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15 Mistakes I’ve Made When Hiring Freelancers Online

hiring freelancer

Avoid them and build quickly to start learning.

I believe in learning quickly. I also believe that prototypes help their maker express their vision and determine if a new product appeals to its target users.

There often comes a time in the early stages of product development where diagrams and presentations need to give way to higher fidelity prototypes. And I’ve been there many times just to be reminded that I lacked the technical skills to ‘build an app’.

A skilled workforce is closer than you think.

In the last decade my technical skills gap (and that of many entrepreneurs) has been closed by online marketplaces that offer to connect you with the talent you need without entering into a traditional, long-term employment contract. I’ve used Upwork, Freelancer, Fiverr and Toptal, to name a few. None of these platforms are new. They continue to evolve to deliver on their visions and as more people rush to supplement their incomes with freelance services, each of these platforms are improving how they manage supplier quality and job timeliness to encourage repeat use by customers.

AirShr would not have started if it weren’t for a software engineer I engaged on Freelancer to build the first prototype. Many ventures start this way. And keep in mind that software engineers are only one of many freelance skills you can hire. I’ve accelerated workflow by hiring experts to draft press-releases, create logos, brand identities and voice-overs as well as outsourcing administration to personal assistants.

I remember my first time.

I remember pressing ‘Submit’ on my first freelance project. The anticipation was palpable.

Would anyone respond?

Who would I end up working with?

This is going to be awesome!

How do I protect my intellectual property?

What IF someone responds!? … Whoa, someone just applied!

Time is your most valuable asset.

Here are the 15 mistakes I’ve made in no particular order when hiring freelancers. Some will seem obvious. Some are embarrassing in hindsight. Embrace each one so you can begin learning as quickly as possible to build and ship a product people will love.

1. My idea is awesome and freelancers will be just as amped as I am to make a great product.

For the most part online freelancers are inspired to develop a strong reputation based on being paid to do great work. And although this is a solid basis for a working relationship, before the project kicks off you are a complete stranger to them and vice versa. Understand that it will be nearly impossible for them to be as excited as you are about your vision.

In my experience experienced and engaging freelancers will want to understand as much as they can, as quickly as possible, to meet and even exceed your expectations. They don’t need to embrace your vision the same way you do so approach relationships with freelancers as ones which will help advance the pursuit of your vision. Anything else is a bonus.

2. I will hire a freelancer on the basis that my IP will be stolen.

This is THE most common concern I hear from aspiring founders following a tech vision. Here’s what I tell them:

1. No one cares about your idea as much as you do and even if a freelancer does, they have to muster all the passion you have to pursue it. In any case there is a very very very good chance that they are freelancing to build the resources to follow their own passion, not hijack yours.
2. You don’t know enough (yet) to know if you actually have IP. You’re building a prototype to learn, i.e. validate a hypothesis about a need and opportunity. If a need and opportunity has been validated it’s more likely that you would be building a team to develop the IP as part of taking a product to market. What stage are you at right now?
3. Your idea isn’t new. It’s a discouraging statement, I know. Here’s the rationale.

Many find these observations confronting. And I appreciate that the desire to protect IP is based on the need for trust between two parties but the bottom line is that you need to be real about whether you actually have IP or not.

Here’s another way to think about it.

In the very early stages of an idea how is someone supposed to help you build a prototype if they don’t understand the situation or use-case they are solving for…? They are there to help you build a product prototype that people will (hopefully) habitually use to improve their lives. And every product needs a business model to be successful. Does the freelancer need to understand the business model to build a product prototype? No. So reveal what’s required to build the product prototype and get learning!

3. Freelancers have done this task before = we share the same context.

Nope. The best freelancers are masters of their craft and can (usually) apply their knowledge to your brief. This doesn’t mean they’ve spent all the time you have on researching / understanding / designing your future state. The project brief should include as much context as will be useful to developing a shared understanding of the objective.

TIP: The best freelancers will ask you questions which in their experience expose the right level of context for them to understand what’s required and how to get started.

4. Collaborating and iterating the product design is part of the deal.

Every version is perfected with iteration. In non-coding projects like drafting press-releases or creating voice-overs (and many others) freelancers will usually include working on iterations as part of the deal. After all they want you to be happy!

In projects involving coding / software engineering you will inevitably want to evolve a design or a feature as you have the opportunity to test versions that your freelancer sends to you. This is where being clear on expectations and milestones is essential.

