Freelance experts can be valuable partners with your company, but getting optimal results from this partnership isn’t as easy as telling them to “fix it,” “figure it out,” or “build a better mousetrap.”

Talk to any startup. I guarantee that they’ll have at least one story of a freelance hiring that went wrong. We’ve worked with dozens of startups that thought they could get by with the help of freelancers to build out their tech products.

The end result?

A “Jenga-like” platform with pieces stacked on pieces ready to collapse. And what ends up happening, is the company puts off an entire redesign to continue to push for customer acquisition goals. Delaying the inevitable complete product rebuild.

Sometimes these scenarios are inevitable for inexperienced entrepreneurs. It’s a learning experience.

But hiring freelance talent should be done with a plan in place.

Drawing on the skills of freelancers can be very beneficial for businesses of all kinds, especially for projects that are out of the ordinary for the internal team working on them. That being said, it is important to prepare for the arrival of your freelance talent and prepare the team or teams they will be working with.

Asses/Project Your Project Needs

The first step in finding a freelancer is assessing your needs in a systematic way.

The worst possible use of an expensive freelancer is hiring them for needs that you don’t fully understand. You want them to hit the ground running, so assess the extent of your needs in advance. Freelancers will also be curious about the length of their engagement with your company, and vague answers will discourage freelancers with other clients to serve.

What will the freelancer(s) do?

  • What work is currently beyond the skills of or time constraints on your employees?

– Is there too much work for your employees or is it too complicated?

– Which skills are demanded by this work?

  • What projects/products/accounts depend on the work being done?

– When are the pertinent deadlines?

– Are you on schedule?

  • What kind of work-load will your freelancer be under?
  • How much work for how long?
  • Will a single freelancer be enough to meet deadlines?
  • Which skills will be most used by the freelancer?
  • Which specific technical skills (eg. Coding with Ruby on Rails)?
  • Which “soft skills” (eg. Communicating, collaborating)?
  • What kind of experience will be most valuable for a freelancer to have?
  • What are the specifics (eg. testing the security of financial services software) that will make a freelancer highly qualified for the work you need done?
  • How soon after the completion of this project will you require the skills of the freelancer again?

-Will you require a different freelancer for upcoming projects?

Answering these questions should give you a clear picture of the work that a freelancer will be charged with, which is crucial in finding the right person for your needs.

Find the Right Freelancer or Freelancers

After you’ve assessed the demands and extent of the work, the next step is finding the right freelancer (or freelancers) to do that work.

Besides finding someone with the right skills and experience, any freelancer you hire should be given a decent understanding of the job they are supposed to do for you.

As you talk with freelancers, walk them through the project or projects they will be working using the information you gathered in the assessment step. Then, ask questions to gauge their interest level and the relevance of their first-hand experience.

  • Have you ever worked on a project like this before?
  • Was it smaller or larger in scale?
  • How did this project go?
  • What was your role in this project?
  • Can I contact the manager you worked with most closely?
  • Does any aspect of your work on this project strikes you as challenging?
    • Does the target release date seem feasible?
    • What will be the most difficult and/or time consuming part of this project?
  • What tools do you usually use for work like this and what resources do you need?
    • What programs/tools are essential for completing your work?
    • How many supporting staff members do you need and what do you need from them?

Have potential freelances walk you through their solutions to the work you need done. Ask them to talk about their direct experience with projects like yours and how they have supported the completion of these projects. It is also good to pay attention to the questions that freelancers ask in return, as people focused on specifics are already thinking of the job at hand.

Prepare Freelance Talent

After you’ve found the right freelancer for your needs, it’s time to put your feet up and watch the work take care of itself, right?

While this would be nice, investing in a freelancer and then failing to orient or prepare this professional is just sloppy.

You want freelance talent to get off to a great start, so clear the path for them and collect all the information that they’re likely to want before they ever make it to your office.

  • What will the freelancer(s) be working on day one?
  • What are the first deliverables that the freelancer will work on?
  • In the first week?
  • In the first month?
  • What information will they need to start their work and do this work optimally?
  • What are the first questions that an expert will likely ask?
  • Which specifics will make this project different from projects they’ve done at other companies?
  • Who will be key in supporting their work?
  • Which employees will work closely with the freelancer?
  • Which employees will the freelancer report to on a regular basis?
  • Are there any details that are outside of a “best case scenario” for their project?
  • Where have you hit snags?
  • Where is the product now and where does it need to be?
  • What are the problems that will require the most of their attention?

No matter what they’re working on, it’s always a good idea to have freelance talent sign Non-Disclosure Agreements prior to starting work for your company. They may be a valuable asset today, but they could be working for a competitor tomorrow and this policy is fairly standard.

Freelance talent can support your internal team on an as-needed basis, but getting your preferred contractors for every project cannot be 100% guaranteed. As free agents, they may be engaged on another project when you’re in crunch time, so it’s important to anticipate these needs and try to coordinate in advance.