How To Successfully Hire and Work With Freelancers
Sep 12
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Dr. Cynthia D. Wiggins

What is a Freelancer?
Freelancing is a form of self-employment with a freelancer working on a job to job basis. Usually the projects will be on a short term basis, so maybe from a couple of days to a couple of months, but it normally would not last for years.
With most freelancers working remotely and not being expected by the the business to come into the office. So you may hire a person in India some person in the UK, some person in Canada, some person in the Caribbean, even though you are located in America.
Can a freelancer work on various client projects?
The freelancer can work on various projects for the client, but in most instances, the freelancer can also work on various projects for themselves because they're considered self-employed. A client may say you are working on X project this one is also similar to that. I want you to work on this, but what I would say is that if the relationship is new that you don't seek to actually employ the same freelancer on several jobs in parallel, simply because you want to reduce your risk.
You're trying to reduce your risk if you know them for a while and you've worked with them on a regular basis. Yes, I would say it would be great to actually provide them with more than one project because it means that you can guarantee the quality of the product or the service that you're getting.
You would not want to have them working on several projects with you because there is a risk with working with a freelancer. They're not employed by you and therefore, if they are sick, if they happen to have any personal issues, you may not be able to get ahold of them and you still have your project to complete.
You're trying to reduce your risk if you know them for a while and you've worked with them on a regular basis. Yes, I would say it would be great to actually provide them with more than one project because it means that you can guarantee the quality of the product or the service that you're getting.
You Can Also View The Video
You can click to watch A Business Podcast With Dr. Wiggins Episode 1 or continue reading below. In this first episode I seek to help you understand what building your team with freelancers would be like by delving into a discussion on how to successfully hire and work with freelancers.
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What are some of payment terms in a client-freelancer contract?
When you're hiring a freelancer, they may ask to be paid on an hourly or fixed term basis. Those are the two main ones, especially if you're using an online platform, but there are also instances where a mobilization fee may be provided or they may ask for a mobilization fee, or they may ask for a retainer, which is similar to a mobilization fee it just means I want something upfront to be able to start this project because it's going to cost me X. You usually have retainers and mobilization fees when you're not working on one of the platforms. The platforms actually help with the mobilization fee by placing money into escrow. You as a business owner will place the money into escrow, and then the freelancer would know that they can actually start the job because you're serious about it. But the escrow on most platforms act like a mobilization or a retainer fee in real life.
When I hire, I tend to hire on a fixed term basis, and that is for a number of reasons. One, it reduces my risk and my cost, so it is not a matter that the freelancer is working on an hourly basis and I'm paying on an hourly basis and quality is not included into that. Because you can easily go way past when the project should be completed and therefore you're paying that cost, while with a fixed term contract, quality is built into it. So therefore, we've decided that this is what the scope looks like for this project, and this is when both of us know that this project has been completed and therefore the money is then paid out. I also think it benefits the freelancer in that if they finish a project early, they're not penalized, and it does not form a bad relationship between them and their clients where the client now starts to question why something is taking so long.
Additionally, for the client, you have instances where you may say, look, I don't know if this person can actually do the job, that they indicated that they can. They may be able to finish the job, but they may finish it at a slower rate than someone who has more experience and again, that affects you. It may benefit the freelancer in that case, but it wouldn't benefit you as the business. So I always go for a fixed term contract. However, with a fixed term contract, you have to understand and know the scope of the project you can't be shifting the scope. It can't be scope creep because in essence, that's also unfair to the freelancer, and it will just mean that the project becomes, problematic in general.
What is the benefit of hiring a freelancer?
The benefit for a company to hire a freelancer is that it helps them with cost reduction. Instead of employing a person where you may have to pay a salary, have to pay their benefits you now how some person who is working with you, will be able to do the very same job, but is self-employed. So you don't have the added cost of hiring some person and paying their pension, but the thing about it as well is that it also allows you to be able to hire some person from anywhere in the world, and therefore you're not limited to where you are and the skill sets that are within your country or within your area.
Considerations when hiring a freelancer.
When you are hiring a freelancer, you should take into consideration that the person is not just a cost to your company the person is actually someone that is bringing a benefit to your company because they're either going to let you be able to focus on something else, more strategic or be able to ramp up a little bit quicker.
