In this post I’m going to discuss deadline management. Successfully managing deadlines is part knowing why specific deadlines exist in the first place, part knowing which are soft and which are firm, and a big part relationship management. Striking the right balance depends on the situation at hand, but generally speaking, deadlines fall into one of three categories and should be managed accordingly.

First Type: The Faildate

Depending on the institution you’re dealing with, and the level of consultant or employee they’re used to working with, a deadline might actually be a test to see if your work is up to their standards. As a consultant taking on a first contract with a high profile client, for example, a deadline could be the point at which you’re no longer considered for future work. And that’s if you meet them, not exceed them.

To beat these kinds of deadlines, you actually have to beat them. Coming in early is the real key to success, but of course your product can’t suffer as a result. You’ll know when these kinds of deadlines are in play if you do adequate research before signing on with a new client or employer in order to find out about their corporate climate.

Sometimes these types of clients will also want frequent, regular status updates, either weekly or bi-weekly, but even if they don’t, it’s a good idea to micro-manage these deadlines by breaking them down into sub-tasks on a fairly small scale. Hourly goal setting might even be appropriate. Good tools for this kind of work include GTD apps that send you notifications on a schedule you set (Things or Remember the Milk are recommended).

Second Type: Firm, But Flexible

This sounds contradictory, but it isn’t. This will cover the vast majority of deadlines you’ll encounter. These are deadlines that are set as firm, and that should be met if at all possible, but that are susceptible to change depending on circumstances and when in conflict with other deadlines.

The key to successfully negotiating these deadlines is finding out why they exist in the first place. If, for example, a deadline exists for the group you’re working with because without that piece of work, another group is just sitting around waiting, then that deadline takes priority. If it exists because it’s based on a reasonable, pre-project estimate of how much time a task should take, then consider it flexible and move on.

Zen is a nice tool to use to track these kinds of deadlines, because it allows you to create custom groups for your different tasks, so you can make your own priority categories depending on the deadline source.

Third Type: Staledate

The final type of deadline isn’t really a deadline at all. It’s the date at which something ceases to really be a concern, and passes into a client or employer’s distant memory. Be careful, because no one you work for will likely admit that these kinds of deadlines exist, so identifying them won’t be easy.

The best way to go about finding your staledate deadlines is by watching ones from the second category you’ve flagged as low priority. Other signs a deadline may actually indicate when you can drop something entirely include a lack of ability to quantify what would result from meeting said deadline, a lack of client stakeholders associated with it, and lax reporting requirements.

Keep tabs on these as you normally would other dates in your usual PM tools, but don’t worry too much about following through until someone important starts asking questions.

Deadlines don’t have to be the movie monsters we make them out to be. Sometimes they’re just a way of saying “we would like this done within a reasonable period of time,” or even “we don’t care about this at all, but we have to pretend to until time X because the policy says so.” If you listen to your deadlines and monitor them properly, the won’t loom so much as pass uneventfully.

How do you manage deadlines?

Image by Flickr user wili_hybrid.

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Just when I needed her most, along came Doris, a free, web-based task management app developed by Seagull Systems originally for their internal use. (Disclosure: Seagull Systems has done development work for one of my projects.) Doris, their personal assistant, turned out to be so helpful that they dressed her up, in the form of a nice UI, and decided to let her help the rest of us get organized, too.

I’ve tried several task management apps and never found one that was quite right. Producteev is a very nice option, but it has more features than I need. Remember the Milk never did anything for me, though many swear by it. I’ve even tried digital Post-its for my desktop. (Don’t go there. They’re cumbersome, harder to deal with than paper Post-its, and very slow to load.)

I was most struck by the simplicity of Doris. I have little time or patience for steep learning curves, and there is literally none with this app.

Once you create an account (just two fields), the first thing you’ll want to do is create groups (one click) for your to-dos. I created one of for WWD article ideas, and one for side projects, among others.

There is no need to set due dates or priorities. Nothing else is required beyond creating groups and adding tasks. You place groups in any order on the page by dragging them. Within a group, you can drag tasks up or down in the list, and you can drag tasks from one group to another.

How does this help you get things done? You simply check your Doris page every day and drag urgent items from their group into the “Today” group. Then you check them off when they’re done and they go into your “History.” There’s a “Tomorrow” group by default, but you could also create groups for next week, next month; whatever you need.

I really wanted simplicity, and that’s what Doris offers.

Doris is still in beta. I provided my feedback right away and said that I would like to be able to collapse groups individually. They responded by saying you can already do that, just by clicking on the group name, and that they’ll be sure to make that more clear. Seagull Systems are constantly improving the app, so do share your feedback: it could have a real impact.

She’s currently available in English and Russian but, pretty soon, approved translators will be able to log in and translate the whole app in 20 minutes or so via a GUI. In the near future, you’ll be able to share tasks with contacts and set Doris up to send you e-mail status reports if you want them. And you’ll soon be able to synch Doris with your iPhone. Look for her in the app store any day now!

Have you tried Doris?Are there other task management apps that work for you?

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Then there are the enterprise level apps that give me a headache to even look at because they cram a gazillion features and functionality into their interface. Or the apps that have robust features that I can’t find or figure out how to use.

