HOW TO HIRE A FREELANCER ONLINE

HOW TO HIRE A FREELANCER ONLINE

www.5crowd.com

You’re working on an important project

and have heard that collaborating with

freelancers online could be a great approach

to get everything done. But there’s a lot of

information out there on where and how to

begin and you’re looking for some insight into

the right way to get the ball rolling. Well, you’ve

come to the right place.

At 5Crowd, it’s our job to connect top

freelancers with the people who need them

and then manage those projects from the initial

briefing to the final deliverable.

We’ve completed hundreds of projects and

thought it would be a good idea to consolidate

and share some of the learnings we’ve had.

With that, we’ve jotted down some best

practices to help you through the process. It’s

kind of like a ten commandments for hiring

freelancers (the only difference is that there’s

eight…and they’re on a PDF instead of stone

tablets).

So here’s the deal...

Introduction

1. Prepare a Detailed Brief

2. Always Have a Contract With Your Freelancers

3. Figure Out Your Budget

4. Post Your Project Online & Find The Right Freelancer

5. Set Milestones and Deadlines

6. Give Clear Concise Feedback

7. Build A Roster of Great Freelancers

8. Build Your Reputation Within The Freelance Community

Table of Contents

The most important step to hiring a freelancer online is to prepare a detailed brief. This is

especially true if the freelancer has never worked with you in the past. A good brief is clear and

concise and can provide guidance throughout the project. It also simplifies the feedback process

later on since you’ll have a document that was aligned-to at the start of the project. There’s a lot

of ways to write a good brief so we’ve included a checklist below.

Include a brief profile of your company

upfront. The freelancer should know who

you are and what you aim to achieve as a

business.

What is the final deliverable you are looking

for? Be really detailed here. For example,

instead of asking for a logo, you may want

to ask for a layered and vectorized AI file

compatible with Adobe CS6.

What are some examples of similar

deliverables you like? Try to include any

thought starters and references to provide

your freelancer with some creative direction

and inspiration around what the final work

product “should look like”. Google images,

YouTube, and Pinterest can be really good

sources for this.

What do you want to achieve with this

project? What are the business objectives?

This context can help the freelancer align to

your vision. It also gives them an opportunity

to go above and beyond if they have great

ideas along the way.

Checklist

5Crowd Tip

Try to put yourself in the shoes of a

freelancer. Does the brief sound like a

project you would want to take on?

Write the brief in a way that inspires

freelancers with a fun challenge. This

will increase the quality and quantity of

freelancers who submit a proposal.

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1 Prepare A Detailed Brief

Who is the audience for your project? What do

you want them to think, feel, and do when they

see the final deliverable?

What is the budget the freelancer will need to

work with?

When is the deadline? Make sure to include

any other key dates including check-ins, draft

deliverables, and feedback calls.

If you really want to geek out on writing briefs,

we’d recommend having a read of these two

articles. They are both solid resources on how

to write a brief for a freelancer:

How to work with freelancers (and get the

results you want)

How to write a design brief for a freelancer or

agency

Checklist [continued]

5Crowd Tip

At 5Crowd, we love doing “Work in

progress check-ins” just to see how the

project is coming along. We find that

more frequent feedback and discussion

helps avoid pitfalls further downstream

by identifying issues earlier on and giving

us more time to course correct. There’s

nothing worse that having a ‘surprise’ as

the project’s deadline approaches.

5Crowd Tip

Even if you’ve got a really simple project,

it’s still worth writing a more formal brief.

The process of writing one will actually

help you figure out exactly what you

want to get out of the project.

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1 Prepare A Detailed Brief

The legal stuff isn’t always the most fun but it’s

super important that you nail this down before

starting any work. From our experience, the

two most important discussions to have are

around the ownership of intellectual property

and the terms around non-disclosure. Both can

be touchy subjects so it’s important to clearly

manage expectations with the freelancer

and have a well-formulated contract prior to

starting the work.

