Better team decisions with AI

1. Frame your decision

2. Work on your decision

• If it's a big or complex decision, break down the decision into smaller parts
  • Prompt: I'm facing a big or complex decision and need help breaking it down into more manageable components. The overall decision is: [INSERT DECISION DESCRIPTION]. Please help me identify the smaller, more specific sub-decisions that make up this larger decision. These might include sequencing choices, resource allocation, stakeholder involvement, timing considerations, or parallel decisions that need to be addressed independently. For each sub-decision, suggest how it could be tackled on its own and how it connects to the overall decision. This will help me approach the larger decision in a clearer, more structured way.

• If choosing one of several alternatives:
  • List alternatives
    • Prompt: I'm working on this decision: [INSERT DECISION] and need help brainstorming alternatives. I've already considered these options: [LIST CURRENT ALTERNATIVES]. Please suggest new and creative alternatives, including radically different approaches, hybrids of current ideas, out-of-the-box options that challenge assumptions, phased or pilot strategies, and alternatives with different resource, timeline, or risk profiles. Aim for 5–10 new alternatives. 

• • List criteria
    • Prompt: For this decision: [INSERT DECISION], I need help developing thorough evaluation criteria. I’ve already identified these criteria: [LIST CURRENT CRITERIA]. Please suggest additional criteria, including financial (e.g., cost, ROI), strategic (e.g., goal alignment), risk-based (e.g., operational or market risks), timeline-related (e.g., time to value), resource-related (e.g., skills or tech needed), stakeholder-related (e.g., customer or employee impact), and quality-related (e.g., scalability or reliability). 

• • Make a table comparing the alternatives against the criteria
    • Prompt: I need to create a comparison table for a decision. My alternatives are: [LIST ALTERNATIVES], and the criteria are: [LIST CRITERIA]. Please build a table with criteria as columns and alternatives as rows. For each criteria, make two columns, one with a text explanation, and one with a rating. Rate each alternative consistently from 1 to 5 with 5 being good and 1 being weak. Highlight the best performer per criterion, and identify clear winners or weak options. 

• • Make a reduced table with the top alternatives against the most important criteria
    • Prompt: Based on a full comparison of all alternatives and criteria, I now want to narrow the focus to the most promising options. Please help me create a reduced comparison table that includes only the top-performing alternatives and the most important criteria. Use the initial table to identify which alternatives scored highest overall or stood out in key areas, and which criteria had the most influence on decision quality or tradeoffs. Build a new table that includes these selected alternatives and criteria, showing both text explanations and consistent 1–5 ratings (with 5 being strong). Highlight the strongest performers and flag any remaining tradeoffs to support a final decision.

• List alternatives
  • Prompt: I'm working on this decision: [INSERT DECISION] and need help brainstorming alternatives. I've already considered these options: [LIST CURRENT ALTERNATIVES]. Please suggest new and creative alternatives, including radically different approaches, hybrids of current ideas, out-of-the-box options that challenge assumptions, phased or pilot strategies, and alternatives with different resource, timeline, or risk profiles. Aim for 5–10 new alternatives. 
    
    
• List criteria
  • Prompt: For this decision: [INSERT DECISION], I need help developing thorough evaluation criteria. I’ve already identified these criteria: [LIST CURRENT CRITERIA]. Please suggest additional criteria, including financial (e.g., cost, ROI), strategic (e.g., goal alignment), risk-based (e.g., operational or market risks), timeline-related (e.g., time to value), resource-related (e.g., skills or tech needed), stakeholder-related (e.g., customer or employee impact), and quality-related (e.g., scalability or reliability). 
    
    
• Make a table evaluating the alternatives based on the criteria
  • Prompt: I need to create a comparison table for a decision. My alternatives are: [LIST ALTERNATIVES], and the criteria are: [LIST CRITERIA]. Please build a table with criteria as columns and alternatives as rows. For each criteria, make two columns, one with a text explanation, and one with a rating. Rate each alternative consistently from 1 to 5 with 5 being good and 1 being weak. Highlight the best performer per criterion, and identify clear winners or weak options. 
    
