Guide for working with freelancers

by Barry on March 22, 2010

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Using freelancers is a great way to solve your staffing gaps if you need to additional coverage because someone is on vacation, you have too much work, or if you need specialized help. There are many benefits to establishing a good relationship and treating freelancers with respect.  I’ve seen too many companies treat freelancers poorly and having hired hundreds of freelancers, and spending time as a freelancer, I’ve compiled tips and guidelines for working with freelancers.  Like all relationships, the goal is to make sure that everyone gets what they want (a win-win).

If you don’t follow these tips, then you risk:

  • Having a bad reputation in the marketplace. The advertising industry is a small industry and we generally know each other.  Freelancers talk to one-another and word spreads quickly about which companies are good to work for and who should be avoided.  Also as the economy turns-around, you will have a much harder finding good people if you treat your freelancers poorly.
  • If you cannot find good freelancers, it can impact your client relationship as it affects your ability to deliver quality products on-time.
  • When you need help on Christmas Eve or Superbowl Sunday, a freelancer with whom you’ve established a good relationship with is more apt to help you out.
  • You can negotiate more favorable rates as freelancers will want to work for you.

Before they start

1. Sign a NDA. To protect yourself, it is essential that each freelance sign a non disclosure agreement. This needs to be executed before you discuss any confidential details and definitely before they start working.

2. Pay them a fair value for their work. While you need to be a good negotiator, don’t coerce them to slash their rates.  If you do, expect that they will jump the second another higher-paying opportunity comes up.

3. Have a clear understanding of the financial arrangement. Discuss how many hours they can work (including any caps and whether overtime is allowed or not), their rate structure (i.e., hourly, daily, weekly, project-based), how long do you need, their tax structure (1099 vs. W2), and when they will be paid.  If you are paying day rates, discuss how many hours they will work an average day, and what happens if they only work a couple of hours.  You typically don’t want to get billed for a full day when the freelancer only worked for two hours. I recommend putting all of this in-writing, which protects both the freelancer and yourself.

4. Understand who you are working with. Freelancers generally can be categorized into two segments. In the first segment, they are freelancers by choice.  They love the life of a freelancer as they can accept or reject any job they want, every job is different, they meet a lot of interesting people, and they have access to many agencies.  Many of the people in this segment like to take months off to pursuit their artistic interests or to travel.  The second group are freelancers by circumstance.  They are using freelancing as a way to pay bills until the right permanent job comes in. I have no hesitation in using a freelancer from either group but you should seek to understand the motivation of why they are freelancing. Have an open discussion as the expectations, such as if they need time off, or if they expect only to be with you for a short time. Again, clear and open dialog is the way to go.


1. Give your freelancers the tools they need to do their job without making them wait for everything to be setup. This means having their desk, computer and access cards ready before they walk in.  If you make them wait two hours for your IT team to setup their laptop, expect to be billed for that time.

2. Introduce them to the project team and to key people in the office.  This includes the office manager, receptionist, IT, HR, general manager, their department manager, other execs, and the accounts payable person so they know who to contact when you don’t pay them in-time.

3. Give them a tour of your office. Show them where the bathroom is, where are the local eateries, and how to find staples and rubber bands.

3. Make sure they know who to contact if they are running late or need to be out sick.

4. Provide the office hours and company holiday schedule. Let’s not have them come into the office on President’s Day because no one told them that was a company holiday.

5. Make sure they know how to get computer help, how to access your file server, how to print, how to use your phones, and how to access voicemail.

6. Ensure that they know how to fill out their timesheets and who to submit their timesheets and/or invoices to.  Also give them the necessary job numbers (if required).  Don’t make them have to jump through six hoops to get paid.

7. Communicate if expenses are allowed, and if so, what are the guidelines for how expenses should be submitted.

8. If they need off-hours access to your offices, make sure that they can get into your office.  In many office buildings, you need a building ID or a special pass to get past security during off-hours.  Also do they need access cards for your office?

Once they are settled in

1. Treat freelancers like employees. As much as possible, treat long-term freelancers the same as you treat your regular employees. Invite them to office lunches, parties, and bagels with the boss. Obviously there may be some meetings you do not want them attending so use your judgment.  For things that take a lot of time like parties and off-site events, I usually tell my long-term freelancers that we would love to have them join but they cannot bill us for their time. Note: your definition of what is long-term may vary but I recommend that anyone who is with you for more than two weeks is treated as long-term.

2. Talk with them. If a problem comes up with their performance, talk with them directly.  Seek to understand if this is a problem that can be corrected or not. If the problem persists, then cut them quickly.  Give them a fair chance but also don’t wait days or weeks if there is a problem.

3. Be transparent. If your needs change or if the client delays or cancels the project, be open and direct with the freelancer.  Let them know what is happening. If you need to let a freelancer go early because the client cut a project, you want to give the freelancer as much time as possible so that they can line up more work elsewhere.

4. Pay OT. Many states (if not all) require that you pay freelancers overtime if required.  The laws vary by state (NY bases overtime based on exceeding 40 hours a week while California bases overtime on exceeding 8 hours a day).  Know the laws in your state and follow them. If you’re not sure about the overtime laws in your state, talk to your HR department.

Wrapping Up

1. Obtain all working files. After the project completes but before the freelancer leaves, make sure that you have all working and source files from them, and that you have personally inspected them to make sure that nothing was forgotten.

2. Pay freelancers quickly. Don’t keep freelancers waiting for their money.

3. Provide references and leads. If you feel that they did a good job for you, don’t hesitate to provide references and leads to them.

4. Maintain your freelance network. Connect with freelancers over Facebook and Linkedin, and stay in touch with them. Freelancers frequently see things that we do not since they work at many different agencies.

5. Keep a spreadsheet. I recommend keeping track of all freelancers you’ve either used or considered using to track their contact information, skills, weaknesses, projects, technical expertise, and performance.

The key to a successful relationship with freelancers begins with having good open and direct conversations, getting agreements in-writing, and putting in the time to maintain and grow the relationship.  Doing so will pay dividends.

Agree? Disagree? Do you have any tips to add?

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