Web Worker Daily

Here’s an interesting little productivity idea from dancingmango: when you’re trying to understand the successes and failures of a system, have the current users of the system write a tombstone or obituary for it. For example, I recently gave up on a particular shareware to-do application, with results that might be summarized this way:

Mike’s To-Do List
2007-2007
Attempted to deliver timely reminders, but couldn’t handle properly scheduling
recurrent tasks.
Ultimately ignored as an unreliable assistant.
Survived by notebook and pen.

By boiling down my experience with this application to just a few lines, I know one critical thing: if I go looking for another application in this space, it needs to handle recurrent tasks properly, or I might as well not bother installing it. Thinking in “tombstone” terms forces me to focus and pare things down to the bare minimum, which is very useful in spotting the essential way forward.

You can use the same technique any time you want to know the 1-3 most critical failures or successes of a piece of software, system, or organization. One caution: avoid the temptation to use this as a way to just take cheap shots at things.