How To Trello Your Project

What to do when your todo list won’t do.

Jess Martin
May 16 · 11 min read
That’s *actually* me writing on the whiteboard, probably bringing forth another Shining Idea.

It happens all the time, without anyone noticing.

You’re excitedly working on the Shining Idea, that one you came up with during a whiteboard session. It’s going great. And then suddenly it isn’t. What’s next? Who’s working on what? Are we done yet? How much is left? Are we on track? Are we working on the right things? Who knows?

You see, you’re not dealing with a simple list of tasks any longer; the Shining Idea has begotten a Project. A Project with dependencies, shifting priorities, deadlines, ambiguous scope, stakeholders, and multiple contributors.

Your todo list doesn’t speak Project. Checking over your checklists won’t help. You’re saddled with a stack of sticky notes and a vague sense of confusion. What now?

Left on it’s own, a Project is a mess. The Shining Idea resonates vision and passion, but a Project requires communication and coordination. We’re going to explore six principles to help you deal with the chaos that results when a Project emerges from the Shining Idea.

Principles, Not Prescriptions

Think of these six principles like a set of Lego bricks. You can take one away, add a new one, step back and reflect, and decide whether you like it. The whole point of Legos is to modify them. Just so with these principles. Play with them, keep what works, throw out the rest.

The only process you should never abandon is improvement. Always seek to improve how you work.

Trello + Projects = ❤️

Trello is a particularly great fit for managing a project that implements the below principles. Throughout the article I’ll discuss and show how to set up a project in Trello to implement each principle.

You don’t need any prior experience with Trello in order to follow along. We’re only going to use the most basic stuff that Trello has to offer: Lists, Cards, and Card Descriptions. That’s it. If you know about those things, you’re good to go. Even if you don’t, I bet you can figure it out.

Let’s dive in!

Here are the six principles in a nutshell:

  • Write down everything and Document All Work In Trello.
  • Start with Four Simple Lists arranged left to right: To Do, Doing, Review, and Done.
  • Work Right to Left, always working on the card that is furthest to the right, yet not done.
  • Divide the work into Goldilocks Cards that are one to two days of work each.
  • Start Cards With Why to provide important context.
  • Don’t get bogged down in the how; Describe The Finish Line, Not The Route.

1. Document All Work In Trello

Write it all down!

Every single task you do to complete a project is work. The first step is to Document All Work In Trello.

This might seem over the top, but the reason is simple: clarity. Writing down all the work that needs to be done forces you to be honest with what it will take to complete a project. Whenever you see all the work laid out in a Trello board, it frequently causes you to rethink your approach or even to reconsider the project entirely. Better to count the cost up front.

But this clarity isn’t just for you. Rare is the project that has no other stakeholder than the person doing the work. Putting all the work in Trello enables you to be clear with everyone about what it will take to finish.

“Done is the engine of more.”

The other reason is more psychological: preserving forward momentum. It feels nice to get things done. Any work on the project that’s done outside of Trello kills the perceived momentum of cards moving to done. The project might look stalled out even though work is getting done. When all the work is in Trello, you get to maximize the good feels as work gets done.

2. Four Simple Lists

Just four! No More!

Start with just four simple lists: To Do, Doing, Review, Done. Resist the urge to add more lists until you feel the friction of not having them.

To Do

Doing

Review

Done

These four lists are all you need to get started.

3. Work Right to Left

No love for starting on the left!

Always start working on the card that is furthest to the right but not yet Done. There are several very practical reasons to work this way.

First, it fights our natural tendency to avoid hard things. Does the following sound familiar? A card sits in Doing because it has that one impossibly complicated part that you can’t figure out. A card sits in Review for a few days because it’s not really clear whether it’s actually done or not and no one wants to have the difficult conversation. Something in the To Do column looks enticingly easy. “I could get that done in an hour!” you think to yourself, forgetting the thousands of times you’ve told yourself that only to discover that it’s harder than you first thought. Finishing things is hard work. Personally, I’ve always struggled with “the last 10%.” Working Right to Left forces me to finish things before moving on.

On the flip side, it feels good to get stuff Done. Overcoming inertia by forcing yourself to make progress on work already in progress can break the deadlock and build that sustainable momentum that’s so precious and powerful.

And finally, it fosters teamwork. I said start with the card furthest to the right, not your card. This isn’t my work. It’s not your work. It’s all of our work. Everyone working on the project wants to see it completed. Just because you haven’t personally worked on something that’s sitting in Review or Doing doesn’t mean you can just skip over it and go pick up a new card from To Do. Reach out and see if you can help. Sometimes all people need is someone to talk them through a roadblock. Be the deadlock-breaker, even if it’s not something you started or it’s outside of your area of expertise.

“Is there anything I can do to help you move that forward?” is a powerful question.

