Matching Guide: 5 Questions To Ask Yourself Before Your Next Freelancing Project

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Bootcamp

5 min readMay 29, 2023

Starting in your freelancing business, you may want to jump on every opportunity that comes your way. It may be tempting to ignore red flags, but brute-forcing your way into a mismatched project can lead to countless hours lost in arbitration.

Instead of grasping for a project that doesn’t highlight your skills, process, or personality, heed early cues to avoid frustration between yourself and the client.

Sometimes this means taking the low and slow approach . . . which may mean less $ and connections in the beginning but will ensure greater business relationships and opportunities in the future.

Creative work, more often than not, requires a collaborative approach. As the designer, you are the facilitator that ignites the creative germination process. However, plants need the assistance of other external influences to grow. The company you are working with is the medium in which this project is growing. Thus, before you sow the seeds of a project, make sure you and your potential client share the same vision and expectations to position your business for fruitful connections and returning customers.

Amazon-Style Delivery vs. Specialty Boutique

Through five years of freelancing, I learned that enthusiasm and a can-do spirit won’t necessarily turn skeptics into believers or low-budget projects into long-term relationships.

There was a pattern with clients I obtained through sites like Upwork versus in-network referrals. Many freelancing site clients just wanted to click “order” like on an online store, avoiding feedback and discovery. I eventually learned (though perhaps too many trials) that you can not will interaction with someone who would like to remain transactional.

If your freelancing business follows an Amazon-like approach, this article may not resonate. However, if consultation and collaboration are a key part of your business, I encourage you to read on to learn from my errors while I was in the starting phase.

Here are five questions to ask yourself before sealing the deal on a contract:

1. What are the client’s basic desires:

Are they looking for a “click and ship,” standard solution or a specialty product?

For anyone starting on a freelancer site, the distinction between standard versus specialty projects can be difficult to distinguish. Some people are looking for consultation and advice along with a product; while others are simply looking for a plugin.

Because of the cryptic nature of many job postings within sites like Upwork, you’ll likely need to get more information from the client about their specific needs and goals. Someone who is unwilling to call or video chat is likely looking for a standard order.

2. Are we on the same page about process?

Be prepared for clients who may be unfamiliar with design processes that ask them for their involvement.

Lay out how you work, your communication frequency, and responsiveness expectations. Be clear about what you’ll need from them, especially during the discovery phase. Not everyone understands design processes, so anticipate their surprise and ask questions about deadlines, processes, and communication.

3. Could I work with this company or person long-term?

With faceless Zoom meetings, minimal communication, and a non-creative, repetitive task, I knew early on that I wasn’t excited about long-term prospects with the client.

During an initial consultation with a studio, I was asked if I would consider transitioning to a full-time employee. I expressed my preference for contracting roles to maintain my business, but the topic was quickly brushed aside, and I secured the 3-month contract.

A month later, a check-in meeting delved deeper into my long-term goals and interest in going full-time for the studio. I reiterated my commitment to growing my business.

Shortly after this check-in meeting, I received a notification that the contract had been terminated. I instantly messaged the President of the company, who had initiated the contract. He responded:

“Hey Elizabeth, the team told me that you have quit this project.”

I clarified my enthusiasm and apologized for any confusion to the manager I was working under, but the manager explained that my reluctance to go full-time made me an incompatible candidate. This surprise ending could have been avoided if we had discussed goals more thoroughly.

Realistically, my “enthusiasm” surrounding the project had more to do with building my portfolio than it did the company or the work. Later on, the employee I completed the check-in with explained that the job, which was technical and non-creative, didn’t seem to pair well with the “creative ambitions.”

Going for short-term solutions is unlikely to drive your passion and commitment. Finding clients with who you authentically share goals will more likely spur a positive feedback loop of your satisfaction playing into theirs. These connections are more likely to return to your services and refer you to others.

4. Is there trust and eagerness to work together?

Is there skepticism or outright suspicion?

A healthy degree of skepticism allows both parties to sus the other out — matching digital metrics with actual qualifications. However, trust is essential in any relationship, especially when you are relied on to make a useful product.

The initial trust may be earned in a variety of ways: your resume, portfolio, and testimonials are some of the ledgers that may be used to cement a level of confidence in your competence. Following the initial impression, the consultation process should make both parties trusting and eager to begin work together.

Your job is to make the potential client as comfortable as possible with your transparency and honesty. However, if by the end of the primary consultation, the air of suspiciousness hasn’t lifted, consider if it will be worth your time; given the greater probability of dissatisfaction and micromanaging that stems from lack of trust.

If you’re still eager to start the project, ask yourself the following to iron over any lapses in the consultation:

5. Have I covered all my bases?

1. Have I fully elaborated on the project details and displayed an understanding of the task?
2. Have I listened to everything the client has said and taken notes?
3. Have I asked for their additional goals and needs along with the associated timelines?
4. Did I go through the ins and outs of how I plan on tackling this project?
5. Does it appear that they understand the process and milestones?

It may feel like a lot to ask yourself before closing a meeting, but it will save you hours of potential remediation from a misunderstanding. For this reason, it’s good to prepare the client for a meeting that accounts for the initial discussion, questions, then reflection.