Trello, Again: Followup

Trello, Again: Followup

To recap: last week I was excited to discover how Trello could manage my entire project backlog with big-picture ease. While some may argue that having a huge back list of “wish projects” is a form of mental masturbation, I look at it a bit differently: my backlog of dream projects is a catalog of what I think is worth pursuing, and is part of my identity as a creative person.

The trick, of course, moving out of the dream domain and into the world of production. And this is where Trello, with its suitability to kanban-style planning, is coming into play.

For reference, here’s what my “DaveCo Personal” board looks like right now, with annotations to show the function of each column.

Current Trello Board Explanation follows:

Maintaining the Big Picture

Most of my Trello board is about wishes, projects, and tasks, but the left-most column has a different purpose. It contains an evolving list of principles and goals used to determine the relevance of every project. This is similar to the When is Something Worth Doing? concept from the Concrete Goals Tracker. It’s kind of like a mentor in a column, providing some perspective to the list making so it doesn’t go completely crazy with ideas that don’t add value or moves me out of alignment with respect to what is important and what is merely interesting.

Tasks Move Left to Right (Mostly)

Each column becomes more concrete from left (possibilities) to right (scheduled, with additional details as needed). As I move the cards, I rewrite their title and descriptions accordingly, and add checklist and due date if they are needed.

Nurturing an Orchard of Possibility

If I have a great idea in the shower and think it’s worth doing someday, I will run down to the computer and create a card in Trello in the Hibernating Projects column as I shiver in my bathrobe. Most of these pile-up in the HIBERNATING PROJECTS column, unless there is an advantage to doing it sooner. Perhaps the idea leverages off something I’m doing already this week, and it’s easy to try out because I’m set up for it.

In most cases, though, I’ll see the card later and may spend some time thinking it through. Maybe it’s actually something I DON’T want that badly, and I’ll delete it. Otherwise, I like to let the idea sit and ripen. I might do some Googling to see if it’s already been done, and find that it has been done already and done well. At that point, I’ll move the card to the DONE THIS WEEK card and close it out by renaming it “Research Great Idea; Already exists.”

If, on the other hand, I find that the field is wide open, I might move the card to the PROJECT BACKLOG as something to definitely look later. At such time, I might open the card and create a checklist of things to try out or do, putting a little more structured thinking into the idea. This lowers the threshold of action for when I come back to it again after a long absence, quickly bringing myself up to speed on procedures I may have forgotten.

Over time, as I review and reconsider every card in the pile, understanding and detail grow. At some point, enough detail and urgency will conspire to move the card out of the nursery and into production. I should add that the magical growth formula here is my attention; just looking at these cards, in the context of my daily continuity, helps each one grow just a little bit. What was not possible two weeks ago may seem utterly feasible today, or perhaps I saw a movie that gave me the inkling of an idea that BAM triggers some new possibility. It really can be that easy.

Moving Tasks into Production

When I’m ready to do some work on an idea, I’ll move it out of PROJECT BACKLOG and into FOR THIS WEEK.

Some of these projects are pretty big and hairy. For example, it took me a while to get moving on the interactive project because I didn’t yet know the best approach. I didn’t even realize this was slowing me down, until I noticed it had been sitting on the list for quite a while. Moving the idea from idyllic “new puppy” phase to the reality of “scooping poop three times a day” is hard work. Plus, when you’re not sure what the project entails, it’s hard to know what to do first and whether it’s “worth doing”. The only way to find out is to get off your butt and trust in your ability to navigate those unknown waters. Only after several dozen hours have been invested will you get a good sense of whether it’s going to pay off.

The idea of spending dozens of hours for an unknown reward is demotivating. Recognizing that, I have started using Trello’s label feature to mark the difficult project cards with ways to start reminders. They provide easy ways to get started on new projects based not on unknown results, but known quantities of time spent doing a certain kind of activity. I know from experience that once I start look at a problem even in the smallest of ways, this quickly leads to ongoing work that is rewarding.

At some point, the idea will see the light of day and get queued up for a week (or “sometime in the next 7 days”) in the PROJECTS THIS WEEK column. This is the pool of projects that I draw from when using an Emergent Task Planner.

Handling Smaller and Emergent Pop-Up Tasks

In addition to big hairy projects, there are the small-scale task cards that don’t start out as dreams or ideas in the shower. I enter them as new cards directly in the PROJECT BACKLOG, DOING THIS WEEK and DOING TODAY columns, based on how actionable I think it is.

