12 tips for working with remote freelancers

I’m a remote freelancer. You’ve booked me for a project. I have, in many ways, been transported into your world, like a visiting alien from another planet. But, remaining securely ensconced in my atmosphere controlled space-explorer vehicle, I view you all from afar.


I need to learn your ways and customs, your cultural rules and behaviour patterns; observing you through a screen, via headphones, deciphering the flow of communication.

I studied the information I had received, prior to my visit. Yet you speak in a strange foreign tongue. Recognisable, yet frequently indecipherable.

But I’m not an alien. I’m an editor. Don’t we all speak more or less the same language?

Don’t speak in jargon and code

Acronyms and other similar codes tend not to help ‘outsiders’ understand their role or task. Especially when there are different acronyms for the same things used by different departments in the whole project set up.

There may be acronyms for teams, job titles, tasks, documents, meetings, platforms, content, digital activities, book components and assets.

“So, as part of the SP1 task, I need to look at the EPN to find the SB2 to determine if the D42 is the correct DCF for the TMP. Bearing in mind that it’s the DK part, not the MK.”

Got that?

The use of specific in-house jargon, in general, can lead to confusion, miscommunication and a feeling of separation until the ‘outsider’ has got to grips with things.

Remember that it’s not hard to unintentionally increase a remote freelancer’s feelings of separation. We’re ARE physically and geographically separate. We ARE remote.

Demonstrating empathy for your colleagues is the glue that holds a remote company dynamic together. Whether it’s their life circumstance, their work experience, or their feelings of inclusion (or lack thereof) in the company, it all starts with listening to remote folks and being empathetic to their situation.

Trello blog: 6 Rules to Live By When You Work In An Office But Have Remote Team Members

Hopefully, this gives a little insight into what it’s like to be a remote freelancer. But this is just one communication issue.

Communication is key

Part of the key to organising a successful remote team is to make sure that all participants feel valued, understood, well-informed and sufficiently well briefed. This is all done using one form of communication or another.

I think freelancers are very aware of this, in-house staff who have spent time as freelancers or as remote workers also get it. Other staff, I think, often have no reference point for what it’s like.

Thoughtful, well-prepared, good quality communication can overcome a lot of the issues.

I will communicate as much as possible because it’s the oxygen of a distributed company.

Automattic company creed.

Reflect and empathise

Project team management and membership require an understanding of the position of each of the team members. If asked to think about it, I don’t think this is too much of a challenge. However, many in-house teams seemingly fail to reflect on and recognise the difference between their physical and geographical proximity, their knowledge of familiar professional behaviours, the exclusive language of their ‘inner circle’ and the potential sensitivity of the freelancer’s position.

It may not be something that occurs to an in-house team, but why not try to at least have some team meetings in which everyone attends from their computer, like the freelancers?

Attending a meeting as a lone outsider ‘on the line’ while an in-house team are together in a room immediately establishes separation. And the audio can be terrible: people sitting further away from the microphone can’t be heard, some people mumble or talk quietly and when various people talk at the same time it does not make for easily understandable communication.

12 tips

Here are 12 things that I appreciate myself and try to pay attention to when managing or participating in a geographically distributed team:

  1. At the start of the project, try to have a video conference call, where you can see each other. Don’t just talk about the project, try to get an idea of the other people’s life and work situation. If it’s a long project, maybe schedule some less formal meetings or a ‘virtual water cooler‘ space.
  2. Make regular contact, even if it’s just to ask ‘How’s it going today / this week?’. Ask if someone needs any support or further information and don’t let too much time go by without checking that information has been received; sometimes spam filters are over-zealous!
  3. Watch out for the pitfalls of written communication. Even if you’re in a rush, be careful not to appear blunt or dismissive. Always read messages back before sending and consider whether they will be understood or could be misinterpreted; particularly if some of the team are not native speakers of the team’s main language.
  4. Organise and create guidelines for communication channels to make everything as clear and efficient as possible. Misunderstandings will waste time and effort. Try not to rely only on email – consider other communication options See here for more of my thoughts on this!
  5. Not everyone works at the same time. Don’t expect instant responses. Be aware of people’s time differences and work schedules.
  6. Create an online space for task management, such as a Trello board, where everyone can access the most important information about what they are doing at any given time. This can help make sure there’s an easy method in place to track and report progress. What’s coming up? What’s in progress? And what’s the status of each task?
  7. Use cloud storage, such as Google Drive or Dropbox for important files, so that updating a document just means amending and communicating the amendments, not emailing out another version.
  8. Be able to connect and communicate in multiple ways. If not Skype, use FaceTime, WhatsApp, Google Hangouts, or maybe a phone call! If you’re in-house, be prepared to be flexible and be prepared to use alternative platforms to the company favourite.
  9. During a web conference, such as on Skype or GoToMeeting, actually use and pay attention to the chat function. For people not in the room, a backchannel such as this offers the opportunity to inform the presenter of audio issues, or to post questions, without interrupting the flow of conversation.
  10. If you’re using platforms on which there is a profile image feature where you can add a photo, use it. Google Drive, Trello, Smartsheet, JIRA, even Dropbox and Office365 accounts now have a profile image feature. If you’re a real person and not an anonymous aardvark or a grey blob, it does actually help.
  11. Celebrate important milestones with the team: Level 4 is done, dusted and in production! Wahoo! Nice work everyone!
  12. Taking things a little bit further (OK, this is fairly out there for anyone who knows academic publishing, but…), why not try automating some tasks and making time to understand how apps and tools can be integrated to automatically update? This can be used with calendars, to do list apps, project management tools – pretty much everything. In turn, this could reduce the need for email updates and those horrible group email chains. What could work to save time and effort? Perhaps an AI automation tool like IFTTT or Zapier could help improve information sharing.

