Howard Dierking

My Workflow

I initially became interested in personal workflow methods and tools when I started at Microsoft in 2006. Microsoft differed from my previous roles in that projects generally required coordination across multiple teams - meaning that there were lots of tasks to manage. Additionally, the corporate culture made heavy use of emails and meetings - meaning that tasks could originate from a variety of sources at almost any time. Without some kind of structure, working at Microsoft could very easily become purely reactionary. And as you may have experienced in your own work, reactionary work may keep you busy, but it doesn’t make you very effective. Most importantly, this kind of work doesn’t feel very satisfying.

So as the barrage of information threatened to overload me, my skip-level manager at the time suggested I read “Take Back Your Life!“ by Sally McGhee. The book provided a process and strategy for using Outlook to manage a personal workflow. This worked especially well for me because at the time, the bulk of my tasks originated from something that came in through Outlook. Over the years that followed, this book along with “Getting Things Done” and “Getting Results the Agile Way” influenced the bulk of the method and mindset I used to try and keep up with my life - even as it was becoming more and more complex and fast moving. I’ve tried implementing these methodologies using a variety of different tools.

I won’t say that I’ve found “the one” in this post, because I have been and will continue to be hacking away and finding new ways to improve my own productivity. However, I’m feeling pretty good about the current approach and tool set that I’m using. So I’ll quickly share that here with you.

Principles

If there’s an overarching theme to all of this, it is be intentional with everything you do. Unsurprisingly, different things work better or worse for different people, because we’re all … you know … different. Some of what I’m going to write about here may work well for you - some won’t. If you’re curious about a technique or tool described here, try it out - but don’t feel like you need to stick with something that isn’t really working for you just because it may be working for me at this point in time.

When getting into the details of a specific process or tool, here are a few additional principles that I have found useful.

Methodology and Tools

So, with the high level stuff out of the way, here’s how I’m managing my workflow at the moment and into the foreseeable future.

Single Kanban Board with Trello

I have found that a Kanban-style workflow works best for me over a more structured framework like Scrum. I think the biggest reason for this is that for a personal workflow, I don’t find task level estimation to be helpful for planning and I therefore find them to be a source of unnecessary obsessing (“is this item 2, 3, or 5 story points?!?!”). I also find some of the resultant artifacts like burndown charts to be a distraction. Now, before you think I’m unfairly bashing Scrum, I think Scrum can work great in team environments - I just find it a bit over the top for my personal workflow. If it helps you, go for it! At any rate, I use a Kanban flow using Trello as my digital board. Because I use the same board for every aspect of my life, I use Trello’s labels for categories such as “work projects”, “personal”, “family”, etc. I do this because I have found it helpful to be able to see at a glance if task-level priorities actually line up with my higher level life priorities. Put another way, if I look at my backlog or weekly lists and see that they are completely dominated by work tasks, I need to step back and re-evaluate.

My Trello Board

Trello is one of those tools that is so flexible, it can be anything you want it to be. This quality can also make it completely unusable if you don’t have a strategy for structuring it in a way that is suitable for the workflow you’re trying to achieve. In fact, I had tried using Trello in the past, and abandoned it when my task lists grew past a certain size. The friction I experienced in this case had less to do with something inherently wrong with Trello and more to do with the fact that I was using the standard “todo”, “doing”, “done” board structure. Therefore, as I’ve built up my current board around how I like to work, I’ve found the following pipelines helpful.

Additionally, you may notice from the picture the colored background for some of the pipelines. Because I want to enforce some self-discipline with my Kanban workflow, I use a WIP limit plugin for Trello. At the moment, I’m only setting limits on my active pipeline (4) and my weekly pipeline (15). As in the case of any agile process, these limits are based on observations about my typical velocity.

Time Tracking

I avoided time tracking for a long time as I didn’t really see the necessity. However, as my role changed and I had to deal with more and more interruptions, managing time quickly became one of the most important skills that I needed to develop. I started tracking my time using Toggl a couple of years ago, but I didn’t really stick with it. However, last year I heard about this simple time management technique called the Pomodoro Technique where you basically slice your time into 25 minute, focused blocks with fixed breaks in between. When I noticed that Toggl had built-in support as a pomodoro timer, I decided to give it another shot and I’ve been happy with it.

My Toggl Dashboard

As you can see, Toggl also provides some handy dashboards so that (assuming you use it consistently) you can see how you’re allocating your time over a given period. I’m not particularly obsessive about this aspect, but it can be useful to see whether how I actually spend my time matches up to how I say I want to spend my time. It also has a nice little iPhone application so that I can track my time without being tethered to my computer. If any Toggl folks are reading this, I would love to see an iPad equivalent, as that’s what I use for most of my technical reading.

Weekly Retrospective and Planning

I have only one “ceremony” in this workflow and that is a weekly retrospective and planning. Rather than describe it in prose, I’ll just show you the Trello card that I duplicate during every retrospective session.

Weekly Retrospective Card

I’ll quickly point out a small handful of things that you may or may not see right away.

Handling Meetings, Email, Slack

Unless you have the luxury of being independently wealthy and working on projects that only you will ever see or care about, you probably have to interact with others as a part of your work. Our professional and personal lives are environments of constant interruption and I believe that our ability to tune out the noise and create the time to focus - to think - is the most important discipline that determines whether we end up being busy or being effective. I’m still struggling to find the right balance myself in this arena, but here are some techniques that I’m currently using.

I hope that some elements of my workflow prove useful to you. At the very least, perhaps this post will have you think through your own workflow with a bit more intentionality. Either way, thanks for reading and if there are specific techniques or tools that work for you, let me know so that I can see how they might fit into my workflow!

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