If I do something that wasn’t planned at all, like spending an hour researching the best stick-style vacuum cleaner, I’ll add that as a new card directly in the DONE THIS WEEK column, with a “+” in front of the card name to indicate it was an on-the-fly task.

Feeling a Sense of Accomplishment

The rightmost columns tend to fill up with things I got done during the week. As it grows, I see how productive I actually am.

After the week is over, I archive it so I don’t have to see old deliverables.

Loose Project Definition

A challenge in project planning is defining the set of concrete actions that actually produce results. This is hard work, and is necessary to transfer wishes like, “I’m going to become the best engineer in the world” into a set of actionable steps with observable results. There is nothing new about this.

I think there’s value in NOT defining those steps right away. For one thing, you may not know what they are. So rather than spend a lot of time wondering what they are, or guessing badly, I’m content to just capture the dream first. It’s the heartfelt yearning that’s driving the resolution in the first place, and it needs to be acknowledged. It’s also the qualitative, subjective measure by which we assess our progress toward the goal. For example, I might have the nebulous wish of being a “great programmer”. I don’t know exactly what that means, but I can put it into my PRINCIPLES AND GOALS columns on the left.

The cool thing is that cards in Trello are easily modified or embellished with additional checklists. A card can start as a wish (e.g.: “be a better programmer”) and then be extended with a checklist that are the actionable steps. Trello allows you to convert checklist items into cards too, so a master “Be a Better Programmer” card can spawn various subtasks that are (1) actionable and (2) produce observable results that (3) are aligned with the original goal. These subtasks can move through the system from left to right, until they are done.

Alternatively, I could spend hours writing up a detailed list of things to do to become a better programmer. This is tedious and difficult to do when you are learning something new by yourself, and such lists end up obsolete quickly as one’s priorities change. I like the idea of broadly defined wishes that are fed by the execution of smaller supporting tasks, because it’s faster and more adaptable.

Wrapping Up

So that’s how I’m using Trello right now, and I’m liking it a lot. It’s been useful as a tool that allows me to see all important project ideas at once, drilling down or moving them with a very simple interface. And since each project is a card with a notes stream and checklists, they become viable mini-project managers when I want to get more formal (but not too formal) about it. I still use the Emergent Task Planner to write down the “Today” tasks, as I like having the paper worksheet to hold my attention for the day’s focus, without the distraction of a computer screen.

Update May 2015

For a large part of 2014, I stopped using Trello because I had developed a kind of “allergy to project planning” and adopted a single-focus approach to managing my projects. This had its pros and cons, but in 2015 I decided to come back to a management system. I’ve readopted Trello in a slightly different manner, based on insights gained from reading¬†The Art of Procrastination.¬†The left-to-right organization is still largely in place, but the names of the columns have changed to reflect a different motivator than urgency.

19 Comments

  1. Andy 3 years ago

    Looks interesting. Somehow I just don’t like the name “Trello”.

  2. Author
    Dave Seah 3 years ago

    I don’t get the name either, and had ignored the product because it sounded like a hip social media flavor of the day thing. It was only when I read that it was from Fog Creek that I looked more closely.

  3. Dan Ostlund 3 years ago

    Here’s the story on the Trello name in case you’re interested:

    http://blog.fogcreek.com/the-agonies-of-picking-a-product-name/

  4. Author
    Dave Seah 3 years ago

    Dan: Awesomeness! Thanks for the backstory!

  5. Lynn O'Connor 3 years ago

    Your Trello looked so cool that I had to try it, and now I”m using it with a close research collaborator –we are listing each project (joint projects for the most part) across the screen, and it is really great. Tasks go on cards, and as we get them done, they’re archived. So far, it’s great.

  6. Author
    Dave Seah 3 years ago

    Lynn: Awesome! Glad it’s working out for ya!

  7. Peter Knight 3 years ago

    Interesting use of Trello. I like the distinction of going from left (possibilities) to right (concrete actions). I have been evolving my own app for personal use and one of the things I want to solve is a better way to deal with stuck projects that go into (temporary) hibernation.

    I have projects that come out and go into hibernation and I want a better overview, but not at the cost of being overwhelmed with the whole array of projects I have. Having a hibernating (but not abandoned) project is good for me, because I often find that by the time I pick up the project again some of the problems I was dealing with can now be easily solved. But right now the process is too random, I’m now thinking of incorporating some way of keeping track of the constraints that are keeping a project moving forward.