There are probably some important things I could have included, but have forgotten or haven’t thought of. Do you have any suggestions? Feel free to comment below to start or join a discussion.

24 thoughts on “12 tips for working with remote freelancers”

  1. A big ‘yes’ to all of these! I’d add to 11 the importance of saying thanks and signing off at the end of a project. I’ve just finished a two-year project with a team based overseas. I did my final handover and said this was me signing off from the project and in return got a very short ‘confirming receipt of files’ response. I didn’t need to have the flags put out, but a ‘thanks for all your work on the project, would have been nice. With huge teams located all over the place it’s easy to forget who’s at what stage of their involvement but I think a project manager should have some idea and sign out with each freelancer at the appropriate time.

  2. Thanks for a brilliant and timely post. I’ve been thinking about #12 recently and looking for alternatives to email communication for remote teams working with in-house teams. I’d love to know more about IFTTT and Zapier as they seem complex to set up at first but perhaps that’s just me. I’ve also been looking at Blink (https://joinblink.com/) which seems really user-friendly but still fairly new. Thanks again for a great post!

    1. Hi Jemma, thanks for reading and commenting!

      In my experience, it’s a start to at least think of the distributed group of freelancers as a ‘team’ at all. Usually, it’s a group of people put together to do different parts of the same project, who never actually interact, but merely receive a brief from and deliver their work to a project manager and then go on their merry (or not so merry!) way.

      On my current project, which I’m just setting up, there are some tasks on which two editors will be sort of working together, so I’m aiming to at least initiate some collaboration. I’ve got everything and everyone in a Trello board, so hopefully this will help.

      I think IFTTT and Zapier seem more complicated than they are, though IFTTT is easier. All I did at first was start playing around with the ready-made actions. I mostly use it for automating content curation or social media sharing or saving. For example, if I add a particular tab to something I save in Pocket, then it automatically creates a note in Evernote; if I clap an article on Medium, it saves it to Pocket; if I Buffer something, it is saved to a line in a Google sheet.

      Blink looks interesting. I’ll have a nose at that! Thanks!

      1. Thanks Richard! I can’t remember if you’ve already blogged about setting up IFTTT but it sounds really useful. I like the automated links from Medium to Pocket to Evernote. Let us know what you think about Blink as it has potential to solve some of the communication barriers that exist.

        1. I think 3 is fundamentally important. If I have to send a ‘firm’ message then I write it, make coffee and re-read before sending to make sure it hits the right note and isn’t too abrupt, and the message is fair to myself. Also, if you’re being employed as an editor or writer you are being judged on your written skills, like it or not, so I feel you need to thoroughly check what you’re planning to submit before it goes out; if it’s shoddy and the punctuation/spelling’s a mess then it’s like going to a manicurist who has bitten nails and chipped nail varnish – it doesn’t instil confidence in the reader.

          1. Hi Nicola, thanks for reading and for your comments.

            Yes, I agree that number 3 is a really important one. For all the reasons you give and also because the repercussions could really hurt future interaction with the receiver. I like your suggestion! Have a coffee and chill before sending.

            On my last project, there were a couple of editors who just kept being late or doing shoddy work and I frequently wrote out a slightly ranty email (without any address added – just in case!) then saved it as a draft, went back later and made it more reasonable before sending!

          2. Hi Nicola! I love the manicurist comparison! I draft emails in old-fashioned Word and then copy and paste into emails before sending. There’s something about Word which makes it easier to check wording and tone before sending. I also save emails to a Drafts folder in the evening and review in the morning before pressing Send, especially when an email arrives after 5pm.

            1. Such a good comparison, Nicola!
              Jemma, I have a 2 minute delay on my email, so after sending it sits in my outbox for a bit. Enough time to quickly retrieve it if I either accidentally sent it too early, or sent it in (slight) rage!

          3. Hi Richard! Fab post, thanks. Completely agree with you about communication pitfalls and the need to celebrate milestones. Another thing I’d mention is thinking about project delays from a freelance perspective, and the lost income it effectively results in. I worked on one project where kick off was delayed, and the inhouse manager asked around other teams to find out if anyone needed a freelance ed for a couple of weeks. Instead of twiddling my thumbs and not earning, I ended up with another project to fill the gap. It meant a lot to me that this inconvenience was acknowledged and addressed.

            1. Hi Emily! Thanks!

              Yes, agree about schedules – that’s happened to me too. Fortunately, I managed to pick up some bits and bobs to fill in time. I’d made sure that this in-house team knew I was annoyed, but obviously, no compensation was offered!

              There’s also my current situation… I’m contracted as an editorial project manager and I’m trying to book freelancers to carry out digital checking, but the specifics of certain tasks are unknown, i.e. dates are, but as it’s a new platform, decent estimates on the actual number of hours the editors will need to complete the work are not yet known. As a result, I’m ‘booking’ editors for dates, but can’t guarantee how many hours work they would actually be paid for during that time. Awkward.

          4. Also, congratulations on writing such a constructive and un-ranty post about this! Not sure I could have managed it! I started to draft something along similar lines 6 months ago but abandoned it 🙂

          5. Reblogged this on Monographer and commented:
            Monographer writes: This week (from 15 Jan 2018) is, apparently, Working from Home Week. To mark the occasion I am reblogging this post by Ricahrd Whiteside on how to make the best use if freelancers who are working remotely.

                    1. Pingback: Practical tips for working with remote workers – FJWilson Talent Services

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