User>Driven

I've been using a new task list manager called Remember The Milk. I decided to check it out when I read that it was one of the first webapps outside Google to use Google Gears to allow offline access. I've been looking for that one single task list manager I could use offline and on that didn't suck like Outlook so I thought I'd give it a try.

Overall I like this little app, but it can't be my one task list tool. It has some inspired touches, but ultimately the fact that it was created on a shoestring by amateurs shows both in usability issues and product management missteps. Here are my thoughts on what works and what doesn't.

A Simple Interface

The interface is uncluttered and readableRTM is overall the most usable web-based task list manager I've come across. It has a simple interface that allows for quick entry and crisp review of task lists. It's quick to add a new task (though slow to add any details). The interface is also readable, very refreshing compared with ultra-busy Outlook.

Easy Categories

It's easy to move back and forth between categories via the tabs, unlike Backpack, OneNote or EverNote which make it harder to find and move between different lists. Tasks disappear when completed (unlike most Outlook views) but are still retrievable if needed.

You can assign priorities to tasks and also attach notes, a critical feature missing from many simple task list managers, including all of the above. These are the minimum metadata elements I think any task list manager needs, but RTM has more.

Tagging Afterthought

Tags provide an alternative navigation mechanism but access is limitedYou can assign as many custom tags as you like to any of your tasks. This allows you multiple cross-category ways of quickly finding or organizing your tasks. My tasks are categorized by venue (the place or manner in which they may be done) within categories like Seated (things I can do at my desk), Puttering (things I can do up and about the house) or Errands (things I have to go out to do). They are also tagged with more general topics like Home_Improvement, Finance, Family or Business.

This is the first time I've seen tagging used in this way and I like the idea. I have to admit, though, that the tags haven't proven as useful as I expected them to be. I think they'd be very useful for business tasks, but personal tasks seem to be easier to manage strictly by category. They would also be more useful if they were more accessible. Only in the Overview can you access the tag cloud that serves as a navigation mechanism.

Nearly There Dating

A feature RTM shares with Gootodo, Mark Hurst's online task list manager, is the ability to schedule tasks for dates in the future. This is a great way to simplify your current list because it gets things you can't work on now out of your view. Unfortunately, this feature only filters future tasks out of the Overview display, leaving them in the category displays which, you will see, one is forced to use often.

Anywhere Access

The nirvana for a productivity nut like me is to have one consolidated task list. To make that happen, you need to have access to your list wherever you are. PDA apps are too limited. Standalone desktops apps are inaccessible if you're away from you PC. Webapps are inaccessible if you're offline - except for RTM, that is, which uses Google Gears to allow access right in the browser whether you are connected to the net or not. You have to login before you go offline, but you can keep working if you then get on the train or walk out of Starbucks. This is superior to Google Reader (the first app to use Gears) which requires you to manually sync before you go offline.

Well-Intentioned Filtering

The overview is simple but mashes all categories togetherOne thing about RTM that does not work for me is the Overview UI. It's meant to be the cleanest, most minimal display in the product and it is well-intentioned. For maximum productivity, you need to focus on only what you're going to work on right now. The Overview filters out anything that's not due today. It also filters out tags and categories, leaving tasks marked by priority and sorted in priority order.

To be readable with more than 4-5 tasks, though, the Overview needs to be organized by categories and needs to allow you to check things off as you complete them. As it is with tasks in strict priority order, you have to read up and down the list to find something you can work on now, rather than just working on the first thing in a chosen category. I end up going back and forth between the overview and the category views trying to figure out what I should be doing.

Then once you've completed something, you have to click through again to the category view to check it off and get rid of it. The app is responsive, but this is too many clicks, too much switching of views.

Clunky Data Entry

Data entry requires three different sets of controlsI said that entering new tasks is quick but it could be much quicker. After you've typed in the text of your task, you're going to want to assign it a priority, put it in a category, give it a date and maybe add a tag or two. To do that you need to use a pull down menu (twice) and a side panel after you've entered the task itself. Follow me here. That's click (the Add Task button), type, click, click, click, click (to assign priority and category via the menu), click, type (to assign the date), tab, tab, type, enter (to enter a tag) - all for one task. All of this should be doable with one form, one click and typing separated by tabs.

The interface looks like it started with a simple design and got busy as successive layers of functionality were added without revisiting the basic elegance that is the best feature of the app. 

Questionable Integrations

Another feature RTM shares with Gootodo is email integration. This is a great idea in concept because people so often use their email inbox as a to do list. Forwarding an email to your RTM account allows you to clean out your inbox and gives you another way to access your central task list. Well, like I said, that's the theory. You have to remember or have your email program remember for you an arcane email address unique to your account. You can't date, tag, categorize or prioritize your task via email. The task arrives in your RTM inbox with the subject line as the task name and the content of the email as an attached note. You then have to add all of the metadata to know what to do with this task.

