We’re now a Freelancer-friendly company (and why you should be too).

By Mark Jones

May 24, 2020


We’ve quickly made the move to working with freelancers to help us get over the constant roadblocks in our business. 

In this post, I want to give some insight into why we’re moving towards hiring more short-term, project-focused help. 

Who are we? 

At Collaboris, we run a network of sites under the “Collab365” brand which are aimed at serving the Microsoft community. 

Our mission is to: 

  1. Help people ‘learn together’ on all manner of topics around Microsoft’s huge product suite. 
  2. Help those who want to work for themselves become full-time Freelancers and not have to struggle to find work. 
  3. Help organizations find remote, Microsoft experts to help them solve the blockers on their Microsoft projects. 

As you can imagine, this is a huge undertaking for us. 

The roadmap and strategy we have laid down to achieve all that is very ambitious. 

We not only have to build new services but also maintain the ones we need to ensure those that consume our services to become highly successful and receive exceptional customer service. 

“Unbelievably” (when I think about it), we currently have just 4 people doing all of that: 

  • Hugo Esperanca: Is the “tech man” who manages the technology side of all that. 
  • Fraser Beadle: Is the “go-to man” for Collab365 MicroJobs. 
  • Helen Jones: Is the “wonder woman” for our virtual summits 
  • Me: I chop and change between all the above, but I am also building the “365ers” as a side project. 

Last year alone, here are some highlights of what we delivered: 

  • We ran 5 large virtual summits with well over 40,000 registered. This required us to create registration pages, lots of Facebook Ads, support attendees, development of our “conference platform”, onboard and manage speakers, run each summit, plus a whole lot more. 
  • We also managed to deliver a massive “regulatory” driven release for MicroJobs to help us support SCA (this is like MFA for credit card payments). 
  • We either wrote or produced thousands of pages across 65 eBooks. 
  • We reworked the Collab365 Community site, removing certain features in preparation for the big move to “365ers”. 
  • We moderated lots of our groups across Linkedin and Facebook with over 100k members on a daily basis. 
  • We 90% built a new platform called the “365ers” to provide a better home for on-demand content. (more news on this really soon). 
  • We onboarded and supported more customers with DocRead for SharePoint. 

We’ve managed to achieve all of that (with just the 4 of us), by some really hard work and huge dedication to the tasks at hand. However, we’ve also started getting help when we need it and where it’s easy to outsource a task. 

Where possible, we’ve automated tasks and processes, but you can only go so far. 

Humans are still essential for creativity and knowledge-based tasks. 

As you can imagine, as we’ve grown our offerings, we’ve found that we need more people to cope. 

Our persistent “hiring” problem… 

Every time we needed someone, the problems we encountered were: 

  • We often only needed skilled people for short bursts of time. 
  • We needed people FAST. We didn’t have the time or resources to recruit people formally. After all, many of our tasks were sometimes 1 hour, sometimes 2 weeks and usually urgent! 
  • When we looked at utilizing the services of contractors or consultants (the nearest to Freelancers) we found they were either outside of our budget and not interested in working for a day or two. 

Freelancers fit that space between doing it yourself and hiring a contractor! 

Given the problems, we needed to find resources that could be up and running in hours, not several days. 

A couple of years back, we’d decided to dip our toes into the world of “Freelancing”. 

I remember it well, I nervously started to look around on the various Freelancer sites and Facebook groups, to find good people without knowing what I was doing, but eventually found someone who fitted the bill. 

Within an hour of contacting them, we were working together. 

Since that day we’ve not looked back. 

For example, right now, we’re working with 5 Freelancers: 

  • To create us some guidance for one of our sites. 
  • To help us with graphics for the 365ers 
  • Developer to help Hugo on a specific tech “challenge” 
  • A copywriter to help me write great content, that’s hopefully not boring! 
  • Marketing person to help me create a set of pages and adverts to promote our new “Book an Expert call” pilot on MicroJobs. 

As mentioned, when we started on the Freelancer path we were a little apprehensive. The whole team was used to working in environments where permanent or long term-contracts were the only way of getting external help. 

I knew to succeed we had to change our mindset. 

Now we’ve changed and gone all-in, we’re LOVING it. 

Word of Warning, be careful going “direct”. 

In the early days, we looked for a marketing Freelancer. I was a member of a large marketing group on Facebook. I hired a person who was very active and really showed they knew their stuff. I paid up-front and after several emails and conversations, I received absolutely nothing. Luckily, in this case, I was able to get my money back after a few weeks and numerous emails, but many aren’t. If you do hire freelancers, use a platform. They take the money upfront and hold it until delivery. This gives you a lot of protection. There’s also no come back on the Freelancer if you go direct, as there’s no “review system” like there is on a platform, a place for you to share your experience so that others can learn from them. 

