Learnings from hiring and managing tech freelancers at scale.

How to best use freelancers, when to use alternatives, and how to avoid common pitfalls.

Since starting ReadyBase in 2017, I’ve learned a lot about managing freelancers and how to best help companies use them. We’ve had the ability to work full range: from fledgeling startups to massive entities like the U.S. Department of Defense. There are a few tenants of truth that I’ve found to hold true regardless of client size.

Freelancers vs Contractors

Before jumping in, I think it’s important to understand the differences between freelancers and contractors. While subtle, they’re a completely different ball games.

At ReadyBase, we consider freelancers to take on multiple clients and projects simultaneously — often at an hourly rate with no agreement on set work hours. In contrast, contractors are typically on one engagement at a time for a full-time duration or a fixed amount of hours/time per week.

While we use the term ‘freelancer’ in a lot of our marketing efforts as a general term, we’ve found that engagements that use contractors and engagements that use freelancers solve different problems.

For the sake of this article, we’re going to stick to the above definition for freelancers.

Freelancers work best for short-term projects.

Having freelancers knock out short-term, “greenfield” (brand new) projects can be a massive win. Using a freelancer reduces the labor cost burden, removes the cost of hiring and on-boarding, and can be a much faster time-to-market on new projects.

Having freelancers knock out short-term, “greenfield” (brand new) projects can be a massive win.

By sharing the freelancer’s time with other companies, you essentially remove the employment burden but get many of the advantages of having an employee.

In situations where you need one-off items like new marketing collateral designed, a landing page coded out, or some additional QA support for your dev team, freelancers can be an excellent resource for your strategic arsenal.

Hiring freelancers is not without its downsides; and as a warning from someone whom has experienced the short-fallings first-hand: for longer term projects or more complicated ventures, consider a contractor instead.

The core concept of freelancing means that the freelancer themselves often get pulled into different initiatives from multiple companies. Occasionally, freelancers will get overwhelmed with work, and if you didn’t have a contract guaranteeing hours (and therefore, you’ve actually hired a contractor), you’re going to feel timelines being stretched, communication suffering, and results dwindling.

When hiring freelancers, prioritize hiring those that have been in the game for a while.

Folks that are new to freelancing are often enamored by the ability to make some extra cash or obtaining the coveted concept of being-your-own-boss.

What we often see is that the magic of becoming a freelancer starts to wear on those that haven’t mentally prepared for the ups and downs of freelancing. Being your own boss isn’t always what it’s cracked up to be.

While we do as much as we can at ReadyBase to vet all of our freelancers and provide a full-time workload to folks whom we’ve actively engaged, we’ve still had a few occasions where freelancers will leave without telling us, or ghost, in the middle of a project and disappear.

Usually, they’ve just been overwhelmed, afraid, and fearful of communicating what they’re going through with us. We always find a new freelancer for our customers at no charge (or discounted, depending on duration of the project) and wish the freelancer the best.

When hiring freelancers, prioritize hiring those that have been in the game for a while.

Treat freelancers with respect.

This one feels obvious, but for some reason we run into situations where freelancers are being treated very poorly compared to full-time employees; almost like they’re second class citizens.

When a freelancer joins your team, they deserve the same confidence and respect that you give your full-time staff.

When one of our customers treats a freelancer poorly, it’s amazing how fast word travels and how difficult it becomes to help support that customer.

If you want the best results from your freelancers, treat them well.

Hire freelancers for what you know.

One of the core entrepreneurial tenants for hiring is this: hire for what you know, learn what you don’t. This rule is even more-so correct when hiring freelancers.

If you hire a freelancer to take on a task that you’re not sure of what the desired result is, the result will be undesirable. That doesn’t mean you have to master design to hire a freelancer to knock out your next one page sales collateral, but it does mean you should know that putting a 2000 word essay on it will lead to poor results.

If you hire a freelancer to take on a task that you’re not sure of what the desired result is, the result will be undesirable.

The unknowledgeable founder issue.

One of the biggest learning lessons (and we’re still learning this one) is to never let a customer hire a freelancer where the customer doesn’t fully understand the medium and outcome.

A great example are startups that don’t include tech founders. Typically, these startups will have funding, a good idea, and an intention to build an app that could be a really good product and solve a good problem. The founders will spend between $100,000 to $250,000 hiring a combination of freelancers, agencies, or both to come up with a solution.

Keep in mind, freelancers and/or agencies are splitting time and mental energy on solving multiple problems for multiple customers. In almost all circumstances, a nuance in implementation will appear that trivializes the success of the startup. Typically, this nuance can appear in how the app was built, how a certain feature works, or how the team approaches solving the problem.

What inevitably ends up happening is that the nuance needs to be reworked and the product becomes non-viable until the rework is made. Typically, the funding is already consumed from feature creep.

The core problem here is that when in a freelancer relationship, the freelancer’s mindset is that of a vendor. You ask for X and they provide X. The freelancer isn’t thinking critically to solve the problem. They’ve got a million others that they’re trying to solve.

In situations where you need to rely on a critical thinker to solve problem, I strongly recommend hiring a full-time contractor (who will be 100% dedicated to the project) or an employee as they’re more apt to bring these critical items up and work through them with you.

Clear direction, clear result.

Freelancers want clear direction and expectation on what the outcome of a project is. The more clearer expectations you can set, the less expensive it will be for you. The interesting thing is, not only is clarity less expensive for you, it will make freelancers far more willing and wanting to continue the relationship.

If it’s complex, hire a contractor instead.

Have you ever had a moment where you were focusing intently on completing a task, and then something distracted you, maybe a noise or a person, and you lost your train of thought? That’s what freelancers go through every day. They get sidetracked by invoicing, new projects, client meetings, and of course… actually doing the work!

This is the primary reason why I recommend hiring contractors for complex or more critical systems for a business.

Larger companies often have systems that are sophisticated and require on-boarding time that most companies (understandably) don’t want to pay for a freelancer to learn. The fact of the matter is, you’re going to have to pay this knowledge tax.

When hiring freelancers, they’re most likely going to be spending only a small portion of their work week on your projects. This elongates the time it takes for them to be effective working with you: if they’re spending 8 hours per week on working on one of your projects, and there’s 80 hours of on-boarding time needed to be effective, it’s going to take them 10 weeks just to be able to start adding value.

For complex situations or where there’s a business need knowledge, use a full-time contractor.

Freelancers still need some oversight and feedback.

This is something I’m guilty of as well: not spending enough time overseeing the work of a freelancer.

In the daily bustle of work, companies hire freelancers to take on work that they don’t have the time to take on. In an ideal world, freelancers could 100% self managed and own the work you delegate to them.

Alas, like employees, freelancers still need some portion of your time to manage them and make sure they’re appropriately doing the work. If you hire a freelance designer, there is still some time commitment required by you to review designs, provide guidance or feedback, and approve the work that’s being done. If you have a developer, you’ll want to commit to making sure that what the developer actually built aligned with what you were envisioning.

When hiring a freelancer, make sure you’re spending a small portion of your time to provide them support and feedback on the tasks and work you’ve delegated.

Need some help hiring or learning how to hire freelancers?

If you’d like to learn more or grab coffee in the Nashville, TN area, hit me up on our contact page or through linkedin.