What's really needed is not to send an email out to a separate task list, but to tag your email with a task, retaining the linkage between the two. This would allow you to complete your task and then get back to the email and let the person who sent it know you've done what they asked. The sprawling open source project Chandler is attempting something like this but they seem to be reinventing Outlook in the process.

iPhone and iPod Touch integration makes more sense than syncingRTM also syncs with Windows Mobile. I don't know why I would want this, though. Either I have a connected device that lets me access the web version of the app, or I have a stand-alone device, in which case I probably want to use the built in task manager. Having my list in two places that I sync once or twice a day would make it too easy for me to get my lists out of sync. RTM has recently added iPhone and iPod Touch integration, though, that looks very slick and makes more sense since you are essentially just accessing one instance of the webapp via a smaller browser.

There are integrations with Twitter and RSS feeds as well but I don't see a lot of utility in these things. More access modes does support the "one list" concept, but beyond web and offline access I'd rather see them focus on core usability issues.

Uncertain Business Model

Windows Mobile syncing was RTM's first paid feature. (iPod integration is the second.) RTM claims to have 300,000 registered users but they recently added a Pro subscription that costs $25 per year. A free version combined with a more sophisticated paid version is a classic business model but there is not enough differentiation here to make me want to upgrade.  I imagine over time they will build more compelling features. I hope they do that (and address some of the issues I've highlighted here) so they can keep the business running. They seem to have been running it for a couple of years now with no revenue, so I give them props for perseverance.

Overall, as I said above, I like this little app. It's got a clean interface, the right basic features, and access when I need it. It's also free. So why am I not raving? Aside from some of the more basic usability issues, the lack of a properly filtered overview and the lack of effective email integration stand in the way of it becoming my one task list manager. Without those things, it just won't scale to the number and variety of tasks I manage at work.

I continue to use it at home for my personal tasks like remembering to do the bills every week or run errands. Meanwhile, I continue to search for that one app that will hold my one, universal task list with ease, integration and sophistication. 

Poor search is one of the many ways in which Outlook sucks. The native Search built into Outlook can only search one type of folder at a time (your inbox, personal folders, archives or public folders). It's also so slow I find it unusable.

A few years back I discovered a great Search plug-in for Outlook called LookOut. It was lightning fast and it not only searched all Outlook folders at once, but it even searched designated folders on my hard drive (e.g., the My Documents folder).

How fast was it? I did a search for the last name of a coworker and the code name of a project we're working on together. It took 3.06 seconds to find 128 documents containing both terms, including emails, meetings, spreadsheets, Word docs. The same search required me to open Advanced Search in Outlook (otherwise it searches subject lines only), only allowed me to search my personal folders, took several minutes and turned up only 39 items. I can't explain why Outlook search is so unusable, but LookOut has made me much more productive.

What's the big deal with search for Outlook? I'll tell you! Good search turns your computer into a database.

I store a lot of the mail I get (and send) permanently. I also have a hard drive full of documents I've created or received. I do this because I often refer to past emails or documents to remind me of past decisions and reasoning, and to base new materials on when I need to create them. A lot of people use their email as a kind of filing system. The problem is finding the material when you need it.

I have a system of folders I keep these things in, but it's hard to remember which I might have filed a specific item in and each folder has gotten quite large on its own. Searching across them all at once and getting results back in a sortable format makes it very quick to locate a specific email or document. I do this several times a day almost every day at work. Imagine if I had to wait minutes every time I did this and then had to repeat the search for different types of folders and on my hard drive before I could find what I was looking for. I would soon give up on searching in this way.

I have a colleague who keeps a set of well-organized folders on his hard drive, one for each of his projects. He saves every document associated with that project in the relevant folder, even saving local copies of individual emails there and then deleting them from Outlook. He has a meticulous filing system that he says never fails him and he can track the progress of every project, document by document. I confess, that kind of diligence is beyond me. I just can't keep up that level of maintenance. And frankly, I don't think I should have to. A fast and comprehensive search tool makes it possible for me to find what I need wherever it lives.

I am still happily using LookOut but you may have trouble finding it for download. Microsoft was apparently so unhappy with how well this freebie worked in comparison to their Desktop Search tool (a separate download that searches multiple folder types and your hard drive, but still much slower than LookOut and with a much clunkier, harder-to-use interface) that they bought the little company and made the product unavailable. Googling LookOut actually took you to the download site for Desktop Search. There was a huge outcry and they actually put the product up again, but only temporarily. You can't download it from Microsoft as of this writing. The only place I could find it for download today was here. I don't know if that will last so I have included a download link to my own copy here. It's freeware, so I am assuming I am not violating anyone's copyright or any laws.