If you’re considering using freelancers, my advice is:  

  • Start small. Find something low budget such as an advisory call. Get a feel for how the platform works and build your confidence. 
  • Create a great “spec” from the outset. Explain what you want to do and also what the deliverables are. I know this is boring for many of us, but honestly, you get out what you put in. Creating a good statement of work allows you to really think about what you want and get the best ROI. 
  • Set a deadline. Don’t just say “tomorrow” if you can wait until next week. Good Freelancers are often busy but strive to meet deadlines. If you want quality work around their schedule and accommodate them, this is a two-way relationship. It’s a good idea to engage with them ahead of time instead of “last minute”. For example, we’re already planning the work we need doing for GlobalCon2. 
  • Be available for regular communications. The longer you leave a Freelancer thinking “What did they want?”, the more they will want to progress and deviate or deliver something a little “off-piste”. 
  • Build good relationships with Freelancers. Treat the freelancers you work with well as once you trust and know they deliver you will want to use them over and over again. 
  • Use a freelance platform. I am not just saying this because we decided to build our own Microsoft-based, freelancer platform. We’ve used (and still do) Fiverr, Freelancer and Upwork to access skills that aren’t just “Microsoft”. These platforms allow you to read reviews and access a massive talent pool. They also protect the payment process (see “word of warning” above). 
  • Protect yourself legally. Get NDA’s, GDPR contracts (etc) signed upfront (if you need them). 
  • Use a platform for payment. These platforms will give you protection because they generally hold the money upfront until the work is complete. There’s also usually some dispute management. 
  • Be nice, leave reviews. When the job is done, take the time to review the Freelancer. This helps them and also helps others hunting for good resources.  
  • Move to remote working. The days of needing to see people work on a desk next to you are gone. Virtually every office-based task can be done remotely. We’ve got tools like Teams and Zoom that make it easy to meet online. If you are open to remote workers, your talent pool suddenly got massive! Think of the cost savings of not having a person taking up a desk. 
  • Break up big projects. This is nearly always possible if you take a step back and plan well. The more you break up a big project into a subset of smaller tasks, the more you can spec them and get a Freelancer to do them. Agile methodologies, such as Scrum work well as they require you to think about things in 1 to 2-week Sprints. 

How much does it cost for a Freelancer? 

Obviously, this is based on skillset, duration of the task and experience. Here are some of the prices we’ve paid: 

  • Create a logo (with 8 variations): 150$ 
  • Create a header image for our Summit pages: 40$ 
  • Write an eBook from a Microsoft delivered session: 250$ 
  • 2 Marketing pages and 3 Ad sets of Ad copy: $800 
  • Investigate a performance problem: $100 

How much should I pay? 

When you first start working with Freelancers you may be confused as to what to pay. (I was). My advice here is to look at existing platforms (especially ones like ours that show pre-packaged jobs). You can find something “similar” to what you need which will give you a great indication.  

If the freelancer platform you choose allows you to ask for “bids” then set a lower and higher budget and see what gets offered. After your first few jobs, you will soon get a good idea about what to pay. 

You can also look to the contractor market and see what a 3-month contractor would end up costing you “per hour”. Once you have that figure you should generally be paying less as the freelancer doesn’t have the cost of traveling to your place of work. Some freelancers obviously may be more experienced than others so prices may vary. 

How to pay the freelancer? 

One of the biggest risks with paying a freelancer directly is that you will often have to pay upfront. The freelancer will naturally be worried that you won’t pay, and you will be worried that you won’t get the work done and lose your money. It’s a big old game of “chicken and egg”. 

Use a freelancer platform that “holds” the money. 

IMHO, this is essential! If you are working with a freelancer for the first time, you will want peace of mind that your money is not released until the job is “done”. The freelancer also is happy because they know that they will get the money if they do the work to your satisfaction. 

Using remote freelancers also opens your market up to most of the world. However, this also presents a problem if you want to work “direct” with the freelancer as it’s often very hard to make international payments with huge fees often being charged. 

Most freelancer platforms can facilitate international payments easily. 

Lastly, it’s also worth noting that if you do register on a freelancer platform and you then bypass the platform, you will almost certainly be breaking their “Terms of Service”.  

How to work with a Freelancer remotely? 

Unlike just a few years ago, we are in an era when there are literally hundreds of options for collaborating remotely. 

Here are a few tips: 

Whichever meeting software you choose to go with (e.g Microsoft Teams, Zoom, GoToMeeting), you will want to ensure a good daily “check-in”.  

This “check-in” maybe via online chat (supplied by the freelancer platform) or you may decide to have a daily stand-up.  

The key requirement is to stay in touch via at least an online chat. 

How to create a good spec 

I’ve mentioned the need to create a great “spec” several times now so here’s an example of what I would do if I needed some help to write an eBook. 

——- START ——- 

We would like an eBook writing for ‘[insert book title]’ session. 

We run large virtual summits based on Microsoft technologies. The sessions are usually based  

As part of our All-Access Pass, we give attendees in-depth EBooks of certain sessions. For this job, we require an Ebook writing up for. 


