silhouette of person holding robot's hand

No matter how experienced someone may be at contracting freelancers, it’s typical to have a little apprehension at the start of each project: worries like, Did I choose the right freelancer? How can I be sure the work gets done on time?

To help you engage talent more confidently, staff from Upwork gathered tips from companies that rely on flexible talent to get projects done. Here are their top suggestions for overcoming common concerns and increasing your chances of a successful project.

How can I make sure I’m choosing the right freelancer for a project?

Most freelancers work remotely from their own location, so you’ll probably never meet them in person. That’s why when vetting talent, it’s important to follow a thorough process and resist taking shortcuts. Sure, it takes a little more work up front, but every company interviewed agrees that the effort’s worth it in the long run.

Take advantage of available info

If you’re sourcing through a freelancing website such as Upwork, review talent profiles, read project ratings and comments, and look at their work quality, certifications, and so on. “Follow a thorough vetting process,” suggests Nathan Drake, CTO at Dental Sleep Solutions. “It may take more time, but it’s worth it in the end.”

Scrutinize from the beginning

When talent answers your project post, consider the questions they ask: Are they strategic and thoughtful? “If they don’t put a ton of effort into answering your job posting, how much effort will they put into your project?” asks Claude Burns, founder and CEO at Office Libations. Observe how well they communicate, and ask questions to verify that they have the experience you need.


If you need certain skills from time to time, it’s smart to create a go-to bench of experts who can provide them. To get started, other companies suggest:

Start small

Nearly every company interviewed suggests that when building a talent bench, start new talent on a small project first. Doing so will give you a chance to review the talent’s work quality and fit.

“Freelancers work independently and control their own schedules. This means it’s important to have clarity around milestones and find the right talent who can manage those milestones on their own,” says Lisa Oda, head of content marketing at Upwork. “Once milestones are met on time and with solid results, you can start to give them larger projects. The beauty of starting small is that you can increase your capabilities while minimizing risk.”

Stick to what’s familiar

On your first few projects, Drake suggests engaging freelancers with skills “close to your comfort zone.” By vetting for skills familiar to you, you’ll be better able to assess if the talent’s the right fit or not.

What do you do when you must contract talent outside of your comfort zone? If you’re a social media marketer, how would you know how to hire a back-end developer? Drake has an easy solution: He invites trusted freelancers to help him with the vetting process. It makes sense, as these freelancers are experts in their field, he trusts them, and they’re familiar with the company, its processes, and the skills needed.


Successful projects require a multiprong approach. Below are the top three suggestions.

Communicate (a lot)

For successful projects, communication is key. This begins even before work begins, with how clearly you write the project description and talk about the results you expect. Build a relationship and make yourself available throughout the project so that the talent feels comfortable reaching out to you if they need additional information. All this helps build trust with freelancers, which helps avoid misunderstandings.

Keep in mind that freelancers run their own businesses, so they work their own schedules and are likely working on other projects too. Don’t expect them to answer emails immediately or attend last-minute meetings. Be sure to schedule any meetings in advance, and let the freelancer determine the time. If you’re working with talent in other countries, be aware of potential cross-cultural communication gaps and how to bridge them.

Quickly end unproductive relationships

“We communicate a lot via Skype. If someone is engaged with you and responsive to working with you, it builds trust that they’re going to work out,” says Eric Olson, VP of development at SoftNAS. But if a freelancer doesn’t work out, Olson says to be quick about ending their contract per the terms of the agreement, and find another freelancer.

Recognize them

Olson’s team is also diligent about taking time to recognize results and making sure freelancers know they’re valued. Recognition comes in many forms, including thanking them for completion of important project phases to leaving a positive review on their profile after a project’s completed.

Mohamed Omar, founder and CEO at Linguistix Tank, believes that recognition is an important part of ensuring freelancers have a positive impression of his company. “Our philosophy is, When they’re happy, clients are happy. That’s why we pay more than average whenever we can,” says Omar.

Move fast—but not too fast

Although freelancing websites and other channels make it faster and easier to directly source talent, keep in mind that you don’t have to sacrifice quality to be agile. “It’s a balance between moving quickly and being diligent about finding the right fit for the work you have,” says Shannon Williams, co-founder and VP of sales at Rancher Labs.