My latest stop in software to try and run my business has been Trello. Unlike Daylite (read my Daylite review), Trello is not a specifically tailored CRM and Project management application.

I say that Trello is not ‘specifically tailored’ because Trello takes a such an open approach to dealing with managing business tasks. You can’t specifically enter clients and then link emails and documents to them. At least not in a way similar to Daylite. You can make a card for a client, throw in their contact information, and then move that through your sales process.


When I started using Trello there was no paid option at all. I’m sure those of you that have been reading my rants long enough will remember a few posts about investing business process in companies with no business models. So why on earth did I trust Trello?

Trello is produced by Fog Creek and they have a solid reputation for good software and long term sustainability. They have a number of other sources of revenue and at the time they had already gone on record saying when they would be charging and what type of things they’d be charging for.

Basically I trusted Fog Creek’s reputation. No startup would ever get a pass from me because they have no history.


Trello is a great free system and it’s wide open so you can do whatever you want with it. This wide open nature is a bit of a hinderance though. It can be hard to find a workflow that suits what you want, since you can do anything.

Trello has great iOS applications and great keyboard shortcuts once you’re in the web application. That still means you don’t have system wide keyboard shortcuts like a desktop application, but it makes it less painful.

Unlike other project management systems, you can’t tie everything to a specific client. You may not be able to find their contact information, along with all their documents across projects from inside Trello. Stepping in to a second application like Evernote can solve that problem though.


The biggest draw back is the lack of data segmentation. It’s hard to get a big picture of your business and what trends are going on with your projects. If you’re a data nerd, you probably won’t love Trello.

Desktop – Well Web Really

Trello does not have a native desktop application. It is a web application and is meant to be used on the web. Sure you can use Fluid to build a ‘native’ application, but really you’re just dedicating a web browser to it. Being on the web means all you need is any computer and your password/username to access your data.

You don’t need to make sure some database somewhere is in sync. You don’t need to make sure that the computer you’re sitting at has the Trello application installed. You really just don’t have to think when you need to work with it, sign on and go.

Web applications aren’t all rose coloured glasses and unicorns though. When an application is not native, you loose any system wide keyboard shortcuts. That means you can’t be working in another application and then send things to Trello by pressing ⌘-SPACE, like you can with OmniFocus or another desktop native application.

I’ve stated many times, I’m a highly keyboard focused computer user. Any application that doesn’t have lots of keyboard navigation is going to feel a bit like a pain to me. Not a deal breaker, but the rest of the applications has to be that much better to keep me using it.

Despite not have system wide keyboard functions, Trello has a lot of keyboard commands. To see them you just press the ? key and a HUD will popup with all the options. All those items are a keyboard focused users dream. Once you have window focus on Trello there really is no reason to touch your mouse.



Trello has a fantastic iPhone and iPad application. They take the standard desktop controls and make them easy to use in a touch device world. I still do 98% of the management of cards from my desktop, but popping in to update discussion on an item is very easy from an iOS device.


You can even get notifications on iOS at many levels. Want to know when anyone updates a card, that is possible. I hate 99.9% of all phone/tablet notifications so I leave them off.

As with any iOS application, you have some drawbacks like not being able to upload files to cards…Remember that’s an iOS limitation, not something that you should be faulting Trello for.

For those of you on Android, Fog Creek has an Android app for Trello and Windows Phone lovers aren’t left out in the cold. I don’t have Android or Windows Phone, but I do trust Fog Creek to build awesome software. A Twitter poll yielded a few responses saying that the apps were fine as well. If you’ve used them and have a review, let me know I’ll add a link here.

Wide Open

Trello is built to be wide open. You can organize a ‘board’ in to any system you want. That allows me to have a process setup to track sales, and have a process set up to track long term projects with many features.

Since I may have many projects for one client on a board, I use the coloured labels as a way to keep track of which items go with a project. I would like an easier way to dive in and out of a specific project for a client, but it certainly hasn’t driven me to try another software system.

This ability to build whatever you want, is also a hinderance for Trello. I had seen and played with Trello a number of times, without ever really figuring out how it could work for me. When I really decided to give Trello a go I spent a morning watching workflow screencasts for any business I could find. I even had the wonderful @markpoppen give me tour of how he is using Trello to organize his business.

Only after investing a day in trying to see the possibilities of Trello, did I feel I could even give it a fair shot. Without seeing the possibilities for organization in Trello I would have spent a bunch of time stumbling around trying to find something that worked. I don’t think that I would have been giving Trello a fair shake with all that stumbling.

Suggested Workflows

If you’re thinking about Trello, here are a few suggested workflows for you to try out. Hopefully these will help you not get lost when you give it a go.

Sales Channel

Here I track all the projects I’m trying to get. Whenever I send an email to a client I also add the gist of the email and a link to the email (MailPlane link) to the card so that I can check it without having to search through my emails.

Each card also gets a due date so that I can keep track of what’s going on and when I need to follow up with someone.

Prospects: – I’ve got an email or call or something letting me know that they are interested. This also contains any sites I think could use my services that I’m going to do some leg work to get.

Meeting Scheduled: – We’ve got a call or in person meeting set.

Estimated: – Sent over an estimate for the work.

Follow Up: – They liked the estimate, but for some reason they are on hold. I follow up on these cards every few months.

Won/Lost: – The cards get a label that tries to segment why I lost the project or green for if I won it.

Long Term: – The agencies and other freelancers I can contact when things are slow. Even those longer term clients that almost always can have some work for you, but just forget to get in touch.

