Artificial Intelligence, particularly generative AI and large language models like ChatGPT and Copilot, have arrived. These chisels and calculators of their time are being met and used with curiosity, inspiration, worry, and pretty much all the gamut of sensation. I used two cool AI prompts that support collaboration and development.

First, I generated 100 critical thinking questions with the intention of mitigating biases and surfacing what’s in the blind spots of a project team that I’m leading (we have missed a few details, so incorporating the practice of asking several versions of the questions “what did we miss?” or “what else might happen?” or “what will our client poke us about?” will enable collaboration and mitigate risks on our team).

Second, I need to improve my attention to detail (see above), so I used some prompts that I found on an Instagram Reel because turning doomscrolling into microlearning is what we should all be doing and there is always time for learning.

The results from my prompts are fine. Not awesome. The thing is, though, that they took eight seconds to create, which gives me way more time and energy to iterate and customize and augment, which feels like the future of work arriving today.

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100 Critical Thinking Questions for Project Teams

A guide to help project teams challenge their assumptions, identify potential pitfalls, and consider alternative perspectives

Introduction

Project teams often face complex and uncertain situations that require them to make decisions and take actions that can have significant impacts on the project outcomes, stakeholders, and organization. To ensure that these decisions and actions are based on sound reasoning and evidence, project teams need to practice critical thinking skills.

Critical thinking is the ability to analyze, evaluate, and synthesize information from various sources, perspectives, and contexts, and to apply logic and creativity to solve problems and generate new ideas. Critical thinking can help project teams to mitigate bias, surface risks, and cover blind spots that might otherwise compromise the quality and effectiveness of their work.

This document provides a list of 100 critical thinking questions that project team members can ask themselves and each other throughout the project lifecycle. The questions are divided into four categories: scope, design, execution, and evaluation. Each category contains 25 questions that are relevant to different stages and aspects of the project. The questions are designed to be simple, diverse, and represent several different cultural perspectives and thinking styles.

The questions are based on two project examples: designing and delivering a full day of learning for 500 employees and implementing a new talent management system. However, the questions can be adapted and applied to any type of project, depending on the context and objectives. The questions are not meant to be exhaustive or prescriptive, but rather to serve as a starting point and a stimulus for further inquiry and dialogue.

Scope

The scope category contains questions that can help project teams to define and clarify the project purpose, goals, objectives, deliverables, and stakeholders. These questions can help project teams to ensure that they have a clear and shared understanding of what they are trying to achieve, why, and for whom.

What is the main problem or opportunity that the project is addressing?
What are the underlying causes or drivers of the problem or opportunity?
What are the expected benefits and outcomes of the project?
How will the project align with the organization’s vision, mission, values, and strategy?
What are the specific and measurable objectives of the project?
What are the key deliverables and milestones of the project?
What are the success criteria and indicators of the project?
How will the project outcomes be measured and evaluated?
Who are the primary and secondary stakeholders of the project?
What are the needs, expectations, and interests of the stakeholders?
How will the stakeholders be involved and engaged in the project?
What are the potential risks and opportunities for the stakeholders?
How will the project communicate with and report to the stakeholders?
What are the assumptions and constraints of the project?
How will the project validate and test the assumptions?
How will the project manage and mitigate the constraints?
What are the potential risks and challenges of the project?
How will the project identify and assess the risks and challenges?
How will the project prevent and respond to the risks and challenges?
What are the potential opportunities and innovations of the project?
How will the project explore and exploit the opportunities and innovations?
What are the ethical and social implications of the project?
How will the project ensure that it adheres to the relevant laws, regulations, policies, and standards?
How will the project respect and promote the diversity, inclusion, and well-being of the stakeholders and the wider community?
How will the project handle any conflicts or disputes that might arise among the stakeholders or the project team?

Design

The design category contains questions that can help project teams to plan and prepare the project activities, resources, and processes. These questions can help project teams to ensure that they have a feasible and realistic plan that covers all the necessary and relevant aspects of the project.

What are the main activities and tasks of the project?
What are the dependencies and interrelationships among the activities and tasks?
What are the roles and responsibilities of the project team members and other stakeholders?
How will the project team be formed, organized, and managed?
What are the skills, knowledge, and competencies required for the project?
How will the project team acquire and develop the skills, knowledge, and competencies?
What are the resources and budget required for the project?
How will the project obtain and allocate the resources and budget?
What are the tools and methods that will be used for the project?
How will the project select and apply the tools and methods?
What are the quality standards and criteria that will be applied to the project?
How will the project ensure and control the quality of the project?
What are the best practices and lessons learned from similar or previous projects?
How will the project incorporate and adapt the best practices and lessons learned?
What are the potential gaps or weaknesses in the project design?
How will the project address and improve the gaps or weaknesses?
What are the potential alternatives or options for the project design?
How will the project compare and evaluate the alternatives or options?
What are the criteria and rationale for choosing the project design?
How will the project justify and communicate the project design?
How will the project review and revise the project design?
How will the project document and archive the project design?
How will the project ensure that the project design is aligned with the project scope and objectives?
How will the project ensure that the project design is responsive and adaptable to the changing needs and expectations of the stakeholders and the environment?
How will the project ensure that the project design is creative and innovative?

Execution

The execution category contains questions that can help project teams to implement and monitor the project activities, resources, and processes. These questions can help project teams to ensure that they execute the project according to the project plan and deliver the project outcomes on time, on budget, and on quality.

