important freelancer characteristics


I had the pleasure of speaking with FreeeUp CEO Nathan Hirsch and FreeeUp CMO Connor Gillivan this past week about what important freelancer characteristics they look for when they make hires. They have a wealth of experience that I wanted to tap, particularly on the topic of these traits that signal a good freelance worker. They were very accommodating, as usual, and had a ton of valuable advice to share.

Below are the questions that I had, and what they had to say about the most important freelancer characteristics.

1.  When you’re looking for a freelancer to do some work for you on one of your businesses, what characteristics are your top priority?

The top most important freelancer characteristics Nate and Connor always look for are skills, attitude, and communication. This goes for any business that they hire freelancers for. They have applied this to hiring people to work with them on their Amazon business, and also when looking for assistants to help them run the FreeeUp marketplace. Any freelancer that they are considering for any task needs to have these top characteristics.

For the skills focus, Nate and Connor said that the freelancer needs to have a strong knowledge base in the area where they’re looking for help on tasks. They want someone that knows more about the skill set than they do. On top of that, skills to them also means the level of experience that a freelancer has. A freelancer need to have actually used those skills for a number of years working on various tasks.

When it comes to attitude, these experienced business owners look for freelancers who are passionate about the skill that they have. They want anyone who’s going to work with them to be excited that they know what they know and enthusiastic about applying it to tasks. If they’re hiring for someone to handle bookkeeping, for instance, they want that person to really love numbers and financial organization.

Finally, they look for freelancers that know how to communicate well. This means communicating on a regular basis to give updates, ask questions, and seek feedback. They want fast responses and frequent outreach when working. They also want freelancers who are bringing their own feedback to the table. These freelancers are the experts in their area. They know more about that area than Nate and Connor do, and will have valuable suggestions to share.

2. What makes these particularly important freelancer characteristics?

Connor says that when you get all of these characteristics in one person, it shows that they are serious about their freelancing business and that they understand how the freelancing world works. When a freelancer lacks in any of these areas, it’s clear that they still need time to grow and mature before being ready to work at a high level.


Nate says that looking at skills is actually one of the most important starting points in the hiring process. Skills are the first on the list because he wants to add skills to his businesses, not just more people with the same skills. He wants to fill in the gaps that exist – Nate and Connor aren’t all-knowing, and they admittedly don’t have a complete set of all the skills on the planet between them. When they look for skills that they don’t have, this is taking care of the business in the best way they can. This way, every business task that needs to get done is going to be handled by someone who knows exactly what they’re doing and is going to get better results than they can in that area.

Anyone can learn skills, and of course years of experience signals a greater chance that someone has learned more skills than, for example, a fresh graduate. No matter what degrees or certificates a person has, however, there is no substitute for real life experience. This is what makes skills one of the vitally important freelancer characteristics, and what Nate and Connor really hone in on when they are looking at candidates. A freelancer needs to have practically applied their skills to related tasks. Moreover, they should be able to demonstrate that they have learned new skills along the way that they have also used while working on various tasks in the area that they are hiring for.


When a freelancer has passion for a skill set, it means that they are doing what they love. Nate and Connor strongly believe that when freelancers are doing what they love, they will come to work every day ready to totally crush it. They will have a great attitude towards their work because they are internally motivated. They aren’t there because they need a paycheck primarily, but because they get to do what they love. They won’t be grumpy about working because they’re tired but rather will get a boost from work because they are having a great time with each task. There’s a saying that work isn’t work if you love what you do, and this is exactly what the FreeeUp founders want to see. They want people who look forward to when work starts and enjoy giving it their very best every single day.


Nate and Connor want people who are responsible about the way they work. Regular communication shows them that a freelancer is focused and productive. They won’t have to chase this person down to find out if things are getting done. They won’t have to wonder if they are working at all. This level of responsibility also shows that a freelancer is proud of their work and are not afraid to say, hey, I’m back for another round!

One of the prominent differences between working with freelancers and working with regular employees is that they aren’t with you all the time physically. You can’t pop over to their desks to find out what’s up. But even so, you shouldn’t have to ask. Nate and Connor want people who are on the ball and will volunteer information. And when there’s a question on their end, they want it answered promptly so that nobody is wasting valuable time, which can hinder operations and hurt business growth.

Communicating issues and looking for feedback shows that a person is pro-active. They are discovering problem areas and bringing them out into the open so they can be solved. They are focusing on looking for solutions and improving the quality of their work. They are confident in their abilities, and put the business before any fears that they might have about showing that they are having trouble. When they give feedback, it means that they are not hiding secrets for themselves, for their own success, but open to really helping the business grow and succeed. This all means that they care more about doing well than about preserving their ego or building up a reputation that isn’t actually real.

3. How did you learn about these characteristics?

Nate and Connor learned that these are the most important freelancer characteristics after running their first business on Amazon for a few years. Back then, they didn’t know very much about hiring, and sort of just went through trial and error to find the right fit. They know that they made a lot of mistakes, but they also took note of those mistakes so they could make better and better hiring decisions as they moved forward.

