How to Build a Team of Freelancers

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Whether your growing business needs to scale quickly, build on your in-house team’s capacity, or create flexible work teams, staying competitive in today’s marketplace means staying agile. For many small and growing businesses, access to the right talent trumps other factors for success.

*The Upwork SMB Survey was conducted online by Bredin, a research firm specializing in SMBs, January 16-19, 2018, and polled 503 principals of U.S. businesses with 500 or fewer employees.

But how do you find the talent you need? For a growing number of businesses, the best option is to tap into the freelance marketplace. Upwork’s Future Workforce Report found that nearly half of businesses (48%) are using flexible workers such as freelancers to scale and access skills they don’t have in-house.

Depending on your project, however, sometimes a single contractor isn’t enough. Instead, you might need a team of freelancers to move ahead. Here’s a look at the steps it takes to start building a team.

1. Break down the scope of work

Not surprisingly, the first step to finding the right freelancers for your project is to identify the types of skills needed to bring your idea to life. By defining the scope of work in a document, such as a creative brief, you can create a detailed reference that may include:

  • Background about your business, industry, and target market
  • Context for your project, such as the problem it solves, the opportunity it leverages, or the competitive landscape
  • Objectives for the project. How will you measure success?
  • Deliverables expected and the types of skills needed to produce them
  • Logistics for your project, including timelines, milestones, budget, and key stakeholders
  • … and any other factors that could affect production

For help getting started, check out Upwork’s Hiring Guides or search the Hiring Headquarters, where you can find more information about a number of skills including data science, web development, social media, and app development.

2. Craft an effective job post for each type of skill

Using the scope of work as a base, write a job post for each of the skill sets you’re looking for that’s engaging, detailed, and professional. The following checklist highlights best practices for creating a good project description:

Checklist of what employers should include in a job post

One common mistake is to be overly brief, especially when posting via Android or iOS: 30 percent of job posts published via mobile devices to the Upwork website are 100 characters long or less.

To help avoid this, prepare for each job post ahead of time:

  • Determine the appropriate payment structure: fixed-price or hourly
  • Consider drafting a detailed project description in another app, then copying it when you go to post your job
  • Highlight two or three must-have skills for each of the skill sets you’re looking for
  • Include a screening question to help make the vetting process easier
  • Do your own search for top talent to share your job post with; an analysis of job posts on Upwork shows that those sent directly to 20 or more freelancers are more likely to be filled.

3. Start vetting proposals

Before you start to receive proposals, it can be helpful to define some qualifiers so that you can quickly identify the proposals you want to prioritize. For example, you can check whether:

  • Proposals follow your directions, if you included a vetting question in your job post
  • Your project requirements—such as hard deadlines or deliverables in specific file formats—can be met
  • A freelancer has the must-have skills you referenced in your job post

You might also set up a quick screening process as proposals come in, looking at criteria such as rate, time zone, and related experience. Don’t have time to individually vet talent? Consider engaging a freelance recruiting consultant to help you hire better and faster.

4. Interview your top choices

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While a proposal can provide a brief introduction—who they are, their skills, and how their experience fits your project—it’s the interview that brings the introduction to the next level. It’s a chance for both of you to speak candidly, to see how well you communicate, and to get a feel for if the freelancer is a good fit.

Be sure to ask questions about the project and the timeline; the freelancer’s experience, interests, work habits, and communication preferences; and how he or she plans to approach the work. Need ideas for questions specific to a certain role or skill? Check out Upwork’s Hiring Guides for interview questions for developers, virtual assistants, designers, and more.

Tip: Opt for a video chat when you interview remote talent. This can create a more “in person” feel and lets you pick up on visual cues.

5. “Onboard” freelance talent

There are always a few processes required when engaging talent, whether they’re remote or on-site. These can include compliance, invoicing and payments, and access to any documentation, data, or systems they need to get started.

Freelancer management systems (FMSs) can streamline and automate processes and paperwork while reducing risk of human error or misclassification. To make sure you’re getting the right forms and documents filled out, consult a legal professional to help come up with a standardized end-to-end process that includes worker classification.

To learn more about what to look for in an FMS, check out this article. And for paying freelancers in other countries, consider a platform such as Upwork Enterprise, which supports currencies in more than 180 countries.

6. Have the right tools in place

Whether it’s sharing deliverables or collaborating on a project, be sure your team of freelancers is set up with access to the right tools and technologies. Start by looking at the types of projects and deliverables your team will be working on, then match them up with the cloud-based tools best suited to the work. Then make sure communication is covered to help you avoid common collaboration pitfalls.

Say you’re working with a team of remote software developers. First, they’ll need a way to communicate and keep track of who’s working on what—say, Slack, Trello, or Google Hangouts. They’ll likely also need a centralized repository like Git to house their code. If they’re responding to bugs around the clock, a bug-tracking and issue-management tool like Jira will keep everyone on the same page.

Each team works differently and needs a different ecosystem—a design team, for instance, has different requirements than a mobile app development team collaborating on a prototype or a remote social team using Google Analytics and scheduling posts. Get ideas for the tools that might work for you with 18 Essential Collaboration Tools for Remote Teams.

With the right people, tools, and communication, it can be easy to grow a team of freelancers and help them work together as a team. If you’re looking for a more turnkey solution, consider hiring a remote agency with all the talent you need under one roof. To learn more, download Upwork’s free Innovative Hiring ebook today.


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Author: Carey Wodehouse

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