How will the project initiate and launch the project activities?
How will the project coordinate and synchronize the project activities?
How will the project track and report the progress and performance of the project activities?
How will the project manage and optimize the use of the project resources?
How will the project handle and resolve any issues or problems that might occur during the project execution?
How will the project deal with any changes or variations that might affect the project scope, objectives, deliverables, or stakeholders?
How will the project ensure and maintain the engagement and satisfaction of the project team members and other stakeholders?
How will the project facilitate and support the collaboration and communication among the project team members and other stakeholders?
How will the project foster and encourage the learning and development of the project team members and other stakeholders?
How will the project solicit and incorporate the feedback and suggestions of the project team members and other stakeholders?
How will the project recognize and celebrate the achievements and contributions of the project team members and other stakeholders?
How will the project ensure and demonstrate the quality and value of the project deliverables and outcomes?
How will the project verify and validate the project deliverables and outcomes?
How will the project test and refine the project deliverables and outcomes?
How will the project deliver and transfer the project deliverables and outcomes to the intended recipients or users?
How will the project ensure and facilitate the adoption and utilization of the project deliverables and outcomes by the intended recipients or users?
How will the project measure and evaluate the impact and effectiveness of the project deliverables and outcomes?
How will the project communicate and disseminate the project deliverables and outcomes to the relevant audiences or stakeholders?
How will the project protect and secure the project deliverables and outcomes from any unauthorized or inappropriate access or use?
How will the project ensure and maintain the sustainability and scalability of the project deliverables and outcomes?
How will the project review and reflect on the project execution?
How will the project document and archive the project execution?
How will the project ensure that the project execution is aligned with the project design and plan?
How will the project ensure that the project execution is responsive and adaptable to the changing needs and expectations of the stakeholders and the environment?
How will the project ensure that the project execution is efficient and effective?

Evaluation

The evaluation category contains questions that can help project teams to assess and improve the project outcomes, processes, and impacts. These questions can help project teams to ensure that they learn from the project experience and generate insights and recommendations for future projects.

What are the main achievements and successes of the project?
What are the main challenges and failures of the project?
What are the main strengths and weaknesses of the project?
What are the main opportunities and threats for the project?
What are the main lessons learned and best practices from the project?
What are the main gaps and areas for improvement for the project?
What are the main feedback and suggestions from the project stakeholders?
What are the main impacts and outcomes of the project for the organization, the stakeholders, and the wider community?
How did the project meet or exceed the project objectives, deliverables, and success criteria?
How did the project align with the organization’s vision, mission, values, and strategy?
How did the project address the problem or opportunity that the project was intended to solve or exploit?
How did the project satisfy the needs, expectations, and interests of the project stakeholders?
How did the project adhere to the relevant laws, regulations, policies, and standards?
How did the project respect and promote the diversity, inclusion, and well-being of the stakeholders and the wider community?
How did the project use the project resources and budget efficiently and effectively?
How did the project apply the project tools and methods appropriately and creatively?
How did the project manage and mitigate the project risks and challenges successfully and proactively?
How did the project explore and exploit the project opportunities and innovations fully and innovatively?
How did the project collaborate and communicate with the project team members and other stakeholders effectively and constructively?
How did the project facilitate and support the learning and development of the project team members and other stakeholders continuously and comprehensively?
How did the project ensure and maintain the quality and value of the project deliverables and outcomes consistently and rigorously?
How did the project ensure and facilitate the adoption and utilization of the project deliverables and outcomes by the intended recipients or users smoothly and satisfactorily?
How did the project measure and evaluate the impact and effectiveness of the project deliverables and outcomes accurately and objectively?
How did the project communicate and disseminate the project deliverables and outcomes to the relevant audiences or stakeholders clearly and persuasively?
How did the project ensure and maintain the sustainability and scalability of the project deliverables and outcomes reliably and feasibly?

Personal development

This awesome Reel from @yourchatgptguide highlights how to use simple prompts to improve proficiency in specific skills as well as build learning plans or systems for enhanced focus and productivity (I just used one of the prompts to improve my attention to detail (recent feedback from family and colleagues tell me it needs to get better).

Here is a possible outline for developing proficiency in attention to detail:

Beginner stage:

Define what attention to detail means and why it is important for your work or personal goals.
Identify the common sources of errors or mistakes that affect your performance or quality of work.
Practice self-checking and proofreading your work before submitting or sharing it with others.
Use checklists, templates, or guidelines to help you follow the required steps or standards.
Seek feedback from others on how to improve your accuracy and precision.

Intermediate stage:

Develop a habit of asking questions and clarifying expectations before starting a task or project.
Break down complex or large tasks into smaller and manageable subtasks.
Organize your work environment and minimize distractions that can interfere with your concentration.
Use tools or software that can help you automate, simplify, or verify your work processes.
Review and update your checklists, templates, or guidelines regularly to ensure they are relevant and accurate.

Advanced stage:

Analyze and identify patterns or trends in your work performance or quality of work.
Set specific, measurable, achievable, relevant, and time-bound (SMART) goals for improving your attention to detail.
Monitor and track your progress and achievements using data or metrics.
Learn from your errors or mistakes and implement corrective or preventive actions.
Share your best practices or tips with others who want to improve their attention to detail.

Practical exercises:

Take online tests or quizzes that measure your attention to detail skills, such as spotting the difference, finding errors, or solving puzzles.
Read articles or books on topics that interest you and summarize the main points or key details.
Play games or activities that challenge your memory, observation, or logic skills, such as crossword puzzles, sudoku, or chess.
Volunteer for tasks or projects that require high levels of accuracy, precision, or quality, such as data entry, editing, or research.
Ask a friend or colleague to review your work and point out any errors or areas for improvement.

Two Cool AI Prompts that Support Collaboration and Development