Frequently Asked Questions

Outsourcing Work to Freelancers 6 questions
  • Is outsourcing similar for all job categories?

    Press release was just an example (refer next question below), and maybe the marketing team should have written it themselves since it’s probably part of their job description, but nonetheless, the process is similar for outsourcing any services or technologies you have no experience with.

    That’s why I wrote “Outsource That – 10 Most Popular Types of Outsourcing Categories” to give you the best chance when getting started with outsourcing marketing and technology services.

  • What if I am outsourcing work in an area that I am unfamiliar with?

    If it is unknown territory it poses a big challenge because this is work that you don’t know how to do. You know what finished product you want but are not sure how to get there, thereby putting you at a disadvantage.

    Let’s say you have been asked by your marketing team to write up a press release, but you don’t have any idea how to do this or where to start. Don’t panic. Start by gathering as much information as you can about the job. This will allow you to understand the requirements before you do anything else.

    Your marketing team has asked you for this so start off by grilling them for information as soon as possible. It’s best to do this over email so you get it all in writing in order to be able to copy and paste things together. You can even act a bit dumb, so they give the most detailed explanation possible. This will help later when you outsource and are writing the project description.

  • What if I am outsourcing work in an area that I have an expertise in?

    You are at an advantage here because you know how this job is performed and understand its rudiments, so you should be able to communicate with your freelancer about the subject in a technical way.

    You can ask applicants about the software used (i.e. accounting packages or others as the case may be) to figure out if they really know what they are doing.

    You can also scrutinize samples of their previous work (although in the case of accounting, privacy issues may arise with work from previous employers).

    Generally, it is relatively easy when it comes to identifying suitable freelancers in your own field.

  • What does it mean to feel empowered with outsourcing?

    I became empowered right from the very beginning which inspired my book “Empowering Your Employees with Online Outsourcing”. I can still picture where I was at the time. The website was called, one of the most popular websites before it was bought out by, the largest crowdsourcing website next to

    To me, it felt like I gained the power to do anything that night. I had been trying to teach myself programming so I could modify my website and suddenly, I found I could get the software and website help I needed for $20 – $30. I didn’t have much money, so all I could do was experiment to see what happened.

  • Is it difficult to become an established employer of freelancers?

    The quality of freelancers improves when employers have good reviews because they have earned more trust. Employers are building a reputation for themselves to enable them to make good hires.

    There are also freelancers working on these websites building reputations, doing what they are good at and getting better with the more experience they get. This makes it easier for them to get approached by good quality employers because of their reviews and proof of past successes.

    Freelance marketplaces can be classed as social marketing websites where people of similar interest come together for similar purposes, posting content for different types of reasons. With outsourcing there is a lot of social proof involved amongst its members. Employers are seeing comments left by other employers and freelancers are seeing the comments left by other freelancers.

  • Were you a successful freelance employer since the beginning?

    Right off the bat, I had a lot of success. I never got ripped off and found that no one was even trying to rip anyone off. I made some mistakes, but I have learned along the way that “you get what you ask for”.

    A lot of outsourcing horror stories are from people who make mistakes themselves then blame the freelancer when the final product is not what they expected. The job of a freelancer is to read the project description and provide what they believe is the requirement, so be careful what you ask for.

Project Management 3 questions
  • Is it helpful to write descriptions with industry jargon?

    If you have enough understanding about what you are trying to outsource and can speak some of the lingo, there is no reason why you shouldn’t succeed. From all my hundreds of experiences with freelancers, I have learned that they are genuine people trying to build a good reputation doing the thing they enjoy and are good at, which inspired my book “Online Freelancers from a Buyers Perspective”.

    They have their own fears too, like not getting paid for their work or getting poor reviews on their profiles. If you find a freelancer that has done three projects and gotten five stars for each, then you know they are good and that they are going to try their best. They need to build a good reputation, so they will work hard not to tarnish their profile with a bad review. Just like you, they need to succeed at their job.

  • Why is a project description so important?

    Now that you have an idea of what to ask for, how do we identify the right freelancer for the job? Your project description is what is going to attract applicants, they will judge you and the job by the way you have written it.

