My GTD Outlook + Blackberry + Plaxo Setup

At the close of my sixth week of an empty inbox (barring a few spikes following a hard-drive crash), I don’t feel too irresponsible responding to Brad’s request to share my GTD setup with the world. I’d say at this point it’s working tolerably well but not at weapons grade, so I’d welcome any suggested tweaks.

Let me start off by noting that the primary constraints around which I have to work are an office email system that’s on Exchange, with Outlook on pc as the supported platform and mail client. Exchange has the benefit of pushing to the supported blackberries too, but that particular combination comes with some unique issues, particularly if you have a limit on server space and have to push archives offline (as I do).

So, in outlook, I’m using the GTD Outlook plugin from Netcentrics. It’s $70, but well worth it imho, and they’ve let me upgrade and had decent support on a couple of re-installs, so I’m happy. (There’s a free trial offer if you want to see for yourself.) Sorry, Mac people, it’s PC only - but I don’t think you really need it anyway.

In GTD, every action has a “context” = where/when you might do it. Every action can also be part of a project. The idea is, at any given time, you can look at a project and see what needs to be done, or look at a context (e.g., “@ office”) and see what your top to-do’s are that you can actually do when in that location. The outlook plug-in uses Outlook’s native task categories to denote context, and its primary benefit is handling: it does things like let you send an email and delegate it to an @Waiting For category at the same time. It also lets you easily add both context and project to a single item (something not easily accomplished in native outlook, and my primary issue with it). Finally, it lets you associate an action with an email and then store them in separate places, which is very helpful except when you lose them.

For me, simplicity is the key to the actions / contexts setup. You need your to-do list to be a dashboard you can really take in at a glance during your day, without sorting through 15 categories of things you should be considering doing. The first time I implemented this (over a year and a half ago), I had way too many contexts, and I spent just as much time looking over all my contexts for the relevant ones as I saved by having them be so precise. Now, my key action contexts are @Yahoo office, @Yahoo calls, @Calls on the Go, @Home, @Waiting For, @Agendas, @Errands, @Lists, and @Someday. That’s it.

I try really hard to park any to-do in one of those areas - and I also try really hard not to let any given category stack up with more than a dozen or two items at the outside. You can’t really have that many priority items anyway, so everything else is something you should try to do, delete, or dump into low priority bins. For a handful of absolutely-must-do-TODAY items, I use the high-priority flag. Once in a while, I add a new context, but only if I’ve thought it through.

If you’re new to GTD, the power of the @Waiting For category is not to be underestimated, and it works really well in this setup. If you’re working out of your inbox as your todo list, there are probably dozens of emails you can’t really do anything about that are just sitting there until you can. Maybe an invitation to a conference you don’t know if you’ll be able to go to yet - simple, park it in @Waiting For and title the action something appropriate (”conference budget approval”). Or park it in your calendar as something you’ll decide after a fixed time. Either way, it’s gone from the inbox and the list of things you scan all day long when you’re looking for actionable items. I have a lot of stuff in that list, and it’s much easier to review it a couple of times a week than to look at constantly.

The other power of @Waiting For is you remember to follow up on stuff. I can’t tell you how many times a week I shoot an email off to someone at Yahoo! and wait to hear a response. This is particularly true when it’s one of those situations where you’re helping someone from outside the company get intro’d internally. It’s very easy to trust karma, delete the original email, and forget all about it - but if you park it in @Waiting For and, on review, notice it’s still there, you can follow up. People are amazed sometimes when I chase down little items like that repeatedly, and you win a lot of credibility taking care of things you’ve been entrusted to in this really simple way.

So those contexts form the basis of my todo list, and since tasks sync to blackberry and you can filter task display on the handheld by category, i can pull up a list of “Calls on the Go” when I’m in my car or “Errands” when I’m at the grocery store. On the input side, I can easily add a new task I think of when I’m on the move or in a meeting - i usually just leave it uncategorized and file whatever’s new the next time I check in from the PC. I also sometimes use downtime to scan @Waiting For to delete items that are no longer open. (If I’m not surfing m.twitter.com.)

The @Agendas category is also powerful. You create an item for each standing meeting you have or each key person on your team, and in the notes field for that item list keep a running list of things you need to remember to talk to someone about but for which you don’t need or want to send a one-off email.  And, of course, it’s all right there in your handheld when you’re having a meeting.
I do take the time to group some tasks into projects, but only certain kinds. For example, Hiring. By doing this, I can pull up the project Hiring and see all the open (and closed) items having to do with candidates in one view. I don’t currently bother categorizing calendar meetings this way, but I think you could.

Filing reference emails is also key - I have a handful of folders that I keep in an outlook .pst file that’s local (not live on the server), and I drop most stuff post-handling into those. They mostly correspond with particular areas of my work responsibility and the major projects within them. Again, the fewer the better, because I frequently have to dig into them to find stuff. I have on general one for “chron”, where I put one-off stuff I want to keep, two general ones for admin (one for sysadmin stuff like password emails) and one for G&A/HR-type office stuff. I also keep a folder called @shortref in my server-synced files so that I can drop, say, the itinerary of my upcoming trip into there and view it from desktop or palmtop. One downside of this is that I can’t access the archives from palmtop or from another computer, and I have to make sure they’re frequently backed up. But since .pst files were not meant to be accessed over LAN/WAN and have a tendency to hang or corrupt when you try, it’s the best I’ve come up with in the absence of an admin assistant.

One problematic element of being in a high-email-volume environment is threaded conversations and ilists. Again, I try to delete or file these quickly once I’ve extracted any actionable elements from them. If i get a long email I’d like to read, I drop it into an @Computer task and mark it low priority.

Finally, I use the Plaxo outlook plugin, which syncs all of my contacts (thus far seamlessly) between my home and work pc’s. You can configure which things you want to sync, and I also sync my tasks and calendar to the web. I’m going to experiment with installing a 2nd copy of the GTD plug-in on my home pc Outlook client (buying the license gives you up to 2 pc’s) and see if that will work too. But web has been fine so far.

Oh, one more thing. I actually lied about having an empty inbox. There’s one email that’s been in there for a month now. It’s red-flagged and marked urgent, and it’s from me to me. The subject line is “GET OUT OF YOUR INBOX”. It’s the only one that I don’t mind seeing repeatedly when I’m in there.