Task2Gather is a pretty straightforward application for managing tasks plus it has an iPhone app which in my book is always a plus. On their site, they define their app as:

“…a free online service for task and project management that organizes your personal, family, social and business lives by keeping all your commitments in one place.”

I have mixed feelings about an app that organizes every aspect of your life although I know my whole like – not just my work – needs it. Still, when I see “organizes your family” on the same app that is supposed to organize my business functions in an efficient and cost-effective way, I get a little wary. But maybe this is the way organizational tools are moving – apps to take care of every aspect of your life because ultimately, they really are inter-related.

In order to get a good feel for Task2Gather, I asked my project manager Marla to test out the tool and give her assessment. Right now we are using Basecamp. I’ve sung the praises of Basecamp before, but these days the number of projects we are managing and the complexity of those projects – each with different combinations of team members involved – is making it harder to keep track of everything.

Marla, in her ever efficient way (thank goodness for organized humans!) came up with a list of pluses and minuses for Task2Gather. Here is what she had to say:

Pluses:

• One feature that my project manager really likes is the stats and reports feature. That could take the place of her weekly past-due reports that she generates by hand in a spreadsheet.
• She also likes that you can assign a deadline that shifts with the project’s priority.
• And she likes that you can see how close to completion a project is, but you have to put in hours spent. That begs to ask the question: Would everyone on our team take the time to enter their hours per project?

Minuses:

• Two things that she feels are lacking in Task2Gather are email reminders and when you post messages or comments, the application doesn’t appear to send copies of those messages to the team members assigned to the projects.
• Also, there isn’t a feature where you can upload file attachments.
• She also feels it is really hard to see the tasks, and especially the deadlines. I have to agree with her on that.

Overall:

Most of the features of Task2Gather are either the same or better than Basecamp and in some cases, just presented in a different way.

After getting Marla’s assessment, I asked Olga Shtaub from Task2Gather to address some of the minuses. Here is what she told me:

1. The emails are currently generated only to inform you if a new project was shared with you or when a new task was assigned to you. To notify about any changes in Task2Gather, there is the “News” feature. “News” contains changes made in Task2Gather like comments, deadline edits, task progress or any other changes that take place and that concern your tasks and projects where you participate. The “News” or changes emerge beside the project or task name and are marked with a bold font. Anytime you log in, you can see all changes and check them immediately. The “News” section is refreshed every 5 minutes.
2. Task2Gather is planning to add a new notification system so users can choose the way they want to be notified by the service.
3. The upload feature in Task2Gather is scheduled for release in the beginning of the next year.
4. The company is planning to change a little bit the UI, design and probably the colors of Task2Gather.

Overall, I think that when it comes to project and task management, it really boils down to not only your needs but your preferences. As cloud working continues to become more and more pervasive, the competition amongst the project management applications heats up in the battle to be better. So while Task2Gather may not end up solving my company’s project management quandries that are often very specific to the way Marla and I like to manage, it could be the perfect solution for another Web worker or Web working team.

What are you using today for project management and task management, and how is that solution really working for you?

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After signing up for a free account, you’ll get a web interface with a box to type. Put in something like “Feed the cat next week” and it will strip off the “next week” part, parse it to get the date, and make the rest the text of your reminder. Then it adds it to the rest of your reminders on the web page. A search box lets you find reminders with particular text, and brighter white is used to highlight the more immediate tasks.

Other features of Deadline include reminders via email or Jabber-based IM, the ability to set reminders by sending email to a personalized Deadline address, and a mobile user interface. For the future, they’re planning an iPhone application, customization, and an API, among other things.

I found Deadline easy to use, though its parsing of English was less full-featured than I’d like (“in a year”, for example, seems to be giving the wrong results). It’ll pop up a box for direct date entry if it doesn’t see any date at all in your entry. Overall, Deadline has less functionality than the most similar service I know, I Want Sandy, but Deadline’s user interface is easier to navigate if you just want to track dates.

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Both of these applications supply ample organizational tools for treating your tasks in strict GTD fashion or reducing them to a flat list: they both allow having a hierarchy of groups and tasks, they both support contexts and tagging. Either one can help you keep track of what you’re intending to do, and remind you when you’re lagging.

What ToDo offers the easiest way ever to build a hierarchy: if you add a subtask, the parent task becomes a group. You can choose what to show on the left-side shelf, from whole projects to single actions, giving you easy access to whatever is important in your mind at the time. You can sort the overall view by project, context, or due date. It supports creating tasks by dragging links in from your web browser, and includes .Mac and Quicksilver integration.

ActionGear hides itself behind a menu bar item and a hotkey (unlike What ToDo, which is a full application). It includes groups which can have nested items within them, though there’s no apparent way to see all of the items in your entire database at once. It also supports embedding files or adding “reference notes” that are not action items. Integration with Growl and Quicklook makes it feel well-integrated with OS X. ActionGear also includes the ability to create smart groups, searching by due date or tag, among other things.

Of the two, I’m liking ActionGear slightly more, though its lack of decent documentation makes figuring out some parts of the interface a bit of a challenge. Both of these applications are available in limited trial versions, and either one can be registered for $29.

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