Project and task management

January 14, 2012

One of the most common questions I get from clients, colleagues and friends is how I manage projects and tasks. Some people think I have an amazing memory. (I don’t.) Some people think I use elaborate, expensive GTD or project management software. (I wouldn’t.) Some people think I’ve figured out a way to squeeze extra hours into the day. (I wish!)

Some of the best advice I’ve ever gotten is to stop storing so many things in my head. The first time I heard that, I was insulted. Hogwash! Of course I can store everything in my brain! But can I tell you something? There’s an incredible freedom in knowing that everything is safely stored outside of yourself. I no longer sit in bed every night and make a list of all the tasks that are bouncing around in my head just so I can go to sleep. Everything is already carefully stored and waiting for me the next day, or next month, or next year.

The best thing I figured out for myself is that you can have both structure and flexibility. It’s not an either/or. I’m an INFJ, and my two strongest dimensions are intuition (N) and judgment (J). Flexibility satisfies my intuitive self, in how I take in information about the world around me; structure satisfies my judging self, in how I respond to that information. The result? A flexible big-picture view paired with a structured detail view.

My three-part system

Part 1 — The keeping of the tasks

Every one of my tasks — from project tasks, like design mockups and revisions, to life tasks, like calling to make appointments and picking up salad mix from the store — live in Things. I have both the desktop and iPhone applications, and they sync over wifi. (Yes, I’m anxiously and very impatiently waiting for cloud-based sync, but true love waits. That’s the kind of love I have for Things.) Each one of my current Allie Creative clients has their own project, and projects are assigned to areas.

New tasks are quickly noted in the inbox, to be sorted into areas and assigned to due dates during a block of administrative time during my day (or when I’m waiting for the attendant to put gas in my car). I steer clear of using my email inbox as a task list, so when a new client task comes in, I copy the details into a new item in Things, acknowledge the task with a quick email reply, and archive the email.

My to-do list was the last thing that I converted to a digital system — long after my calendar, address book and many other things — and the transition was totally worth it. I’ve used a host of systems (with some top contenders being Basecamp, Flow and Teux Deux), but I always come back to things. Again, true love.

Do I still jot down quick task lists on paper? Definitely — especially when there’s a lot on my plate and I’m trying to get my head around things and prioritize. I have eight different kinds of to-do lists in my desk. But knowing that there’s a permanent, comprehensive storage location that’s outside of myself is such a relief. It’s like the difference between trying to carry a dozen eggs in your bare hands and placing them in an egg carton.

Bonus: You’ll impress your friends when you remember to bring them the book they asked to borrow two months ago at your last dinner date.

Part 2 — The quick reference

There’s one small gap in my task management when it comes to projects, and that’s the quick reference or at-a-glance view. Or, more accurately, views, plural. Being able to see the full list of all my projects and all of their sub-tasks is great, but I’m often looking at 20 projects and hundreds of tasks. Trying to quickly decipher the big-picture view can be challenging. It’s hard to see the forest for the trees.

For awhile, I used tags (within Things) to generate views, but the tag management wasn’t working well in my flow. I was already using (and adoring) Simplenote (for iPhone) and Notational Velocity (for Mac) for managing notes and other kinds of quick reference items, so I added a project quick reference to my notes. I list all of my projects in two ways: by date and by size. In the date schema, I have sections for:

  • now — things that are due, or that I’m working on, either today or this week as a whole
  • next — things that are on deck
  • then — things due anytime after next week (that I can work on this week or next week if I have extra time)
  • on hold — things that are waiting on another party
  • upcoming — things that are on the docket but haven’t started yet (like scheduled projects)

At the end of each day, I take two minutes (at most) to update this list. And at the end of the week, I spend 5-10 minutes strategically shifting things up — or figuring out what I need to do to spur a project out of a holding pattern.

In the size schema, I have broader buckets that are more unique to my workflow. One bucket might be for projects with 20 hours or more remaining until completion; the next bucket may be for projects with around 15 hours remaining. There might be design projects in both buckets, but they’re differentiated by scale. I often play around with these buckets and adapt them to what suits me best. And that’s what’s great about a simple text-based list: It takes 30 seconds to try a new sorting method, and 30 seconds to switch it back. The strength of my task management system (part 1) is structure; the strength of my quick reference (part 2) is flexibility.

Part 3 — The wrangling of the files

This is probably the simplest part of my flow. I tried using Basecamp for file storage; it drove me crazy. I tried demanding that all project notes and copy live on Google Docs; it was impossible. So I went back to the simplicity of folders and files. Every client has a folder. Every client folder has subfolders for projects and assets. I use (fairly) consistent naming conventions for the files and folders, but it’s not perfect. And yet I’m never unable to find a file. I call that a successful system.

I still use, and love, Google Docs, especially for what it’s designed for: collaborative documents. If I’m working with a project manager, we can know that we both have the most up-to-date copy of the client’s website content. If I’m working with a copywriter, I can make comments and request revisions without a complicated, six-quote-level email thread. I also use Google Docs almost exclusively for spreadsheets, since it handles spreadsheets so elegantly. But I’m not afraid of having documents on my local computer, either.

Anything else?

I’m an organization junkie. I’m always thinking about how the things I do now help or hinder Future Allie. I believe that expending a small amount of extra energy to do things right now keeps small things small (and keeps big things manageable) later.

But if that all this sounds like too much — or if you need a good starting place to figure out your best flow…

  • Start doing a 10/15 split. Spend 15 minutes at the end of the day checking out, and spend 10 minutes at the beginning of the day checking in. My three-part system usually takes care of these check-ins/outs through osmosis, but there are days when coming back to the 10/15 split is invaluable and necessary. If you don’t like your current task/project management system, or don’t have one at all and feel overwhelmed a lot of the time, start with the 10/15 split.
  • Try heatmapping your productivity. By figuring out when you’re at your most productive, you’ll figure out the best time to start tackling things like project management and file organization. For example, if you’re at your creative peak from 2-4 in the afternoon, that’s not the time to organize your task list; it’ll feel like a chore. But if you’re a bit slower to get rolling in the morning (like me), setting due dates and categories for tasks might be just your speed at 9 a.m.

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  1. Allie,
    I love this! I need this! I can hardly understand a word of it though… so I’m going to go over every detail, look up each link, and then come armed with questions! Thank you for opening up your organizational genius to help the rest of us unravel our chaos!

  2. Thanks for sharing. Always a big tour to get things aligned, and I’ve always admired how you do so much and also allow yourself Fridays off.



  3. Allie Girl, this is fantastic. I totally agree with Diane though, I don’t understand it, but would love to set it up and get organized. Thank you for sharing. Can you do a training day for us??

  4. Allie – I love this, too. But, like Diane, I can hardly understand a word of it! I don’t yet have the tools you mention (iphone – my plan isn’t up for a change until April; I don’t have a mac or any nifty technological toys yet). To some degrees, that in itself, keeps my life more simplified. And being fairly organized, sticky notes and lists have kept me in line so far. But I do like the idea of prompts and reminders, because sometimes an old sticky note disappears into the background. So…I think we need a workshop, put on BY YOU! …once I get some technology to actually bring to the workshop! Thank you for sharing.

  5. I think maybe you have a book in you. . .

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