Outsourcing: 5 Stages from Pain to Pain-Free

Outsourcing work to others can be challenging. In some cases, it may feel like a mistake. You may have lost money and time attempting to leverage your time and money to get a task done.

Making the decision to outsource is good. We’ve seen and read loads of examples of companies and individuals who have managed to use outsourcing to grow their business and get more work done. These people have been able to reach and make a greater impact just by figuring out the outsourcing game.

How do you know if it’s time to outsource?

One of the most obvious reasons to outsource is if you have too much work. If you’re fortunate enough to have too much to do and not enough time in the day, then you may want to consider outsourcing some of your tasks to someone else.

Perhaps, there are tasks which you do, that you do not enjoy or are not the most skilled at. These tasks may be better served by leveraging someone else’s experience and talent.

If you have tried to outsource work, then you may have experienced some of these situations:

Your Pain Points

Finding Reliable People

Today, thanks to the internet, finding people to help you is easy. Market places like Upwork.com or Freelancer.com or Fiverr.com are filled with freelancers who are climbing over one another to win your work. There is no shortage of people.

The problem is that you may have found someone who did a terrible job. They are not responsive. They did not listen or follow your instructions. They did not deliver on your expectations. You were left disappointed, frustrated, upset or maybe even angry.

Paying The Right Price

Price is a contentious issue. There is no guarantee that if you pay a higher fee, that the person you choose will deliver. There is also a risk that you pay too low and that the quality you expected is not on par. In our opinion, going for cheap is not recommended.

Where Do You Find The Right People?

We’ve already mentioned a few platforms where you can find people to help. With more choice comes more confusion. Some platforms are known for cheap resources for small tasks. Other platforms list people who are amazing at complex and intricate work. The platform you choose to find people on, is a personal preference. We believe that each platform has its merits, pros and cons. At the end of the day, it really does not matter where you chose to find your people. Just that you have a process to find them. More on this below.

Time Zones and Holidays

If you choose to work with people outside of your local area and contract people from the internet, chances are that they will be in a different time zone and may even be on the other side of the world. This may bring challenges in terms of communication, because while you are sleeping, they are working and vice versa. There are loads of freelancers who will adapt to your working times, but this may not always be the case. Be respectful of people’s time, but make sure that there is some overlap in times for meetings and communication.

Other cultures may follow a different calendar because of their religion or cultural background. Keep this in mind when finding someone to work with.


Again, depending on who you outsource your work to, may bring up language barriers which you may not have experienced before. You may find people who communicate really well, despite the fact that English is not their primary language. Again, build this into your process.

Technology Challenges

You may have had a situation where the freelancer was not familiar with a tool you use, and because of that made mistakes and maybe even abandoned the project altogether. Be sure to find people who are ok with using what you have. In some cases it may not serve you well if you already have a process in place and the freelancer refuses to work within your parameters and technology stack. Keep this in mind and do not settle if this is the case.

Security and Privacy

You may have had a situation where you shared your login details to someone and they did not honor that trust. You may have lost data and found your website compromised. Not a nice situation to be in.

Outsourcing The Pain-Free (or Less) Way

We can’t really say that the strategies below will eliminate the pain and frustration completely, but implementing these processes may help you a great deal.

We will address each of the problems above one by one.

Stage 1: The Job Post

Irrespective of which platform you choose to use to find people, be sure that you write a clear, conscience title and description of what you need help with. Avoid being vague and ambiguous. People who read the post should know exactly what is needed, understand the deliverables, the timeline and your expectations. This will make them ask themselves if they are capable of doing the work. This is stage 1 in the disqualification process.

Some platforms allow you to ask specific questions related to your job post. We recommend asking questions which directly talk to their personality and values. When evaluating applications, look for clues which talk to their character, their values and work ethics. Match the responses to your values, your culture and your work ethic.

Stage 2: Mini Tests and Prompts

In some cases we use the question prompts to ask people to do a simple test as part of the application process, such as an online personality test. Their responses may surprise you, and those who do not complete this step, are disqualified. Stage 2 in the disqualification process.

Stage 3: Chat/Email

During the application process, depending on the platform, you may have an opportunity to discuss the work in more detail with the freelancer bidding for the work. This again is an opportunity where you can eliminate candidates for the work. If their written English is too casual, has spelling errors or they are not as responsive to you as you expect, disqualify them immediately, i.e. stage 3.

Once you have a shortlist of applicants, book them for a meeting at a specified date and time that suits you. Make sure this meeting is a video call using Skype or zoom. Zoom is great because if you end up not selecting one of your interviewees they cannot harass you via the recruitment platform or on Skype. The meeting id is unique to that session. During the interview as similar questions to the ones you posted on the initial job post and compare their verbal responses. Ask open-ended questions to get them to talk. You want them to talk for 80% of the interview while you listen and evaluate them. Even if you have found someone who seems great, we encourage you to end the meeting telling the candidate that you will get back to them in a few days. The logic behind this step is to ensure that you have already gone through all the people on your interview list to eliminate the possibility that the next person you interviewed will be better than the one you have just met.

Stage 4: Video Interview

The video interview has a number of benefits:

  • Do they have a good internet connection?
  • Do they communicate well?
  • Are their verbal communication skills as good as their written skills?
  • What environment are they working in?
  • During the meeting, do they get disturbed or are distracted?
  • Do they show up for the meeting on time?
  • Are they open to discuss their working times, holidays and cultural days?
  • Do they have the tools necessary to get the work done i.e. camera, microphone, laptop or pc?
  • Can they follow instructions?

Each one of these questions could be potential deal breakers for you to eliminate the person from your short list. If there are a few things you could live with, and you feel are not that important to the job, then so be it. Use your gut to get a feel for the person. Look in to their eyes and see who they really are and see how comfortable you feel by speaking to them directly.

Do not settle, just because you want to save time. The more time you spend evaluating the person doing your work, the better it will be for you in the long run.

Stage 5: Mini Assignments

At the end of this process, you may find yourself with a short list of 2-3 good candidates. We suggest giving a small assignment to all 3 people with a specific deadline and narrow requirements. The one who completes the task to your liking will ultimately be rewarded the project. You may want to keep in touch with the other two candidates as you may need them as a backup if your star performer is not available or you expend your tasks to outsource.

So You Found Someone to Outsource: What now?

Now that you have found someone, there are few things to keep in mind to be sure that the person lives up to their promises.

  1. Use a project management tool like asana.com, trello.com, wrike.com or any other task and deadline based tool to manage and communicate and track the progress of the work.
  2. If your job is based on hours, keep an eye on what you are billed. Measure the work based on how long you think the task should take and the quality of the output. If the person takes longer, don’t fret. This may be part of your process to letting go of some tasks.
  3. Be sure to give reasonable deadlines and communicate your expectations.
  4. Use a password encryption tool like lastpass.com or 1password to protect your passwords, your data and web assets.
  5. If needed, you may require your new freelancer to complete an NDA to protect your client and your interests. Be sure that this is stated up front and used as a stage to disqualify candidates.
  6. Setup regular video call meetings to discuss progress, be human and show interest in the person who is helping you out. They are human too and do need some love and attention too. Work does not always need to be transactional. Develop the relationship.


Outsourcing can be exceptionally difficult the first time. We feel that creating a process to find the right people is imperative and we hope that this 5 stage guide helps you in finding the right resources.

Comment below to tell us what you think and share your process with us. Perhaps there are stages you have implemented and we would love to hear about them.

Burhaan Pattel

Burhaan Pattel

Founder of Bridgeight - Digital Bridge Builder, Certified Google Ads Partner, Facebook Marketer, Funnel Builder & Coach.

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