    
• Your team prioritizes the alternatives directly or develop a scoring mechanism
  • Prompt:  Please help me create a scoring mechanism that assigns appropriate weights to each criterion based on its importance, defines a consistent scoring scale (e.g., 1–5 or 1–10), and applies it across all alternatives. Then calculate total weighted scores for each option, rank them from highest to lowest, and identify any close calls or ties that might require further consideration. Also include a brief explanation of how each score was derived and any insights about the strongest or weakest options.

• If a go / no go decision:
  • List pros/cons of the decision.
    
   
  • Turn the pros/cons into list of reasons to go and not go
    • Prompt: I’ve listed pros and cons for this decision: [INSERT DECISION]. Please convert these into more actionable and specific lists: "Reasons to proceed" (benefits and positive outcomes) and "Reasons not to proceed" (risks and downsides). Add any reasons I may have missed, group similar points, and make them measurable where possible.
      
    
    
  • Rank the reasons to go by importance (Critical, Essential, Important, Unimportant)
    
   
  • Generate a Go / No Go comparison
    • Prompt: I'm considering a Go / No Go decision: [INSERT DECISION DESCRIPTION]. Please help me generate a structured comparison by organizing the reasons to proceed ("Go") and the reasons to hold back ("No Go") into four priority levels: Critical, Essential, Important, and Unimportant. For each side, group and label the reasons accordingly, making sure they reflect both the strength of the argument and the potential impact on the outcome. Where possible, make each reason specific, measurable, and actionable. This breakdown should help clarify the weight of each consideration and guide a more confident decision.

3. Make the Decision

• Ask team members to write down their gut for the decision and share it
  
  
• Consider a potential decision and write it down
  
  
• Get people on the team's feedback.
  • And/Or use AI to simulate the feedback of a variety of roles, stakeholders
  • Prompt: I'm considering this decision: [INSERT DECISION DESCRIPTION] and would like simulated stakeholder feedback. Please think through the right set of roles that should provide feedback for this decision given our context. For each, offer both supportive and critical feedback. Optionally, add a specific role and their perspective if I insert one.
    
    
• Play devil's advocate on the decision and tell you why it's a bad idea
  • Prompt: I'm considering this decision: [INSERT DECISION] and want you to play devil’s advocate. Please argue against the decision by highlighting risks, questioning assumptions, identifying what could go wrong, flagging resource or timing issues, and challenging whether it aligns with my goals. Provide strong critical reasoning to stress-test my thinking.
    
    
• Do a pre-mortem or write a press release on the decision
  • Prompt: I'm about to make this decision: [INSERT DECISION] and want to conduct a pre-mortem. Please imagine the decision failed badly and write a scenario describing what went wrong, when it started, who was affected, what was missed, and the root causes. Then outline preventive steps I can take. Afterward, write a “press release” describing the successful outcome of this decision to help me visualize a positive future.
    
  
  
• Check the decision against your values and your goals
  • Prompt: Please evaluate this decision: [INSERT DECISION] in relation to my values and goals. My values are: [LIST VALUES], and my goals are: [LIST GOALS]. Provide an alignment score for each value/goal (1–10), highlight conflicts, identify opportunities to strengthen alignment, suggest adjustments, and assess overall consistency with who I want to be and what I aim to achieve.
    
  
  
• Expand on possible second and third order effects of the decision
  • Prompt: I’m considering this decision: [INSERT DECISION] and want an analysis of its ripple effects. Please identify second-order effects like team or process impacts, third-order effects like culture or market responses, and fourth-order or beyond effects such as unintended consequences or systemic changes. Include both positive and negative potential impacts across short- and long-term horizons.
  
  
• Have team members express their ideas and their emotions about the potential decision. Encourage honesty and take the emotions seriously.
  
  
• Iterate on this step and working on the decision until you are satisfied or time is up.
  
  
• Make the decision tentatively, take it to superiors, stakeholders etc...

4. Record, Act on, and Learn from the Decision

• Record the decision and the reasons for it
  • Prompt: Please create a decision record for this decision: [INSERT DECISION]. Include the decision made, date, decision makers, and stakeholders consulted. For context, explain the problem or opportunity, alternatives considered, evaluation criteria, and key decision factors. For implementation, list next steps, timeline, resources needed, and success metrics. Finally, outline a review plan with a future review date, evaluation focus, and triggers for revisiting the decision.
    
    
• Write down what success will look like and how you will measure it
  
  
• Write down when you will revisit the decision or do a retro and do so

Next Steps