If you’re reading this, you might be interested in the idea of hiring freelancers, and you even might have already tried it before.
A little about my situation - a couple years ago, I tried to hire freelancers and I failed. From that point, I vowed that I could just do everything myself.
But as the months went on, and my businesses kept growing, I found myself drowning in work (especially email).
This blog post is about how I successfully found, hired, onboarded, and now work with a small team of freelancers.
In this post, I’ll take you through my process and what worked for me, and will go over the 3 main points:
- Should you hire freelancers and start outsourcing?
- How to hire really talented freelancers on a budget
- How to onboard and train freelancers
Who is guide this for?
Hopefully, this post helps someone that were in a similar position to me:
- You’re bootstrapping a business or side project and want to start outsourcing, but not really sure how/where to start
- You are doing this on an extreme budget.
- You are looking for the best quality of work possible.
I want to stress, again, that this guide is if you’re trying to hire on a budget, and you’re willing to have some patience in the hiring and onboarding process, to save money.
If you have the cash/resources to hire $40/hour US-based freelancers, then you should do that.
But this post is about hiring talent overseas at as low as 1/10th of that cost.
For some context, with this strategy, I was able to get good quality work at $3-5/hour.
Should you start outsourcing?
You must ask yourself this question first.
Should you be outsourcing your work right now?
I believe that outsourcing should be the last viable option , and here’s why:
Do you have the money?
The first issue with outsourcing and hiring is that it costs money, forever.
Do you have the budget to hire someone? And will you be able to pay them on an ongoing basis, potentially for many months/years?
If not, then I would consider doing the work yourself until you can get the money for it.
One of your goals will be to retain good freelancer talent, and I think that hiring for one-off jobs is less than ideal, because you will spend a lot of time just looking for good talent, and also training them. You want to find someone that’s good, and keep them for as long as you can.
Having someone constantly helping you is a recurring expense, so if you don’t have enough money then figure out how to make money.
Are you actually that strapped for time?
Do you feel like you are drowning in work every day and can barely keep up?
If the answer to that question is not “fuck yes”, then you might want to think about how you can be more productive individually before taking the leap and hiring people.
Are these tasks you need to be outsourced truly blocking you from working on more important things? I think it’s important to deeply think about that.
Can you automate these tasks instead?
Can you automate what you are looking to outsource? In most cases, yes.
I’ve also scraped websites and emails for thousands of leads using bots and APIs. Get creative.
If you don’t know how to write code that can automate things, then you can learn, or you can also use things like Zapier.
It may save you a lot of money in the long run.
Can you build dashboards that save time/money?
This is what I like to call the digital “last mile”.
For shipping companies like FedEx, the last mile in the shipping process (to get the parcel to the customer’s door) is the most expensive mile.
As a programmer or with no-code tools, you can figure out how to build dashboards around your tasks, so that your freelancer only has to do one specific task, rather than all of the complicated stuff around it.
For example, for Starter Story, I have a freelancer helping me with outreach.
Instead of telling her to “email 20 businesses a day”, I built a simple dashboard where all she has to do is enter basic information and click a button to send an email.
Once the email sends, it loads up a new page to fill out.
A couple hours of coding is saving many hours per week of work and also streamlining the process and leading to less room for error.
Have you actually done the tasks yourself?
If you’re looking to be the most efficient in outsourcing work, then you need to be hyper-familiar with the actual work involved.
It should feel like you’ve done those tasks so many times that you could do them in your sleep, and at this point you just need someone to repeat those keystrokes for you.
Why is it important to be hyper-familiar with the work?
- So you can understand how long it takes
- So you understand the full process, edge cases, things that can go wrong.
- So you can explain it in detail to your freelancer.
- So you can make sure it actually works (for example - how do you know cold email works for your business if you’re not on the ground floor trying it out?)
Understanding the tasks at a deep level will save you a lot of time and money.
How to find an amazing freelancer (on a budget)
Ok, so you exhausted all of your options, and you’re ready to hire - let’s talk about finding and hiring great talent.
How to find good freelancers that are cheap? It’s really hard.
After my first failed attempt at outsourcing, I went back to the drawing board on hiring freelancers. I went about it in a more calculated way than before.
Most importantly, I was open to being patient and taking the time to learn the skill of outsourcing through some trial and error.
I will take you through my process and what worked for me to find a couple really amazing freelancers:
Step 1: Create a job on Upwork for the skill you’re looking for
(Note - I use Upwork because it seems to be the best but same principles should apply to any freelancer network)
It doesn’t really matter what you write in here, this is just to attract applicants. Keep it short, I guess.
To start, you’ll want to go for the lowest rates, or the cheapest, entry-level freelancers.
The quality pool is much lower, but if you’re willing to put in some work in the beginning, you can find some true gems, and save thousands over the lifetime of your business.
Step 2: Create a general task that you can send to all freelancers
Now, you’ve got dozens of freelancers applying for your job, but how to find the best talent? Hire them and give them an insanely specific task.
Once you start a contract with them, send them a message with very specific directions on what you’re looking for.
Why get specific? Because it’s a really easy way to see if they “read the fine print” and are detail-oriented. That’s what you’re looking for. This is how to gauge the quality of their work.
The task does not need to be what you are hiring them for, but it’s best if it’s somewhat related. It’s also great if you can get something out of it, too (like getting extra leads for your business)
Here’s what my offer proposal looked like (I suggest zooming in on this and reading the whole thing):
See how specific I was getting?