    Let’s say you post your project and you get 20 replies, which can happen easily especially for writing projects. You need to develop the art of skimming and rejecting the cover letters you don’t find attractive. Some ways to quickly scrap profiles is by discarding ones that don’t have any useful information, provided no sample work (depends on type of project), or have poorly written cover letters (e.g. uses all caps or all lower case).

    Quickly eliminate cover letters with slang, familiarity, or anything that is not professional or a turn off, hopefully then you have narrowed down your bids.

  • Why is project management important?

    I’m not the most disciplined person, a lot of things about project management put me off. I’ve created a book called “Managing Outsourced Projects with SPEED” and it is dedicated to, you guessed it, managing outsourced projects. SPEED is an acronym for a frame work I developed that helps navigate an outsourced project online. I keep it quite basic and it is helpful when first starting out.

    This is not meant as an ad for the book. I’m just saying that you don’t have to use Gantt charts and spreadsheets and all those other things because at the end of the day it is between you and your provider and how you work together over the computer.

Budgeting 5 questions
  • Is it acceptable to limit funds for a specific task?

    It’s fair to have a budget, outsourcing allows you access to a range of providers where there are some people willing to work within your budget.

    If it is lower than you might think acceptable, add it to your project title so people find it easy to avoid if they think it is too low e.g. “10 Articles about Dog Training – Budget $20”.

  • Can you explain the math behind budgeting?

    Let’s say I hire Sue to design me a logo for $30. Now that is USD$30 and let’s say Sue lives in New Zealand (because it is easier for the sake of this exercise).

    My budget of $30 USD ($45 NZD) subtracted from Upwork fees 20% gives us $24 USD ($36 NZD), which is what Sue the freelancer earns.

    That means that if I set a budget of $30 on a project, I know it will cost me $45 and I know the freelancer will only get $24. It seems odd that people would work that way, and you can see why they would be tempted to work off the site then make payments through PayPal.

  • Can a projects value be based not on money but more about desire to have?

    It’s all about VALUE. Sometimes value will be your motivation. How much do you desire the outcome, and how good do you want it to be?

    Say you have just written your thesis. It’s taken you three months, you love the result, and you know it’s a winner, but you also know your English is very poor.

    Would it be worth spending $30 to have it edited and proofread by a professional?

    Think about it. There is only so much you can do alone, so wouldn’t you appreciate as much help as you can get? You only have so much money, but you would be surprised how far it can go. Let’s go through some math.

  • What if I always offer a limited budget because I am trying to save money?

    Depending on how you go about this, certain attitudes will be picked up on and may cause a sense of distrust. At the very least, promise good reviews and try to hire people looking for their first project. This way, you will enjoy getting a good review too. Try to be a mentor and pay them back with kindness.

  • What if I have a limited budget for a project?

    I very rarely negotiate prices. Usually, if I get into a conversation where my budget is being questioned, I just say thank you for your time and move on, I know that might sound arrogant but let’s back up. First, let’s look at three scenarios that lie behind most pricing decisions:

    From the Outsource That Professional Book Series:

    An excerpt from the Conclusion of our book: Tips for Selecting and Hiring the Best Online Freelancers…

    So, for the job to end well, it must also start out as perfect as possible. Do not be afraid to get into the nitty-gritty details before the actual freelancer search process. Preparation must always be a priority in any aspect of life, in any industry. Hiring the right people to do the job will make all the difference to the success of your company.

    All in all, the general principle could be summarized in 3 short sentences:

    • A happy workplace means a happy worker
    • A happy worker means a job well-done
    • A job well-done means a happy employer

    And you, quite literally, have the world at your fingertips. It’s up to you now whether you just read it or act on it.

    Online outsourcing is one of the most effective and profitable tools used by business owners today, and it is my mission to help you use this tool to your benefit and get the most out of it by finding and hiring the best freelancers available.

    I have provided you with key tips for finding and attracting skilled and qualified candidates so that only the best work is delivered to you. I hope you have enjoyed this book and it has given you the expertise and courage that you need to find success in your outsourcing journey and all your business projects. The help you need to succeed is out there.