4. Goldilocks Cards

Find that just-right-size!

Strive for Goldilocks Cards: not too big, not too small. When I speak of size, I’m talking about the time that a card takes to complete. Each card should represent about a half-day to two days of work, max.

“This one’s too small…”

Never forget that every minute you spend in Trello is not The Real Work™. Trello is meta-work that facilitates The Real Work™. You will never finish the project by moving things around in Trello. It’s incredibly tempting to spend time futzing with your tool — it feels like The Real Work™! It’s not. The Real Work™ is work that moves the project one step closer to Done. Go do that.

“This one’s too big…”

“This one’s just right.”

Pro tip: I don’t recommend referring to yourself as “self” out loud. Give yourself a more interesting name like “Birdman” or “Sassy Minx” and use that instead.

5. Start Cards With Why

Why start with anything else?

Now that you’ve Documented All Work In Trello and split everything into Goldilocks Cards, what should you write about the card beyond the title? Start by describing Why the work needs to be accomplished at all. A few sentences will do.

Why start with Why? It’s all about context. The person doing the work might do it differently if they knew the purpose it was trying to accomplish. They might suggest a change to the Finish Line (see next principle). They might argue it doesn’t need to be done at all, which is the biggest win of all: the only thing better than getting work done is not doing work that should never have been done. Starting Cards With Why helps us see the forest, not just the tree in front of you. And when you’re in task execution mode, that can be enormously difficult and tremendously valuable.

Try to frame the Why in terms of the person for whom the project is being done. If you’re writing software, it’s the user. If you’re planning a surprise birthday party, it’s probably the person who’s about to be surprised. If you’re putting together a marketing campaign, it could be the target customer.

If you’re stuck writing the Why, try the 5 Why’s exercise. Start with “why do I need to do this task to complete the project?”

6. Describe The Finish Line, Not The Route

Tell me where we’re going!

Once a card has a Why, a title alone is not sufficient to describe the work that needs to be done. And just as importantly, the work that should not be done. Two people reading the same title will envision two completely different results. So, what should you write?

Describe the Finish Line, what it would look like for the task to be complete. Don’t worry about how to get there.

It’s easy to get sucked into describing how to do the task, particularly when you know how to get it done. Let’s say the card is “Bake a cake.” The Finish Line would describe things about the finished cake. Should it be blue? Write that. Should it be delicious? Write that. Should it have at least 3 layers? Write that. Two cups of flour, or three? That’s how. Don’t write that. If this card is Done and you end up with a delicious three-layer blue cake, then do you care how many cups of flour were used to make it? No, you don’t.

Another way to think of the Finish Line is to write what is necessary for review. Once the card is sitting in the Review list and someone is trying to determine whether it’s done or not, the Finish Line should allow them to easily say “done!” or “not done!”

One caution here: don’t go overboard. A few lines is normally sufficient. Cards are placeholders for conversations. If whoever is working on the card doesn’t have enough detail, make sure they know to reach out to you to ask for clarification.


That’s it. Six principles as a simple starting point for any project. Resist the urge to make it more complicated, at least at first.

Let’s look at those principles one more time:

  • Write down everything and Document All Work In Trello.
  • Start with Four Simple Lists arranged left to right: To Do, Doing, Review, and Done.
  • Work Right to Left, always working on the card that is furthest to the right, yet not done.
  • Divide the work into Goldilocks Cards that are one to two days of work each.
  • Start Cards With Why to provide important context.
  • Don’t get bogged down in the how; Describe The Finish Line, Not The Route.

You might notice that the first three principles focus on the flow of work, while the last three focus on how to describe a single task. The principles could be further summarized:

  • Principles 1-3: Document all work in four simple lists and work right to left.
  • Principles 4-6: Break down work into day-long tasks that start with why and describe a clear finish line.

Think back to that whiteboard session. The one that brought forth the Shining Idea. Behold again the shimmering vision of that Shining Idea. The Project has no purpose other than to bring that Shining Idea into Reality. Remember that. Don’t fall in love with process and start mistaking it for The Real Work™.

Well, what are you waiting for? Go move some things to Done. ☑️

What now?

  • 📖 READ! 📖 This article grew out of Why You Should Use Trello For Damn Near Everything. Check that out for a refresher on why Trello changes your brain for the good.
  • 🗣 SHARE! 🗣 I was a project newbie once. I’m sure you know a struggling someone who needs this article. Share this article with them! I had them in mind as I was writing it.

Acknowledgments

Thanks to Jason Rudolph, Glenn Vanderburg, and Lauren Moon for reviewing drafts of this article.

Jess Martin

Written by

Engineering Manager, @LambdaSchool. Co-founder, First.io. Bringing web products to market. Building tools for a better tomorrow.