When I discovered Trello, I’d been actively looking for a project management system that worked for me. I’m a solopreneur, freelance writer, and WordPress site builder, so I was delighted to discover a tool that would work with my multiple business personalities.

I also, however, needed a system to use with the clients I manage and collaborate with when building their sites on WordPress. It proved tricky because my WordPress clients are mostly non-technical people. Some of them can barely handle email. Others are ok with technology and just prefer to have someone else get their site up and running for them, and most are in the middle somewhere.

If you’ve ever done any design-type work with clients, you know that some of them have a clear vision of what they want, and others … well, let’s just say they don’t.

BT (Before Trello), I figured out a workflow with my WordPress clients that started with having them fill out a detailed questionnaire. Theoretically, it would provide everything I needed to know to build their site for them. And for some — those who had a clear vision — it worked beautifully.

For others, though, communication quickly degraded into a death spiral of confusing and contradictory emails.

How, I wondered, could I use Trello to collaborate with clients?

The Experiment

I got a request to put together a WordPress site for an art studio. The client wasn’t the studio owner, but another freelance writer, Rod, who had landed the website gig as part of the project. We exchanged several emails, and then he asked if I ever used a project management program for team projects.

“Aha!” I thought. “The perfect guinea pig.”

I suggested Trello, and we were off and running.


First, I created two To-Do lists, one for me and one for Rod. Mine included all my normal steps for installing WordPress and setting up the site. Initially, Rod’s list included items like, “Log into WordPress and Change Your Password,” “Provide JPG or PNG images to use on site,” “Designate custom icons for homepage,” and “Create a version of the logo image on a transparent background.”

To make the board visually interesting and relevant, I used one of the artist’s paintings as the background.

Rod caught on quickly, although at the start he often updated or added a card in Trello and also emailed the same information. Gradually, though, the emails diminished and all our conversations took place on Trello.

Since then, I’ve worked on two more projects with Rod and Trello has been involved from the get-go.

In each of the two later projects, I created a list at the start called Status Updates. That list, which contained only one card,  became the conversation catch-all for the project. We still commented on individual cards, but general questions and answers, thoughts, suggestions, and file uploads were added to this one. This provided a history, as well as a single repository for attached files.


Now, Rod would much prefer that all communication be by phone or in person. That’s how he rolls. However, he’s come to appreciate the ways Trello can make a project easier. Here are a few of his favorite aspects of Trello:

  1. Having a separate board for each project
  2. The ability to move easily between projects using the Boards menu at the top
  3. The ability to easily move tasks from “to do” to “done”
  4. The ability to hold a running conversation which “functions like a dedicated e-mail communications channel between participants.” How about that?
  5. Email notifications. “That feature eliminates the problem of having to open Trello again and again throughout the day to check and re-check for any project activity. Excellent idea!”  
  6. Attachments. He likes that you can “upload one time to the Trello board instead of hunting for your team members’ individual email addresses.”
  7. Attachments can come from multiple sources like Dropbox, Google Drive, your computer, OneDrive, or Box.

Lessons Learned

When I began working with WordPress clients, it took a little while to create the systems I have in place for working with them. After a while, I was able to list the most common questions and concerns, and address them proactively. I created checklists to make sure I had all the information and materials I would need to build the client’s site.

Introducing clients to Trello is no different. Naturally, your collaboration system with your clients will depend on:

  • The type of work you’re doing together
  • How willing your clients are to learn something new

Before you jump in with both feet and add all your clients to Trello, create one or two collaboration boards you can learn from, to see what works for your clients.

For these initial forays, it’s a good idea to pick the client carefully. Choose someone with whom you have a good rapport, and who isn’t afraid to learn new tools and new technology.

Then introduce Trello one step at a time. If you’re like me and you “got” Trello right away, remember that won’t be true for everyone.

Think about it in terms of making a smooth onboarding process. What can you do to make the client’s initial experience with Trello easy and comfortable?

The “Aha” Moment

If you’ve done a good job, you may be pleasantly surprised one day when your client does what Rod just did to me. He disappeared from the current Trello project board for a while, so I reached out by email to see what was going on.

He responded to let me know he’d hit a rough patch, and wondered if we could schedule a phone call.

“Let me know what time works for you on the Trello board,” he requested.

A sure sign that your efforts are working. Job well done.

Check out a sample Trello board based on Susanna’s workflow:

Screen Shot 2015-11-23 at 5.40.11 PM

More sample boards found on the Trello Inspiration Page

Freelancing is smoother when all the apps and tools you’re using are working together in a central space. Learn how Trello Business Class can power-up your potential with Google Drive, Evernote, and video conference integrations, to name a few.

How freelancers can improve client collaboration with Trello