    Take advantage of it – make it happen.

    From the book Tips for Selecting and Hiring the Best Online Freelancers – Outsource That.

Finding Freelancers that are a Good Fit 8 questions
  • What about freelancers without any job experience?

    Let’s talk a bit about newcomers: young, fresh university graduates in India, the Philippines, Indonesia, Russia, all over the world, people who have never had a job or worked for an employer online or offline.

    There are a lot of young people, and adults as well, joining freelance websites with no job history or sample work, with graduation photos as profile pictures. If you’re going to work with them and accept their cheap prices, try to drop the role of employer and instead act more like a mentor. If you guide them, both of you will have greater success.

  • Is it logistically difficult working with a freelancer in a different time zone?

    With online outsourcing, unless you only hire people in your country/time zone, you are going to have to work with people in different time zones. To some this might make them uncomfortable but once you get used to it, it is not too bad.

    In New Zealand, I know that in the Philippines everyone is going to be starting their day during my lunch time so it gives me time in the morning to prepare work that I can pass it on in the afternoon. While their workday spills over into my evening, I can work with them at home once I get home from the office, if need be.

    That’s one example of how conflicting time zones can work. India comes online in the early evening and, is still online in my early morning. I can give them work at night and check it the following morning, this is another example of making the time difference work.

    If you hire one or more people on an hourly basis you would be surprised how willing people are to work through their night and sleep through their day if you prefer them to be available during your working hours. This is easily organized and is common practice.

    When working on most projects, time difference isn’t much of a problem. All you need do is to work out the best times to communicate and this can be done through the private message board of the freelance website you work on. You might only find that you need to communicate every two or three days depending on how well the project is understood by the freelancer.

    I have only mentioned India and the Philippines so far. Countries like Venezuela, Russia, Poland and other European countries are online when I am online during the day so there is no shortage of help when it is needed.

  • How can I avoid dishonest freelancers?

    Once, a freelancer misrepresented herself to me for a writing project. She had a US profile, a great cover letter, and our interview went well. Despite this all, what I got back was crap. It appears she had outsourced it to someone who had no real grasp of the English language. I shut down the project in disgust.

    Now this was rare for me, but I wasn’t willing to get in a conversation about it, I had waited a week and I was busy at the time, so I made a two-minute video pointing out the errors. After sending this video to the freelancer, I never heard a word back, my money was refunded, and I moved on.

  • How do I know if freelancer credentials are legitimate?

    So, what about genuine credentials? On freelance websites, freelancers post their profiles and list their education, specifying whether they have a diploma or a doctorate in a field of work. Ask yourself, what sort of credentials do you need in a freelancer?

    If you want to hire someone who has a law degree, for example, then you might start off by looking for someone who says they have a law degree and has done several projects like yours and received 5-star reviews. That is proof that they are qualified.

    Online Freelancers are more than just a bunch of qualifications. Have a look at our blog post “7 Things to Help You Understand the Online Freelancer“.

  • Can I invite qualified freelancers to my my job opening?

    Most freelance websites have a place you can search for freelancers and invite them to your project, so take advantage of this service. In your searches, you will find people who work in the area you seek and have had many satisfied customers. Be careful about hiring outside of your country for certain projects, though.

    Let’s say you are hiring a lawyer to write you some contracts and you get a great offer from a man that has studied law in Singapore, but you live in New Zealand.

    Like me, you would have to get a local lawyer to look them over before you could use them safely.

    We have a book that covers contracts “Using Contracts when Outsourcing to Online Freelancers.”

  • Should I be intimidated by expensive freelancers?

    Freelance websites give you the evidence you seek. Maybe the more experienced people are more expensive, but they often have lots of good reviews. Don’t be intimidated by people that have hourly rates of $120. I have had them bid on $30 jobs that I know will take them at least 3 or 4 hours and they perform just as well as people with hourly rates of $12.

    You must realise you have the one thing freelancers need: money. If your budget is $30, all they need to know is the task and they will do it, simply because no one else at that time is offering them an alternative. If freelancers were sitting there while a dozen different employers were placing bids on their time, it would be a different story.

  • Why should I screen a freelancer by reviewing past experiences?