  • The eBook should be a minimum of 3000 words. 
  • Although you can start with a straight transcript, the Ebook should be rephrased to suit the reader. (Many of the phrases will relate to what they’re doing on the screen).
  • We require clear screenshots inserted. 
  • The content should be spell-checked and ran through Grammarly. 
  • Please don’t share the eBook or the MP4 that we will send. 

What we’ll send to carry out the work:

  • The MP4 for you to download. Please take screenshots from this. 
  • An example of a great eBook that we’ve delivered previously. 


  • We’re always looking for writers to create eBook’s, so if we’re happy we will ask you to do more. 
  • You will learn the topic really well. 
  • We will name you as the author on the eBook (as well as the original speaker). 


  • 250$ 


  • 20th March 2020 

If you would like us to check what you’ve done at any stage, please send us over a draft so that we can feedback ASAP.  

Please contact us with any questions. 

——- END ——- 

The example above is for an eBook, but if you needed something like dev doing, you might want to also include documents such as: 

  • Screen Mock-ups (using a tool like Balsamiq Mock-ups) 
  • Process Flow Diagrams 
  • Constraints (e.g. anything that the solution needs to work with or within). 
  • Functional/Technical Specs 
  • Test Cases 

Do you allow access to your systems and data? 

As with permanent employees, or contractors you need to ensure your data is both safe and secure. 

To lower your risks, consider the following: 

  • Use Test systems: Provide access to a test system with anonymized data only. 
  • Share your screen: Do a “screen share” with the freelancer where you can control what gets shown. Ask the freelancer not to use any screen recording software. This may sound obvious, but some may do this so that they can refer to it later. 
  • Screenshots: Send screenshots to the freelancer and obfuscate any sensitive data with tools like Snagit. 
  • Create Sample Data: Export sample data into a package allowing the freelancer to work with that. 
  • Still need access to ‘live’?: If you do need to give “live access”, then make sure you limit the duration and permissions of the account to an absolute minimum. As soon as the freelancer is finished be sure to revoke all access. In addition to this, you should ensure you create a separate account. If your system supports it, you can and enable logging and auditing to monitor what data that account accessed. 
  • Use the Firewall: You can also set a firewall rule to only allow the freelancer to access your system from a certain IP Address. 

It’s also a very good idea to get the necessary legal agreements signed to cover you against data protection legislation such as GDPR and DPA. 

All things considered; this is a risk every business needs to undertake for any person that interacts with their data. Many of the processes above also apply to FTE’s, consultants and contracts. After all, any employee can expose data either with malicious intent or accidentally.  

Fixed price or variable? 

Most of the work you will do is “fixed price”, this is why it’s important to create your spec really well from the outset. The freelancer can only deliver what you ask for. On sites like ours (listed below), we not only allow you to ask for bids from our freelancer talent pool, but we are also encouraging them to create pre-defined MicroJobs. Our theory is, the closer they get to what you went the more successful the outcome. In many cases, they may already have done what you need so all you need to do is purchase it and then ask for customizations. 

We’re really encouraging all of our Freelancers to do this, see this post ‘What would I do to become a successful full-time Microsoft Freelancer?’

What if it all goes wrong? 

If you’ve written a great spec and remained in daily contact with your freelancer then this will likely ensure a successful outcome. However, from time to time thing can go wrong for many reasons.  

You will need to select a freelancer platform that can manage the dispute process. The dispute process usually results in one of the following outcomes: 

  • The freelancer wins and keeps the money 
  • The buyer wins and keeps the money 
  • A partial refund can be awarded, usually with a compromise and an agreement to continue. 
  • Or, more preferably an agreement is reached to continue the work to get the job done. 

We are ‘dogfoodin’ Collab365 MicroJobs 

Due to our experience, we noticed a gap. Many of the big Freelancer sites are generic, offering “all things to all men”. When we tried to find Microsoft related help, it was really hit and miss and buried 4-levels down in the site structure. 

As you do, we set about building our own Freelancer platform, specializing in Microsoft skills

When you’re building out a new Freelancer platform, it’s essential you use it yourself to experience what it’s like (aka “dogfoodin’”).  

On MicroJobs, we’ve had Freelancers complete the following: 

  • Write us #Office365 Related eBooks 
  • Build us a Speaker onboarding solution using #PowerAutomate, #PowerApps, #MicrosoftTeams, #MicrosoftForms, and #SharePoint. 
  • Create EBooks and technical guidance. 
  • Created a team training series of videos. 

Simply using it ourselves has caused us to make many tweaks, improvements. 

So the big questions are: 

  • Have you started to engage with Freelancers? 
  • If not, what’s holding you back? 

Mark Jones

About Mark Jones

My goal is to help 1000 Microsoft experts have more freedom by selling their skills, working from wherever they choose.

To achieve this, I want to help educate via these sites:

👉 Collab365 Summits - Massive virtual conferences for Microsoft products
👉 Collab365 Today - Aggregation site for the best community blogs
👉 Collab365 Community - Huge blog site including plenty of Microsoft content

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