Take into consideration as well that anyone can hire a freelancer. It can be a non-profit. It can be an individual who's trying to start a business and is in the startup phase of the business. You can be a sole trader, a LLC, but you can also be a global organization. A lot of bigger companies may seek to hire, either staff or agencies instead of saying, I will look at a freelancer in performing this task, but that is also open to them. I would say that the main thing that you need to focus on is, what am I gaining as an organization or individual by hiring a freelancer? And then what is the return on my investment? Because that is essentially what a freelancer and hiring a freelancer is. It's an investment and you expect a return out of it.
Take into consideration as well that anyone can hire a freelancer. It can be a non-profit. It can be an individual who's trying to start a business and is in the startup phase of the business. You can be a sole trader, a LLC, but you can also be a global organization. A lot of bigger companies may seek to hire, either staff or agencies instead of saying, I will look at a freelancer in performing this task, but that is also open to them. I would say that the main thing that you need to focus on is, what am I gaining as an organization or individual by hiring a freelancer? And then what is the return on my investment? Because that is essentially what a freelancer and hiring a freelancer is. It's an investment and you expect a return out of it.
Consider whether using a freelancer is best for your business?
As a business owner or a professional, you also have to do some sort of introspection and determine whether or not you are willing to give up autonomy to another person to perform this task, and are you in a place where you can manage the person and this project?
You should have an idea of the skills that are involved in performing the tasks that you want to provide to a freelancer or give a freelancer to work on, even if you don't know how to actually, perform the task. So say for example, you may not know how to develop a website but you want someone to develop your website. What I would suggest that you do is that you actually go online and you try to have an understanding of the skills that are involved. That is so that when you are specifying what the freelancer needs to do and the type of person that you're looking for, you know if the person meets the needs for the project or for the business that you have. Because it's very important that you have an understanding of the skills. And it is not that a person may tell you something that is incorrect or try to cheat you out of money, but it's simply to ensure that when you get to the quality stage that you can say the person had meet the requirements for this project. Because we started out knowing that the skillset for this project was X and you don't have a different expectation of what the project will look like, and then the person's skillset does not match up to what you envision in your mind.
Consider as well, the cost of the project.
If you want to let the freelancer tell you the cost of the project that you have scoped out and indicated that you want them to do in your mind, you should have what a project of the type and size should actually cost. And that is so that you know if somebody's overpricing you or if they're underpricing you, they may be underpricing so that they could get the job and actually try to change the terms and conditions, when the job is already assigned to them because they know it makes it a little bit difficult for you to then move on from them. Or it may simply be that they don't clearly understand the scope of the job and you know that maybe if you want to work with them, that you have to go back and say, look I think that you're underpricing me, maybe you don't clearly understand the scope I want to work with you, do you want to relook the scope of the project?
The other thing when it comes to pricing is that you are not looking for average, um, price for the project because an average, average takes into consideration the highest and the lowest to come to average. What you're looking for is the usual cost for a project, and that is simply so that when somebody comes to you with a cost, you can say, okay, I think that this is a fair cost.
Sometimes what I will hear from freelancers and individuals who work with clients is that they costed it at X and the client did not have any issue with it, and therefore that meant that they could have increased the price of the project, but that's not necessarily the case. And I could say in my own experience, when I don't object to a cost, it means that me and the freelancers were actually exact in what this project should actually cost. If they had gone a little bit higher, maybe I would not have mind, but if they were much higher than I had in my mind, or which they originally, priced it at, I would've said, okay, well this person is not for me, or they're overpricing the project. And I say overpricing because I don't normally, and I wouldn't advise a business owner to haggle with a freelancer. They have their own costs, they should be able to have the experience to be able to cost appropriately if you have a problem with how they are costing I would just simply say to move on and seek to find someone else. I would also say in costing, what I seek to do is get at least three quotes, and I can tell you without a doubt, if you get three quotes, there'll be one that's really, really high, there'll be one that's really low and it'll be one in the middle.
[00:11:57] It is much easier now to determine pricing for any job. If you are online, you can look at a platform such as Upwork, you can just look for the project and in most instances, you will see the freelancers that work on a similar project and you can just note the price that they would have been paid for a project similar to yours. Yes, you don't know full details or you don't know how long the project actually lasted, especially if it's a fixed one, but, you still will have a general idea. 99 designs and Fiverr tend to have set costs for set projects. They will allow you to work out the details for such projects, so it's very specific. It may say you are going to pay 500 dollars for a freelancer who is at this ability and they will do X, Y, and Z. That's how, Fiverr and 99 designs are, Upwork is a little bit different.