- I asked them to only find businesses between a certain Alexa rank
- I asked them to only find businesses in a certain industry
- I asked them write out a unique sentence about their business - this also helps to gauge their English skills
Step 3: Hire lots of freelancers, and fire fast
With this method, you will be hiring a lot of people and asking them to do the smallest job possible (<5 hours of work).
This will be enough time to gauge if they are good, and that they read the instructions, and followed through.
If they did not follow your instructions or they did a bad job, pay them for their time and end the job.
Keep hiring people until you find one that you know is great. When you find them, you will know.
I went through 12-15 freelancers until I found a couple that were really good, and I’m still working with them today.
Training, onboarding, and retaining freelancers
Congrats! You have hired a freelancer (or maybe a small army of them) on the cheap.
Now it is time to actually work with them.
Onboard slowly, it will take months
If you went the route of finding some affordable freelancers on Upwork, then it’s time to start onboarding them.
Here’s another thing that I totally screwed up on my first go-around - I threw everything on my freelancer and expected them to know how to do it.
This time, I took a more calculated and iterative approach.
For my case, here’s how it went for one of my freelancers:
- She started adding leads to a Google sheet, and I would manually upload them.
- Then I taught her how to upload them directly.
- Then I had her help with data entry tasks for our tools database.
- Then I showed her how to share stories on Hacker News.
- Then I showed her how to follow up with referrals.
- Then I brought her on to help with email work.
- She started with transactional ones and she learned how to use Pigeon to update the status of interviews and send automated follow-ups.
- She upgraded to learning how to handle more complicated emails.
- I taught her how to create and send the newsletter.
- Then I taught her how to publish content on Starter Story.
- The list goes on...
We went through all of this slowly, over the course of 2-3 months.
And now all of those tasks mentioned above are no longer on my plate. Hours of work every week vanished.
Now, the only thing I do for Starter Story is build features and work on revenue-generating tasks.
It’s an amazing feeling to not be bogged down with all of those day to day tasks, especially email.
Help your freelancers to improve their skills
If you’re going the route of hiring affordable freelancers, then you have an awesome opportunity - to teach.
From my experience, the freelancers I’ve hired are very eager and willing to learn.
Often times, the tasks you give them might be the first time they have ever done it - and for them, that can be huge for their career and future as a freelancer.
Continue to give your freelancer tasks that challenge them, help them improve their English skills.
You have an opportunity to get some great work at a great price.
Document vigorously (and use Loom to demonstrate tasks)
Use Google Docs or even a Google Docs wiki to document everything possible - you will save a ton of time when you hire your next freelancer or need to hire a new one.
If you want to save a crap ton of time, check out Loom - it’s a Chrome extension that allows you to quickly record your screen (with audio) and explain processes.
Rather than spending 20 minutes on an email explaining how to do a complicated task, you can just record yourself doing that task in two minutes and send that off.
I’ve recorded 123 videos for my freelancer since starting!!
Don’t blame the freelancer - take ownership
One thing that bothers me is when people talk down on the idea of outsourcing work because “you get shit work”.
You are getting shit work because:
- You don’t know how to identify talent
- You’re not willing to take the time to train someone
- You’re not taking ownership of your own business - you’re expecting someone you hired to take ownership (and that will never work)
Just like anything, with hiring employees or contractors, you are their manager and ultimately the responsibility for everything is on you.
When something goes wrong, it’s not their fault, it’s your fault. It’s your responsibility to fix it and make sure it doesn’t happen in the future.
Use a CRM to collaborate & stay organized
You may want to look into using a CRM or (even just a spreadsheet) to keep track of things with your freelancer.
Since we have hundreds of interviews in progress for Starter Story, we both use Pigeon together to be able to tackle work and move forward while both having context on where everything is at.
It also allows us to add notes inside the Gmail interface. If you plan on working with a freelancer (specifically a VA that might be helping you tackle your inbox), you should definitely check out Pigeon for Gmail.
Tracking time and paying your freelancers
What I love about Upwork is they handle all of that, they keep detailed logs of everything and payment is automatic once a week and I can pay by credit card. I don’t have to think about it.
If you’re worried about the freelancer going rogue or logging more hours than they are actually working, then I’d suggest re-reading the section about finding good talent - with a good freelancer you should never run into that problem.
Also, give raises and bonuses to your freelancers!
You will become a better manager
I wouldn’t take this guide verbatim. This is just what worked for me.
But one thing I know for sure is that through this process you will learn so much:
- You will learn how to identify talent and strong candidates
- You will learn how to train and onboard employees
- You will learn how to have patience when you need something done
- You will learn how to better document processes
- You will become a better decision-maker
- You will learn how to build a team
- You will learn more empathy
- You will identify countless holes in your business, or processes
- You will experience the power of work getting done while you sleep
- You will see the power of outsourcing and you will wonder how you ever lived without it!
You might run a small business today, but these soft skills are invaluable for the day when you’re running a 250 person company (if of course you ever envision that).
Anyone can do your work, don’t think you’re the only one!
One thing that I’ve learned through this process is that I am constantly surprised by how much better my freelancer is than me at most tasks.
I’ll read an email reply (done by my freelancer as me) and really love their response and how they handled the situation.
Anything can be taught. It’s just if you’re willing to let go of your ego and stop thinking that you have the special sauce to get it done.
Sure, there are businesses that can thrive with a solo founder doing everything, but you might be surprised by what you learn outsourcing.
You should also use “we” when talking about your business. You have employees now, it’s time to grow and scale!
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Hey! 👋I'm Pat Walls, the founder of Starter Story.
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