3 Hacks for Hiring the Right Freelancer/Contractor

Why Hiring Freelancers Is Tricky 

Hiring freelancers or contractors can be a game-changer. You get specialized skills, flexibility, and cost savings compared to full-time hires. 

But here’s the challenge: the freelance market is crowded, and it’s easy to waste time (and money) on the wrong person. Missed deadlines, poor communication, or mismatched expectations can derail projects. 

The good news? With the right approach, you can dramatically increase your chances of finding the right fit. 

Here are 3 hacks to help you hire the right freelancer or contractor every time. 

Hack 1: Define the Process Before You Hire 

Most hiring mistakes happen before the first interview. If your process isn’t clear, you’ll attract the wrong candidates. 

What to do: 

• Write a clear job description (deliverables, timeline, budget). 

• Define success upfront—what does a “good result” look like? 

• Use your project management tool to track applicants, tasks, and milestones. 

📌 Pro tip: Document your freelancer hiring process once using SOPs or BPMN diagrams. This makes it repeatable for future hires. 

Hack 2: Shortlist and Test Candidates Before You Commit 

Not every applicant deserves your time. Filtering candidates early saves you headaches later. 

How to shortlist effectively (on platforms like Upwork): 

• Check ratings & reviews: Look for consistent feedback across multiple projects. 

• Evaluate portfolios: Focus on relevant work samples, not just polished showcases. 

• Assess communication: Pay attention to how quickly and clearly they respond. 

• Look for repeat clients: This signals reliability and long-term value. 

Once you’ve narrowed the list, don’t rely solely on profiles or promises. Put candidates to the test. 

What to do next: 

• Assign a small paid trial task before awarding the full project. 

• Test not just skills, but also communication, reliability, and ability to follow instructions. 

• Compare trial results across candidates to make an informed choice. 

📌 Pro tip: Keep the test task relevant to your project so it contributes value even if you don’t move forward with the freelancer. 

Hack 3: Set Up Clear Systems for Collaboration 

Even the best freelancer will struggle without clear workflows. 

What to do: 

• Use tools like monday.com, Asana, or Trello to assign tasks and track progress. 

• Agree on communication rules (Slack, email, weekly check-ins). 

• Automate repetitive workflows (e.g., payment reminders, status updates). 

• Store all deliverables and feedback in your centralized knowledge hub. 

📌 Pro tip: The more structured your system, the less you’ll need to micromanage. 

Final Thoughts 

Hiring the right freelancer or contractor doesn’t have to be a gamble. By: 

1. Defining your process, 

2. Shortlisting candidates with clear criteria, 

3. Testing before committing, and 

4. Setting up strong collaboration systems, 

…you’ll build a reliable network of freelancers who deliver quality work every time.