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Introduction 
Getting started outsourcing with freelancers can seem complicated, so we created this 
quick start guide to get you on the right path. 
In this guide, you’ll learn about 
● How to get started hiring 
● How to begin working with freelancers 
● How to resolve issues that come up 
● How to scale up using freelancers long term 
This guide is filled with best practices and helpful tips and tricks to outsourcing & 
scaling your business effectively. 
Enjoy! 
 
   
 
 
Hiring Freelancers 
Ready to get started hiring? Here’s what you need to know when making your first 
hires. 
Determine What You Should Outsource First With A Simple 
Exercise 
If you aren’t sure who you should hire first, use a simple exercise to bring some clarity. 
If you’re overwhelmed & wearing too many hats: 
1. Write down a list of all the things you do on a day to day basis 
2. Take a look at the list and think which would be the easiest ones to get off your 
plate. Think about things that take up a lot of time, but don’t move the business 
forward 
3. Select the tasks and decide which level of freelancer you need (see the next tip). 
If you’re trying to execute something new that you don’t know how to do: 
1. Get clear on what the end goal is 
2. Get a base level of understanding on how you think you’d like to accomplish it 
3. Hire an expert to help you flesh out what actually needs done 
 
Hire The Right Level Freelancer For Your Needs 
Want to know how much you should be paying for a freelancer? We like to divide it up 
into 3 groups to help bring some clarity. 
1. Basic Level ($5-$15 / hour, depending on location) 
 
 
These are “followers.” They are fast learners, but you’ll need to train them to follow 
your system and show them what you want them to do.  
They are best suited for accomplishing basic tasks and following systems and 
processes that you already have set in place that require no previous specialized skills. 
2. Mid Level ($10 – $30 / hour, depending on location) 
These freelancers have a specialization, or previous experience in certain areas. 
You won’t have to train these freelancers on their skill set, but they generally will need 
guidance on what you’d like to accomplish. 
3. Expert Level Freelancers ($20-$57+ / hour, depending on location) 
These are freelancers with high level skills and experience. They are consultants, 
strategists, and planners, and are useful in certain cases to execute the most difficult 
and skill-intensive tasks. 
Expert level freelancers are a good fit if you don’t have a process in place yet, or you’re 
looking to execute a new strategy. 
 
Save Time By Hiring Pre-Vetted Freelancers 
Finding a good freelancer can feel like digging for a diamond in the rough. 
You often need to dig through hundreds of applications and messages, then spend 
your time interviewing multiple applicants over the course of a few weeks. 
Instead, you can save a massive amount of time by hiring pre-vetted freelancers with 
our service from ​FreeUp​. Instead of interviewing hundreds of applicants yourself, we do 
the work for you by pre-vetting freelancers for skills, communication, and attitude.  
 
 
We only let the top 1% of applicants onto the platform, which means for every 100 
people that apply, on average we only let in 1.  
So if you’re looking to bring on 1 more person to your team, you could interview 100 
like we did, or just use FreeUp and cut straight to the top! 
Click here to sign up for a free account​. 
 
Sometimes Cheap Is Expensive 
As the saying goes, you get what you pay for. You’re not going to get an “expert” for 
$5 per hour. Be realistic with your budget and pay what needs to be paid for the right 
person for your business.  
“A players” may be more expensive upfront, but often can do the work of 3-5 normal 
freelancers, at a better quality, with better results, even faster.  
Don’t be fooled by the cheap prices, and instead focus on hiring for quality. You’ll be 
much happier in the long term. 
Ask About Their Computer & Internet Connection Upfront 
When you outsource, make sure to ask about computer & internet connection. Not 
everyone has a great connection or a great computer, so it’s important to verify this in 
the beginning.  
At FreeUp, we vet and verify internet connections with a tool called ​Speedtest.net 
which can confirm the freelancer’s internet speed. 
Ask your freelancers about their connection (get proof) and computer situation so you 
don’t run into any surprises! 
 
 
Use Test Projects Before Onboarding 
Before fully hiring and onboarding a freelancer, it’s a great idea to give them a small 
test project to make sure it’s a great fit for both of you.  
Choose something that can be done in 30 minutes or less, and is directly related to the 
job that they will be hired for. Pay them for this time.  
This will be a good indication of their skill, effort, and communication before you go 
through a full onboarding. 
 