One thing I miss from Daylite is the data segmentation. I wish that there was a better way to really find out overall why I don’t get projects. That is one of the biggest failings of Trello, no real data analyzation is possible.

Long Term Client with Ongoing Work

Future: Any item that sounds like a good idea, but we are not working on right now. It’s the same thing as a ‘Someday’ list for you GTD people.

To Do: All the things that we are currently working on. I make each major item a single card.

Bugs/Issues: Here we can create a new card of we want, or we can move an existing card in to the bug area, if we find something.

Doing: When I’m working on a specific card, I put it in this list. Helps clients see what is happening when they look at the board.

Done: When I think I’m done a card I put it in this list so that everyone knows it’s time to review the work.

Approved: Typically this is really where a client can step in. They’ve taken the card, checked out the features and they agree that it’s done.

Once something is in the approved list it typically sits for a while. Once it’s sat I end up archiving it, since having 100 cards there starts to get a bit much to deal with.

All Project board

Another board I keeps is an ‘overall’ board for the projects in my business. Small enough projects (like a basic theme build) just get a card here with a bunch of lists. Larger projects get a card that simply tracks the overall status of the project.

I’ve found this useful so that I can see how loaded down with work I am. If I’ve got 8 cards on the go for projects and 3 upcoming, I need to find a way to push the start dates for those 3 out. If I’ve got one on the go and one starting soon, better start hustling to get more work.

Upcoming: – Holds all the approved work that is starting at some point in the future.

In Progress: – Stuff I’m working on right now.

Waiting for Approval: – These projects are almost done, just tying up the last loose ends so I can get paid.

Completed: – It’s done and been invoiced.

Paid: – The client has paid the invoice. Yes I use Ronin for billing which tracks all the payment stuff for me, but I like seeing it here as well.

Clients Across Projects

One thing Trello doesn’t do is track assets for a client across projects. I have one designer that I work with on many projects. We open a board for each and track the work for the project inside the board.

I’ve found more than once I end up looking all over to try and find an item for this specific colleague. Since it’s spread across a bunch of project boards I sometimes end up looking all over to try and find what I want.

I’ll write later how I’ve started using Evernote to deal with this weakness of Trello. Basically I have an Evernote notebook for each client and tag items for a project. I send emails in from MailPlane or IFTTT and the new Evernote reminders help me out a bit. Make sure you watch the video on the blog post.

Just How Busy Am I?

Another thing I miss in Trello, is a way to answer the question:

Exactly how busy am I right now?

I’m trying to sort that out by using paper, but I’m not sold that I really have the answer. Trello doesn’t offer me a solution, but I never had one before so it’s not something I was really expecting Trello to solve for me.

Wrap Up

So do I like Trello? Yes I do. I’ve been using it for about 5 months now to manage my business. Yes I do use Evernote for some things, but Trello is great.

9 responses to “Does Trello work to Run Your Business?”

  1. Dan Avatar

    I would recommend checking out Gtdagenda for an online project&task manager.

    You can use it to manage your goals, projects and tasks, set next actions and contexts, use checklists, and a calendar.
    Syncs with Evernote, and also comes with mobile-web version, and Android and iPhone apps.

    1. Curtis McHale Avatar
      Curtis McHale

      Thanks for the recommendation, but it’s unlikely I’m going to try it. The UI doesn’t lead me to believe that it’s worth my time. Not that I need the best designed app out there, but it needs to look decent.

  2. John Parris Avatar
    John Parris

    Thanks for the review and showing how you use Trello. I’ve been tracking projects in WP, but the lack of an easy, quick mobile app that ties into it has me looking elsewhere. I’m giving Trello a shot now, and your post has helped me. I’m curious to hear more about how you use Evernote with it.

    1. Curtis McHale Avatar
      Curtis McHale

      What have you been using on WordPress to track projects?

      Still working on the Evernote post, no real ETA. I do have a post up later this week about being fast in Evernote though. That will help you be quick with Evernote at least.

      1. John Parris Avatar
        John Parris

        I’ve been using WP Project Manager with some minor mods. It lacks some things like project archiving and categorization, and I’ve thought about adding them myself – I just haven’t had the time to dive in.

        The lack of a good mobile interface has been my biggest annoyance. He does have a paid add on for the front end, but I haven’t tried that and can’t speak to how well it may or may not work on mobile.

        I really like owning my data and would love to make it work, and of course it being in WP is nice and means I could do lots of things with it down the road. I’d like to add some features and maybe do a custom front-end theme that works well on mobile… but you know how that time thing goes.

        1. Curtis McHale Avatar
          Curtis McHale

          I’ve looked at that and it hasn’t ever inspired me at all, at least it hasn’t inspired me to use it.

          Actually none of the WP based project plugins look like much at all. I keep tinkering with my own (which would have a proper mobile interface) but there is that time thing. 😛

          1. John Parris Avatar
            John Parris

            Hehe yup.

            I first looked at that plugin last year, and it was horrid. I came back across it again about 2 months ago and it’s quite a bit different. I’m like you though, not really inspired by it. There are some nice features, but it feels a bit cluttered.

            I noticed some people on Github are offering to pay to have featured added to it. If time could be found, I’m betting there’s a market for a really well done PM plugin/ecosystem.

          2. Curtis McHale Avatar
            Curtis McHale

            You should take a look at my GitHub profile.

          3. John Parris Avatar
            John Parris

            Just followed you and will check out the project.