Using Controlio to Manage Your Freelance Team

Freelance management is unlike anything we’ve done before. Distributing work across multiple time zones clouds accountability. Without someone looking over their shoulders, how do we hold people accountable? And how do we make sure we are getting our money’s worth? These are just some of the questions I found myself asking three years ago when I started working with remote teams for the first time. Using time tracking tools like Controlio helps make remote management less like babysitting. I will go over some of the strategies I developed.

Technology Allows Remote Freelance Management

Controlio is just one example of technology that can help remote managers refine their approach. When I first started working with remote teams, I was worried that my hired help was just going to log in, leave their computer unattended, and walk away. I was unsure of how to use the available resources and tools. When I first started hiring remote contractors, I was very worried that my hired help would end up just logging in, leaving their computer unattended, and walking away. I was very worried that my contractors would end up just logging in, leaving their computer unattended, and walking away. This level of uncertainty is where time tracking software comes in. With Controlio, I don’t have to obsess over the presence of my contractors, but I can be certain that work will get done. I can feel confident in myself as a manager, and I can feel confident in my contractors. I will be sharing some of the strategies that I have developed over the years.

Understanding this separation is important for effective collaboration. The moment I changed my thinking from “managing employees” to “collaborating with independent agents”, everything was different. I stopped micromanaging day-to-day operations and developed my management style to focus on specific projects with definable and measurable outcomes. I also created a management system that didn’t require me to conduct check-ins; instead, I provided the system to set accountability against defined objectives.

Freelancer Relationships

Open and vague expectations are the end of productive working relationships with freelance workers. With the lack of a structured office environment, freelancers need to have a very clear understanding of everything that the freelance worker needs to accomplish. That is, what success looks like for the reasonably described task.

I have started to spend tremendous effort, before I even look for freelance workers, to clearly and accurately describe what I expect the end result to be. Rather than “help me with my marketing,” I provide the result as “achieve an increase of 500 subscribers to the email list each month using content upgrades and lead magnets.” In this way, I am able to provide a measurable result, “manage social media,” and also describe my expectations of “post (2) unique platform-appropriate posts each day, and respond to all the comments within a 2-hour time frame.’’

These goals also have the purpose of attracting the right freelancers. I have also utilized the goals to set clear goals that I can use to define success or failure and also set control limits to avoid using subjective descriptions.

Using the Controlio Tool from the example above, I have also added consistency to the process of defining goals or expectations and measuring freelancer performance. Controlio also provides transparent accountability for diligence and effort with a clear definition of time and task usage, and provided that both freelancers and their clients establish specific goals, the freelancers and their clients would be able to objectively understand their expectations and the realities of performance.

Tools for Managing Remote Freelancers

Chat Apps

Remote teams communicate all day long, and the right tools make it easy to know what team members are doing. I have a Slack account. Each day I post a message on the Slack board, ⎡Channel➜Name⎤⎦, to communicate with team members and to clarify what I want done. I can collaborate with team members on a project without my involvement.

However, I realized one major drawback in using software tools for communication—endless meetings through structured project management. I try to hold meetings when issues can be solved via Slack or outside the project management tool.

Tools for Managing Tasks

These apps create a connection between short- and long-term goals and day-to-day tasks. Trello is great for simple tasks, while more complex tasks are best supported using open project management tools such as Wrike or OpenProject.

The secret to choosing a project manager app is to correlate it to the current state of your business. I have watched businesses improve severely from poorly designed project-manager business apps that no one works with.

Time Management and Measurement

This is when using the Controlio app is recommended. Unlike typical timers, Controlio will break down levels of incoming work and not just calculate work hours. They will also accurately measure the productivity of your work.

The app automatically tracks all programs in use, and depending on the work’s specifications, it will measure activity levels and classify the work as productive or non-productive.

Controlio can change your business for the better. With it, you can see not only the times your freelancers are clocking in and out but also actual patterns of behavior. I noticed a freelance writer who spent nearly two-thirds of her time on a single article in the research phase. With this insight, I was able to make changes to increase her output twofold.

Managing Freelance Teams

It may be hard to accept, but freelancers are not always a cheaper option than hiring employees. This is especially true when you are looking beyond simple hourly rates.