Don’t Give Everything To One Person 
Entrepreneurs fall into a common trap. Hiring is hard so they make a bunch of bad 
hires. Then they find someone they like. So what do they do? They load that person up 
with everything.  
This can also be risky if that person quits, so it’s a good idea to spread out your hires! 
 
Ask About How They Take Feedback 
Don’t work with people who get defensive. Work with people who can take feedback 
and improve based on it. They will add the most value to your business in the long run. 
 
 
 
Find Freelancers That Underpromise & Over-Deliver 
Are you interviewing a freelancer that sounds too good to be true? Do they claim they 
can do it all?  
Surely there are some supercharged A+ player freelancers that can do it all, but it’s 
uncommon. If you have someone promising that they can do it all, it can be a cause for 
alarm. 
The best workers are honest about timelines and expectations. Be wary of freelancers 
that set unrealistic deadlines. 
 
Get Transparency About Who’s Doing The Work 
Some freelancers are solo, some subcontract small tasks, others operate as an agency. 
Make sure to ask about who is going to be doing the work and set the expectation of 
transparency. 
 
Tap Into An Expert’s Knowledge And Let Them Lead 
Don’t hire an expert and then ask them to do it your way. Hire experts to bring their 
own strategy and expertise to the table. Set expectations upfront on the type of 
collaboration and relationship you want to have. 
   
 
 
Getting Started Working With 
Freelancers 
Hold A Formal Onboarding With Freelancers 
After deciding on who to hire, it’s time to give a formal onboarding. This is a great way 
to welcome a freelancer into your business, get them familiar with your processes, and 
establish expectations upfront. 
In the onboarding, you’ll want to: 
● Welcome them to your business 
● Introduce them to key personnel 
● Share an overview of what they need to know about your business 
● Create necessary accounts and/or give them access to key resources  
● Set expectations about communication 
● Set expectations about work hours 
By taking extra time to make sure they have everything they need, they will feel much 
more welcome and invested in your team. 
By clarifying and setting expectations from the beginning, you’ll both be on the same 
page and this will help solve issues that could creep up later.  
A good kickoff meeting can be the difference between success and failure with a 
freelancer. 
 
 
 
Share How Their Work Impacts The Company 
Give your freelancer context into the “why” of the work you are assigning to them.  
This gives their work purpose, you’ll get more buy-in, and you’ll see an overall 
performance increase by taking the time to do this simple step. 
 
Set Clear Expectations & Deadlines 
Create a clear set of expectations on everything that is important to you. 
● When you want them to work (should they be on slack, or on chat?) 
● How you want them to communicate (do you prefer email, asana, etc?) 
● When projects should be completed 
● What to do if they have questions or run into issues 
When getting started with projects, create clear project scopes, provide guidelines, 
and set deadlines for completion. Show them what it should look like when done. 
The clearer the instructions, the better your results will be. 
 
Put Everything In Writing 
When working with freelancers, make sure you establish ownership of the work upfront. 
Get everything in writing before work begins and have the freelancer agree to it in 
writing as well. 
 
 
 
Create & Update SOPs 
SOPs (or Standard Operating Procedures) are the backbone of efficient work. These 
documents clearly define how a process should be completed. 
Start by writing a basic, documented SOP for each task you’d like your freelancer to 
complete.  
This can be as simple as a google doc with instructions and steps. 
If a task comes out different than you originally expected, go back to the SOP and 
adjust it so that it doesn’t happen again, provided they continue following the 
instructions. 
 
Use Short Screencast Videos To Help Explain Tasks 
Want to speed up your communication? 
Shoot a quick screencast video to explain how you’d like a task done with software like 
Loom​ or ​Soapbox​. 
These softwares allow you to easily show your freelancer what you mean, and is perfect 
for explaining clearly what you’d like done! 
 
Assign 3-5 Small Weekly Tasks To Each Freelancer 
Give each assistant 3-5 small weekly tasks to do on the side of their core work. It’s a 
quick way to get small, time-sucking things off your plate and see how the freelancers 
work with more responsibility. 
 
