Are we tackling a problem that can be resolved with a checklist?

Summary

Problem	Description	Example	Hallmarks	Can a Checklist Help?
Simple	Easily knowable.	Procedure for receiving goods	Following the steps brings a high likelihood of success	Yes with procedural steps.
Complicated	Not simple, but still knowable.	Deployment procedure for software	Unanticipated difficulties are frequent but predictable. Timing and coordination are serious concerns.	Yes with more detailed documentation for dealing with unexpected outcomes.
Complex	Not fully knowable, but reasonably predictable.	Organizational change.	Outcomes for complex problems remain highly uncertain.	Limitedly - the problems in this space need to be further broken down for better management.
Chaotic	Neither knowable nor predictable.	The Weather.	Many pieces operating together in a system.	Nope - if you cannot repeat the result - you cannot make it a checklist.

Simple

Simple problems that need a disciplined result suit checklists.
When you are able to articulate a series of steps that will produce the same or similar results in all scenarios you know you have a great candidate for systematization.

Complicated

Most information system problems are of this nature. They need the interaction of many people or are larger than what can be recalled by a human.
These kinds of problems are also suited to Checklists.

Complex

Complex problems need to be broken down into smaller parts. Then a checklist can become useful. For example making a checklist to "Improve business revenue 50%" will not work. You should split these into sets of repeatable tasks that drive towards that goal. An achievable, quantifiable result should be at the heart of a good checklist.

Chaotic

Danger Will Robinson, Danger. If you cannot articulate, explain and predict with any great certainty steps that will effect an outcome you should not try to capture these in a checklist.