There are a lot of hidden costs that go into hiring freelancers. Marketplace fees, time spent managing new freelancer accounts, and time spent carrying out training. When you consider the training and management time spent, the costs of hiring a freelancer can quickly outweigh the hourly rate.

I always try to approach freelance work by imagining our end goal. If I can estimate that an additional 500 email subscribers could generate revenue of $2,000, I can justify spending up to that amount to hire a freelancer.

I am trying to hit the goal of moving away from hiring the bottom-tier freelancers. The end goal is to get results that go above and beyond our expectations.

Quality freelancers know what they are worth, so it is important that they are working above your expectations.

Having Controlio removes the pain of juggling supervision with self-direction. While freelancers aren’t being micromanaged, management can keep track of the freelancer through work patterns and productivity.

I explain Controlio to freelancers very frankly. In my onboarding, I describe what is being tracked, how I review the data, and how my goal is to improve the process, not to call anyone out. A lot of my clients only trust me more because of my frankness. Perhaps the greatest part of this process is that I create mutually trusting relationships with freelancers because I am so open with them.

Ensuring accurate and punctual payment is essential for maintaining a strong relationship with a freelancer. Late or questioned payments are the fastest way to lose talented collaborators and damage your reputation as an employer.

For project-based work where hourly tracking doesn’t make sense, I establish clear milestones with partial payments. My process with Controlio is that there are no billable hour disputes because Controlio has generated an invoice based off tracked time that is the only source to dispute a billable hour. It is completely based off of the data that is clear and without question.

This allows freelancers to have consistent pay as well as have structured checkpoints to review the work.

Most people have questions. So let’s answer the most common ones.

Q1: How do I keep freelancers from thinking they are being controlled by having to use time-tracking software? \

Almost every time I use Controlio, I explain to the freelancers why I use time tracking software. I let them know it is to improve workflow and to bill accurately and not to monitor them in any negative way. Most people actually find this information helpful, since they are focused more on the metrics to improve their own work, as opposed to the opinions of a subjective manager. This is, to be transparent, a way to build trust instead of micromanaging people.

Q2: Should I pay freelancers by the hour or by the project? \

This is determined by the type of work required. Customer care and community management positions need continuous engagement, and they are best paid as hourly employees. Other work, such as writing and designing, is best done on a project basis, as it provides a motivation to work efficiently. While I have freelancers doing hourly work, I use Controlio and pay project freelancers at milestones, regardless of the time they spent on the work.

Q3: How do I build loyalty with freelancers if they can leave at any time? \

This is a matter of fact. Freelancers have a foot out the door, at least to one client, far more than employees do to one employer.

I have chosen to accept certain realities regarding my work, especially pertaining to the freelance industry, and I believe there are ways to make these business partnerships work both ways. This can largely be done through fair payment, clear guidelines & expectations, quick payment, and a certain level of professional mutual respect. The most effective and valuable freelancers stay (and are not loyal, but are loyal to the mutual benefit of the professional relationship) because the relationship benefits them. Controlio helps define and remove the grey issue of whose expectations and the prescriptive, controlling manager’s metrics, and thus frustrate the freelance professional.

Q4. Where do you see the biggest pitfalls in your management practices around your first freelance hires?

Freelancers cannot, and should not, be hired for the vague, undefined, and immeasurable. It is a classic entrepreneurial error to hire a freelancer with the mindset of “I need help” and without defining the form that help should take. This leads to mutual frustration. It is essential for someone looking to be an effective manager to document in detail how the tasks, the outcomes, and the metrics that constitute success are to be defined and approached. Controlio works here because, in the final analysis, the measurement of time is task and project specific, therefore eliminating the vagueness of the task.

Last Thoughts

Freelance management is a different skill set from conventional management. Effective freelance management offers the greatest yield. With optimal management, freelance teams achieve a level of outcome (and efficiency) greater than that of traditional models of employment.

Essentially, managing freelancers, like managing employees, is about control and the professional attitude adopted toward the freelancers.

Controlio enables this approach by giving objective data about productivity and time usage while avoiding the burden of endless meetings and check-ins.

Whether this is your first time hiring a freelancer or you are managing dozens of them, remember that incentivizing properly, communicating clearly, and using data to operate are going to lead to success, while working off of assumptions will lead to failure. The freelance revolution is permanent, and managing remote teams is a necessary business skill for entrepreneurs.