Hiring freelancers does not necessarily equal saving money + accessibility + bigger hiring pool.


The Consequences Of Working With The Wrong Fit


I hired close to 80 freelancers in my career. The consequence of working with the wrong freelancers in my case can be summarized to a total of: 3 wasted years, over $50,000 in worthless hours worked and over 100 upsetting and frustrating days. The benefit has been at least 6 times the loss over the same period.


Now, what’s a bad fit?


This all depends on your needs and their expectations. What’s a bad fit for you, can be a great fit for other entrepreneurs. Let’s use an example.


You’re looking for a programmer to help you build the first version of your app.


You did your research to define the features that this app needs to have.


You hire a freelancer and provide detailed specifications about the application.


The programmer starts working. She/he has other projects but carefully planned and estimated the completion of your project in 25 days. This programmer organized her schedule to be able to complete two projects one of which is yours within 25 days so she can start another one by the time wireframing and designs of this third upcoming project are complete.


10 days later, you call her asking for 2 more features because after speaking with 20 more potential app users, you realized that the majority of your potential users will use these two features but not the first. Now this programmer -who by the way only follows waterfall development strategies – needs to go back to the planning stages and make the necessary adjustments. A week later, you get back to her asking to remove a feature. The programmer needs to make other adjustments now and most likely won’t be able to finish on time for the new project to start as planned.


With this, she is frustrated, you are frustrated, and neither want to work with each other anymore.


Notice here this had nothing to do with the qualification of the programmer. It was simply an example of a bad fit.


Every single bad hire I made wasn’t due to contractors’ capabilities to complete the tasks. It was because our interests were not aligned.


The same programmer, would do a fantastic job in a different setting – mostly in projects with set and final specifications, clear expectations and final deadlines. In this case, a good contractor would take the time to carefully understand everything upfront, do the necessary planning and get to work to finish on time. No sudden changes or additions.


Taking the time to find the right fit is key for cost minimization and output maximization.


A Freelancer Evaluation Checklist


First, an interest and better yet passion for startup development. If they don’t care or know enough about startups, they won’t understand what it means to work in such environment.


Questions to ask: Do you use Product Hunt? Are there any current startups that you believe have a lot of potential? Why? Have you built a startup or was part of building one?


Second, an interest in the idea. I’ve had freelancers go as far as giving recommendations to improve my suggested approach to building the product, and I’ve also had freelancers rushing me to start the work without asking any questions or making any comments.


Questions to ask: Do you have comments or suggestions about the idea and our plan in general?


The second point in the list leads us to,


Purpose. It’s normal that one of the main reasons behind contractors’ interest in my proposal is money. What’s dangerous is if it is the only reason. You’d be able to recognize their motivation by how fast they want to start and careful they are in getting the needed information to make a planned and well thought estimation. If they’re trying to start as soon as possible without further planning, know that they’re just looking for another project.


Questions to ask: What’s your technical approach for this feature? Which part of the scope is still unclear for you?


Fourth, availability. Although the future is uncertain in many ways, it’s very important to discuss the future since the beginning. As an example, if their plan is to pursue their own venture or join a large company in the next 3-6 months, you may be better off working with someone else unless your needs for their skills are just temporary.


Questions to ask: How many projects are you currently working on? Any plans after completing this project? What do you see yourself doing a year and three years from now?


Fifth, attitude. This cannot be emphasized enough. Proving the worth and usefulness of an idea is challenging and stressful enough. The last thing a founder should have to deal with is an argument over scope changes every time there is one. If the contractor doesn’t understand this, you should definitely look for someone else.


Questions to ask: What’s the most frustrating part of your job? What sequence do you follow from start to finish of the project? How do you describe a complete project?


Sixth, access and responsiveness. If you’re located in San Francisco, California and your team is in Manila, the Philippines, the difference in time between the two is 15 hours. If 5 or 6 pm is when they call it a day, the only solution is for you to work by night or vice versa. This is inconvenient and impossible to deal with over time. Also, access isn’t just about how close they are, it’s about how easy you can get hold of them. All of these very important variables must be discussed in the beginning and accounted for in your hiring decision.


Questions to ask: What does your working schedule look like? What’s your favorite communication medium (Skype, phone, email, etc.)? Have you worked with a client overseas? Tell me about the project.


Last but certainly not the least, qualification. Can they do the job? More importantly, can they do it with minimum supervision?


Questions to ask: I see you’ve been doing this for X number of years, how many projects did you complete in this period? Which one are you most proud of? Why? Which one are you least proud of? Why? How do you find answers to your questions when the answers are not online? Do you have a mentor(s)? Are you part of any groups in your field?




Consider all of the steps that you take to ensure a fit between you and the freelancer, theory. No matter how much proof you find, nothing is confirmed until you work with each other. For some jobs, I typically do a mini test project and for others, I make sure the first milestone in the project is a way to test the fit. To avoid delays and frustrations, I make sure I hire the freelancer at least two weeks before the target start date. This way, if things don’t go well, I would have time to hire someone else.


Make free mistakes.


BTW: more details about finding your most valuable complement (freelancer) can be found in the bootstrap a startup program. 2+ hours of actionable strategies, methods and examples made to guide you through starting and building a startup venture under limited to no resources.

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