    For example, I’m now working on my 2nd mobile webapp and I’m completely at a standstill because I haven’t been able to find a good solution for syncing data. I’m kind of waiting to see if a perfect solution surfaces instead of coding my own one which would be a huge undertaking. I guess if I were using this type of kanban organization the tasks for this project move left into the backlog column. What happens when the backlog becomes indescribably long?

    this got me thinking about process…thnx!

  8. Svet 3 years ago

    The name is very optimistic for me and as far as I can see the tool is rather complex and ideal for PMs. I can say that I have used another tool which is Comindware task manager for many different projects and when I have been reading about Trello I found that they have a lot in common.

  9. Author
    Dave Seah 3 years ago

    Peter: I find that I have the same reaction to hibernating projects, with similar positive-but-unpredictable results. I’ve given up on trying to plan them, which helps me relax, but it doesn’t help me achieve a factory-like precision in being productive. On the other hand, I gave up on that model too, preferring the fruit orchard metaphor for productivity instead. Likewise, when the backlog becomes indescribably long, I just don’t worry about it. I might go in and prune out some ideas that don’t really grab me anymore, or I might move them out of backlog and send ’em back to the bush leagues. I think people with huge creative dream project backlogs tend to NOT have a shortage of interesting ideas. I try to keep the “this week” and “doing today” pile my main focus (I wish I could color code them red or something), and I make sure that this column is relatively few in card count ala ETP principles. My ability to focus is very much dependent on my ability to ignore everything else that doesn’t matter. Without that, I’d find all these cards piling up overwhelming. I don’t let them judge me, and I seem to be doing OK.

  10. Author
    Dave Seah 3 years ago

    Svet: You’re right…it does sound very optimistic. I imagine it in a chipper British accent. I haven’t heard of Comindware…I just checked out their website and could not find a simple screenshot or demo video, unfortunately, to evaluate it. Too bad!

  11. Jack Fine 3 years ago

    Hi David – I love the way you’ve laid out your board on Trello. I read thru your post several times and I’d like to hear more about the way you’re using the color coded labels to “unstuckify” projects. Would you please elaborate a bit more?

  12. Author
    Dave Seah 3 years ago

    Jack: The color-coded labels are doing a couple of things:

    • Since most of the cards don’t have a color label, cards WITH labels stand out. I use the labels very sparingly, and only on projects that are important (income related) or difficult (unstuckifying)

    • Cards related to pressing matters get assigned a due date also.

    There’s room for only 6 types of labels, so after using up the red one for “business”, I have five unstuckifying procedures:

    • Do a 15 minute surge of work. Starting enormous projects is quite daunting if you’re fixated on wanting it to be done. Committing to 15 minutes of work on it, though, is a lesser mental burden, and often unlocks more time.

    • Do a 2 minute gather. Sometimes, it’s hard to get started if you don’t have everything ready, especially if it’s a boring project. I’ll spend 2 minutes gathering the stuff I need, then call it quits for a while. Then next time, I’ll have everything I need in one place and am ready to go. That is, if I don’t just start doing the project once all the materials are gathered.

    • Do a 5 minute evaluation. Sometimes, it’s just that we haven’t looked at the project hard enough, so it remains a nebulous cloud of don’t wanna do, but don’t know what the doing entails either. Spending 5 minutes to break it down and really challenge those assumptions helps chip away at the uncertainty. What might come out of it is a very short action plan or checklist.

    • Do a 5 minute structural outline. Sometimes we just feel a bit lost. Spend a few minutes mapping out the shape of the project, what connects to what, and then you can figure out your entry point. This is different from the 5 minute eval in that you produce a kind of map, rather than a checklist or strategy.

    • Do a 15 minute brain dump. I find it therapeutic to just write out what I’m thinking in a kind of free association. The result is a clarity of mind. You don’t have to do this in writing, either…you can spend 15 minutes explaining to a friend. From clarity often comes purpose.

  13. Mark Coleman 3 years ago

    Hi David,

    I enjoy following your design journey.

    I have a question about the use of checklists in cards, how do you manage the tasks in the checklists for a particular card, do you sit the card in the “In progress today” until tasks are done, or do you as you mentioned split them out into task cards of their own? I’m not sure how the latter would work, as it loses context once it’s burst out from the checklist, do you rename the card to maintain context??

    I use RememberTheMilk, with lists and lists for projects client and personal tasks (300+ tasks), but the volume is so large and looking at it all it’s so “listy” and overwhelming that using something like a kanban board seems easier to focus on.

    Do you think using other boards to “hide” the other projects is a better way and then pull to the front main board, or should they all live in the hibernating and backlog lists.

    Thanks for any of your insights.