    As you sort through the bids you have received there will be one that speaks to you; it will feel right. Once you’ve done your due diligence, checked out the freelancer’s details and made sure they fit, reply in a professional manner.

    Once you provide the rest of the guidelines for the job and have some discussion of the expectations, the freelancer can begin the job, it really is as easy as that.

  • How can I effectively narrow down the best freelancer for the job?

    Start looking at your budget and the range of bids you have received. If you have listed a $30 budget, the chances are all the bids will be $30, but at least one will be $300 dollars – insane right? Maybe not. Some copywriters charge huge fees but the results they get are huge in comparison, so you may want to consider that. It’s another learning curve stepping into the world of copywriting but if you have the budget, go for it.

    Conversely, a $5 bid may seem weird but then, this person may be willing to work for almost free if they get a good review. The calibre of this applicant may be surprisingly good, or they could be a dud. If you do hire this applicant to do the work and the return is great, you may want to pay the original budget just to say thank you and make it worthwhile to the provider.

The Process of Hiring and Working with a Freelancer 4 questions
  • Are freelancers usually willing to revise their own work?

    This happened again with another writer who had done a lot of work and asked me to give her a chance in correcting it. I said yes, but cautioned her that if the work needs editing, I wouldn’t accept it and she agreed. Even though I waited a while, what was eventually delivered to me was immaculate and a high quality. It is not that common for freelancers to outsource their own work when they get overloaded, I sometimes suspect it has happened, but I can’t be sure.

    There are several training courses and coaches for training freelancers, that recommend freelancers outsource their overflow to stop them missing deadlines. Just like anyone, freelancers make mistakes, but they really should check the work thoroughly before passing it on to the buyer. A little advice would be telling your freelancer you will only accept work from him or her and not a third party.

  • Should I provide mentorship to emerging freelancers?

    If you are on a bootstrap budget, then mentor some of the newcomers and benefit. Just be sure you are going to give clear, concise instructions and be prepared to pay for the mistakes you make. It hurts when you must pay for something if it is useless, but it’s not fair if a freelancer spent a week following your sloppy instructions and goes unpaid. If you do have to admit you are wrong, it’s a good feeling when you sense their relief and gratitude for you being humble.

  • What happens once it is time to hire a freelancer?

    If you have been interviewing a freelancer and are ready to hire, you can send a final invitation to hire, depending on what website you are using. This tells them you are happy and gives them the final decision. When you send the invitation to hire, you can change the terms of the project description (optional).

    Be sure to edit it to cover everything you have discussed in the interview to match what you both agreed to. This way, when freelancers accept it, they will have agreed to the new terms. This serves as a great fall back if anything goes wrong with the project and you must go into mediation with the freelance website support staff. This proof of what you agreed to will help you get a refund from them if you are not happy. I have more advice in my book: “Tips for Hiring the Best Online Freelancers“.

    There is a bit more to it, but generally, if you find someone with proof of past successes you will come out on top. Believe me, your first successful project will stun you with the high quality you receive for the little money you spent.
    Most freelancers just want a job and to prove themselves deserving of a good review so they can start to build their profile. Now that you have learnt more about freelancers, let’s take you through how best to overcome the challenges language and time-zone differences bring to the client-freelancer relationship.

  • When should I start interviewing freelancers to hire?

    Hoping to start up a dialog, some freelancers will ask questions, and how you manage this depends on the type of person you are.

    When you first make contact with a freelancer it is classed as an interview. Having a freelancer to guide you through the steps may be exactly what you need, but if you are the type of person who finds it hard saying no, you may get hooked into hiring the first person you talk to.

Communication 4 questions
  • What do I do if a freelancer speaks a different language?

    Language barriers are something you may run into, but you don’t have to. You can always hire only people from your country, it’s still cost effective, it depends on how you look at it. Let’s say you live in the US and you hire a US graphic designer for $12 an hour, this is still much less expensive than hiring an employee and it’s a lot cheaper than hiring a professional designer in the yellow pages. Its more expensive than hiring someone from another country for $5 to $8 or thereabout but if it helps you to feel secure then it’s a great place to start.

