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Hiring your first freelancer

Sooner than later, you’ll hit some walls that will hinder your progress. Some of these walls can be overcome with more “firepower,” and outsourcing can be a great idea if it's done right.

September 13, 2020

Hiring your first freelancer

Whether you are a single co-founder or small team with initial funding, sooner than later, you’ll hit some walls that will hinder your progress. Some of these walls can be overcome with more “firepower,” and outsourcing some of the team’s tasks can be a great idea, as long as it’s done right. 

Why are you hiring in the first place? 

“I need someone to handle our marketing, i.e., social media and SEO of our new SaaS service. I’ll just hire freelancers on Upwork.”

If you’ve never said something similar yourself - you’re a better person than me. Many entrepreneurs start with a misconception that one can solve a problem by throwing some money at it. “I don’t know how to program, so I’ll hire a development studio. I’m not a marketing expert, so I’ll just use a marketing agency. I don’t enjoy writing but using a freelancer platform. I expect to have an impactful industry blog within a year”. The reality is that you’d better spend your time and money talking to other entrepreneurs on how they dealt with a specific challenge and educating yourself on how to deal with those challenges, especially in the early days. You might even be better off spending your time bringing in a co-founder who can complete you. Either way, very few problems solve themselves with a bit of money, and delegating a full business function is probably a bad idea. 

Should you hire a consultant or a freelancer?

Freelancer, consultant, contractor, off-shore, outsourcing. Many people interchange them for many reasons, and it doesn’t matter. What does matter is that you have in mind precisely what you’re looking for and that you don’t hire a freelancer to do a consultant job regardless of how they define themselves. 

So what is the difference between a freelancer and a consultant?

In short - you pay a consultant to advise you on what you should do. You pay a freelancer to do a job you can define well. Let's go back to the statement: “I need someone to handle my social media and SEO for my new SaaS service.” If this is all you know about marketing, a freelancer won’t do you much good. You need to do a lot of strategizing and planning before you execute, and for that, you need an expert consultant. 

Consider these statements:

  • I have a solid understanding of the tasks that need to be done to achieve the goal.
  • I know how to define the tasks, their schedule, and how to judge the result fairly.
  • I can write a brief about the task that a professional can take and execute on.
  • I can measure all the critical aspects of a delivered task, including quality, maintainability, etc.
  • I have a fair estimation of how much such a task would cost with different degrees of expertise.

If you don’t feel comfortable with these, you should consider hiring a consultant to frame your needs and define the tasks. You can also use a consultant to help you manage tasks owned by freelancers.

Jonathan Stark, who consults freelancers, came up with the below matrix (published in his webinar), to help freelancers climb the altitude matrix and provide more strategic value to their customers. It can also guide entrepreneurs on the type of hire they need.

Jonathan Stark altitude matrix

How are others hiring for this task? Research

You want to get some sense into the task you are creating and understand the jobs listed in the market for such tasks, the language used, and their costs.

  • Map the relevant online marketplaces for freelancers for this task and focus on the one that serves your research best. Keep in mind this is just the research stage, and you don’t need to hire a freelancer using this platform. Even if you plan to engage using a local board or even using your network, there is great benefit in using the online platforms for research simply due to their accessibility and scale.

The most popular freelancers platforms are:

Dedicated platforms for software development freelancers

Dedicated platforms for marketing freelancers

Look for other job offers and job descriptions of the same task.

Write an internal task scope definition

The goal of this step is to force you to put down your thoughts into a document. 

When I first suggested creating such a document, it felt like a complete waste of time. After all, I’m about to document, to myself, my thoughts. But that is precisely the point of this step. To frame things and move them from vision to building blocks you can use. It will force you to go from the “I want someone to deal with my marketing” to a more specific and broken down task - or acknowledge you need a consultant job to help you frame that.

I prepared an internal task scope definition template you can use.

Write an external-facing job post

This step aims to structure what you’re looking for and communicate it efficiently to the candidates. A well-structured job post can help filter freelancers with a good fit for your needs and prepare both parties for the next steps of the engagement, including the interview and hiring. 

Keep in mind to be realistic both in your specification as well as your expectations.

I prepared a job post template you can use.

