A gap in task management: discontinuous work

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I’ve written a great deal on what we call the 3D workforce — decentralized, distributed, and discontinuous. As I characterized it for a webinar last year:

Teams are mobile and geographically distributed, and they extend beyond the boundaries of a “corporation” to freelancers, customers, and supply chain partners. Timeshifting and multitasking force work to be discontinuous, and demand loosely coordinated, short-term projects. Decentralized teams get less oversight and are relying on results-only work styles.

I’ve been talking with a lot of task management product managers recently, as I gear up for the 2016 Task Management Narrative, an in-depth look at a long list of task management tools, including Asana, Azendoo, Basecamp, Clarizen, Flow, Producteev, Wrike, Smartsheet, Todoist, Trello, and others. And I have lit upon a problem regarding task management that none of the tools seem to address.

My work is discontinuous. So the actual work associated with any given task is likely to be performed in a fragmented way: two hours yesterday, 45 minutes today, and 4 hours over the weekend. Task management tools are designed to allow me to deal with some aspects of my work — such as assigning a due date (quite a common feature) and perhaps a start date (a much less common feature) — but the discontinuous reality of actually getting things done is not well supported.

In my case, I use a daily technique for planning my work — as do many others — but it is not actually supported by a computerized tool: I use an Action Notebook, designed by Behance, and each morning pick the tasks that I am going to work on, and write them on the righthand page. [Note: this is not exactly the version of notebook I use, but the differences don’t matter.]

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You’ll see that there are only seven of the task areas (in blue) on the right hand page. Based on my immense laziness but equally great self-awareness, I know I can only accomplish a few things each day, because life and me. My technique is to plan on working on one task that will involve an hour or more of my time, which I designate as the top-most, and I write ‘1/1’ and then the work I plan to do, like ‘1/1 write up A gap in task management: discontinuous work’. I allot two slots for working on two activities in the 1/2 hour to 1 hour range, such as phone calls, and I denote them as ‘1/2′ and 2/2’. I am still an optimist because I believe I can accomplish three tasks taking (in principle) less than a 1/2 hour, which I denote ‘1/3’, ‘2/3’, and ‘3/3’. There is one additional slot available at the bottom, which is a wildcard for the unexpected.

That’s it. 1 2 hour block of work + 2 45 minute blocks of work + 3 30 minute blocks of work = 2 +1.5 +1.5 = 5 hours. The rest of a prototypical day is consumed by lunch, emails, unexpected requests, dithering, and miscellaneous activities.

And I seldom have a day go as planned. Circumstances intrude. A call is rescheduled. An unexpected opportunity leads to a proposal. Again, because life and me. So, very often I start out on Tuesday making a list and including things that I never could get to on Monday.

Your mileage may vary.

The point I am making is not the specifics of how I manage my time each day — and each week, in a less refined fashion — but that I am trying to schedule my work each day, and it is not well-integrated with my calendar or my task management solution. There are some exceptions, such as telephone calls or other meetings, which are always scheduled on my calendar (Google Calendar), but in general my day-to-day participation in the tasks I am working against is captured only in my work journal, and not in my task management tool of choice (Todoist, at present).

What I envision as a solution requires a few new features, or refinements of features.

Treat tasks as discontinuous — Instead of modeling tasks as though they are monolithic, they would be better modeled as a discontinuous sequence of fragments. This is something like the way that time trackers work, although I am less interested in the keeping track of time aspect, and more on the planning side.

Likewise, we have the general concept of subtask, but that is used in a different way, means to break a more abstract task into a collection of tasks that can be distributed to multiple individuals, and undertaken possibly in parallel. Subtasks also are used to capture dependencies across phases or stages in projects, which isn’t what I am getting at. Even if I were to use a solution with subtasks and task dependencies, I would still want to plan around discontinuous chunks of work making up those tasks and subtasks.

Surface daily and weekly planning in calendars with other scheduled activities — As Mike Monteiro at Mule Design put it,

Most people don’t schedule their work. They schedule the interruptions that prevent their work from happening. In the case of a business like ours, what clients pay us to make and do happens in the cracks between meetings, or worse, after business hours.

So I would like to *not* use a work journal to enter my 1/2/3 task plans everyday. I would rather do it within my task management tool. Imagine a daily planning regime, where I would pick today’s tasks from my task management tool’s task list, and for each I could allocate a hypothetical time range — in my discipline , 2 hours, 45mins, and 30 mins — and have those task fragments associated with the appropriate tasks as a new sort of metadata, something like comments. At the end of each day — or the next morning — I could indicate — with check boxes, notes, etc. — whether in fact I actually did work on the task as planned, and when (if I care about the when). So at any point I could look at the history of the work done on any task, and the days when I did that work.

And it would be best if my task management tool had a real ’round-trip’ sync with my work calendar, so I could drag my work fragments around other calendar events, and my plans regarding the fragments would show up on my calendar, allowing me to sidestep the calendar/work paradox that Mike Monteiro wrote about. (Even better would be an AI ‘bot that would move fragments around on my calendar based on my preferences, like scheduling the 1/1 task for early morning, when my concentration is best, and moving tasks involving calls and meetings to the afternoon.) Since the actual work I plan to do would actually show up on my work calendar, others wouldn’t schedule an unexpected meeting right in the middle of me writing this blog post.

The Takeaway

It’s possible to imagine that I could phony up a way to do discontinuous tasks with a lot of manual work, today. I’ve tried at various times with various task management tools, but those have always been unsatisfactory and very time consuming.

The key takeaway is that supporting how we actually work — not a simplified and incomplete analog of it — requires complex tools that are designed for that purpose. The reality is that today’s task management solutions don’t reflect the 3D world of work, or do so only in a drastically minimized way. The vendors that push in that direction will likely be the victors in this marketplace.