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How to Hire Agency Help on Upwork


Could you take on another 3 projects this month?  How about another 3 projects this week?  What about 3 projects today?

No matter who you are or the size of your agency, at some point you’ll face the reality of limited bandwidth.

I’ll never forget sitting across the table from one of the largest HVAC companies in town.  The proposal meeting was going amazingly well and they seemed to be really impressed with my proposal.

They were asking all the right questions.  It almost seemed like they were going to hire me on the spot, even with the higher rates I decided to add at the last minute.

But then, the dreaded words came out of their mouths….

They said, “Mike, I love it.  Let’s get started.”

I was horrified.  

This may sound crazy, but I was hoping they’d tell me, “No thanks.”  Or at least delay giving me a decision.  You see, I was so swamped I just couldn’t take on any more work.

I saw my nights and weekends vanish before my eyes.  Yes, the money was great, but my soul was crushed.

It seemed like only yesterday I was trying to figure out how to get more clients but now I had the opposite problem and I knew I needed to find some help.

Over the years I’ve figured out how to hire people to help me do the work and I want to share with you my top 4 tips for hiring on Upwork.

1. Hire for a Single Task

When I first started looking to hire help, I made the mistake of trying to hire my replacement instead of hiring for the individual tasks I most needed help with.

Most agency owners don’t realize how unique they are.  In order to launch an agency, you have to be good at lots of different things and be comfortable wearing a lot of different hats.  So, when we look for help, the tendency is to try and find someone just like us!  The truth is if there is someone out there with your exact skillset they are either very expensive or your competitor.

Instead of finding a super-skilled generalist, zero in on the exact tasks that are the most time-consuming.  By dividing the help you need into single tasks, you’re more likely to find a specialist who can be hired for a good rate while maintaining a high level of quality.

For example, instead of looking for a digital marketing expert, look for someone who specializes in just Facebook (or whatever service you need.)  You could even get more specific to find multiple resources who specialize in different aspects like Facebook account creation, ad management, copywriting, or design.

In our agency, we deploy a “leveraged service model” where much of the hands-on or administrative work is done by a third party, where client management and strategy are handled in-house.  

2. Filter Out Bots & Bad Applicants

When I first started hiring on Upwork, I was overwhelmed by lots of flakes and people who couldn’t do the job after I hired them.  

I almost assumed hiring on a platform like this doesn’t work. Instead, I found some ways to more quickly get connected with the right people.  

One of my favorite hacks when hiring on Upwork is to include this question buried in the middle of the job post.  I ask, “What is your favorite food?  Please open your cover letter answering this question.  This is your first test!”

You would be surprised how many people don’t reply to this question.  This tells me either they think I’m joking OR, more likely, they never read the job description.

If you want to cut your applicants in half up front, and get connected with the right people, try that hack.

3. Hire 4. Fire 2

No matter how awesome a candidate seems before you hire them, you’ll just never know until you start working with them.

Hiring a candidate on Upwork and narrowing it down to only one candidate was really hard and that’s why I like to hire several people for the same position at the same time.

I’ll hire up to 4 people for the same job and start them with a test project which is representative of the work they will be doing for me.  When you actually start working with them, you’ll not only get to experience the quality of their work, but their ability to communicate and willingness to take feedback.

If you hire 4 candidates, it’s likely you’ll quickly know you made a bad hire within the first 10 days of working with them.  You should expect candidates to be their best during this trial period so if you feel something is off, trust your gut.  It probably is.

And, who knows, when you hire 4, maybe you find two amazing candidates who will give you extra reliability and plenty of bandwidth to scale. 

4. Train, Train, Train

The best hire in the world still isn’t going to be a mind reader.  You need to teach them what to do, even if they already have experience.  Too many Upwork hires end badly simply because they didn’t have everything they needed to succeed.

It can be easy to neglect training your new hire especially when you’re already swamped.  It’s hard to admit, but hiring someone to help you will probably initially make you MORE busy not less.  It’s going to take some time before you’ll feel the effects of their work.

Putting in the time to train and give your new hire feedback is worth it.  Plan to work with them, provide hands on feedback, record loom videos and explain the steps you want them to take.

The bottom line is if you want a great candidate to really shine, spend time with them.  It’ll pay off dividends.

Upwork can be an amazing way to connect with talent across the globe and one of the fastest ways to create more bandwidth in your agency.  If you’re swamped with client work and hoping the next client delays their project or hires someone else, it’s time for you to find some help.

If you want to learn more about how  to use Upwork to grow your agency, apply for a call with our director of coaching. We’d be  happy to help you get started.