If you are offline, what you can do is that you can actually call persons who perform the type of service that you want and let them send you proposals or let them send you information on what the project would cost you. Sometimes you can simply just Google and see some of the costing and for similar projects. Even if you are not on Upwork or if you are not on Fiverr or you're not on 99 designs, just simply sign up and seek to search for the information.
Consider the project timeline
There are a lot of things that are involved when it comes to determining the timeline for a project. Skillset is one of those that will determine whether or not a person will be able to finish it very quickly or whether they will take a little bit longer because they have a learning curve that's involved there.
The other thing that you may seek to do to reduce the risk when it comes to timelines, is that you hire an agency instead of an individual because an individual, especially for very big projects, they can only realistically work on that project and therefore sometimes if the project goes on longer than they had expected, they are not paying their bills, and then they come to you and then it makes the relationship very complicated. So if a project is not, like say, proofreading or, editing something, and it's more in the realm of social media management or web development, to reduce your risk when it comes to time, I would say to get an agency versus an individual.
Consider the management of the project and freelancer.
There are a lot of things that are involved when it comes to determining the timeline for a project. Skillset is one of those that will determine whether or not a person will be able to finish it very quickly or whether they will take a little bit longer because they have a learning curve that's involved there.
The other thing that you may seek to do to reduce the risk when it comes to timelines, is that you hire an agency instead of an individual because an individual, especially for very big projects, they can only realistically work on that project and therefore sometimes if the project goes on longer than they had expected, they are not paying their bills, and then they come to you and then it makes the relationship very complicated. So if a project is not, like say, proofreading or, editing something, and it's more in the realm of social media management or web development, to reduce your risk when it comes to time, I would say to get an agency versus an individual.
Consider the management of the project and freelancer.
The management of the work with the freelancer is a very important one. You now become a project manager and you are no longer the individual that's actually doing it. So you have to take into consideration that you need to have either where they're messaging you on the platform , or you actually have some check-in times that you all have agreed on. Also if you have the project in milestones, you know that there's a set time when they're supposed to deliver X, Y, and Z.
I would say when it comes to communication, that you make sure that anything that was said verbally, is also placed in writing or recorded, and that is to make sure that if you miss something, you can actually go back and look at the recording. I know with Upwork that if there is a dispute regarding a freelancer saying, they want to be paid, but the project is not finished, but the client is taking really long, Upwork, will go back into the messages and see, whether or not the dispute should be on your side as a client or on the freelancer's side. Sometimes, depending on the cost, they will just say, I will give the freelancer the money and I will also, reimburse the client, but communication is very key there.
For larger projects, for example, web development, some persons may develop a project plan for you. I would say this, the development of a project plan does not mean that the project will actually be on time. Sometimes you can spend more time trying to develop the project plan than actually doing the project, and therefore that's just a waste of everybody's time. If the person does not have good project management skills, they still are not going to get the project on time. I would say meet, have some checkoffs and some checklists and say, okay, well we're supposed to come back at X time; we know that the scope is X and you say to the freelancer, I want to be able to, launch or have this project finish at X time, and therefore they're working back and say, okay, well I will give you this task at X time, or this milestone will be finished at X date, and that is to work back or work forward to the project end date. But things happen, I would say, one, give yourself grace if you are not finishing a project on a date that you expected it to be finished. But I would also say by mitigating some of the risk by using , an agency versus an individual can help with that.
Another critical business consideration is where do you locate freelancers for your project?
It is very easy at this stage to find a freelancer. There are couple of platforms now that offer freelancing services and they are between a client and the freelancers. So Upwork is one of the bigger ones. 99 designs is also one that I use specifically if there's design work that needs to be done. If there's ebook, if they're PowerPoint presentations , if there is any design work that needs to be done, I use 99 designs, and that is because of how 99 designs is actually structured. You can have a contest and post a job and say this is the details for the job, and then persons will bid on the job. By bidding on the job, they are actually providing you with designs. So in instances where you may not be able to determine if a freelancer's work, will be to the quality that you want it to be on 99 design, specifically with design work, you can tell whether or not, through the contest, feature that they have, whether or not the standards that you have, they have. And not only that, whether or not they have a base look that you're looking for, and then you can work with that person and there's specific stages that you will start then placing the money into escrow, but it isn't from the beginning. Then you work with one or two people and then you move on like that. But I find that that structure is very, very good to work with.
