My Workflow v2

Posted by Howard on Tuesday, February 22, 2022

Some friends of mine recently released a podcast episode on the topics of attention management related tools, and it turned out that one of the resources they referenced was an old blog post of mine on the topic; so maybe that’s a decent place to start and see what’s worked out, what hasn’t, and what new circumstances necessarily change strategy.

As I read back through that post, most of the reasoning behind my need to get more organized still holds true - there’s a lot of cross-group coordination, inputs come in from a number of different sources, and as a result there’s a tendency for work to become almost entirely reactionary. In my current role, there’s one additional challenge. It may not be a wholly different challenge than those that I described facing at Microsoft, but it certainly feels more acute. At higher levels of management, it can almost be seen as a virtue to focus on responding to the needs of the teams reporting to you and abdicate (I think the positive spin word is “delegate”) the vision to others. Typically, we justify this by saying that we’re “shifting left” or empowering teams to innovate or something similar. Now don’t get me wrong - delegation and empowerment are good and necessary things - but not when it comes to vision. Maybe I’m the exception in this view, but the most important part of a senior leader’s job is defining, clarifying, communicating, and driving a consistent vision throughout and across the company. In order to successfully accomplish this, you have to aggressively protect time to think, research, and experiment in many of the same ways that the 30 year old me had to figure out early on in my time at Microsoft.

So with that bit of philosophical soap box out of the way, here’s how I think about time and work management.

First, the principles. I still believe that without some kind of guiding rationale, applying any one of these tools and techniques is applying someone else’s experience and hoping that you magically get their results. But obviously, you’re not any of those people - so the right starting point is to define the core things that you want to accomplish with a system or tool that you plan to use. In my case, the core principles still hold true - in fact, I was pleasantly surprised to see that some of the changes I’ve made are even more strongly aligned with my principles than I had realized (I guess that validates that they were the right ones). You can read the explanation in the original post, but here’s the quick synopsis:

  • Single task list
  • Process over tools
  • Minimize the number of tools

So what’s changed since the original post? I still use Toggl for time tracking and still use it largely in the context of pomodoros. The most notable change has been in my combining tasks and note taking into a single, software tool called Roam Research. I’ll talk about the reasons for the changes and then spend a very small amount of time talking about the tool as there’s so much to it that I wouldn’t be able to do it justice anyway.

So why change?

First a word on note-taking. I still love writing on paper and have amassed a pretty impressive collection of full Moleskin notebooks over the last several years. Aside from serving as a reminder that I did lots of stuff and maybe some periodic nostalgia, the simple fact for me was that these notebooks didn’t really benefit me all that much. This is because the information was locked in those notebooks, unrefined and disconnected from related information that would have benefited my overall knowledge. (If you want to go further off the deep end into thinking about how to make note taking more intellectually useful, look at the zettelkasten method.) Roam is optimized around connecting information into a single graph of data - and you probably know how much I love graphs - so there was an immediate appeal. The more I used it, the more I found a natural rhythm for capturing and refining notes, thoughts, and todos (more on this last one in a second) into one or more linked nodes in the graph. I also got an iPad pro with pencil recently, so I’m still able to take notes as if I were on paper and easily move them into Roam for refinement - so it’s a bit “best of both worlds”.

But what about tasks? I was using Trello and probably more importantly, I was trying to manage my personal workflow using all of the agile buzzwords, tools and techniques. Again, maybe I’m the exception here and you are killing it with your personal scrum backlog, but for me, trying to operate my personal life as if it were a SDLC was pure garbage. A few notable points of friction.

  • you are one person, which means that your WIP limit is always and necessarily 1. Trying to estimate (or achieve uniform sizing of work units) proved an utter waste of time for me, as it didn’t achieve anything other than taking away time that I could have spent doing…you know…the actual work.
  • the time difference for me between keeping a “groomed backlog” and just looking through all of my TODOs when choosing the next thing was negligible. And worse, if I strictly operated from a prioritized backlog, I often ended up working on the wrong things. For teams, I get it - you want to try and create as much stability as possible. However, that’s just not how life works for a person (If it does work that way for you then you have clearly unlocked some life secrets that I need you to teach me asap.)
  • using an independent tool for task management means that you’re probably having to do a bunch of manual task creation and that information - despite your very best efforts to add notes, etc - will be missing much of the context that initially surrounded it. The net effect of this will be context switching and copy/pasting.

At the end of the day, acting as though I was a 1-person software development team was adding process/ceremony without benefit, so in line with my principles, I simplified. One cool feature of Roam (not unlike tools like GitHub or GitLab now offer) is the ability to add a little bit of metadata to a line and turn it into a TODO. In fact, you don’t even need to worry about the specific metadata - you just hit on the same line and that line becomes a TODO. Because everything in Roam is a linked graph, I can then easily jump over to a page that has all of my TODOs on it in one place. These days, I just take a look at the entire list and choose the next thing to work on. But the biggest bonus here for doing this in Roam is that there’s no loss of context. Even though I have a global view of all TODOs that I work from, I’m still capturing them in their original context, whether that’s meeting notes, my research journal, etc - so no more looking at a task and having no clue why it’s there.

So in sum, my principles still hold true, and in that spirit, I’ve streamlined 2 different workflows (and tools) into 1. It’s not perfect - never will be - but it’s continuous improvement. And isn’t that the point of all this?