Be reasonable and flexible if you can. It’s

actually a good sign if a freelancer has a few

questions or asks to change a clause in the

agreement because it means they are taking

the engagement seriously. With a quick Google

search, you can find dozens of templates with

standard terms to work off of but it’s always

best to seek independent legal advice. From

our experience, a good contract includes the

following elements:

5Crowd Tip

For the sake of flexibility and ease of

replication, it is definitely worthwhile to

create a template (or set of templates)

for your work. It can be really useful to

reference a ‘work order’ in Schedule A

that is customized and appended to

each agreement. You can then have a

general contract without sacrificing the

specificity needed for each project.

The names and contact information (including

phone numbers) of all people/parties

involved. This can be really useful in the

11th hour!

A brief outline of the work the freelancer will

be doing. This could be a list of deliverables,

milestones, or deadlines. Writing this down

drives clarity up-front and accountability

throughout a project.

Language around who will own what (or all)

aspects of the work product once completed.

Make sure to define when the project will be

considered complete.

Clearly laid out compensation terms including

the amount to be invoiced, what the payment

terms are, and how payment will be made.

2 Always Have A ContractWith Your Freelancers

Descriptions of any limitations around

confidentiality. If the nature of the work is not

sensitive, that’s great. However, if it is you may

want to spell this out so that it doesn’t end up

unexpectedly on a freelancers online portfolio.

An outline of what happens if the project

doesn’t go as expected. What happens if the

freelancer doesn’t finish the project on time?

What happened if the deliverables are not

satisfactory? What happens if you need to

cancel the project halfway through?

5Crowd Tip

We make use of electronic signatures to

streamline all the paperwork and create

a full digital audit trail. We really like

HelloSign since it integrates well with

Gmail. You may also want to check out

DocuSign and EchoSign.

Continued...

2 Always Have A ContractWith Your Freelancers

Before you approach a freelancer, nail down

your budget. It’s a good idea to have a

number you’d like to spend and a maximum

as well.

If this is your first time working with a

freelancer, it may be difficult to know what a

reasonable budget is. Also, since each project

is unique, it can be difficult to benchmark your

project against similar ones. Setting a good

budget that attracts great freelancers without

spending too much comes with experience.

We find that most people new to the world

of freelance end up setting too small a

budget. This ends up precluding many great

freelancers from participating in the project

which creates additional risk that the project

will run over it’s timeline and budget.

When it comes to freelance, just like anything

else, “you get what you pay for.”

3 Figure Out Your Budget

All right, you have your brief, your contracts

and your budget. Now you need to find your

freelancer!

There are two primary ways to find freelancers

online. You can either contact freelancers

directly through directories like LinkedIn,

Dribbble, or Vimeo or you can post your job on

a marketplace like Elance, oDesk, or Freelancer.

There are pros and cons of both approaches.

Contacting individual freelancers directly can

be a time consuming and tedious manual

process. However, it’s usually free to do and can

elicit a high response rate - especially if you

personalize each message. Most freelancers

will have their own website with a portfolio and

their preferred contact method. If someone

doesn’t have an online collection of their past

work, they should probably be dropped from

consideration. Bear in mind that with these

‘cold’ messages, you risk coming across as

spam in their inbox. We would recommend

keeping the message short and to the point.

The marketplaces let you to tag your brief

by the skill set you’re looking for. They will

syndicate your job out to lots of freelancers

and solicit interest for the job. You’ll get some

great collaboration tools including a workroom

where you can chat with the freelancer and

share files, a time tracking system to drive

transparency, and escrow services to build trust

with the freelancer. However, it’s easy to get

lost in the shuffle if your job doesn’t stand out

and since anyone can sign-up as a freelancer,

there’s a lot of profiles to dig through before

finding someone that works.

5Crowd Tip

5CrowdTip

Be careful in assuming that a great

portfolio means the freelancer does great

work. Quality is more than just the work

product and you won’t get a great sense

right away of how well the freelancer

manages timelines or budget, how open

they are to feedback, or how responsive

and professional they are.

It’s worth seeing what comes up when

you Google, Facebook, and Twitter the

freelancer’s name. This will help you get a

sense of who the person is based on how

they present themselves online.

