How to Hire on Upwork

Upwork’s wealth of high-quality talent, detailed bios, and ratings is unmatched. Over the years, I’ve hired at least 25 people through Upwork, and it has significantly contributed to my success. Here are some of the key strategies I’ve developed for hiring effectively on Upwork:

1. Avoid Paying for Boosts

I’ve found that paying for boosts is unnecessary. High-quality candidates consistently apply without the need for extra promotion. Save your budget and focus on evaluating the natural influx of talent.

2. Wait 24 Hours Before Reviewing Applicants

Patience is crucial. By waiting 24 hours after posting a job, you can get a clearer picture of the range of talent available. This waiting period allows you to identify both the standout candidates and those who might not be the best fit.

Don’t be constrained by Upwork’s suggested salary ranges. You can often find excellent talent at more reasonable rates.

4. Avoid Hiring Through Agencies

Hiring through agencies increases costs and introduces unnecessary middlemen. Directly engaging with freelancers ensures clearer communication and a more personal connection with your hires.

5. Conduct Quick Phone Screens for Large Applicant Pools

When faced with 50+ applicants, quick phone screens are essential. I use Calendly to set up 15-minute slots and invite about 30 candidates to interview over the period of 48 hours. This process (brutal for the interviewer) quickly filters out those who may look good on paper but fall short in areas such as communication skills, internet quality, and authenticity of their experience.

6. Follow Up with In-Depth Interviews and Work Simulations

After the initial phone screens, I usually identify a few strong candidates. I invite 3-5 of them for longer interviews that include work simulations. This could involve pair programming, writing customer emails, or designing components together. It’s a practical way to assess their skills and compatibility with your workflow.

7. Hire Two Candidates as a Safety Net

To mitigate risks, I often hire two top candidates. This strategy acts as a hedge against unexpected issues with freelancers. Typically, at least one of the two will prove to be a successful hire.

8. Be Cautious with Part-Time Freelancers

Hiring part-time freelancers (20 hours or less per week) can be challenging. They often juggle multiple jobs, making it difficult for them to prioritize your work. Full-time commitments generally yield better results.

9. Embrace International Talent

International freelancers can be as competent as those in the US and often at a lower cost. The quality and affordability of global talent are impressive. Additionally, international contractors are usually highly motivated to work with US companies, bringing enthusiasm and dedication to their roles.

10. Require all communication to happen on Upwork

When I post a job on Upwork, some freelancers invariably try to figure out my email address and email me, find my phone number and call me, or even start live chatting me on my company website. I tell anyone who does this that all communication must happen on the Upwork website. That way, I can stay organized, reduce distractions, and manage the speed of the hiring process.