7 Things to Consider Before Engaging a Freelancer

By Connor Gillivan - Dec. 15, 2017
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Editor’s Note: This is a guest post by Connor Gillivan – CMO and co-founder of FreeeUp.com. His opinions are his own.

It is not uncommon for business owners to feel overwhelmed at times. Running a business takes a lot out of a person, and there comes a time when help is needed. Hiring a freelancer to take on some of the day-to-day tasks can be a big help without being a huge financial burden. If you hire the right person for the job, they will be a valuable asset to your business.

Hiring any freelancer, let alone the right one for you, is not a task to take on lightly. Particularly because you are hiring someone that you may not even meet face to face, the interview process becomes that much more important. Your success hinges on the questions that you ask and how well they work to determine the right fit.

Here are 7 things to consider before you bring a freelancer on board to help you and your business.

1. Skill sets and core competencies

The first topic that you should dive right into is your candidate’s skills and talents. Ask them about their background and how it brought them to work in the field that they are in today. Ask them to describe what they feel they are best at, and why they see this as their top skill or competency.

More than just the skills themselves, notice how your candidate talks about them. Do you sense confidence in the way they describe these skills, or do they seem to be unsure about what they are saying? These signals are important clues to what they can really do.

Along with core competencies comes the experience that your candidate has. They may not be able to tell you exactly who they worked for and what specific projects they completed, but they should be able to give you a few clear examples of what other freelance experience they have under their belt. Experience is a great teacher, and you will be able to tell a lot about their maturity from the way that they talk about their previous freelance projects.

2. Work schedule

You might be impressed by a freelancer’s knowledge and skills, but it is essential that they can work to a schedule that fits your requirements (and deadlines!). You may not need them to work specific hours, but you need to understand what you can expect in terms of deliverables.

Does your freelancer have other commitments, whether work or personal? How much time do you need, and how much time can they set aside for you on a daily or weekly basis? How flexible are they, or what level of flexibility can the job tolerate? And don’t forget to ask when they can actually get started.

Freelancers can be awesome additions to any company, but one thing to note about them is that, for the most part, they prefer to work on their own schedules. Many will be able to give you set hours if you need them to work alongside you or another member of your team. Make sure that you clarify this in advance, however, so that you are both clear on the time commitment and schedule that you need to be followed.

3. Communication style

Determining how your freelancer communicates is the next step. You are not hiring a full -time employee that you can call into your office any time you like. Your freelancer could be working from anywhere in the world, in a completely different time zone. Establishing communication guidelines early ensures that you can keep in touch with your freelancer while they are on the job.

Ask about what their normal work day is like and when they are available for meetings. They might be able to have a quick chat with you outside of working hours, but you want to make sure that you don’t expect them to give up their family time or sleep. Set times that you both agree on for when you can get together to sort out any questions or obtain additional information.

Note also how the freelancer responds to your request for clear expectations on communication. Hesitance could be a signal that your freelancer may not be good with keeping to deadlines. Not being able to reach your freelancer and not getting tasks completed on time are both detrimental to your business.

4. Attitude and values

Does your candidate actually enjoy what they do? This is a very important factor in their work life that can heavily impact their performance. Ask them how they feel about the task(s) you are looking for them to work on.

If they haven’t talked a lot yet about their previous experience, ask them to give more examples of similar jobs that they had in the past or are working on currently. Getting your candidate to talk more will give you more hints about how they conduct themselves. You can gauge their general attitude in this way by looking for clues around how they view their work.

Ask your candidate about difficult situations that they have found themselves in over the course of their freelance career. Ask them how they handled the problem. You can also ask specifically about dealing with a difficult client or co-worker. Freelancers can tend to be less outgoing since they typically work alone, so it is crucial to know how well they can manage relationships.

Your company will always be unique, no matter how many similar projects your freelancer has taken on over the years. As you explain your expectations, provide some additional information about your company. Tell the freelancer a little bit about how you like things done. Introduce examples of other team members that they will be working with. Ask your freelancer if that works for them.

5. Future outlook

Even if you are not hiring for a long-term position, you still want to know what level of commitment your new freelancer has. You might need their services again, or you might actually expand, making room for a longer term (or even permanent) position.

When screening a freelancer, come into every conversation with all the possibilities in mind. Besides, a freelancer who has long-term goals shows a level of maturity. Also, you want to know the degree of loyalty that a freelancer has. By being willing to commit to a long term project, you can tell that they are a true professional who knows the impact that they can have on your business.

6. Questions for you

Make sure that your potential freelancer knows that they are free to ask you any questions that they might have about the project or the company. Some freelancers can be hesitant to express their concerns. This is particularly true if you are interviewing a candidate from a culture where it is not acceptable to ask but only to follow directions.

Open up the floor to them and encourage them to speak up and share any suggestions that they might have about the position … ideally before the project begins! Since this is their field of expertise, you might be surprised at what more they can contribute to your company. They could very well have some ideas that you hadn’t thought of.

7. Moving forward

When speaking to a potential freelancer, give them a clear idea of when you plan to make your selection. Freelancers – especially the best ones – are not going to be sitting around twiddling their thumbs. More so if your job or project is part-time, they will likely have other offers and interviews lined up or other schedules to adhere to.

Taking these tips into consideration, you will be able to quickly determine the reliability and competence of your freelancer. They will also help you to discover which candidate is best suited to the job you need filled and to your company culture as well.

Pay close attention to how your freelance candidates responds. Their answers will give you valuable hints about who they are and how they work. Keep your needs and the needs of your company in mind throughout the process. If you are interviewing several freelance candidates, having a checklist to note how well each of them matches up can make the task much easier.

Connor Gillivan is an author, serial entrepreneur, and CMO and co-founder of FreeeUp. When he's not bringing together hundreds of freelancers and business owners, he's mentoring entrepreneurs through his site, ConnorGillivan.com.


Connor Gillivan

Connor Gillivan is an author, serial entrepreneur, and CMO and co-founder of FreeeUp. When he's not bringing together hundreds of freelancers and business owners, he's mentoring entrepreneurs through his site, ConnorGillivan.com.

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