Anatomy of a Checklist

Insights on the science of task lists

Sumedh Jigjinni
5 min readMar 5, 2014

Task lists have been utilized to keep track of things to do. They are manifested as grocery lists, checklists, etc. They live everywhere such as in notebooks, loose pages, post-its, and even on our digital devices. In The Checklist Manifesto, Atul Gawande popularized and validated some of our assumptions regarding the checklist as a powerful tool to ensure we get things done in a standard way. As I have been building Catalist, I have taken a hard look at what a task list has been, what it is today, and what it can be with regards to productivity at the individual and team level. Thanks to some comprehensive customer development, many insights have emerged and I’m now here to share them.
Task lists are collections of tasks, or items that need to be completed. They vary in terms of complexity based on the resources needed to complete them. This can be boiled down to high-level strategy, mid-level tactics, and low-level operations.

Relationship between 3 levels of tasks

Each level informs the scope of the goal and thus the relative ease. Depending on the stakeholder, this ambiguity can be healthy or harmful. The brilliance of task lists are their flexibility, but their downfall is also in their usage inconsistency. When people write out their tasks, they tend to hover around one of these levels since it falls in line with their level of thinking at that time. Since each individual has a comfort preference when it comes to these levels, it is difficult to force a user to the more basic level, like tactics. Part of this is a comfort not only in scope but also comfort in cognitive load, or how much one can maintain in their mind without relying on separate tools and content.

For this reason, Catalist has focused more on the relationships between tasks. By having a user identify the relationship among tasks, Catalist can surface the optimal choice of constraints to ease the cognitive load off the user. So what are these types of relationships? Tasks fit within a spectrum of independent and mutually exclusive.

Drawing cards from a deck is independent since it will influence future draws; Rolling dice is mutually exclusive since it won’t influence future rolls

If independent, the tasks are more related and logically fit within a goal. When mutually exclusive, the tasks don’t inherently relate but they still satisfy a need the user has set. It can be confusing to categorize tasks as such but it makes sense when breaking things down further. Independent tasks vary on whether they must be completed linearly. In project management, this is identified as milestones, and in the interface world, these are steps in a wizard. An order exists by which each task must be completed sequentially from the first task to the last task. (It gets more complicated still when imagining feedback loops within these systems which makes completing certain milestones more difficult.)

One must cross each stone like milestones to get to the other side like in such a linear system

Other independent tasks are not linear but do relationships among all the individual tasks. In these cases, order is not important but each task contributes a discrete amount to the greater goal. This contrasts with mutually exclusive tasks which do not have these same types of relationships among the tasks.

So how do we leverage these task lists for future use? When a user creates a task list, they are essentially making an investment. This only provides returns if it helps them directly with a future task list. Repeatable task lists are a key component to productivity and a defining trait of Catalist. Not all task lists are worth repeating but for times when a process is used on multiple occasions, a repeatable task list can be a godsend. The task list has to become a template that will manifest itself within the right context for it to actually work on a repetitive basis. We can call this a standard or a habit. By the way, this also applies to specific tasks and not just the task list. When a task list is repeated, each instance of that list has some relationship. If it is on a chronological cadence (e.g. daily/weekly/etc.), then the frequency of the task list trigger is constant. It is also important to set the relevant point of the trigger (e.g. 4pm/Wednesdays). The typical usage of this is paying bills, submitting hours, or performing car maintenance. Essentially each instance is necessary at that point in time. Time is the typical usage of repeatable task lists.

However, instances can vary in other contextual ways, such as by entity. Often we need to invoke a repeatable process for a set of people such as customers, investors, or team members. This has been demonstrated through CRM tools and Trello to keep track of these agents as they move through a system. Each instance is a coordinate of both milestone and entity. These tools capture the instance visually but lack the necessary support to place them in a greater task list or a task management solution. In these cases of variance by entity the point of trigger is a different issue completely. Time is still relevant but in ways more relevant. The trigger is now based on an implicit or explicit constraint. Idle time captures how long an entity has stayed within a particular bucket and is more of a count-up approach. However setting a specific time limit or even manual due date increases urgency and thus actionability of the particular task.

This is the type of logic Catalist leverages to help limit user input and maximize user value. It’s important to understand the system at its most basic level to be able to leverage the relevant capabilities for target usage. By approaching product design and development in such a scientific manner, one can achieve a more powerful least common denominator for multiple contexts irrespective of industry, vertical, or function.

Sumedh Jigjinni is a productivity expert whose insights have led to Catalist, a new task management solution. Compared to other offerings, Catalist emphasizes focus, pacing, and priorities. This helps entrepreneurs, freelancers, and office managers know what needs to get done now. Sign up to learn more about the beta & other productivity insights: Catalist — Track your Tasks

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Sumedh Jigjinni

I care deeply about productivity, mindfulness, & growth. Founder of Catalist, a fresh approach to task & time management.