

  1. Have we clearly defined the scope of work we need completed and the related skills and experience  a successful freelancer should have to undertake it?
  2. What criteria will we use to measure the success of the freelance relationship and the work submitted?
  3. Who will this person need access to on our team or on other teams and what sort of background materials or resources will they require to do their work? Have we made arrangements for them to receive this support?
  4. Who will be the freelancer’s key contact on our team? Is this person equipped to manage the freelance relationship effectively?
  5. Have we developed clear policies around intellectual property and confidentiality?

To ask the freelancer:

  1. How frequently do you prefer to check in with your clients and what’s your preferred communication channel?
  2. How are you most comfortable receiving an assignment (scoping call, written brief, etc.)?
  3. Are you most comfortable with clear directions and defined deliverables or with more iterative projects?
  4. How do you define a great client relationship? What makes a great client for you?
  5. How many other projects are you currently working on? How much of your time is committed to each project?

To ask the freelancer’s past clients:

  1. How was the project you worked together on structured? Which party proposed the structure?
  2. How did you communicate with this person? How would you assess their communication skills and the overall communication process?
  3. How proactive was this person in soliciting your feedback and how responsive to incorporating it?
  4. Did the deliverables created by the freelancer meet your expectations? If not, did you express this? How did the freelancer respond?
  5. Would you work with this person again or recommend them to a colleague? Why or why not?

Bringing on a freelance creative to increase your team’s capacity and to benefit from specialized expertise will never be risk-free, but you can set yourself up for a successful relationship if you invest time in thorough vetting, info gathering and expectation setting. Your team and your new collaborator will thank you.

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