Agile-Flavored Pomodoros

Recently I wrote about the importance of working on The Right Things, and in order to walk my talk, I’ll share the techniques I use to keep on track.

My personal project time is between 6–8:30 am on weekdays, which isn’t a massive amount of time (and honestly I do sometimes sleep in a little). However, I know from experience that, with a little discipline, even 90 minutes is enough to do meaningful work. When I say “discipline” what I mean is more of a process, a system, or maybe a habit. Since labels are fun I’ll call it “Agile-Flavored Pomodoros”.

Trello cards are splendid.

My morning routine

I start every “session” the same way—by reviewing my Trello board. It shows me what task I’m currently working on, and if I had to stop mid-task—as is often the case when working in small bursts—I will have notes written in the card, guiding me into what I was focusing on before last stopping. The board also shows me what to do next, in prioritized order, so when I’m done with one thing I never have to think much of what to do next. Having a set up like this has allowed me to push a project forward even when all I have is one-to-two hour chunks.

People who are familiar with “agile” will feel familiar with what I’m describing. That’s not a coincidence. I’m heavily inspired by the way I and others have gotten work done when in an agile environment. Someone feeds tasks—also called stories—into the pipe, and I pick the next one up. There’s no thinking required. I can get to work immediately. A virtual assembly line.

I complete a story, mark it as finished and move on to the next one. I pause for a moment, because it’s not ready. The definition of done isn’t there. I refuse working on a task before knowing how far I should go with it. Not knowing when to stop has come back to bite me so many times before. So I spend a few minutes contemplating what would be the least amount of work, that still allows me to say with a good conscience that I completed the task. Drawing imaginary lines in the sand—the key is not what I must do, but rather what I must not do.

Now I’m ready. I put on some ambient chill music, set my timer, and sink into twenty-five minutes of deep concentration. When the time is up I take one-to-five minutes to shortly reflect upon whether I’m headed the right way. If needed I’ll do some minor course-correction before embarking upon another twenty-five minute session. Rinse and repeat.

Notice that I don’t spend too much time thinking about what to do. It’s all laid out like a smorgasboard of things to work on. It allows me to take a deep-dive into details when working on a task, while I can rest assured that my cumulative effort moves the needle towards an overarching goal. This is essentially pairing an agile-inspired Trello board with the Pomodoro Technique, and it’s my favorite way of getting things done.

I want to try it! How do I get started?

You could just take what you like from the above and add it to your workflow in any way you see fit. However, there are a few things I keep in mind in order for it to work effectively for me.

A. I should not have to think about what to work on—I can start immediately
B. I can determine when a task is completed—I know when to move on to the next task
C. The “big picture” is already set—I don’t have to worry about it

My solution to [a] was described in the section above—I have a curated and prioritized list of “stories” to choose from.

Knowing how to determine whether a task has been completed or not [b] can be done in a bunch of ways. Writing this down is sometimes called “definition of done”, and ideally the definition is formulated so that everyone who reads it understands it the same way. There are various techniques for ensuring good definitions—S.M.A.R.T. Goals is an example—but personally I find it to be a tad too much work. I’m usually content with making a checklist inside the Trello card. (Note: if I was working with someone else I’d spend more time on formulating clear goals.)

The final piece of the puzzle [c] is to not have to worry about the “big picture” too often. The “big picture” is really just another expression for “project scope”. One common mistake is having a project that’s too ambitious. For example, many people who want to make video games dream of making blockbuster size games right away. It’s sometimes easy to forget that those projects take years to complete by teams working full-time—sometimes hundreds of people. Thinking too big, too soon is setting yourself up for failure. Deciding on making Tetris instead of Grand Theft Auto 5 could be the decision that marks the difference between even being able to finish.

The Big Picture

At the beginning of each project I do an exercise I call “The Big Picture”. This takes me usually one-to-two hours, and consists of brainstorming ideas, sifting through and scoring those ideas, and finally assembling them into the structure I’ve promoted above. Sometimes, if I feel like I’ve lost direction and can’t regain it, I’ll do this exercise again mid-project.

1. Brainstorm

Write down everything that would be cool. Don’t scrutinize in this step. Everything is allowed, and it doesn’t matter how fitting or unrealistic it is (What about lasers? Lasers, guys!). Quantity is better than quality.

2. Cut and score

Take all the ideas from the brainstorming and start cutting away things. This is the step where you remove stuff that might make the project too fat. Remember, by putting in too much you’re increasing the risk of making the project too big. Save the ideas you cut for future projects.

When I’m done cutting ideas I put the remaining ones into a spreadsheet, where I categorize them. I then assign each idea (or “feature”) a point value between 1-3 for awesomeness and for effort. This way I begin getting a sense for how much work each feature will take. Watch out for stuff that requires a lot of effort yet contributes only a little awesomeness. Be sure those ideas really are worth the effort. Sometimes, completing them will enable you to create a bunch of great things, but other times they might only be a waste of time. It’s your call, so be sure to make “calculated gambles”!

3. Prioritize

With the scoring step out of the way you should now be able to see the shape of your project scope, “The Big Picture”. Choose how to organize them (for example decreasing awesomeness and increasing effort), and then you’ve got a backlog. This is the list!

I’m not religious about putting everything in score-order—it was after all just a bunch of guesswork. I like to get a few easy wins in first, before jumping into something that might take a little more effort, followed by a few easy wins, and so on. If I’ve built something that I assume will make my life easier I like to make it immediately prove its worth by doing a few tasks that supposedly should have become easier to complete now that the fancy new feature is in.

(4. Work)

At this point I’ll have enough direction to last for quite a while, so I’ll jump into it. If you’re like me, every now and then you’ll lose track of time while focusing on a particular task. In order to remind myself of how much time I’ve spent I’ll set a timer for twenty-five minutes (inspired by the Pomodoro Technique). After the alarm goes off I take a one-to-five minute break. During this break I’ll usually write down how I’m feeling about the task, if my current approach is working, and anything else I find noteworthy. Sometimes a single sentence is enough—other times my thoughts span multiple paragraphs. The reason for doing this is because I believe that many challenges will reveal their solution when re-examined with the wisdom gained from experience.

Wow. You’re at the end of a long post. I welcome you to comment on my approach or share your own, whether similar or not. Tweet me. @marcusstenbeck