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Cracking Upwork: A seven step guide to securing top-tier talent


If you’re a small agency outsourcing short-term work to contractors you may have browsed Upwork, a freelancer platform that promises access to top talent from around the globe. But these platforms can mean hours of sifting through irrelevant listings and, much worse, poor quality results and delivery. So, are freelance platforms worth using? After years of fine-tuning my Upwork strategy, I believe they are. Here are seven steps I follow to get successful results every time.

  1. Use the right keywords. At Capulet we often coordinate campaigns in countries outside of North America, so we source local artists to ensure the content aligns with cultural and language norms. Based on location, language and experience, descriptors can vary dramatically. Before posting a job description, study prospective profiles to learn how freelancers describe their skills and use those descriptions in your post headline. The right keywords will attract the right creators.
  2. Write a comprehensive brief. Good talent will appreciate the effort. Great talent will read it. A detailed creative brief sets expectations and serves as a reference point to keep both parties aligned throughout the project. Here’s an example of a creative brief I developed for an anti-malaria campaign Capulet supported alongside global nonprofits in Sub-Saharan Africa.
  3. Pre-scan for talent. Scanning profiles ahead of posting a project description saves time and overwhelm when responses start to flood in. As you scan, save profiles that meet your criteria to a “wishlist” and invite those creators to bid on the project once it’s live. This step is especially helpful for budgeting as most creators publish their preferred rate.
  4. Set a fair budget. Unfortunately, many hiring folks see platforms like Upwork as a connection to cheap labour. If you prioritize price over experience, quality and communication skills then it’s doubtful your project will succeed. Being equitable, especially when working with freelancers in parts of the world with less economic privilege, will help establish a baseline of trust that every project requires. Set a fair budget and leave a buffer for additional edits or scope creep.
  5. Only review applicants who provide samples. Before posting a job, select the option to ask applicants a few questions. I always ask them to share work experience and samples similar to what’s outlined in the creative brief supplied in the project post. This is your chance at a sneak peek of their work style, attention to detail and communications skills.
  6. Work and pay on milestones. I find breaking the project into milestone delivery and payment installments keeps everyone happy, especially project managers like me who take deadlines seriously. Top tip: Milestones also provide useful pause points, which allow you to go in a different direction with another freelancer if you aren’t getting what you need.
  7. Practice empathy. Building relationships with creators from different parts of the world with diverse experiences, styles and ideas can give your campaign the spark it needs. Which makes it important to anchor your project with empathy, care and generosity when  working across time zones, languages, and cultural norms. A successful project partnership also demands a solid project management plan and frequent check-ins.

When you provide clarity, define expectations and practice gratitude, working with freelancers can be rewarding, ultimately producing effective campaigns and meaningful collaborations.

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