Written by Carey Wodehouse
A lot goes into hiring someone who will (hopefully) be a good fit for your team. They need the right mix of skills—both technical and interpersonal—and they should be adaptable, motivated, and enthusiastic about the work. Hiring someone is a time-consuming investment, and going back to the drawing board after a new hire doesn’t work out can be a big setback, especially for small businesses bringing in help during a busy period.
Fortunately, hiring freelancers can be cost-effective and fast, if you know where to look—and what to look for.
So what should you keep in mind when deciding if a freelancer is the right way to go? Here are some tips on what to look for and questions to ask along the way.
When hiring an employee, it’s a conundrum hiring managers face: Which is more important, the right skills or the right attitude? Both are desirable, but the wrong attitude—not a lack of technical skills—is much more likely to lead to a hire not being a good fit. In his book “Hiring for Attitude,” CEO of Leadership IQ Mark Murphy states that 89% of new hire failures are caused by attitudinal reasons, whether it’s for things like lack of coachability or emotional intelligence.
Attitude is a significant consideration when hiring a freelancer as well. Freelancers are often brought in specifically for their skills, which may work fine for short-term projects. But with more collaborative projects and contracts trending toward longer-term engagements, attitude can’t be ignored.
The first few steps of the freelancer hiring process typically focus exclusively on skills—the kind of information readily available online through portfolios and profiles—so it’s crucial to build in other opportunities to gauge attitude in your process.
Culture fit may seem like a secondary concern when it comes to remote workers, but the truth is that it still matters. Any freelancers you bring on will still be partnering with your employees, so you’ll need to make sure they can work with them.
When gauging whether a freelancer is the right fit for your team there’s more to consider than whether they have a positive attitude or not. Oftentimes there will be specific qualities that may be more appropriate, desirable, or helpful in your business or industry. These qualities will depend on the culture of your organization.
In our article “4 Ways to Preserve Company Culture When Hiring Freelancers,” Brenda Do writes, “Remember, individuals—whether employees or freelancers—don’t bring your culture with them on their first day working with you. Culture is something you preserve through your actions and processes.” So while you may not be able to gauge if a freelancer meshes well with the rest of your team on day one, it’s a factor you shouldn’t be willing to let slide down the line. If it seems like someone isn’t jiving with your culture, revisit the engagement.
Tip: Behavioral interviews and probing questions like “How do you approach conflict with a client?” can help you uncover if their attitude aligns with yours.
It’s easy to stay motivated when you’re in an office, attending regular meetings, and interfacing with your boss at your desk. For managers, having someone around the corner makes it easy to drop in and see how things are progressing, have off-the-cuff conversations, and stay tuned in to an employee’s performance. But for freelancers, who are all business owners juggling the demands of their clients and running a business, you won’t have the same access to them. Having the flexibility to be off-site is a big draw, not a barrier to doing great work. The key to success is rising to the occasion when hurdles happen.
Tip: Look for the freelancer who takes initiative and has an entrepreneurial mindset. Know that hiring a freelancer isn’t necessarily a “set it and forget it” scenario, but finding someone who is self-motivated and passionate about their work is a good sign they’ll be invested in your project’s success.
Nothing brings productivity to a screeching halt quite like poor communication. Start paying attention to how a freelancer communicates from the beginning of the engagement process. Do they respond promptly to emails? Do they avoid scheduling unnecessary meetings? Do they require follow-ups?
In the beginning, a little extra communication is good to get freelancers on the same page with you and the project. Look for someone who asks a lot of questions, which shows they understand the project and are thinking about how to approach it. But be aware of how much time you spend communicating beyond that. They’re supposed to help speed things up, not slow you down.
If you’re engaging a freelancer outside of the U.S., be aware of any cultural differences that might make communication feel “off” to either party. It can be easy to misread different communication styles and jump to the wrong conclusions without a little cultural insight.
Tip: It’s OK for a freelancer to do their own thing if they’re motivated and understand the project. However, if a freelancer repeatedly falls off the radar until minutes before a deadline and misses the mark, that might be an early warning sign they’re not a good fit.
Many small businesses work with freelancers for longer-term engagements. That’s why it’s important to find someone who puts client service first and adjusts to the way you do things. Freelancers have to be good listeners, clearly understand deliverables, and be excellent communicators. Otherwise, you’ll be spending more time appending or editing their work.
Whether you take an Agile approach or use a chat messenger to stay in touch, it’s helpful to have freelancers on board with your processes. Not everyone loves change or adding extra process, but being adaptable and open-minded will help them integrate into your workflow and processes.
Tip: A good way to gauge this is a small first project. If that goes well, open the floor for them to suggest improvements. If they can even further improve or streamline a process, they’re a great fit who’s going to add value to your organization.