1- Lay of the Land

1.1- Goal definition

What do you want to achieve?
What is your goal?
Why is it a good and valid goal?
What benefits or value will achieving this goal bring?

1.2- Difficulty

Has anyone already achieved this goal? Who are they and how did they proceed?
What role does luck play in the achievement of this goal?
What personal experience do you have with this goal or similar goals?
Have you already tried to achieve this goal? What went wrong, if anything?

1.3- Requirements

What re the most difficult parts of the process of achieving this goal?
What resources or capabilities do you need in order to succeed?
What obstacles or challenges do you anticipate facing along the way?
What support or help will you need in order to overcome these challenges?

1.4- Stakeholders

Who will be affected by your efforts to achieve this goal?
What are the interests and concerns of these stakeholders?
How will you involve stakeholders in the process of achieving this goal?
What feedback or input will you solicit from stakeholders along the way?

1.5- Resources

What resources or assets do you have at your disposal to help you achieve this goal?
What additional resources or assets will you need in order to succeed?
How will you acquire or access these resources or assets?
How will you allocate and manage these resources or assets to maximize their impact?

2- Past experience

2.1- What already exists

How did people who have already achieved this goal proceed?
What can you learn from their experiences?
What ideas or practices can you reproduce from their successes?
What mistakes or failures can you avoid by learning from their experiences?

2.2- Best advice

What advice or guidance have people who have already achieved this goal provided?
How has this advice been time-tested or proven to be effective?
What common themes or trends do you see in the advice that has been provided?
How can you apply this advice to your own efforts to achieve this goal?

2.3- Lessons learned

What lessons have people who have already achieved this goal learned along the way?
What challenges or obstacles did they encounter, and how did they overcome them?
What insights or insights did they gain that you can benefit from?
What mistakes or pitfalls can you avoid by learning from their lessons learned?

3- Creative solution

3.1- Brainstorming

Can you think of any new ways to achieve your goal?
How can you cultivate a mind of alertness and openness to new ideas?
What are some creative approaches or methods that you can use to generate new ideas?
How can you involve others in the brainstorming process to generate more ideas and perspectives?

3.2- Idea generation

Are you trying to create something totally new, or are you building on existing ideas or solutions?
What are the key drivers or factors that will determine the success of your solution?
What are the potential risks or drawbacks of your solution, and how will you address them?
How does your solution compare to existing solutions, and what sets it apart?

3.3- Solution development

How will you refine and develop your solution to make it more effective and impactful?
What tools or techniques will you use to test and validate your solution?
How will you involve stakeholders in the development process to ensure that your solution meets their needs and expectations?
How will you iterate and improve your solution over time to maximize its effectiveness?

4- Options assessment

4.1- Criteria development

What are the different ways that you can achieve your goal?
What criteria will you use to evaluate and compare these different options?
How will you prioritize and weight these criteria to reflect your goals and priorities?
How will you collect and analyze the data or information you need to evaluate the options?

4.2- Option evaluation

How will you score or rate each option based on the criteria you have identified?
How will you combine the individual scores to produce an overall score or rating for each option?
How will you consider the potential risks and drawbacks of each option in your evaluation?
How will you compare the overall scores or ratings of the different options to determine the best one?

4.3- Decision-making

Based on your evaluation, which option do you believe is the best choice?
How confident are you in your evaluation and decision?
What additional factors or considerations will you take into account before making a final decision?
How will you communicate your decision to stakeholders and ensure that it is implemented effectively?

5- Enhancement

5.1- Differentiation

How can you differentiate your chosen option from the competition or other alternatives?
What unique or distinctive features or benefits does your option offer?
How can you communicate or showcase these features or benefits to potential customers or users?
How can you leverage your differentiation to gain a competitive advantage?

5.2- Competitive advantage

What are the key drivers or factors that will determine your competitive advantage?
How will you measure and track your competitive advantage over time?
How will you defend or protect your competitive advantage against potential threats or challenges?
How will you leverage your competitive advantage to grow and expand your business or organization?

5.3- Value proposition

What value does your chosen option bring to customers or users?
How does this value compare to the value offered by competitors or other alternatives?
How will you communicate and promote this value to potential customers or users?
How will you capture and retain the value that you create for customers or users?