Your project is designed to get you to a learning outcome, not a perfect product. When your prototype functions in a way to help you learn and you’re embarrassed to send it to people to test, you’ve achieved a minimum viable experience — ship it and get learning!

TIP: If you expect, without discussing prior with your freelancer, to keep iterating on your initial design one of two things will happen:

1. It will become expensive because the freelancer will charge you the standard hourly rate; or
2. Under a fix-fee project your freelancer will become frustrated and possibly quit because they are being asked to do more than the original scope.

5. The freelancers hourly rate is the proxy for quality.

Not necessarily. When assessing the quality of freelancers on face value I look at (in order):

1. Number of projects / hours worked and the corresponding average rating
2. References given by their customers
3. Price

I favour freelancers with a large number of projects / hours and an 90%+ rating with favourable customer references.

During any freelancer review I also look for RED FLAGS including:

  • 100% rating across a small OR large number of projects / hours worked — no one is perfect.
  • Large proportion of one-word or templated customer references — doesn’t inspire me with confidence that these customers are real.
  • Price is too cheap — If a price is too cheap then quality will almost always be compromised and philosophically I believe it’s important to pay people what it takes for them to do their life’s best work.

6. Freelancers must work at Apple / Google / LinkedIn / Facebook / Pinterest /… by day and freelancer by night.

Um, no. People who work at these companies aren’t generally freelancing on the side.

7. Cultural differences won’t be too big an issue.

Do not underestimate the value of a different cultural perspective when building a prototype, it can be enormous. However, clear communication is the essential ingredient to progress and when this is compromised speed to delivery and therefore speed of learning slows.

If communicating during the interview process with a freelancer is difficult, consider this a sign of things to come.

8. The platform (ie Upwork, Freelancer, Fiverr and Toptal) vets every freelancer.

Each of these platforms has a continual focus on increasing quality but don’t mistake this to mean they comprehensively vet each freelancer. In some cases the platform will promote certain freelancers due to their sustained high performance with customers or they may even have a dedicated concierge service to help you find the freelancer(s) you need. Ultimately, who you hire is up to you. Hire wisely.

9. I’ll work out who to hire when I see which freelancers have applied to work on my project.

It’s dangerous to be guided by the quality of applicants who have applied to take on your project. Be clear on the qualities an A-team freelancer should possess before you submit the project online and measure candidates against that expectation. It seems simple but it’s easily forgotten.

10. When I agree to hire a freelancer it will an exclusive working relationship.

Don’t expect this. The economics of freelancing usually mean that a freelancer supports many clients simultaneously. This only becomes an issue when a freelancer does not apply the appropriate level of focus to projects. The core of this issue can usually be traced back to a lack of realistic, clear and agreed project milestones.

11. Freelancers working for agencies are the same as freelancers working independently.

Not true. The agency model usually involves a very articulate and convincing business development person securing projects which they then hand-off to other people to deliver. Unfortunately I’ve had very low success with this approach and as a result prefer working with independent freelancers.

12. As soon as I press submit (to publish the project) I’m committed to hiring a freelancer.

The project only starts when you hire the freelancer and not before. You can always withdraw the project from the platform without hiring.

13. The only way to hire a freelancer is wait for them to find my project.

In many cases you can reach out to a freelancer you have identified as a potential fit and encourage them to apply.

14. Email is the best way to communicate with my freelancer(s).

There are a variety of ways to communicate with freelancers. My preference is to use Skype for regular check-ins if the project term is longer than one week and then use a messaging service like Slack to go back and forward on other questions.

The bottom line with communications is to use which ever medium is going to accelerate progress and reduce ambiguity.

15. Skill = skill proficiency.

Freelancers generate business by selling their skills. They will market the languages they code in, the programs they design in and the disciplines they bring to the table, to name a few. Remember that this is marketing. Possessing a skill and being highly proficient in that skill are two completely different things. In addition to their online reputation, check their education credentials where possible, it will give you a sense of their pedigree.

Also, be aware that many freelancers are self-taught. This can be a good and a bad thing. Good because people can develop and monetise new skills; bad because they may not possess foundational knowledge taught as part of a formal education. This can manifest in different ways but ultimately quality can be compromised.

Is your experience the same? Are there other classic mistakes or learnings you’ve taken away from working with freelancers?

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