4 Post Your Project Online& Find The Right Freelancer

The marketplaces charge fees to post your job, take a markup on each payment and may also

charge a fee for currency conversion.

Shortlist and InterviewAfter you’ve received a few proposals on your project, pick the ones that you have the best

feeling about and set up some interviews. We’d recommend holding the interview over the same

medium that you plan on communicating with the freelancer during the project. This will ensure

that any technical issues or differences in communication preferences are caught up-front before

a work engagement begins.

It can also be useful to structure the interview process with a rubric so that you can assess and

evaluate each candidate against the others. Rubrics also help you quickly identify potential gaps

with a specific freelancer. Beyond the technical skills, some of the things we look for are great

communication skills, flexibility, patience, and resourcefulness.

5Crowd Tip

Pay attention to all the details during

the interview. Were they punctual for

the interview? If they showed up late,

did they give you a head’s up? These are

early signs that the freelancer may be a

good or bad fit with what you’re looking

for.

4 Post Your Project Online& Find The Right Freelancer

Here are a few interview questions to consider:

1. What is your current availability?

2. Do you foresee it changing over the coming days or weeks?

3. What are your working hours?

4. Are there specific times throughout the week where you’re not free to chat?

5. Have you done a project similar to this one?

6. Can you provide some relevant work samples for me to review?

7. Are you open to doing work-in-progress check-ins throughout the project?

8. How much time do you typically need to complete an assignment of this kind?

5Crowd Tip

Many freelancers (especially the great

ones) have the luxury of choosing their

clients and deciding what work they want

to take one. Remember that the interview

is really a two-way discussion and that

you’re real goal should be to assess fit

both ways. Although you are discussing

the scope of work of a project, don’t be

surprised if you start getting asked some

questions yourself!

4 Post Your Project Online& Find The Right Freelancer

By this point, you’ll have a lot of information

about your top candidates and it’s time to

make a decision. If you can’t decide between

two freelancers, try doing a paid trial run with

each one on a very small project or on the first

milestone of a project. You’ll be able to get a

much better sense of what it’s like working with

each of them and which one you prefer.

One decision you may have to make is whether

or not to hire a freelancer based overseas. This

has some clear advantages and disadvantages.

The allure of getting work being done while

you sleep ais amazing and you may be able to

get a fresh perspective on your project that

you might not find locally.

However, depending on the project, it may be

nice to have someone who understands your

local culture. If you need a quick revision and

your freelancer is across the globe, you might

need to wait a full day to hear back. Also,

be mindful that you may have to overcome

a language barrier to communicate with the

freelancer.

Select A Freelancer To Work With

4 Post Your Project Online& Find The Right Freelancer

To keep your project from veering off course,

we highly recommend setting milestones and

deadlines. These are predetermined check-ins

where a certain amount of work is required

to be finished and delivered. That way, if

something isn’t quite as you envisioned it, you

can get the project back on track or quickly

cut your losses if you feel that the arrangement

isn’t working out.

The number of milestones should be

proportional to the size of the project and the

frequency of deadlines should be based on

your comfort level. For smaller and simpler

projects, setting up a single delivery date and

then making revisions after you’ve seen the

final work product may actually be the path of

least resistance.

5Crowd Tip

It’s often a good idea to hold a “kick-off

call” at the start of each project. You

can keep it short but it gives both sides

the opportunity to ask any outstanding

questions. We find that a short kick-off

call gets everyone excited about the

project and brings clarity to what needs

to be done which ends up saving time

and cutting down on email.

5 Set Milestones & Deadlines

Congrats - if you’ve made it this far, you’ve now been sent the first draft of the work product by the freelancer! It’s time to give feedback.

Feedback for freelancers is especially important because they are often working solo and don’t have the structure of an office environment to

providing ongoing guidance and coaching. Good freelancers take feedback well and learn from their mistakes. But it’s really important to stay

constructive and professional. The good news is that if you followed Step #1 in this guide, you’ll have a great brief to reference in your feedback and

the process should be fairly straightforward.

