Dylan Sigley takes us through 8 Tips for Hiring Freelancers on Upwork

“Hi Dylan Sigley, I have been running my own drop servicing business for a while now and am starting to sign up lots of clients. I was wondering if you could share some tips for how to hire freelancers on Upwork?”

Thanks for the question. Yes, I can give you some good advice since I have hired literally hundreds of different freelancers over the years and now teach others how to as part of the Dylan Sigley ‘Drop Servicing Blueprint’ course that I teach.

Here are 8 tips that will help find great freelancers on Upwork, so that you can scale your business and deliver an exceptional service to your clients.

1. Find Freelancers with A High Job Success Score

My first tip is to go for freelancers that have a high job success score. Every Upwork freelancer eventually gets a job success score, otherwise known as JSS for short.

If you view a freelancers profile, for example “Dylan Sigley Web Development”. It will show you their JSS score. The score is out of 100%. Freelancers that maintain over 90% JSS for 16 weeks in a row are given ‘top-rated’ status, which means these freelancers have provided their customers with great work, consistently.

When you’re hiring freelancers, ideally you want to go for talent with a ‘top-rated’ status, because you want the best you can afford. But when you’re starting, a 95% or even a 90% JSS, will likely get you the job done to a pretty decent quality.

Hiring these top freelancers almost guarantees you’re going to be dealing with a professional that firstly knows what they’re doing, and secondly, communicates quickly, effectively, and has a history of delivering great service to other clients.

2. Hire Freelancers Who Communicate Quickly and Clearly

Drop servicing is all about fulfilling your clients’ needs by providing a high-quality service that is delivered promptly. You need a freelancer who’s going to reply quickly, communicate clearly, and just make life easier for you, so you can deliver excellent service to your paying clients. What you don’t want is a freelancer who has inconsistent communication. Can you imagine trying to follow up with a freelancer about a project they’re working on, only to hear back a day later, or finish the product delivery late and just make excuses? That’s just not going to cut it in your drop servicing business.

Hiring contractors and freelancers off Upwork is a great start. You’ll want to start there, but over time you’re going to want to lead a team that works exclusively for you, potentially as an employee. If they’re going to join your team in the future full-time, they’re going to have to be able to communicate clearly and be reliable.

3. Check Their Prices

My third tip is to hire an affordable freelancer. To make money with your drop servicing business you need to be able to charge your clients more than you have to pay your freelancers. This can be tough because often the best freelancers charge the most. To overcome this problem, you can look to hire freelancers in countries like the Philippines who can deliver high-quality work and at the same time do it at an affordable price.

Upwork has a search filter that lets you search for freelancers that charge a specific amount per hour. You can also hire freelancers on a fixed price basis, which also works great, it just depends on the type of work. You just have to work out your budget and then use the search filters to find freelancers who fit within your budget.

You want to take your time and find the best picks for your business that you can afford. If you find that over time a freelancer is providing a lower quality than you need, or isn’t receptive to feedback, then you can quickly replace them. This is better than hiring quickly and then giving them tons of second chances when they’re just in it for a paycheck rather than helping you grow and scale your business.

4. Write Detailed Job Postings

If you post detailed job listings you will get better responses from freelancers as they will know exactly what you are after. One tip I give people is to include a few hidden questions in your job postings. This will let you know which freelancers are reading the whole posting and are paying attention to it. One way you can try this on Upwork is to write something like “when you apply for this job at Dylan Sigley Services please include the words ‘blue dog’ at the top of your proposal”. It’s a really simple, quick, and effective way to check your job details that have been read by freelancers who apply for your job.

5. Hire Freelancers Who Are Open to Feedback

If you want to be a boss, you are going to have to start thinking like a boss. As a good boss, you’re going to have to give feedback to your team on what’s working well, and what’s not. At the end of the day, you’re the one hiring and paying them. You’ve got to be respectful, but if a freelancer isn’t doing something correctly, and they’re not open to changing their ways, then it’s best to move on and hire a freelancer who is open and receptive to feedback. You should also be open to feedback yourself. In some cases, a freelancer you’re hiring for a very specific service may well know more about the service than you do, so be open to their feedback and recommendations. Think of it as using their skills and knowledge as a learning opportunity to help improve your business.

6. Find Freelancers Who Have a Track Record

The next tip is to find freelancers who have a track record on Upwork and have earned money on the platform. The more money they have earned, the more it shows you that they are trustworthy, communicate well, and deliver their services to a high standard. For example, if I was looking for a freelancer for a role at ‘Dylan Sigley Services’ I will hire the freelancer that has earned $10,000 on UpWork over a freelancer who has only earned $1000 on the platform.

7. Make Sure They Have the Right Skills

My next tip is to make sure that you find a freelancer that has the right skills. If you’re hiring an ad specialist to make you YouTube ads, then you want to ensure you’re hiring an expert for this specific job, not say a generic ‘advertising expert’. For example, while there may be a freelancer that has a lot of experience with Facebook Ads or LinkedIn ads, you’ll want to find the ideal match for your service and make sure they have YouTube ad expertise. To find the right person, look at how long they have been doing it for and if they can communicate their skills clearly (they should if they know what they are talking about). You can also check their portfolio and testimonials from past clients to see how well they have performed in the past and if their past clients are satisfied with their work.

8. Try Before You Buy

My final tip is to give freelancers a test. A top success score, testimonials, previous work, and communication style can give you a lot of good hints about what they’d be like as part of your team, but nothing beats a paid test to see how they fit into your business. Everyone works differently, and you’ll never know for sure how it’ll work out until you put someone through your system. So give them a test so that you can check for yourself that they know what they are talking about. For example, if you are looking for a copywriter you could ask them to write a 500 word article explaining what the Dylan Sigley Drop Servicing Blueprint course is all about.

The Bottom Line

There is a lot that goes into hiring great freelancers for your business, and Upwork is a fantastic place to start when you’re trying to build and grow your first drop servicing business. If you can find freelancers who have a high job success score, communicate well, are affordable, open to feedback, have the right skills, have a good track record, and can pass a test then you have found your ideal freelancer.

You’ll be delivering projects to happy clients and earning good money in no time.

Dylan also discusses the best approaches for entrepenuers to achive a work life balance.


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