    Starting with a fixed price project is safer and you will still get your US provider, unless you meet someone else along the way.

    Let’s talk about writing for a moment, there are lots of reasons you might use writers and I recommend you use an English writer from an English-speaking country if you want good quality writing. I would also say that there are a lot of foreign people living in English speaking countries who are not great writers make sure you get samples before you hire anyone.

  • What are the most annoying things freelancers do when communicating?

    You start up a dialog with someone and they only use 3 or 4 words in every message, avoid them. If they are not going to make the effort, it’s not worth it.

    Another pet peeve, you spend hours planning a project, you write a great project description, you attach a brief to the project explaining what you want and how you want it presented etc. You post it on a freelance website and get lots of bids. Suddenly, you get someone who bids half of your budget and you get excited, so you start up a dialog. Their opening question is “What do you want?”

    Either you are a bad planner and communicator, or you begin to doubt yourself, seriously!

  • What are some tips to communicate effectively with freelancers?
    1. Use simple language
      Use simple language and keep emotions out of it as much as possible. If you get a reply that you don’t understand, check that they understood your message properly.
    2. When on the phone or Skype, speak at a steady pace
      Speak slowly and be specific. Use words that you know they will understand. Don’t interrupt the other person and always say thank you and use good manners.
    3. Use screenshots, diagrams, and other images when communicating
      Use whatever tools you can find to get the message across. Make sure you itemize each step so they can follow your instructions easily.
    4. Regularly check for comprehension
      Before hitting “enter”, have a careful look at what you just wrote in your message, quite often you can’t edit your messages and if you rush you may write things that have double meanings, or you might misspell their name.
    5. Religion
      One thing you must always remember is that freelancers in different countries have a lot of religious beliefs and can be easily offended by offensive language or spelling their names wrong.

    Be sensitive and polite and you shouldn’t have any problems. If you are prone to anger or anxiety, take a short break and come back refreshed. It’s not worth ruining a working relationship by overreacting and hurting people’s feelings.

    Somethings we make a big deal about things, but really, they are small if we know how to manage them properly. Next up we learn that we don’t need a huge budget to work with online freelancers, and still get value for money.

  • What are the best strategies to communicate with freelancers?

    Communications a big deal on freelance websites, you need to be able to communicate with freelancers and get your requirements across. There are lots of different types of communication:

    • Writing
    • Phone
    • Skype
    • Messenger etc.

    Phone or video messaging will give you a better idea of who you are dealing with, but writing can be more specific, and you can take time planning and editing until you come up with the perfect description and set of requirements.

    A great tool is screen capturing software like Snagit, you can record the desktop, speak your requirements and you can save it and recall it later. It is great for marking up corrections because you can say what you think is wrong and how it can be corrected.

    Project management software like Basecamp is a great tool because there are so many different types of communication like built-in messaging etc. too much to go into here.

Intellectual Property 2 questions
  • How can contracts be useful to protect intellectual property?

    This is one area where you must be very careful and you must use contracts. One other thing you must also be aware of, freelancers are online to do projects in their area of expertise, that’s all they want to do, and they want to get successful and build a good reputation. It takes a special person to take an idea for a product or an app and make it real and then market it and get rich, these are things that you are good at, don’t hire a copy of you, hire a specialist in the area where you need work done.

    If it’s a 3D model of an idea you are considering, or a market research report, or even a product description, these are projects you can safely outsource online because there are lots of people who specialize in those things. People aren’t sitting there trying to find ideas to steal, or at least I have never come across one in the twelve years I have been doing this.

  • Are there ways to protect intellectual property?

    Freelance websites give you the evidence you seek. Maybe the more experienced people are more expensive, but they often have lots of good reviews. Don’t be intimidated by people that have hourly rates of $120. I have had them bid on $30 jobs that I know will take them at least 3 or 4 hours and they perform just as well as people with hourly rates of $12.

    You must realise you have the one thing freelancers need: money. If your budget is $30, all they need to know is the task and they will do it, simply because no one else at that time is offering them an alternative. If freelancers were sitting there while a dozen different employers were placing bids on their time, it would be a different story.

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