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How to hire freelancers and create successful collaborations in the age of the digital nomad

Hiring remote employees and freelancers has become a trend in the new generation of digital nomads. The ubiquity of wifi and laptops has given young workers the possibility of working from any place in the world while discovering new cultures and countries, with places like South America, Southern Europe, and Southeast Asia having become popular destinations. 

Companies also benefit from this trend. It removes the need for a physical space to work, and in the early stages of a company, relying on freelancers and remote workers allows for a better handling of the budget, allowing them to grow without spending a lot of resources.

But it’s not always sunny in Remote Working Valley – there are plenty of examples of bad experiences that have led to situations that generate distrust in the remote based working style. It’s not uncommon that a lot of money is spent, and even after a lot of time and effort the outcome could be negative. However if things are properly managed and reviewed, most of these problems can easily be prevented.

Throughout the process, clearly-defined roles and expectations, and frequent communication are key.

If not properly managed results can be very upsetting and negative for the involved parties – this is why it’s important to define everything with thorough detail. Every project should have a very well-defined scope of work, an allocated budget and time frames, the project should also require a role/position that will be filled by the candidate that goes through all the interview process and gets to the end. Many times a bad or ambiguous definition of those elements elevate the risks that come with remote hiring and may lead to a failure of the relationship and/or project.

If you want to reduce or mitigate the risks of failing when taking on remote workers, you can follow these four steps:

Define the scope of the project

Every project, no matter how small, must have a clear written scope that summarises its goals, responsibilities and timelines. It’s of extreme importance that you clearly and unambiguously define the scope of your project, as failing to do so will increase the risks of a poor outcome.

In order to define a proper scope you must clearly write down the project’s details, including each of its deliverables, milestones, budget, timing considerations and the specific tasks involved. Your scope must answer the question, “What is the task you need to complete or the problem to solve, and what’s the outcome you expect?” The response should include a lot of details and understandable language for the level of work you’re seeking. 

Break your project down into tasks, and assign specific roles to your remote workers, including necessary milestones and expected deadlines. Share this information and make sure it is always available to your workers.

Publish the job

Once you have your scope defined, you can head to the popular platforms that connect companies with freelancers, like UpWork, Fiverr, NomadList, Freelancer, LinkedIn, StackOverflow and many others. Be sure to analyse them and choose the ones that best suit your project’s needs. You can also ask for referrals from people you already work with. 

After choosing the platform, create an attractive job posting with enough information to engage the people you will be interviewing afterward. Make sure to include a lot of details and as much information as you can to describe the job to be done. If the announcement is done properly, attracting the right candidates will be much easier.

Remember to include requirements regarding level of education, skills and past experience. Make a budget and fee expectations for the job, keeping in mind that more experienced people demand more compensation for their time. You should also define the expectations regarding the availability of the remote workers to work on the project.

Think of the job posting and the hiring process as a marketing campaign, in which candidates become your audience that you need to engage with the goal of attracting the best candidates to work with you. To accomplish this you should use empathy, tell a story that resonates and communicate with your candidates frequently. 

Interview several people

When you’ve found candidates that respond to your posting, do your research and choose several people to interview. Ideally you should develop a process in which the candidates are evaluated and removed if they don’t fit with the project’s needs. Then choose several channels of communication to assess the candidates and remember to consider their location, since an extreme change of time zones could affect workflow.

Afterwards you’ll want to define the structure of the interviews. This will vary depending on the needs of your project. If your project requires technical skills you might want to include a technical test for candidates to complete, or you could choose to generate a formal structure of interviews to evaluate candidates from a formal perspective, you could also conduct your interview as an informal conversation and ask open ended questions, each of those styles should match a goal that helps you determine whether the candidates are fit for the role you’re looking to fill. 

It is often recommended that in the process you evaluate education skills, and work experience as well as previous work samples, but also remember to pay attention and evaluate personality traits, motivators and overall attitude towards the project.

Pick your choice and start working

Once you’ve interviewed your candidates and have made a decision on who will be the one filling the position, it’s time you reach written agreements between you or your company, and the remote worker, most common documents that are shared in the process are freelance contracts, non-disclosure agreements, non-compete agreements and letters of agreement.

Depending on your project you could need one or the other, but the idea is that the major terms of work like scope, deliverables, payment terms, timings, deadlines and confidential information are specified in the agreements you choose to use.

Evaluating workers through a trial period in which you assign smaller tasks of the project will allow you to assess their abilities more quickly and determine if they are fit for the role. When they start, remember that you should create a healthy remote working culture, in which people will feel comfortable working with your project.

Lastly, it’s of great importance that you frequently engage through several communication channels, I know I’m being very persistent about communication, but hey, it’s because it’s really important! Establish frequency of messages and daily, weekly, or bi-weekly meetings – and if you’re managing a lot of people at the same time, it’s recommended that you use a simple project management tool such as Trello.

Samuel Villegas
Samuel Villegashttps://innovationhackinglab.com/
Samuel Villegas is a serial entrepreneur and the CEO & co-founder of Innovation Hacking Lab. Passionate about contributing to human-centered global transformation, innovation, entrepreneurship, business methodologies, and information technologies, he loves helping fellow entrepreneurs and innovators in their ventures.


  1. Thanks for the tips, Samuel! Knowing what the right traits to look for are in a remote worker will go a long way to helping you ensure that those you will hire are indeed the best for your organization.

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