I found an interesting article about contextual decision making.  "A Leader's Framework for Decision Making," an article in Harvard Business Review, is about tailoring your decision making approach based on the context.  You can use the Cynefin Framework to figure out which context you're operating in, so you can choose the most effective response.  The key is whether to categorize, analyze, probe or act.

Context's Characteristics
The Cynefin Framework includes five context types:

• Simple - Repeating patterns and consistent events; Clear cause-and-effect relationships evident to everyone; right answer exists; Known knowns
• Complicated - Expert diagnosis required; Cause-and-effect relationship discoverable but not immediately apparent to everyone; more than one right answer possible; Known unknowns
• Complex  - Flux and unpredictability; No right answers; emergent instructive patterns; Unknown unknowns; Many competing ideas; A need for creative and innovative approaches
• Chaotic - High turbulence; No clear cause-and-effect relationships, so no point in looking for right answers; Unknowables; Many decisions to make and no time to think; High tensions
• Disorder - This context is particularly difficult to recognize because of multiple, competing perspectives.  The recommendation is to break it down into its constituent parts and assign it to one of the other four realms.

Fact-based Management
Simple and complicated are part of the ordered world.  How to respond as a leader in simple and complicated scenarios:

• Simple - (The Domain of Best Practices) - Sense, categorize, respond; Ensure proper processes are in place; Delegate; Use best practices; Communicate in clear, direct ways; Understand that extensive interactive communication may not be necessary.
• Complicated - (The Domain of Experts)  - Sense, analyze, respond; Create panels of experts; Listen to conflicting advice.

Pattern-based Leadership
Complex and chaotic are part of the unordered world.  How to respond as a leader in complex and chaotic scenarios:

• Complex - (The Domain of Emergence) - Probe, sense, respond;  Create environments and experiments that allow patterns to emerge.  Increase levels of interaction and communication.  Use methods that can help generate ideas; Open up discussion: set barriers; stimulate attractors; encourage dissent and diversity; and manage starting conditions and monitor for emergence.
• Chaotic - (The Domain of Rapid Response) - Act, sense, respond;  Look for what works instead of seeking right answers; Take immediate action to reestablish order (command and control); Provide clear, direct communication.