    Cheers, Mark

  14. Author
    Dave Seah 3 years ago

    Mark: Those are great questions. Lessee…

    (1) checklists in cards

    Some background context first: I think of them as steps in a recipe, as opposed to task todos. The difference is that a recipe’s steps aren’t crying out to you to be DONE RIGHT NOW, unless you happen to be cooking, whereas “todos” (to me anyway) have an implication of “you should be doing this now to get it out of the way”, which I find stress-inducing.

    I use the column position of a card to set its immediacy. I actually may move a card back and forth between the “TODAY” and “THIS WEEK” and “BACKLOG” columns depending on how “top of mind” it is; the checklist maintains continuity of the actions that must be performed. In other words, I often use the cards to keep track of a project scope, not just a single task, especially with more complex projects.

    I haven’t so far promoted checklist tasks into their own cards very often…I think I did it once for a task that was taking a long time, and when I got to a place that felt like a milestone, I split off the last checklist item into its own card so I could stuff the original card into the DONE pile. It’s true that I lose context / connection with the original card, but I don’t use Trello to boss me around on such thing. I AM THE CONTEXT, not Trello or the cards. I use Trello to help remember what I have going on, so I don’t forget things. The cards also are capable of holding commentary and checklists, so that helps me remember what I was thinking at the time. I am pretty consistent in keeping progress-related notes in Trello (I like to see those cards move toward completion)

    I like the idea of having other boards to hold other projects, but there’s no way currently in Trello to make them link, or move lists back and forth. I think this is one of the things their team is looking into. For detailed project work, I use Basecamp to maintain detailed task notes and progress; Trello is used to remind me “what’s on deck” at a particular time.

    In summary, I use the cards in Trello to maintain awareness of projects both complex and simple so I don’t forget anything. I use checklists for projects that need to be broken down into steps, or if I’m figuring it out as I go along. Sometimes a project card can be a single task (e.g. “get Vietnamese sandwiches”) or something more nebulous (e.g. “establish business practices”). As my understanding of the project changes, I will often rename the cards. For something like “establish business practices”, that may turn into a checklist, and then it may split into multiple cards. It’s not important to me that the cards all remain linked together contextually; what counts is the TANGIBLE RESULTS produced. I am the main context, and knowing that I’ve finished and completed certain tasks means I have more resources or have advanced my position in some way.

    Dave

  15. Mark Coleman 3 years ago

    Hi Dave,

    Thanks for the prompt and considered reply, I’ll have to mull over it all over the next few days and do some experimenting with my current workflow. I guess I just need to push through the fear of not having each task being so detailed in my “what’s on deck” view. It may be that I can use RTM in the same way you use basecamp.

    Thanks again for your help and response.

    Cheers, Mark

  16. Author
    Dave Seah 3 years ago

    Mark: Good luck!

    If you find yourself using all that detail, maybe it’s necessary, or it may be a way of working through stuff.

    For example, I like to write in paper notebooks when I’m working stuff out with my fountain pen, but I almost never go back and look at what I wrote. The process of writing is what sets the tone for what I need to do, and I come away with clarity. It seems kind of wasteful in retrospect to do all that writing, but it serves the purpose of creating useful results (clarity), and it’s kind of fun to look at if I choose to do so some time in the future.

    Feel free to drop me an email if you’d like to chat further! I love talking about people’s workflow to figure out how we’re doing it differently!

  17. Mark Coleman 3 years ago

    Thanks David, I’ll shoot an email once I get my head above water and can breath some sense into my workflow :-) Cheers

  18. Briana Pierce 2 years ago

    Brilliant implementation! I have been struggling to use the GTD methodology (or some mutant offshoot) for awhile now; I like many of the concepts but simply creating the structure for it is a bit overwhelming. I’ve been playing with Trello for awhile now, and tend to keep a physical Kanban board for my work tasks. I really like the way you set this up, and am looking forward to seeing how it works for me.

    Thanks for sharing, and have a great weekend!! :)

  19. Bryan Harris 2 years ago

    Really nice write up. Liked the way you handle ‘pop-up’ task. Many days they completely take over the day. Thanks for sharing with us! I’ve been using Trello for over a year now. Huge fan! I made a web app call http://emelloapp.com that integrates email with Trello. Thanks for sharing!

A message from Dave:

I really believe we all benefit when we share our own perspectives on common experiences. It would be great if you added your own anecdotes and comments, even if you don't necessarily agree with the premise of the post; that's just good conversation in my book. The house rules are "treat each other with kindness and respect" and "enjoy the flow of ideas!"

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