6- General advice

6.1- Planning

What is your overall strategy for achieving your goal?
What are the key milestones or objectives that you will need to reach along the way?
How will you allocate and manage your resources to support your plan?
How will you monitor and evaluate your progress to ensure that you are on track?

6.2- Execution

How will you execute your plan to achieve your goal?
What are the key activities or tasks that you will need to complete?
Who will be responsible for completing each of these activities or tasks?
How will you coordinate and align your efforts to maximize their impact?

6.3- Monitoring and evaluation

How will you monitor and evaluate your progress to ensure that you are achieving your goals?
What metrics or indicators will you use to track your progress?
How will you collect and analyze the data you need to measure your progress?
How will you respond to setbacks or deviations from your plan, and how will you adjust your plan as needed?

7- Antifragility

7.1- Detecting fragility

How specialized or complex is your chosen option or approach?
How much do you know about the subject or domain in which you are working?
What are the potential risks or drawbacks of your chosen option?
What could go wrong if your chosen option fails or underperforms?

7.2- Being robust

How can you make your chosen option or approach more robust or resilient to potential risks or challenges?
How can you anticipate and prepare for potential setbacks or failures?
How can you design or build in contingency or backup plans to help mitigate the impact of potential failures?
How can you test or simulate your chosen option or approach to ensure that it is robust and resilient?

7.3- Gaining antifragility

How can you design or build in flexibility or adaptability into your chosen option or approach?
How can you leverage failures or setbacks as opportunities for learning and improvement?
How can you harness the power of feedback and iteration to drive continuous improvement and growth?
How can you leverage the potential upside or upside of your chosen option or approach to gain a competitive advantage?

8- Sanity check

8.1- Embracing reality

Is your chosen option or approach realistic and achievable given your goals, resources, and constraints?
How does your chosen option or approach align with the values and priorities of your stakeholders?
How does your chosen option or approach compare to other options or approaches that you considered?
What assumptions are you making about the feasibility or effectiveness of your chosen option or approach?

8.2- Feedback loop

How will you collect and use feedback to improve and refine your chosen option or approach over time?
What metrics or indicators will you use to measure the success or effectiveness of your chosen option or approach?
How will you monitor and analyze these metrics or indicators to track your progress and identify areas for improvement?
How will you incorporate feedback into your plan to adjust and adapt your chosen option or approach as needed?

8.3- Judging the solution

How does your chosen option or approach align with your goals and objectives?
Are there any potential conflicts or contradictions between your chosen option or approach and other goals or objectives that you have?
What is the probability and potential payoff of the outcome that your chosen option or approach is expected to produce?
What are the perspectives and opinions of other people who have evaluated your chosen option or approach? Are these perspectives and opinions credible and relevant?

9- Implementable plan/ Design thinking

9.1- Plan development

What are the specific steps and actions that need to be taken to develop the plan?
Who is responsible for each step or action, and when will it be completed?
How will the plan be structured and organized to ensure it is effective and achievable?
What resources, tools, or other support will be needed to develop the plan?

9.2- Prototyping

What are the key components or features of the plan that will be prototyped?
How will the prototyping process be carried out, and what methods will be used?
What is the intended outcome of the prototyping phase, and how will it inform the development of the final plan?
How will feedback from stakeholders and other sources be incorporated into the prototyping process?

9.3- Testing

What are the key aspects of the plan that will be tested, and how will the testing be conducted?
What are the criteria or benchmarks that will be used to evaluate the plan's performance during testing?
What adjustments or changes may be needed based on the results of the testing phase?
How will the testing process be coordinated and managed, and who will be responsible for it?

9.4- Plan execution

What are the key tasks or milestones that need to be accomplished to execute the plan?
Who will be responsible for each task or milestone, and when is it expected to be completed?
What resources, tools, or support will be needed to execute the plan effectively?
How will progress be monitored and reported, and how will any challenges or obstacles be addressed?

9.5- Plan evaluation

How will the success or effectiveness of the plan be measured and evaluated?
What are the key metrics or indicators that will be used to assess the plan's performance?
How will feedback from stakeholders and other sources be used to improve the plan or make adjustments as needed?
How will the evaluation process be structured and managed, and who will be responsible for it?