Outsourcing 101 Course Podcast

Managing your freelance workers

Episode 16 of The Free Outsourcing 101 Course


In this episode James Mackay goes over the can-be-stressful subject of managing freelance workers. Learn the tips for an efficient workforce. Check out http://outsourcing101course.com to sign up for The Free Outsourcing 101 Course that includes 15 video tutorials and much more!

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Hello my fellow outsourcers and welcome back to another episode of the free Outsourcing 101 Course podcast. In this episode we are going to talk about managing your freelancers. If you’re not careful, managing your freelancers can become a full time job. It can become very frustrating and very unproductive.

So right up front you have got to set yourself goals and lay down your expected outcomes. Critically you need to avoid being a micro manager or being one of those people who peers over the virtual shoulder of your employees, because let me tell you now, you are going to find your productivity slides and your freelancers are going to find very quickly that it gets frustrating.

Upwork has a cool little feature for outsourcers called the “work diary” and the work diary actually allows you to see screenshots. These are randomly captured during the period your freelancers are working.

Now, it is tempting to log on there repeatedly and to have a look and see what they are doing. Most important you want to make sure that they are actually working for you and not Skypeing or Googleing or whatever they might be doing.

But, in all of the time that I have been doing outsourcing I have only ever once seen one of my freelancers not doing their assigned task. So generally speaking you don’t need to worry about that. What you can do is use the work diary to make sure that what they are doing is heading in the direction that you want them to.

For instance: It’s easy to see what a graphic designer’s working on but it’s a lot harder from a screenshot to see what a sound engineer or a web developer is doing.

I’m not a technical person and I certainly can’t read programming code, so when I see that in a work diary I just have to assume that the code on the screen has to do with the job that I have hired them for. So let’s talk about how we go and manage our freelance staff.

There are three general ways that I try to keep things efficient and they are all online solutions, and they all involve me and my freelancers.

So the 1st step is:

Content Management

2nd step is:

Setting Goals and Tasks

And the 3rd step is:


Now, when we are talking about Content Management we are talking about managing files and so on. It’s critical that you have a well-organized and well-managed method of handling files.

So what I mean by that is, you could use something like “mail big file” or simply use email but very quickly different versions of files and will end up getting confused and mixed up and you will be in a world of hurt. You won’t know the status of your files, you won’t be able to keep track of what’s going on and your freelancer will probably end up getting confused as well.

One thing you can do here is to simply go ahead and use Dropbox. And Dropbox is free up to a certain level and gives you storage for whatever amount of gigabytes they are offering at the moment.

If you don’t want to use Dropbox you can use something like Google Drive or any of those other online cloud storage providers, however, it is critical that you provide access to your freelancer so they can upload, download and share files from there with you.

Now, there is a bit of trust involved because if your team is working on confidential files, you need to trust that they are not going to share them with anyone else.

The 2nd part of what we do when we are managing our freelancers is to make sure we set goals, tasks and to-do’s. I have been using the online project management software Basecamp for something like 10 years. I still use Basecamp Classic because it’s the one that I’m in-love with and I really can’t see the point in upgrading to the new Basecamp.

However, if you want to jump on to Basecamp.com you can get a very cheap project management system up in a way and I THINK they still have a free system…

I use the plan that costs me about $20 a month and that seems to be more than I need. It’s got lots of storage space and project limits and so on…

Now what we do with Basecamp is use it as a project management tool. Other suggestions might include Trello or Asana but to be perfectly honest I did sign up for those and found that they didn’t do anything that I couldn’t do on basecamp so I just stuck with what I know.

Basecamp is a project management tool that allows me to set what the Army would call the ”commander’s intent” so I can say to my freelancers: “Okay team, what we are trying to do is to build an ecommerce website” or “We are trying to build mobile app” and then I can go through and explain what we are trying to do, bit by bit: “The mobile app will do A, B, C it should run on X, Y, Z platforms, we will put it in The AppStore, etc… etc…”. I just go through and explain what’s going on.

At this point you do need to share your business idea and goals with your freelancers so they understand what’s going on.

There’s no point trying just to say “well I don’t want to share my idea with them” because if you don’t share your idea with your team, they are really not going be able to provide the solution that you need. The next thing you want to do with basecamp once you’ve done your commander’s intent is to set up the to-do’s.

Now you can group the to-do’s under different things so you might say “Ok, we are making a mobile app so we have to-do’s in a number of different areas…

No. 1 is for the the AppStore, and then you list all of the to-do’s to do with the Apple Appstore. Sign up for an account, Get the Apple authorization code, etc etc.