We find that the key to good feedback - whether positive or negative - is to be very specific. If there’s one area where the remote barrier of

freelance tends to manifest in a challenging way, it’s during the feedback process. Instead of describing visual changes to a website, try attaching

a screenshot with sticky notes on it. Instead of suggesting a change the third scene in a video, try including the exact frame that you’re referencing

(e.g. “at the 0:47 mark”). This may end up taking more time, but you’ll end up actually saving a lot of time in the long run by preventing back-

and-forth clarification. As an added bonus, having good feedback dialogue acts to strengthen your business relationship with the freelancer and

motivate them to do great work with you.

5Crowd Tip

There are some great cloud collaboration tools

that you can use to streamline the feedback

process. Google Docs is great because you

can see the revision history and get alerts

when comments have been resolved. For

graphic design, a tool like GoVisually is great

for gathering team feedback with clear version

control.

6 Give Clear Concise Feedback

5Crowd Tip 5Crowd Tip5Crowd Tip

Feedback can be really effective when

both sides can talk it through. Hopping

on a quick phone or Skype chat is a really

great idea. However, it’s also helpful to

have it written down as a reference and

to document what was communicated.

After speaking on the phone, send

through an email with a recap of the

feedback you just communicated and

you’ll be well on your way to being a

feedback pro!

For more tips on working with freelancers

from out of town, check out our blog

post on creative ways to overcome

remote working barriers.

If you’re hiring creative services, you

should really consider developing brand

guidelines (if you don’t have them

already). Brand guidelines will help

freelancers quickly learn what your brand

is all about and what the rules are around

it.

We find that having these cuts down

on the number of rounds of revision by

providing clear instruction on the tone

and style with which you want your brand

expressed. Although it takes some time

to make brand guidelines, it will definitely

save you a lot more time by becoming

a default briefing document for your

projects.

6 Give Clear Concise Feedback

Freelancers specialize in different areas and many have very specific areas of expertise. As you

work more and more with freelancers, you will begin to develop a ‘roster’ of people with varied

expertise. It’s important to strike a balance between working with new freelancers and working

with familiar faces.

WHEN TO USE A FREELANCER YOU’VE

WORKED WITH IN THE PAST

You’re under tight timelines and need a

predictable deliverable

The project you are working on is very

similar to one that the freelancer has

completed in the past.

You haven’t worked with a particular

freelancer in a while and want to keep the

relationship warm.

WHEN TO USE A FREELANCER YOU’VE

NEVER WORKED WITH

You have some flexibility in time and

budget and can test out a new freelancer.

This is a new project and a freelancer

you haven’t worked with yet has a lot of

experience and expertise in this area.

The freelancers you usually work with are

booked up and can’t focus on your project

at the moment.

7 Build A Roster Of GreatFreelancers

Whether it’s small talk over Skype, project

feedback on a conference call, or emails about

billing, remember that your communication

with freelancers becomes their total impression

of you. It is really important to always do right

by people. The freelance world is increasingly

connected and although there are now millions

of freelancers out there, it can actually feel

very small at times. Put in the extra effort to

make sure your freelancers are taken care of.

Develop relationships and keep them invested

in your business priorities. You’ll end up getting

great referrals from your freelancers, higher

engagement, and a better final product with

each project.

8 Build Your Reputation WithinThe Freelance Community

Almost any work that can be done at a computer can now be done online. We think that’s pretty

awesome.

5Crowd is a Toronto based venture leading the way in connecting enterprise Marketing and Sales

teams with a flexible, just-in-time freelance workforce. We curate and manage a private network

of the world’s top freelancers that we call our Crowd. We handpick the best, guide them through

a multi-step vetting process, and then collaborate with them deliver great results on each project.

We’re on a mission to unlock the power of freelance and share it with the world. So if you’re

interested in working for us, or working with us, give us a shout. We’ll grab a coffee and go from

there.

If there’s something we haven’t shared

that you’d like to know, give us a shout!

Coffee’s on us!

About 5Crowd

647 874 1507

blog.5crowd.com

Thanks for reading!

How To Hire a Freelancer Online