Anyway, I hope everyone gets as much out of LookOut as I do. Post your experiences in comments below or head over to the Productivity forum to discuss. 

I attended the Boston installment of the FogBugz World Tour this morning held by Joel Spolsky, the author of Joel on Software and cofounder of Fog Creek Software.

The software includes bug and enhancement tracking features like those in Bugzilla with a wiki for managing requirements, discussion boards for you and your customer, and project management software that uses your developers estimates and (critically) your developers historical accuracy at estimating. It wraps these features together in one of the smoothest, lowest-effort Ajax UIs I've seen to produce a suite of tools for managing the software development process.

Joel himself was the first person I met at the seminar and I got the chance to shake his hand and ask him a few questions one on one. He is low-key, articulate and funny, just like his blog. Some of his memorable lines at the seminar included:

We're on roughly a 1-year release cycle. If you are on a more like a 6-year release cycle, you're probably on the Vista team at Microsoft.

FogBugz handles email because, as we all know, all applications eventually become email clients.

We don't have an offline mode because it turns out it's easier to get internet access on planes than it is to get offline synchronization to work right. 

We use FogBugz internally to manage our projects. We don't use Microsoft Project because the software development team for Microsoft Project doesn't use Microsoft Project.

That last quote brings me to why I think Fog Creek has been able to produce a product in FogBugz that is so neatly tailored to the needs of software developers and development organizations. Joel and his crew are so very user-driven in my estimation because they themselves are the users.

The company's motto is "Building the company where the best software developers in the world want to work." They are famous for providing privacy and large monitors for all of their developers, for eschewing VC capital, and for doing very little marketing outside of Joel's blog. Joel says the most reliable way to grow revenue that he's found is to simply release a new version of the product. This all contributes to their focus on developers and since they are developing tools for developers, there arises a virtuous cycle.

Let me give you an example of how this works. In an interview with Robert Scoble, Joel described why there aren't a lot of reports on developer productivity in FogBugz. He says it's because lazy managers use these kinds of reports against developers and that creates a disincentive for using the bug tracking software, which in turn actually makes it harder to manage the development process. Joel's intimate familiarity with the reality of software development processes makes it possible to look at a feature request from what he calls an "anthropological point of view," rather than simply a prioritization or implementation point of view. What he's really saying is that Fog Creek is user-driven rather than feature-driven.

I don't know if Joel and crew would be as good at putting themselves in someone else's shoes. In fact, I'll bet the relative lack of success of another of their products, City Desk, is related to the fact that it's not really a product for developers. Or rather it is, but it shouldn't be. I've tried the software and it's really attempting to solve the problems of web content producers in small organizations. Unfortunately, I think it takes a developer-oriented approach to that set of problems, limiting its appeal to those developers who sometimes have to act as content producers.

Good designers instinctively know that a "clean" and "uncluttered" design is more effective in conveying information. Unfortunately this kind of gut feeling isn't always enough to stop clutter from creeping into designs for everything from websites to store signage to brochures and product packaging. Also, it's hard to quantify clutter. How much information is too much?

Researchers at MIT have may now have a way to help. According to MIT News, researchers "modeled what makes items in a display harder or easier to pick out. They used this model, which incorporates data on color, contrast and orientation, to come up with a software tool to measure visual clutter."

By itself, a clutter detector might be interesting to researchers and designers on a sort of academic level. The MIT folks, however, took things a step further and actually demonstrated experimentally that their measure of visual clutter affects human performance in information retrieval. Again according to MIT News the researchers "found good correlation between the time it takes to find a symbol in a map and the amount of clutter according to their measure."

So design purists, now you have the proof that too much information undermines its own usefulness and a tool to measure exactly how much is "too much." You can even download the tool, written in MATLAB format, from MIT's site for free.

What's your favorite overly dense, hard-to-use visual display? My perennial favorite is airport signage. Ever notice that despite the incredible number and variety of signs at airports that when you get off a plan at an unfamiliar gate you usually have no idea which way to go?

Fantastic list of Google Maps mashups. I found nearly every one del-icio.us-worthy.

The one I stuck on my Firefox Bookmarks Toolbar right away is the phone number locator. It allows you to type in the area code and exchange of any phone number (say of a number you don't recognize that just called you) and see where that exchange is located on Google Maps.

I typed in my own number and it says I live several towns away from where I really live, but that may be because I have VoIP and, frankly, it was close enough.