Out of all the good and bad hiring decisions, they found that skills, attitude and communication are the top three most important freelancer characteristics that make for the best hires.

4. What other traits would tip the scales in favor of one candidate versus another if they both possessed the above?

A freelancer who has a very organized and professional presence online is something that definitely makes them stand out. When the partners search for freelancers to hire for business needs, it’s always online. Most of them work from distant parts of the world, and this is where they live and promote their offerings.

For example, when they go to Facebook or LinkedIn to do a search, it’s important that freelancers have a presence. Not all good freelancers will have or be willing to share a social profile for privacy reasons, but they should always have a professional one where they post their skills and work history.

It’s also a good sign when freelancers show professionalism. The internet for a freelancer is their calling card, their resume. A professional profile and professional conduct on the platform shows that they are responsible freelancers who are serious about work.

Another huge plus is someone who invests in their online presence. For example, Nate and Connor are impressed by a freelancer who creates and shares good content. This means that they are passionate about and invested in their area of expertise. In the end, it also points to how seriously they take their freelance business.

5. Conversely, are there any important freelancer characteristics that tell you someone is not going to be the best fit?

Apart from the opposite of the above – not showing a high level of expertise or past experience within the skill set they claim to offer, unenthusiastic attitude towards the tasks, slow responses, etc. – there are a few red flags that Nate and Connor look for.

From Connor’s perspective, one sign that a freelancer might prove to be a bad hire is poor reviews from past clients. They don’t just take reviews at face value, but want to see if a client was upset enough to warrant a review and find out why that happened. Most business owners are super busy, so if they took the time to warn others about someone, there has to be something to it. The same goes for good reviews, of course, and the partners also explore those to see what the story is.

Nate adds that another important freelancer characteristic that tells them someone may not be a good fit is when they show signs that they are only focused on making money. This usually means that they are not happy about what they do, and maybe generally unhappy about working. They have to, and so they do it. Either way, they are not going to bring a positive vibe to work with them, and this bad attitude can be infectious – pretty soon, as Nate has personally experienced, you might find that good workers are starting to complain and slack off because the bad apple has spoiled the bunch.

6. Where do you draw the line – when, if ever, is a good fit good enough?

Our general rule here is, Don’t Settle. Nate and Connor like to keep looking until they find that freelancer who is an amazingly good fit for their needs. It might take some time, but from experience, it’s totally worth it. If you rush and make a bad hire, even if it’s not really bad but not really good either, you will end up wasting time anyway, and this hurts your business more than taking your time to get it right the first time.

7. Is this any different from when you’re looking for a freelancer to join the FreeeUp marketplace?

FreeeUp’s standards for freelancers were built from what Nate and Connor learned in hiring for their first business. Everything that they hold true for their own hiring needs is a part of the process that they built for FreeeUp. It’s all part of how they find the top 1% of freelancer applicants to join the marketplace. They want only the best freelancers there who are ready to work with high level clients and perform at the highest level.

In a Nutshell

So there you have it, straight from Nathan Hirsch, the online hiring guy, and Connor Gillivan, the marketing man behind the FreeeUp marketplace. Skills, attitude and communication are the areas where you want freelance candidates to excel. If they also show a high level of professionalism and a drive to share about their expertise, then you may have found the perfect one. Watch out for poor reviews and a focus on the money when you search and interview, though, as these can ruin everything.

Do you have any important freelancer characteristics that you want to see in a candidate? Don’t ignore them just because they’re not on this list – it’s a basic one, and there are lots of other important freelancer characteristics that can help you find your man. It’s important, after all, that you find the right fit for you, and this often means looking for a candidate that fits your personal preferences. Write them down and vet for them as you search.

If you want more tips about hiring for specific tasks, browse through our blog – we have a ton of content on how to find, interview and onboard for different skill sets.


Julia Valdez

Julia Valdez is a professional teacher and decades-long lover of the art of words on paper, the stage and the big screen. She spends most of her time doing freelance content and project management, community volunteer work with the Philippine Advocates for Resilient Communities, adventuring with the Greenhouse Christian Fellowship, and sharing lots of laughs over little crazy things.


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3 thoughts on “Interview: What Are the Most Important Freelancer Characteristics You Look For?

  1. Skills + Attitude should go together. If someone has the skills doesn’t care about working to be better and owning mistakes, I would definitely not work with this kind of person.

  2. Hello, Julia. I have to admit you have strong points there. As a freelance content writer with years of experience, I have to agree that most clients look for these characteristics. It might also be interesting to mention the quality of communication. A freelancer can communicate promptly and on a regular basis, but it should be kept polite at all times. Also, freelancers often struggle with finding the right dose of humor to indulge in when talking to a client. I believe that is also something to ponder.

    1. Hi Rawiyah, excellent point – there should always be that level of professionalism where you don’t cross the boundary unless you are sure that your client is comfortable with it and that it will add value to your working relationship.

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