When you assign a task, you can actually put who you are assigning it to and when it’s due by. And now, you go through and assign all of the tasks that you can think of for each component of your project. We have a list of to-dos for the AppStore, and then We have a list of to-dos for designing the app, and then We have a list of to-dos for developing the app.

So, all of these are different phases so you go through and list them all out and then create a to-do list for each one.

Don’t be unrealistic with your to-do dates. Tasks do take time and what the lay person thinks take 5 minutes will probably end up taking a developer half an hour.

So, just bare that in mind, don’t be unrealistic and don’t be upset when a freelancer does take half an hour for something that you expected might take 5 minutes.

One thing that always seems to happen when an outsourcer hires a new freelancer is that there’s a thing called “feature creep”. This phenomenon occurs when the outsourcer decides that they want a extra features after development has begun.

Here’s an example: the developer starts working on the agreed features and as they work on the project the outsourcer gets feedback and has a look and then realizes “Ohh hang on if that’s going to be like that then we need to put in this feature and that feature. “

So, the project that started off with 100% of features soon blows up to 110, 130, 150 percent of the original task. If you have very well-expressed what you are trying to achieve with that project, then the developer would have gone ahead and planned 100% of the project. But, once you start bringing in extra features their initial plan might have to be turfed out. All of a sudden a small feature may actually throw out your whole plan.

So, you have to be cognizant of the fact that your freelancer isn’t going to be able to necessarily achieve the things that you think are small features but actually have larger, overriding consequences.

This is just something I found over the years, if you can get away with it then great but I’m just saying be warned… manage your expectations and understand that this could take a while.

Now what you do with the to-do’s is actually assign them to the freelancers. When they complete the task, they log onto basecamp and they tick them off. It works really well.

But we don’t use basecamp for day-to-day communication, as it’s more for objectives and goals. For day-to-day communication, we use a thing called “Slack” S-L-A-C-K.com. It’s a free messaging service, very similar to Skype except a lot more powerful.

You can use Skype if you have already got that. It’s a good, basic way to get started but I have found that Skype does have limited capacity to handle files if you want to attach a file to Skype it does seem to take quite a long time to upload and download, with Slack it integrates with the number of different file management and sharing apps so it seems to work a lot more easily.

So, files aside I do think Skype has missed the big opportunity here, they thought the world would go for audio communication so they built that platform around Skype “calling” but unfortunately for them it seems that text chat is still going strong.

Now, avoid the temptation to be texting your freelancer every 5 mins… “how’s it going?”, “give me an update”, “can you show a screenshot blah blah blah blah blah…”

Bear in mind there’s a concept called “the managers and makers”.

Now, you as an outsourcer are adopting the role of manager, your freelancer who’s trying to complete the task for you is in the role of maker.

Now makers and managers have different mind sets and a maker will like to sit down and work uninterrupted for 3 or 4 hours to try and complete the task. They get in the flow, they get the momentum, and they just want to keep going.

And manager on the other hand, is really good at delegating and really good at multitasking and says “right I’m doing boom this list here and I’m doing that design over there, I’m doing that to-do list” and you think you’re doing a great thing but managing all of these different tasks once and trying to get your… you know multiple freelancers working and answering your questions and trying to get your responses back in on time and so on and so forth…

But what you’re doing is actually having a negative effect. All you’re doing then is really just making it more difficult for your freelancer to get on with the task that you have set them.

What you can do is say… let’s just say you’re doing a design task and you set a to-do list for your designer and you want them to design a logo or 5 draft logos. You might say to them “Ok I want you to spend 1 hour and do as much as work in 1 hour as you can and then supply me with screenshots of what you have done at that point. So, if you set the parameters upfront they know inaudible 55 minutes designing a logo and then 5 mins preparing the screenshots. Make sure you tell them a time and say “I will check back in with you at X” and they will be more likely to be able to show you something.

Now, if you try and interrupt them and send them occasional or informal messages on Slack or Skype then they’re going to get disrupted, the work that you are paying for will be inefficient and the solution won’t be as good as if you adopt manager and maker roles and let them just do their thing.

So, those are the 3 online tools that I use to manage my freelancers. It doesn’t matter where you are in the world they are all web-based, doesn’t matter where they are either because so long as they have Internet connection they can jump on and work with Dropbox, work with Slack, and work with Basecamp.

And if you set the parameters to manage your freelancers and you allow them to understand what you expect from them and then you follow up in an appropriate manner with appropriate communication then I think you’ll find things will work a whole lot easier.

Thanks for tuning in once again to the Free Outsource 101 Course podcast. I look forward to speaking with you again on the next episode, which is “4 biggest mistake outsourcers make”