Overcoming Massive To-Do Lists

As much as we try to avoid it, there are times when our To-Do Lists become overwhelming.  This is true across virtually any team - or individual - within any organization, regardless of size.

As a Product Leader, I have often been confronted with this problem.  Over the years, I have evolved an effective methodology that reliably produces positive results.

This easy-to-implement methodology has proved successful both for my work as an individual and for large teams I have led.

The methods consists of four elements:  Time Period, Categorize, Classify, and Prioritization.


Step One: Set A Time Period

The first step is to set a time period to address the initial block of tasks on your list. It may take several - sometimes dozens - of these blocks to resolve your entire list.

For first-timers, I recommend setting your period for one week. This will allow to focus and achieve some quick success while learning the method. When working on my personal “To-Do” list, I typically set my time period for one week.

When leading teams, I typically set the time period at two weeks. This aligns with the typical “sprint cycles” of agile software development teams.

I tend to use the term “sprint cycle” for these time periods, regardless of whether I am leading a software team, or not.

Step Two: Categorize

The second step is to identify which of the items on the task list will be included in your initial sprint cycle.

Effectively, you create two lists, Active Items and Backlog Items.

Active items should include items that you will could accomplish in a highly-productive sprint cycle. In reality, you may not complete all of the active items in your first sprint. That is ok. You should expect to have some items roll into the next sprint cycle.

Items that are not being addressed in the sprint cycle are placed in the Backlog. You will then revisit, “groom” the backlog, and pluck out new items to include in the Active items list for your next sprint cycle.

One last step is to look at the items on your Active list and identify which items have Dependancies, which are tasks that need to be accomplished before work on this task can commence.

Step Three: Classify

This step involves identifying the tasks before you and categorizing them in terms of Urgency and Difficulty.  There are three levels of each.  This leads to tasks being assigned into one of nine categories.  These categories are later prioritized.

Here are the steps to the prioritization process:

  1. Compile a comprehensive list of all tasks on your To-Do List.

  2. Scrub the list to reduce duplication and to sub-divide larger tasks into actionable elements.

  3. Categorize the Urgency of each task in terms High, Medium, and Low

  4. Categorize the Difficulty of each task in terms of Easy, Medium, and Difficult

  5. Populate the categorized tasks into Table 1 (below).

  6. Evaluate the matrix and make any adjustments for Dependancies. For example, you cannot logically have a task in Cell 3 that is dependent on a task in Cell 5 being accomplished in advance. You must either 1) move the Cell 5 task into Cell 2, or 2) move the task in Cell 3 to Cell 6.

Table 1:  Item Categorization

Step Four:  Prioritize

With each task assigned into nine categories, we now prioritize the order which we will tackle the tasks in these categories.  Table 2 (below) details the order in which we will focus our work efforts.

Table 2:  Task Prioritization

This prioritization starts by addressing the easiest and most urgent tasks in Cell 1 first.  The most difficult and least urgent tasks - Cell 9 - are addressed last.

Before commencing work, it is important to look at the items in Cells 3 and 6.  We are delaying work activity on these tasks, which may prove problematic.  If possible, subdivide some of these tasks into smaller (less difficult) tasks and reassign into Cells 1,2,4, and 5.  This will help you address these items quicker.

Here are some notes on the prioritization rationale:

  1. We start by addressing tasks in Cell 1.  This will allow you to quickly complete some of your urgent tasks, removing stress from the team.

  2. There is a tendency for urgency to change over time.  In particular, tasks assigned with medium urgency often become more urgent with time.  For this reason, we address the tasks in Cell 4 second.  This allows you to quickly remove additional items.  This lessens the odds of “medium urgency” changes, allowing you to better focus on the tasks in Cell 2 and Cell 3.

  3. After completion of Cell 3, we focus on tasks in Cell 5.  Once we complete the items in this call, we are in very good shape.  That massive list of items is now greatly reduced.  Also, the stress of urgent items is less of a problem for the team.

  4. Before addressing the final four cells, now is a time to review these remaining tasks.  Often, the requirements for some of these lower priority tasks disappear, further reducing your list of remaining tasks.

  5. We finish off the To-Do List by address the easier tasks in Cell 7 and Cell 8 first.  From there, we address the more difficult in Cell 6 and Cell 9.


Step Four:  An Alternative Approach

Several times, when managing larger product and software development teams, I have split the developers into two teams and taken an alternative approach.  These teams are affectionately referred to as “the hares” and “the tortoises.”

The Hares are focused on clearing the items off the list and only work on the easier tasks.

The Tortoises work more deliberately, focused on the more difficultly tasks.

Care should be taken when deciding which team associates are assigned to.

Below is a Table detailing this alternative approach.

Table 3:  Alternative Prioritization: Split Teams

Conclusions

Implementing this approach to dealing with overwhelming To-Do Lists reliably produces successful outcomes.  Occasionally, I make modifications to this framework based on circumstances.

That is okay.  The end goal is to get the tasks completed as quickly as possible while avoiding delays to realizing your business objectives.  Whatever works…

Another benefit of this approach is that it is easily understood by the members of your team.  Teams like structure and this logical process helps them better focus, avoid stress, and realize better results.

It is gratifying when I run into former team members and they advise that they have adopted this approach in their new endeavors.

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