Getting (and Staying) Organized

During the past year-and-a-half as a software development manager for a local consulting firm, I’ve tried a number of different tools and techniques to keep me organized.  As my role expanded to include business development, hiring, and project management tasks, there’s been a lot more to keep track of.  I meet weekly or twice-monthly 1-on-1 with each team member on my current project.  “Move it out of e-mail” is my primary objective for getting organized.  The rest of this post will elaborate on the specific alternatives to e-mail that I tried on the way to my current “manager tools”.
Outlook
Beyond e-mail and calendar functionality, Outlook offers a To-Do List and Tasks for keeping organized.  Both provide start dates and due dates.  The To-Do List is tied directly to individual e-mails, while Tasks are stand-alone items.  I abandoned the use of task functionality pretty quickly.  I used the To-Do List as recently as July of this year, but I see it as a bad habit now.  I rarely end up clearly the various options to flag an e-mail for follow-up (Today, Tomorrow, This Week, Next Week, No Date & Custom), so they become an ever-growing list where I only very occasionally mark items as complete.  In addition, the search functionality in Outlook never works as well as I need it to when I’m trying to find something.
Lighthouse
Once I passed the six month mark with my employer, I felt comfortable enough to introduce weekly 1-on-1s as a practice on my project.  After a couple of weeks of filling out a paper template from these guys for each team member on my project, the need for a better solution became readily apparent.  Lighthouse is the name of the company and their product, a web-based application for managing your 1-on-1s with staff.  After the free trial, I chose not to renew.  While I like Lighthouse, and the cost wasn’t prohibitive, my employer wasn’t going to pay for it.
I liked the ideas in Lighthouse enough that I tried to build a simpler, custom version of it myself.  Increasing work responsibilities (and the birth of my twins, Elliott and Emily) erased the free time I had for that side project.  Lighthouse maintains a leadership and management blog that I’ve found to be worthwhile reading.
Trello
I first started using Trello years ago for something not at all related to work–requesting bug fixes and enhancements to a custom website my fantasy football league uses.  I didn’t consider using it for work until I was re-introduced to it by a VP who uses it to keep himself organized.  Once I reviewed a few example boards and set up a board to moderate weekly business development meeting, new possibilities for its use revealed themselves very quickly.  As of today, I’ve got 4 different boards active: 1 for “hiring funnel” activities, another board for business development tasks, a 3rd for project-specific tasks that don’t fall into a current Scrum sprint, and a 4th board as a general to-do list.  The last board turned out to be a great solution for capturing information from my 1-on-1 meetings.  It also tracks my progress toward annual goals, training reminders, and other “good corporate citizen” tasks.
The free tier of Trello service offers the functionality that matters most:
  • create multiple boards
  • define workflows as simple or complex as you need
  • create cards as simple or complex as you need
Markdown formatting, attachment support, due dates, checklists, archiving, the ability to subscribe to individual cards, lists and/or boards and collaborate with other team members of Trello combined with the key functionality above has helped me become much better organized and able to communicate more consistently with my team members and executives in my organization.  The search capability works much better for me than Outlook as well.
I’ve only gotten a handful of co-workers in my organization to adopt Trello so far, but I keep recommending it to other co-workers.  I’d like to see our entire business unit adopt it officially so we can take advantage of the capabilities available at the Business Class tier.