Naturally, we think freelance marketers can be a phenomenal resource. But as with any employee—and especially a remote one—it’s a good idea to have some strategies in place that can help us make the most out of their expertise. We spoke with Aneesha Rao, Founder and CEO of Lantera Labs, a company that consults with enterprise and SMB companies alike, and Kaleigh Moore, a freelance writer for SaaS and eCommerce with over six years’ experience in the field, for their insights.
According to Moore, the best marketers are very clear about what they want, who their target audience is, and have a solid, easy-to-navigate onboarding process for anyone they bring on board. “They're also really good at communication and are always happy and available to answer questions,” she says. “They have all of the important strategy details ironed out before they dive into a new project and have metrics in place that serve as benchmarks—rather than just winging it.”
It’s a cliche for a reason—not every horse is going to be a great fit for every racecourse, and not every approach is going to be ideal for every freelancer. “With freelancers, the guardrails I implement depend entirely on the level of expertise the freelancer has, and the extent of my relationship with them,” Rao says. “With an experienced content or design marketer, I let them have at it, and give a basic schema of project scope. With someone I'm working with for the first time, or someone who is less experienced, I usually provide examples (especially for design) for things that I like, and things that I don't like. I'd say with content marketing, I'm very involved in the feedback and iteration process for copy for the first few assignments, and then I hope that feedback process creates a system of understanding where the content marketer is able to roll up their sleeves and really deliver content that wows.”
If you have a problem with freelancers flaking out on you, remember that they’re people, too. When we don’t interact with people face-to-face, it can be easy for our interactions to be impersonal and feel almost fake—and that’s going to make flaking out a lot more attractive. “I think freelancers can be flakey if it's just a job,” Rao says. “if you communicate with someone one-on-one, set expectations, and invest time in building a relationship, it's like any other relationship. I happen to think that culture is created everywhere, and regardless of whether or not someone is in-office, remote, a contractor, or employee, they're contributing to your team and organizational culture. I think an org culture is super important to maintain and invest in; I think it's in the best interest of everyone at the company, and the company itself.”
With freelancers, stuff often comes up. So if you need something turned in in 72 hours, ask for it to come in in 48. A good freelancer will get work in on time or ahead of time frequently, but life has a habit of getting in the way of the best intentions. “I always pad my deadlines and work hard to deliver ahead of schedule, as this really wows clients and helps them keep things moving along,” Moore says.
“I love communication; I think it's key,” Rao says. “I'm also a bit of an obsessive project manager, so I have a KANBAN for everything (seriously, I'm doing my laundry with boards these days). So, for communication I use Slack, for PM, I use Notion. I think it set expectations to set a sprint with your team of full-time or freelance talent, plan for the week, and then reflect on what has been done well and what could have been worked on. I think there's almost a blame culture that exists in all employment, not just freelance employment, and that concept of ‘What haven't you done?’ is something I try to shy away from. Instead, it's more like, ‘How did we grow this past week, together?’
Rao I set soft deadlines and plan sprints in 6-week intervals. I think if something is getting pushed back for over 3-4 weeks, that's an item to look at, and evaluate how important it is. I think also a 6-week time period is a pretty not-insignificant chunk of time in which you can reflect, think about ways to become better, etc. I have a deadline for everything, but within a sprint, if deadlines get moved, I think that's part of the process. If something doesn't get done entirely within a sprint, that's part of the reflection.
We can all agree that keeping the conversation going helps prevent “freelance flake,” and keeps everyone on the same page. But not everyone agrees on how this is best handled.
“I think freelancers should readily be providing updates, and if they're not, you should ask for them,” Moore says.
Rao disagrees—not about the value of communication, but in terms of how it happens. “I think efficient and strategic project management precludes the need for check-ins,” she says. “If everything is set up, then the work should be completed in the timeline set forth. When deliverables are delayed, usually that's stated in a sprint recap meeting, with an updated due date. Deliverables get delayed; we all want to do more in our work day than we have the space (mental, physical, etc.) to do. I like to think about work productivity as a kind of ebb and flow.”