I tend not to work with Fiverr, and that is because of how they're structured. The freelancers will indicate the cost that they will give you for a project, and sometimes they will say, okay, well I'm only giving you one or two revisions. And realistically that is not to a business or a, client's benefit. It isn't that you want the ability to give revision ad nauseum and go back and forth and change scope or anything like that. What it does is that it limits you to quality of work and really and truly as a business owner, your main thing should be quality of the work that you get and not simply if a person meets a hard and fast number of revisions that they have.
Another critical business consideration is where do you locate freelancers for your project?
It is very easy at this stage to find a freelancer. There are couple of platforms now that offer freelancing services and they are between a client and the freelancers. So Upwork is one of the bigger ones. 99 designs is also one that I use specifically if there's design work that needs to be done. If there's ebook, if they're PowerPoint presentations , if there is any design work that needs to be done, I use 99 designs, and that is because of how 99 designs is actually structured. You can have a contest and post a job and say this is the details for the job, and then persons will bid on the job. By bidding on the job, they are actually providing you with designs. So in instances where you may not be able to determine if a freelancer's work, will be to the quality that you want it to be on 99 design, specifically with design work, you can tell whether or not, through the contest, feature that they have, whether or not the standards that you have, they have. And not only that, whether or not they have a base look that you're looking for, and then you can work with that person and there's specific stages that you will start then placing the money into escrow, but it isn't from the beginning. Then you work with one or two people and then you move on like that. But I find that that structure is very, very good to work with.
I tend not to work with Fiverr, and that is because of how they're structured. The freelancers will indicate the cost that they will give you for a project, and sometimes they will say, okay, well I'm only giving you one or two revisions. And realistically that is not to a business or a, client's benefit. It isn't that you want the ability to give revision ad nauseum and go back and forth and change scope or anything like that. What it does is that it limits you to quality of work and really and truly as a business owner, your main thing should be quality of the work that you get and not simply if a person meets a hard and fast number of revisions that they have.
You want to also consider contracts and non-disclosure agreements when hiring a freelancer.
On all of the platforms, like any internet based company website that you go to, there are always terms and agreements. There are general terms and agreements for using the platform, but then they may have freelancer client agreements as well that you should go through. It allows you on those platforms to be able to say, I have my money placed in escrow. If there's an issue, I don't have to pay it out. If they don't meet the quality that I am trying to meet. I don't have to approve the job until they actually meet that.
If you are offline I would also say that you seek to have a contract and agreement with the person. Sometimes, relationships as wonderfully as they start may sour in the process of you approving the project. You want to make sure that there's a clear indication in the contract of who's supposed to do what when money is paid out, and as I said, this is offline. You also want to read contracts to make sure that they are not simply in favor of the freelancer, because the contract, for the most part will come from the freelancer. And if it seems to benefit the freelancer have nothing, in how if something happens and they don't fulfill their obligation, what then happens or what they will do, you know, that you don't wanna work with that person. I would say make sure that you are fine with the contract and don't just simply agree with the contract and to sign a contract because you want the project started. Because you could start the project early with the intentions of it finishing in a week, and because the contract is worded badly or it is written badly, you have issues and the same project lasts you five, six months. I would say make sure that the contract is written in favor of the client as well. That is one of the reasons I tend to hire persons from a platform, because the platform already has , for the most part, built in safety nets, for me, feeling comfortable that a person who does not fulfill their obligation to me will not be able to, actually be paid.
You should try to make sure that if a project is done offline or if you hire a freelancer offline, and even if you hire a freelancer online, that there's a non-disclosure, aspect written into any contract that you sign to. You don't want that the project that's done for you, that they can use some of the images either in marketing or for promotional purposes, and then your intellectual property is out there. And you don't want them to tell your secrets or your business secrets to other persons. A lot of people have lost businesses simply because they did not ask someone to sign a non-disclosure agreement as horrifying or as pedantic as it may seem, and boring as it may seem to ask someone to sign in non-disclosure agreement. If they did not give you, it is in your best interest to either ask them to sign one, meaning you give them one or ensure that they create one that you sign.
