"Tasks" and "Puzzles": Easier Work Management with Categories

As a project manager who supports over 100 active projects at a time, I have a decent volume of personal tasks or actions to manage in order to keep those projects on track.

This isn’t easy, and I’ve developed and combined many strategies in my 8 years in the field to keep my own workload manageable, from philosophical shifts to tactical workflow habits.

Today I’d like to share one of my favorite new tactics that makes managing my own tasks both easier and more effective. It has made immediate sense to my team and others I’ve shared it with, so the learning curve is negligible, and the benefits come quickly.

Categorize Your Work Items

My simple tactic is this: every time a new work item comes to me, I label it as either a “task” or a “puzzle.” You can think of these as categories, tags, labels, or buckets—whatever works for your brain or whatever options you have in the software program where you track your tasks.

Perhaps you can already tell what my categories mean, but here’s what they mean to me:

• A task is something that, even if it includes a number of sub-items that need to happen in a series, doesn’t require me to figure out much of anything. It might take a few minutes or a few hours, but it won’t be too taxing on my brain, and it isn’t likely to surprise me by how long it takes.
• A puzzle, by contrast, requires me to solve a problem of some kind, or perhaps even define a problem before I can solve it. I don’t know in advance all the individual actions it will require of me, and whether it takes minutes or hours, I probably won’t be able to predict its time requirement in advance. Puzzles also tend to require more brainpower.

Please either steal my categories and use them yourself, or take inspiration from the general idea of task categories to come up with your own!

Using Categories Effectively

Simply using labels like “task” and “puzzle,” or thinking of your work in different types or categories, may bring you clarity about the nature of each item. But there are a few more aspects to the system in which I use these categories that really helps me organize my workdays in powerful ways.

Capture all your work items in one place.

I find I need to see all my tasks in one list and all my puzzles in one list in order to manage and work through the items on those lists effectively. I currently do this within our shared company project management software, but in another work environment I could see myself doing this in another shared digital space (a document or a spreadsheet) or my own personal list (to-do list software or a physical notepad). Any of these would work, but the point is that all my work items are in one place, and in that one place, I have a section for puzzles and a section for tasks.

How do I get everything in one place? In short, diligence and a commitment to doing so. I personally have 3 written ways I can receive work requests (email, instant messaging, and project management software) and 3 verbal ways (by phone, during a meeting, and a pop-in at the office). Capturing verbal work items on my one list is easier because I write them there directly as I receive them, adding the label in the process of capturing the work. Moving email or IM work requests over to my PM software takes a few more steps, but once I’ve done the work of copying and pasting the information to my list with a category, I find I’m able to work through my tasks and puzzles with much more calm and focus.

Prioritize within categories.

The main reason I love having all tasks or puzzles captured in their own section of a list is that I can then put items in priority order within their section.

I think we sometimes get stuck trying to prioritize within a single list of all our work items because items differ from each other along multiple continuums—how much time or effort they’ll take, how soon the deadline is, how important they are to the company, etc. But using categories like tasks and puzzles, I’ve removed that first continuum (how much time or effort they’ll take) from the equation. With one less factor to consider, prioritization gets easier.

As much as possible, I try to make prioritization part of work intake. So I capture the work item with any notes/context, label it “task” or “puzzle,” and then immediately try to place it in the correct location on the task or puzzle list based on its priority relative to the items already on the list. Prioritization of individual tasks doesn’t have to be perfect, so just make the best priority estimate you can in 5-15 seconds.

The key to getting away with only prioritizing within categories, however, is making sure you have a system for giving each category regular time and attention. I am currently experimenting with two similar systems: puzzles in the morning, tasks in the afternoon, or one puzzle first thing in the morning, and tasks for the rest of the day. You could also block specific hours on your calendar to work on the various categories, adjusting how much time each category gets as you observe how quickly you work through the items and whether you’re meeting the necessary deadlines.

Try pull-based work within categories.

Another thing I really love about implementing everything I’ve described above is that it sets me up to de-emphasize stated or perceived deadlines. Instead of using a push-based system where I try to achieve all the work “pushed” to me by the stated deadline, I simply pull the next item off my task or puzzle list at the next designated time to work on it. When I’m finished, I pull the next item—this is a pull-based system. This has done a lot to decrease my stress and increase my satisfaction during my workday, and using categories with effective prioritization are part of the backdrop that makes it possible.

Of course this will be easier or harder depending on how meaningful the deadlines really are on your tasks. I encourage you to let Cal Newport challenge your thinking on how flexible the timelines on your tasks really might be. But even I had to add something to my task and puzzle system—a third “category” of work that is basically all my time-sensitive items. Typically these are reminders for me to check in on the progress of a project and most of these items don’t take very long, but anything that’s especially time sensitive goes on this list in order to free me to use a pull-based approach for tasks and puzzles.

Do puzzles first.

One of the problems I had before I implemented this system is that I would naturally do all the easier items (tasks) on my mega to-do list because, well, it was easier, and I liked making quick progress through my list because it fed the fantasy that I could end the workday with a clear list. The trouble was that I spent so much of my day context-switching between smaller items that by the time I got down to the puzzles left on my list, my brain was too fried and I didn’t have the brainpower left to do them. So puzzles would get pushed off too long, relative to their priority.

So as part of my new system, I work on at least one puzzle each day before I do anything else—even reading email or IMs!—so that I don’t start that frantic context-switching that drains the brainpower I need for puzzles. It’s challenging to put off people who are asking for things, but it has gotten easier with practice and commitment, and as I observe how many more puzzles I get done with less stress, and how nothing really breaks when I wait until 2-4 hours into my workday to start answering messages.

This part wasn’t my idea. I’ve heard encouragement to do the hardest thing first from multiple sources in my life, including via the metaphor of “eating the frog,” courtesy of Brian Tracy. So between encouragement in the ether, and the fact that what I was doing wasn’t working, I now find the discipline to start my day with the hardest thing. Observing the beneficial results has helped me keep it up (most days anyway).

Put it all together.

So my current, actual workday looks like this. Between whatever meetings are on my calendar, I:

1. Work on one puzzle until it’s finished, or until my lunch break.
2. After my puzzle or after lunch, I start working through my emails, IMs, and other new work requests. I answer easy emails or IMs immediately. For harder ones, I turn them into a work item in my puzzle, task, or time-sensitive item section of my list.
3. I work through the day’s time sensitive items until I finish them, or until the workday ends.
4. If time is left, I work through tasks until my workday ends.

I don’t always keep up this system perfectly. I’ve had days when I couldn’t focus on puzzles at all because I was tired, or I had a crazy meeting schedule and needed to adjust. But the point isn’t that I’m rigid about my system; the point is that I keep coming back to it and keep trying (another way of thinking in which Cal Newport encouraged me). My roughly 80% success rate is a huge improvement on what I was doing before. My brain used to feel fried at the end of nearly every workday, and now that only happens maybe one day a week. That’s a major win!

I’m sure your system won’t look exactly like mine. But I hope you can see plenty of ideas in my system that you can adapt into a system that works for you. Meaningful work categories are a great cornerstone of personal work management, and intelligent workflows around them can preserve joy and satisfaction in the workday of a project manager who has an inevitable tornado of demands swirling around them.