 
 
Schedule Weekly 1-on-1s For Feedback 
Set a schedule for 1-on-1s to make sure you’re giving consistent feedback.  
During the 1-on-1 you can: 
● Ask them about how they are doing personally and show them that you care 
about them 
● Get updates on project status 
● Give feedback on work done 
● Clarify goals 
● Help remove any roadblocks they have 
This also gives you a chance to review their work in stages to avoid being disappointed 
once the project is complete. 
A 15-30 min 1-on-1 meeting performed consistently can make a massive difference in 
your success outsourcing! 
Build A Relationship With Freelancers 
You can make people sign all the NDAs in the world, set up lastpass, and watch over 
their shoulder every day, but there is no substitute for building a strong relationship 
with people. 
Ask them about their life, their family, and what they want to accomplish. Show an 
interest in them as a person and establish rapport.  
Building strong relationships protects your business over everything else. 
 
 
 
Be Honest With Freelancers & Get Explanations 
If you don’t understand something a freelancer is doing, ask them to explain.  
For example, if you’re working with developers and don’t understand the terminology, 
tell them upfront. Ask them to give you clear explanations that a 5th grader would 
understand. The best developers can translate what they are doing into a simple form 
that you can understand. 
 
   
 
 
Resolving Issues 
When working with freelancers, you’ll inevitably run into issues from time to time, but 
that’s no reason to worry. Follow this simple advice to resolve problems quickly and 
get back on track! 
Don’t Settle For Subpar Work 
If your team is not performing at the level that you want, and you’ve given consistent 
feedback, don’t be afraid to part ways.  
Let go of the low performers, bring in new talent, and reset expectations with 
everyone. 
 
Don’t Assume, Always Verify 
As a business owner, it is easy to get upset and frustrated when something goes 
wrong. Enter a conversation looking for information first. Once you get the information 
then you can decide what action to take.  
By starting off upset, you can miss out on learning the big picture. Ask people for their 
side of the story and then go from there. 
 
Don’t Force A Freelancer To Stay 
If someone wants to quit, in general it’s best to just let them go. Convincing someone 
to stay rarely works out and usually ends up in a bigger mess. 
 
 
 
Reset Expectations If Necessary 
If a VA / freelancer who has done great work starts going downhill, do the following to 
reset: 
1. Pause work 
2. Have a meeting 
3. Reset the expectations during the meeting and don’t leave the meeting until 
you are 100% on the same page in writing 
4. Restart work 
5. Hold them to those expectations 
6. If the issue happens again, repeat.  
7. If you don’t see progress replace 
  
 
   
 
 
Scaling Up With Freelancers 
Maximize Productivity By Giving Each Full Time Employee 
A Freelancer To Work With 
Do you have full time employees? Give them all a personal virtual assistant to maximize 
their productivity.  
Your full time employees are doing work at their salary that should be done by less 
expensive labor. By giving them each a freelancer to delegate lower level tasks, this 
allows your business to skyrocket productivity without skyrocketing costs. 
This also trains them to practice delegation, which everyone needs help with! 
 
Tap Into Freelancers For Knowledge & Ideas 
Ask freelancers about their systems and processes they have created throughout 
building their freelance business.  
The good ones will have ideas for you to implement, and it will make it a lot easier for 
your business. 
 
Create A Career Path / Incentivized Structure 
All great freelancers are looking to grow their business, just like you.  
 
 
By creating a clear path for them to grow within your business, or an incentive 
structure, it will help motivate them to perform. 
When your business is small, it will be hard to define this path, but realize that it will be 
vital for keeping top talent onboard long term and will keep them focused on growing 
your business.  
 
Keep People Focused On Their Strengths 
Don’t try to teach people to be good at their weaknesses. From a business side, this is 
a bad investment because it’s often too difficult to execute. 
Instead, focus on maximizing people’s strengths and have them avoid doing things 
they are not good at. 
 