Let's now look at the steps for successfully hiring a freelancer.
The first process for hiring a freelancer is to post the job. It doesn't have to be as detailed as a job description, but you want to actually post a job either on any of the platforms that they have for freelancers. If you're doing it in person, or over the phone, just specify via email or some written method, simply be cause it's in writing you got to be a little bit more detail, there's little area for somebody misunderstanding or misconstruing something that you said, in a voice or a telephone conversation. So I would say put it in writing.
Shortlisting the applicants is the second step in the process.
Fit assessment is step number three in the process.
Make sure that you place things in writing even if it's just messages or just emails, if you had a verbal conversation, make sure that you say, okay, in writing, this is what we discussed. So that, again, you all can determine if you're on the same page and there's nothing nefarious in that. The freelancer, may do it and you just go in and say, okay, yeah, we discussed that. This is fine. No let us add this. I said this and this. It shouldn't be seen as a combative process because it is really just them covering themselves, meaning freelancer, or the agency and you covering yourself, this is a normal course of business. So I would advise you to actually make sure that you have things in writing after a verbal discussion.
The final step in the process is quality check, approval and payment.
Shortlisting the applicants is the second step in the process.
When you do get applicants for the job, you need to start shortlisting the persons that you want to go forward with, want to have an interview with, and the shortlisting, on Upwork or any of the other platforms is very easy, you're just going through and saying, look, I'm going to reject this one. They don't normally see that you've rejected it and you're working with the considerations that you have from before, any job posting. So you're looking to see if the person has the skillset that you're looking for. If the application that they write seems very generic or it seems specific to you and your needs. Now we have AI tools that will write emails and proposals for persons, so you have to see if you have more than one person with the same type of generic proposal, and weed those persons out. I tend to look for success rate as well with that individual if they're doing things on time. I look to see proposal wise, if they have the skills that I actually want. I have realized that with covid, you get, a lot of persons now that may have started out in one field, branching out into another, and there's nothing wrong with that, but if their base, experience is not what you want, you have to determine whether or not that's the person that's for you.
Fit assessment is step number three in the process.
There's more to working with a freelancer, than simply if they meet the skill sets that you have. It is a relationship and you have to understand if you and the person can work together if you're of similar mind.
In step four you will refine the terms of service and contract.
During the conversation with the freelancer you flush out what this project should look like. Yes, you had a post, or you originally in real life went to a person to say, I want to hire you for your services. They may have a set contract, that is great. Ensure that what you all agreed on verbally is also within the contract.
Step five is where you will manage the project.
Recording sessions can be very helpful. And it doesn't have to be video, the person may be working at home and don't want you to necessarily see their home but you can actually have voice recordings.
Make sure that you place things in writing even if it's just messages or just emails, if you had a verbal conversation, make sure that you say, okay, in writing, this is what we discussed. So that, again, you all can determine if you're on the same page and there's nothing nefarious in that. The freelancer, may do it and you just go in and say, okay, yeah, we discussed that. This is fine. No let us add this. I said this and this. It shouldn't be seen as a combative process because it is really just them covering themselves, meaning freelancer, or the agency and you covering yourself, this is a normal course of business. So I would advise you to actually make sure that you have things in writing after a verbal discussion.
The final step in the process is quality check, approval and payment.
Either offline or online there'll come to a point where, there's either a last payment if it's milestone base, or stage base, or you are seeking to approve the entire project. And really and truly what you need to do is a quality check. Take for example, if it is development work that was supposed to be done and it's a website that they were supposed to complete, you need to go through and make sure that everything you want this website to be able to do it can actually do. So you are going in and even if they tested it, you also go in and you test it.
I only sign off after I've gone through all the edits and therefore, I am fine with all of them. I've asked you the questions and therefore I will sign off, but there must be quality checks.
With website design, it is not simply if the website is performing the task, but you are also, testing for errors within that actual design. A quality checking in any case is very, very important to say I am fine with providing the money because you can't get back the money after you've approved it, after you've given anybody money it's a difficult process to try to get back the funds that have already been given and they may have left with your money and you still don't have the project, or the service or product that you actually wanted. So I would say make sure that the last stage is a quality check before you sign off.
You can see the full video of my podcast A Business Podcast With Dr. Wiggins on youtube here.
You can see the full video of my podcast A Business Podcast With Dr. Wiggins on youtube here.