Successfully Onboarding a New Freelancer: Four Questions to Answer

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Successfully Onboarding a New Freelancer: Four Questions to Answer

Great – you found the perfect freelancer to contribute to your next big project. This rockstar talent has agreed to your terms and is ready to get to work. So take a breath – the hard part is over, and now it’s time to get the wheels in motion to make the collaborative effort with your handpicked freelancer a huge success.

There a number of essential questions you need to run through with your handpicked freelancer to ensure a pleasant and productive partnership. Here are a few of the most important ones:

Agree on the Rate and Move on.

Compensation discussions can be tricky and time consuming, but they don’t have to be. When working with a freelancer, be clear from the start about how much you are willing to pay and on what terms. It’s also important to research what rates they might expect. The Internet is full of forums and free advice for freelancers and with a simple Google search, you can find out what they might expect on sites like Leaving Work Behind. If your allotted sum doesn’t match up with their expectations, consider whether the value they offer is worth it to you to spend extra money on, or whether it’s the right move to respectfully find another collaborator.

Communicate Your Brand Identity.

Upon settling on a satisfactory rate for both parties, one of the most critical actions you need to take is to explain values as an organization. This goes beyond understanding what your organization does; it includes helping them understand your brand and what your organization cares about. What are its core values, and how do they typically translate in your work? Given these values, what are expectations you have for contributing freelancers? What are things that they should prioritize over others? Providing the right context is a prerequisite to having a successful working relationship with a freelancer.

Establish KPIs, Key Players and Goals.

As Seth Godin says, “the less people know, the more they yell.” Once your handpicked freelancer has a sense of your organization’s values, be explicit about the tools and information they need in order to succeed on their specific project (Ask them to sign an NDA if necessary). Who else is working on the project, whom they should know? What do they need to read in order to understand the project thus far? What has your client already expressed about the direction of the project? What will failure look like?

These are important questions for you to answer so that your handpicked freelancer is brought up to speed. It prevents mistakes that could have been prevented if only they had had the right information.

Develop Effective Communication Systems

Two people’s expectations can be very different, and seeing eye-to-eye is an ongoing process. In her book, Lean In, Sheryl Sandberg explains this dilemma quite nicely, “I learned that effective communication starts with the understanding that there is my point of view (my truth), and someone else’s point of view (his truth)… When we realize and recognize that we can see things only from our own perspective, we can share our views in a nonthreatening way.” Working with freelancers is no exception. Make sure you have a well-oiled communication plan to make sure your visions do not stray too far from each other. Make sure you know how often the freelancer is to update you on their progress, and what communication platforms you will use. What aspects of their progress matter to you? What is the best way for them to reach out and get help if needed?

Communication routines are imperative. They can vary depending on an individual’s preferences. One person might have the freelancer, for example, email them at the end of the day with a bullet point list of their progress. Another person might have them send updates when they have finished a substantial step of the task. And so forth.

Regardless of the specific routine you establish with them, ask the freelancer to start using your organization’s tools as soon as possible. Slack, Jira, Trello and Asana are all popular, efficient choices. Using one of these systems will help you keep track of what’s going on if you’re working with multiple freelancers, but you need to take the time to introduce them to these systems. If your organization uses Coworks, for example, walk them through the parts of the website where you’ll be communicating and sharing files, and let them know if this is how you will be making payments.


These questions are among the most important to ask when starting a collaboration with anyone — and in particular, with short-term collaborators. By systematically thinking through what it is you want to happen with your new freelancer, you can ensure that you get a quality result. There are other benefits, too: with each successful relationship you establish, there’s an opportunity for further collaboration — with this freelancer or with others. You have strengthened your organization’s reputation as a quality place with which to work.

Extra Pro tip: you can ask your trusted freelancers for referrals, they are often happy to help.

By | 2017-05-09T05:40:51+00:00 May 9th, 2017|Productivity Hacks, Remote Work|0 Comments

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