Choosing and vetting your freelancer

Look at the freelancer portfolio of past jobs

In some cases, a freelance job results in an asset that is publicly available and is visible to all. For example, a blog post, website design, or video clip. For these kinds of jobs, you should always look at examples from their past jobs. You should expect to see at least ten jobs they can reference. If they don’t have enough in their portfolio, simply ask for more if they don’t have more, they can share, merely move on, or make the educated decision that his hiring is a hire risk. It can still be attractive if the cost is low.

In back-office/strategy jobs, the freelancer will have difficulty sharing their past job outputs as they are primarily confidential. That said, you should ask them to details at least five examples they can provide

  • Customer industry - e.g., a SaaS service for accounting 
  • Customer point of contact role - e.g., CEO/CMO
  • Customer task - e.g., create a content strategy. 
  • Customer output - e.g., keywords research with 1000 search terms analyzed, 50 blog posts ideas, competitive analysis, post calendar, vetted freelancing writers DB.
  • Reference to talk to the customer and get a recommendation 

Past jobs results should be as similar to the ones you expect

If you get some reference work and identify it’s close to what you need, but lacks quality, style, or simply different from what you expected, move on. You are most likely to get a result closer to the references than what you had in mind, regardless of how good your brief will be. As that is the case, identify freelancers whose work body is as close to what you are expecting as possible.

Interviewing your freelancer

  • Take me through your best customer project in the last quarter
  • What worked well?
  • What needed to improve?
  • Give an example of a project that was a total failure?
  • What did you learn?

Traits you should be looking for

  • Understand you and communicates well
    If the freelancer is fantastic, but the two of you can’t corporate efficiently due to language, culture, timezone, or anything else, the project will fail. Best to move on. 
  • Responsive
    It’s tough to identify this in the vetting stage, but you should set the expectations early.
    How do you expect to communicate? On slack? On messenger? Linkedin? Email?
    How soon will they likely reply to each medium? What if there is something urgent? 
  • Follows a straightforward process - preferably a combination of someone who has enough experience to provide you with a blueprint to a successful process, or can be flexible and adjust to yours. 

Test the water first

Compared with hiring a full-time employee, a freelancer engagement is usually more limited in time and scope. As that is the case, when working with a new freelancer, always try to hire them for a subset of the task or add a milestone checkpoint that will enable you to pull the eject in case things don't work out. Don't surprise your freelancer with this but better set the expectation that you are using a limited test period/cost to make sure you cooperate well.


These aspects of the hiring are outside the scope of this post but you should be aware that this point can’t go unnoticed, especially if you’re hiring freelancers directly. 

You should consider:

  • Hiring structure (employee/invoiced employee/freelancer)
  • Legal contract
  • NDA
  • Ownership of the result (especially in creative tasks)
  • Usage in freelancer’s portfolio

If you are hiring using the online platforms, you should notice the legal and financial coverage you enjoy on them. If you are hiring freelancers directly, you should be very diligent in understanding the legal, financial, and tax situation. It can vary greatly depending on the hiring location as well as your freelancer location. 

You are hiring for a task - but there will be future tasks

While you might have a single task in mind, you'll encounter many talented people during the hiring process. Some might be too busy to take on your assignment, while others might be too junior level or too expensive for your budget. It would help if you managed them in an excel sheet for future jobs. Overall, except for the people you hire to do the task, your hiring process should also enrich your freelancer's DB with new freelancers you'd like to work with within various seniority levels and price points. Depending on your future task, you may already have a shortlist of freelancers you can do with, making the process much faster and more efficient.

Once the job is done

If you felt the freelancer did well, you should spend the time to provide a detailed review within the used platform and LinkedIn profile page. 

If you felt the process was missing, highlight if this is something you can improve in your process or highlight the freelancer’s feedback. These will serve you in future freelancers as well as employees hiring.

What’s a Rich Text element?

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Static and dynamic content editing

A rich text element can be used with static or dynamic content. For static content, just drop it into any page and begin editing. For dynamic content, add a rich text field to any collection and then connect a rich text element to that field in the settings panel. Voila!

How to customize formatting for each rich text

Headings, paragraphs, blockquotes, figures, images, and figure captions can all be styled after a class is added to the rich text element using the "When inside of" nested selector system.

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