How to Successfully Work With Freelancers | Proposify

How to Successfully Work With Freelancers

As a small agency or business striving to grow and manage that growth, at some point you’ve likely arrived at the cross roads of “Do I hire more employees or should I look for sub-contractors?”

8 min. read

Kevin Springer is a long time entrepreneur, co-founder of Proposify, and the former owner of a web design agency. Jennifer Faulkner is a marketing and communications consultant who has been freelancing for the past six years. Since we’ve worked on both sides of this coin (and with each other), we thought it would be helpful to share some tips on the best ways to work with freelancers to the benefit of your business.

While it’s very exciting when you land large projects, if you’re a small company, sometimes those large projects require extra bench strength or a skill set that you may not have on staff to get the job done, and it can feel overwhelming. But the project may not be so large or enough of a long-term commitment to warrant hiring fulltime employees. That’s when freelance professionals such as copywriters, online marketers, developers, and designers can save the day.

Let’s start at the very beginning. It’s a very good place to start.

Sound of Music references aside, this is the first golden rule of working with freelancers. Whether you need some extra help on a specific project that you just won or on an existing job that’s moving into a new phase, get the freelancers together with your team as early in the project as possible. That way everyone can benefit from each other’s experience and expertise, give input, and develop the best plan of attack right from the get-go. Not only will the project itself go more smoothly but the end result will be the best possible.


"This can be a very frustrating situation as a freelancer. For example, sometimes people will design a whole website or an ad and then call me and say, “All we need now is copy!” The problem is that without exploring what the actual copy needs might be at the beginning, they’ve gone ahead and designed full pages when maybe the information requires only a small call-out, or vice versa. It’s the same if your designer designs an entire website and THEN you bring in the developer, you may be in for a nasty surprise about what can and can’t be done within the budget scope or even realm of internet possibility. Involving a freelancer from the beginning could save you from costly mistakes later.”

So you might be asking yourself, “Ok, you convinced me – I promise to involve freelancers from the beginning. But how do I choose that freelancer?”

Finding Mr., or Ms., Right

Many of us in the agency and freelance world have come from larger shops so we already know the players; who to use and just as importantly, who NOT to use. Maybe some of your former co-workers have gone out on their own as freelancers. The advantage of this kind of hook-up is that you already know their work ethic, their style, and you likely already share a good rapport, which is so important, especially when working on creative projects. You can also start with word of mouth recommendations from industry colleagues who have had similar work done recently, from local agencies, or clients.


If you’re meeting with a new freelancer for the first time, don’t be shy about asking them how long they have worked in the area, and whether or not they have experience with projects similar to your own. You can also request client references to verify the information, to find out about about the quality of work, timeliness, and whether or not they would ever hire the contractor again. Ask for a portfolio or work samples. Don’t be concerned about offending anyone by requesting this kind of background information. Reputable contractors won’t be offended because they will have nothing to hide.

Apples to Apples

Now, you need a plan. One of the most important factors that contribute to the success of a project for everyone involved – you, the client, and freelancers – is to have a well-articulated project plan that clearly lays out the expectations and scope of the project. This will make sure everyone knows what’s involved, what it’s going to cost, and when you’re going to get it done. With a good project plan, you can ask your freelancer for an accurate estimate to prevent scope creep.


As I freelancer, having a detailed plan means I can give an agency a more specific stick-to-it estimate because I fully understand what’s expected of me. Grey area can be hard (and sometimes expensive) to price.


Scope creep happens at two levels. For the agency owner, it could happen from both the client side and the freelancer side so you want to be sure that plan is detailed and clear to keep things between the ditches. The quote from the freelancer should include a full break down of services/expenses that meet project requirements, the timeframe for completion, any expectations once project is finished, the amount of down payment if any, and a payment plan.

When you’re reviewing estimates from freelancers, it is critical to remember that the lowest bid is not always the law. Examine quotes carefully to figure which contractor provides the best service, is the most experienced, and seems most capable of completing the project to meet your client’s expectations, in the best timeline possible. Remember, you get what you pay for and sometimes, that ain’t pretty.

Things to be Aware of:

  • Your freelancer may ask for a deposit on the job. Depending on the size and timeframe, this is reasonable request. We suggest not more than 50% upfront.
  • Contractors who are vague – you need that detailed estimate.
  • Freelancers who pressure you for a quick hiring decision or offer a discount for an on-the-spot hiring.
  • If the person is going to be working with your internal team, make sure it’s someone who fits in with your corporate culture. You want the team to have a good vibe that will produce great work.

Sign on the Dotted (on)Line

Once everything has been agreed upon, your next step is to get everything in writing. Like the project plan, contracts should be detailed and specific. It is always a good idea to have a lawyer draw up or review the contract, but if that is not in the budget, check out Docracy. The piece of paper, or contract, describing work to be performed, detailing the project, and quoting a price for the project, is a legal document, binding to all parties who sign it.

For that reason, make sure you read the contract carefully before signing it. Make sure all aspects of the project are accurately described, and that everything promised and agreed upon is included. Never sign any document you have not read carefully, or that contains only vague references to vital aspects of the project. Once the contract has been signed, the contractor is not legally bound to promises not included in the contract.


Surely we don’t have to convince you of the almighty importance of open, regular communication. We both LOVE Basecamp and have used it for years. It helps everyone stay on top of things – agency, freelancer, and client. Whatever project management tool, you use, USE IT. And especially use it to keep in touch with the freelancer.

If you have any questions or concerns about the progress of the project, don’t hesitate to speak to your contractor. Have regular meetings and check-ins so that neither side is blindsided.

Remember, project success is a two-way street. Be flexible when minor changes occur that won’t affect the appearance, function, or quality of the project and in turn the freelancer will likely be flexible with you when you might need a little extra help. Just be sure to keep written track of any changes.

Now, that’s a problem.

Hopefully having followed all the previous steps, there will be no serious problems. The most common problems that come up when working with a freelancer are delays and misunderstandings about the scope of the work.

If a serious problem does come up and you and your freelancer disagree, it’s important that everyone stay cool, regardless of how dire the situation may appear on first blush. Set a time for you and your contractor to get together, discuss the problem and go over the contract. Get all sides presented if it involves other people. If the problem is not resolved, get the opinion from a colleague; if the situation gets super serious, discuss the situation with your lawyer.

Be Open to Ideas

Working with freelancers can be extremely beneficial to your company (Jennifer: If I do say so, myself) They can give you the flexibility to expand and contract your employee base as needed, they can allow you to win bigger or different business due to their experience, and they can inject a new spirit of ideas into projects. Remember that you hired them for a reason – their skill and expertise - so be sure to get your money’s worth and be open to their input.


When I had an agency, we developed a number of mutually beneficial, long-term relationships with some great freelancers. They became extensions of our staff and it was great to know we had a toolbox of talented go-to people when we needed them. The relationships worked because of respect, earned trust, and clear expectations.


As a freelancer, my bread and butter is based 80% on subcontracted work. I work hard to develop long term relationships with agencies to be the person top of mind when they need an extra hand. Just like your full-time employees, if I’m treated with respect, you’re going to get more than you bargained for. In a good way.

Hopefully this has helped give you the basics of working with a freelancer. Do you have any tips we should add to this list?

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