Become Your Freelancer’s Favorite Client 
Think of creative ways to make yourself their favorite client, and they will perform even 
better for you. 
● Ask them who their favorite client is and why  
● Make strong communication a priority 
● Respect their time. 
● Honor your word 
● Build a personal relationship with them 
Give Positive Feedback & Motivate Freelancers 
Keep freelancers you hire motivated with the following: 
 
 
● Tell them you appreciate them 
● Share their wins publicly 
● Point out something awesome they did in the past month 
 
 
   
 
 
What’s Next? 
Ready to get started hiring freelancers and scaling up your business?  
Click here to join FreeUp. 
Have any questions? 
Book a call here​ or just shoot us an email at support@freeup.net 
 

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quick-start-guide.pdf

  • 1.  
  • 2.   Introduction  Getting started outsourcing with freelancers can seem complicated, so we created this  quick start guide to get you on the right path.  In this guide, you’ll learn about  ● How to get started hiring  ● How to begin working with freelancers  ● How to resolve issues that come up  ● How to scale up using freelancers long term  This guide is filled with best practices and helpful tips and tricks to outsourcing &  scaling your business effectively.  Enjoy!         
  • 3.   Hiring Freelancers  Ready to get started hiring? Here’s what you need to know when making your first  hires.  Determine What You Should Outsource First With A Simple  Exercise  If you aren’t sure who you should hire first, use a simple exercise to bring some clarity.  If you’re overwhelmed & wearing too many hats:  1. Write down a list of all the things you do on a day to day basis  2. Take a look at the list and think which would be the easiest ones to get off your  plate. Think about things that take up a lot of time, but don’t move the business  forward  3. Select the tasks and decide which level of freelancer you need (see the next tip).  If you’re trying to execute something new that you don’t know how to do:  1. Get clear on what the end goal is  2. Get a base level of understanding on how you think you’d like to accomplish it  3. Hire an expert to help you flesh out what actually needs done    Hire The Right Level Freelancer For Your Needs  Want to know how much you should be paying for a freelancer? We like to divide it up  into 3 groups to help bring some clarity.  1. Basic Level ($5-$15 / hour, depending on location)   
  • 4.   These are “followers.” They are fast learners, but you’ll need to train them to follow  your system and show them what you want them to do.   They are best suited for accomplishing basic tasks and following systems and  processes that you already have set in place that require no previous specialized skills.  2. Mid Level ($10 – $30 / hour, depending on location)  These freelancers have a specialization, or previous experience in certain areas.  You won’t have to train these freelancers on their skill set, but they generally will need  guidance on what you’d like to accomplish.  3. Expert Level Freelancers ($20-$57+ / hour, depending on location)  These are freelancers with high level skills and experience. They are consultants,  strategists, and planners, and are useful in certain cases to execute the most difficult  and skill-intensive tasks.  Expert level freelancers are a good fit if you don’t have a process in place yet, or you’re  looking to execute a new strategy.    Save Time By Hiring Pre-Vetted Freelancers  Finding a good freelancer can feel like digging for a diamond in the rough.  You often need to dig through hundreds of applications and messages, then spend  your time interviewing multiple applicants over the course of a few weeks.  Instead, you can save a massive amount of time by hiring pre-vetted freelancers with  our service from ​FreeUp​. Instead of interviewing hundreds of applicants yourself, we do  the work for you by pre-vetting freelancers for skills, communication, and attitude.    
  • 5.   We only let the top 1% of applicants onto the platform, which means for every 100  people that apply, on average we only let in 1.   So if you’re looking to bring on 1 more person to your team, you could interview 100  like we did, or just use FreeUp and cut straight to the top!  Click here to sign up for a free account​.    Sometimes Cheap Is Expensive  As the saying goes, you get what you pay for. You’re not going to get an “expert” for  $5 per hour. Be realistic with your budget and pay what needs to be paid for the right  person for your business.   “A players” may be more expensive upfront, but often can do the work of 3-5 normal  freelancers, at a better quality, with better results, even faster.   Don’t be fooled by the cheap prices, and instead focus on hiring for quality. You’ll be  much happier in the long term.  Ask About Their Computer & Internet Connection Upfront  When you outsource, make sure to ask about computer & internet connection. Not  everyone has a great connection or a great computer, so it’s important to verify this in  the beginning.   At FreeUp, we vet and verify internet connections with a tool called ​Speedtest.net  which can confirm the freelancer’s internet speed.  Ask your freelancers about their connection (get proof) and computer situation so you  don’t run into any surprises!   
  • 6.   Use Test Projects Before Onboarding  Before fully hiring and onboarding a freelancer, it’s a great idea to give them a small  test project to make sure it’s a great fit for both of you.   Choose something that can be done in 30 minutes or less, and is directly related to the  job that they will be hired for. Pay them for this time.   This will be a good indication of their skill, effort, and communication before you go  through a full onboarding.    Don’t Give Everything To One Person  Entrepreneurs fall into a common trap. Hiring is hard so they make a bunch of bad  hires. Then they find someone they like. So what do they do? They load that person up  with everything.   This can also be risky if that person quits, so it’s a good idea to spread out your hires!    Ask About How They Take Feedback  Don’t work with people who get defensive. Work with people who can take feedback  and improve based on it. They will add the most value to your business in the long run.     
  • 7.   Find Freelancers That Underpromise & Over-Deliver  Are you interviewing a freelancer that sounds too good to be true? Do they claim they  can do it all?   Surely there are some supercharged A+ player freelancers that can do it all, but it’s  uncommon. If you have someone promising that they can do it all, it can be a cause for  alarm.  The best workers are honest about timelines and expectations. Be wary of freelancers  that set unrealistic deadlines.    Get Transparency About Who’s Doing The Work  Some freelancers are solo, some subcontract small tasks, others operate as an agency.  Make sure to ask about who is going to be doing the work and set the expectation of  transparency.    Tap Into An Expert’s Knowledge And Let Them Lead  Don’t hire an expert and then ask them to do it your way. Hire experts to bring their  own strategy and expertise to the table. Set expectations upfront on the type of  collaboration and relationship you want to have.       
  • 8.   Getting Started Working With  Freelancers  Hold A Formal Onboarding With Freelancers  After deciding on who to hire, it’s time to give a formal onboarding. This is a great way  to welcome a freelancer into your business, get them familiar with your processes, and  establish expectations upfront.  In the onboarding, you’ll want to:  ● Welcome them to your business  ● Introduce them to key personnel  ● Share an overview of what they need to know about your business  ● Create necessary accounts and/or give them access to key resources   ● Set expectations about communication  ● Set expectations about work hours  By taking extra time to make sure they have everything they need, they will feel much  more welcome and invested in your team.  By clarifying and setting expectations from the beginning, you’ll both be on the same  page and this will help solve issues that could creep up later.   A good kickoff meeting can be the difference between success and failure with a  freelancer.     
  • 9.   Share How Their Work Impacts The Company  Give your freelancer context into the “why” of the work you are assigning to them.   This gives their work purpose, you’ll get more buy-in, and you’ll see an overall  performance increase by taking the time to do this simple step.    Set Clear Expectations & Deadlines  Create a clear set of expectations on everything that is important to you.  ● When you want them to work (should they be on slack, or on chat?)  ● How you want them to communicate (do you prefer email, asana, etc?)  ● When projects should be completed  ● What to do if they have questions or run into issues  When getting started with projects, create clear project scopes, provide guidelines,  and set deadlines for completion. Show them what it should look like when done.  The clearer the instructions, the better your results will be.    Put Everything In Writing  When working with freelancers, make sure you establish ownership of the work upfront.  Get everything in writing before work begins and have the freelancer agree to it in  writing as well.     
  • 10.   Create & Update SOPs  SOPs (or Standard Operating Procedures) are the backbone of efficient work. These  documents clearly define how a process should be completed.  Start by writing a basic, documented SOP for each task you’d like your freelancer to  complete.   This can be as simple as a google doc with instructions and steps.  If a task comes out different than you originally expected, go back to the SOP and  adjust it so that it doesn’t happen again, provided they continue following the  instructions.    Use Short Screencast Videos To Help Explain Tasks  Want to speed up your communication?  Shoot a quick screencast video to explain how you’d like a task done with software like  Loom​ or ​Soapbox​.  These softwares allow you to easily show your freelancer what you mean, and is perfect  for explaining clearly what you’d like done!    Assign 3-5 Small Weekly Tasks To Each Freelancer  Give each assistant 3-5 small weekly tasks to do on the side of their core work. It’s a  quick way to get small, time-sucking things off your plate and see how the freelancers  work with more responsibility.   
  • 11.     Schedule Weekly 1-on-1s For Feedback  Set a schedule for 1-on-1s to make sure you’re giving consistent feedback.   During the 1-on-1 you can:  ● Ask them about how they are doing personally and show them that you care  about them  ● Get updates on project status  ● Give feedback on work done  ● Clarify goals  ● Help remove any roadblocks they have  This also gives you a chance to review their work in stages to avoid being disappointed  once the project is complete.  A 15-30 min 1-on-1 meeting performed consistently can make a massive difference in  your success outsourcing!  Build A Relationship With Freelancers  You can make people sign all the NDAs in the world, set up lastpass, and watch over  their shoulder every day, but there is no substitute for building a strong relationship  with people.  Ask them about their life, their family, and what they want to accomplish. Show an  interest in them as a person and establish rapport.   Building strong relationships protects your business over everything else.     
  • 12.   Be Honest With Freelancers & Get Explanations  If you don’t understand something a freelancer is doing, ask them to explain.   For example, if you’re working with developers and don’t understand the terminology,  tell them upfront. Ask them to give you clear explanations that a 5th grader would  understand. The best developers can translate what they are doing into a simple form  that you can understand.         
  • 13.   Resolving Issues  When working with freelancers, you’ll inevitably run into issues from time to time, but  that’s no reason to worry. Follow this simple advice to resolve problems quickly and  get back on track!  Don’t Settle For Subpar Work  If your team is not performing at the level that you want, and you’ve given consistent  feedback, don’t be afraid to part ways.   Let go of the low performers, bring in new talent, and reset expectations with  everyone.    Don’t Assume, Always Verify  As a business owner, it is easy to get upset and frustrated when something goes  wrong. Enter a conversation looking for information first. Once you get the information  then you can decide what action to take.   By starting off upset, you can miss out on learning the big picture. Ask people for their  side of the story and then go from there.    Don’t Force A Freelancer To Stay  If someone wants to quit, in general it’s best to just let them go. Convincing someone  to stay rarely works out and usually ends up in a bigger mess.   
  • 14.     Reset Expectations If Necessary  If a VA / freelancer who has done great work starts going downhill, do the following to  reset:  1. Pause work  2. Have a meeting  3. Reset the expectations during the meeting and don’t leave the meeting until  you are 100% on the same page in writing  4. Restart work  5. Hold them to those expectations  6. If the issue happens again, repeat.   7. If you don’t see progress replace            
  • 15.   Scaling Up With Freelancers  Maximize Productivity By Giving Each Full Time Employee  A Freelancer To Work With  Do you have full time employees? Give them all a personal virtual assistant to maximize  their productivity.   Your full time employees are doing work at their salary that should be done by less  expensive labor. By giving them each a freelancer to delegate lower level tasks, this  allows your business to skyrocket productivity without skyrocketing costs.  This also trains them to practice delegation, which everyone needs help with!    Tap Into Freelancers For Knowledge & Ideas  Ask freelancers about their systems and processes they have created throughout  building their freelance business.   The good ones will have ideas for you to implement, and it will make it a lot easier for  your business.    Create A Career Path / Incentivized Structure  All great freelancers are looking to grow their business, just like you.    
  • 16.   By creating a clear path for them to grow within your business, or an incentive  structure, it will help motivate them to perform.  When your business is small, it will be hard to define this path, but realize that it will be  vital for keeping top talent onboard long term and will keep them focused on growing  your business.     Keep People Focused On Their Strengths  Don’t try to teach people to be good at their weaknesses. From a business side, this is  a bad investment because it’s often too difficult to execute.  Instead, focus on maximizing people’s strengths and have them avoid doing things  they are not good at.    Become Your Freelancer’s Favorite Client  Think of creative ways to make yourself their favorite client, and they will perform even  better for you.  ● Ask them who their favorite client is and why   ● Make strong communication a priority  ● Respect their time.  ● Honor your word  ● Build a personal relationship with them  Give Positive Feedback & Motivate Freelancers  Keep freelancers you hire motivated with the following:   
  • 17.   ● Tell them you appreciate them  ● Share their wins publicly  ● Point out something awesome they did in the past month           
  • 18.   What’s Next?  Ready to get started hiring freelancers and scaling up your business?   Click here to join FreeUp.  Have any questions?  Book a call here​ or just shoot us an email at support@freeup.net