Kinds of Thinking (& Prompts for More Thinking)

By: Dr. Tovah Sheldon

Naming different kinds of thinking is not new, and neither is thinking about thinking. Yet, in today’s complex and fast-changing world, the ability to think well matters! It also matters that we are intentionally working to strengthen and expand how we think. Below are eight kinds of thinking, along with brief definitions and prompts to help you reflect on and intentionally grow each one.

1. Strategic Thinking
2. Critical Thinking
3. Systems & Symphonic Thinking
4. Analytical Thinking
5. Paradoxical Thinking
6. Self-Awareness & Metacognitive Thinking
7. Creative & Design Thinking
8. Intuitive Thinking

Before we explore each one, it is worth stepping back to consider the bigger picture. Concurrent and interconnected use of the different kinds of thinking shapes how we make decisions, relate to others, lead, learn, and contribute to the world. Overrelying on or neglecting a particular kind of thinking can become a limitation, affecting both our processes and our outcomes. The initial prompts below are designed to help you think more broadly and more intentionally about how you are approaching your work, your thinking, leadership, and learning:

• Which kind of thinking may be most helpful or beneficial in this situation?
• Which kind of thinking do I tend to lean on most? Why?
• Which kind of thinking might I intentionally grow, practice, and get better at? Who do I know that practices this kind of thinking regularly?
• In what ways might overuse of one kind of thinking be limiting me or the outcomes I’m working towards? 
• In what ways might we ask others to make their thinking visible, or name the kind of thinking they are using?
• For this particular group, what kind of thinking is missing that I could bring forward?

Although these prompts might not hit home quite yet, I suggest you return to the above broader questions after exploring the specific definitions and prompts below. My hope for you is that this resource sparks further inquiry, deeper awareness, and continued growth. 

I also hope you will challenge my thinking, share how this resource could be more useful, and help us all show up better together.

8 Kinds of Thinking

1. Strategic Thinking

Definition:

Strategic thinking is a future-focused, systems-aware mental process that integrates curiosity, feedback, and long-term insight to understand how internal and external forces shape collective direction or advance an individual for long-term success. It involves slowing down to question assumptions, seek diverse perspectives, and generate novel possibilities that anticipate emerging trends, risks, and opportunities. A tangent of Strategic Thinking is anticipatory thinking, which is the cognitive process of proactively exploring potential future challenges and opportunities to prepare for them.

Prompts:

1. What future possibilities or trends could influence this situation, and how might they shape the long-term outcome?
2. What assumptions am I making about the future? What evidence do I have for or against them?
3. Who else is affected by this decision, and how might their perspectives reveal opportunities or risks I haven’t considered?
4. If I zoomed out to a 30,000-foot view, what larger patterns or shifts become visible? 
5. What would success look like in 6 months, 2 years, or 10 years from now, and what choices today move me toward that?
6. What emerging external forces (social, economic, cultural, political, technological) could disrupt this plan?
7. How might I position myself or my team to thrive, not just respond, amid uncertainty?
8. What aggregation of technical and tactical moves could strategically impact me in the long run? Why? What are others not noticing that I need to notice?
9. If I deliberately slowed down right now, what new strategic possibilities might I notice that could advantage me or my team in the future?

2. Critical Thinking

Definition:

Critical thinking is an intellectually disciplined, metacognitive process of analyzing, evaluating, and synthesizing information from observation, experience, reflection, and communication to arrive at well-reasoned judgments. It requires questioning assumptions, recognizing ambiguity, examining evidence, and understanding who benefits from particular narratives or expectations. In Brené Brown’s terms, it includes ‘critical awareness,’ which is the ability to see how social messages and power structures shape beliefs and behaviors, so individuals can challenge unfair expectations and choose responses rooted in clarity and truth rather than shame or bias.

Prompts:

1. What assumptions am I or others making? How could those assumptions be challenged?
2. Whose voices, experiences, or data are missing from this conversation?
3. How do power, privilege, or social expectations shape the way this issue is being framed?
4. What evidence supports this conclusion, and what evidence contradicts it?
5. What alternative explanations or interpretations could also be true?
6. Who benefits from the current narrative, and who might be harmed by it?
7. If I step back and reflect on my own biases, how might that shift my interpretation?

3. Systems & Symphonic Thinking

Definition:

Systems thinking is a holistic approach to understanding complex problems by focusing on the interconnectedness of parts, the underlying structures that drive observable behaviors, and the feedback loops that shape how a system functions across time as well as in different contexts. It requires looking beyond surface-level events to identify deeper causes, invisible patterns, and dynamics, while also recognizing that changes in one area can create ripple effects across the whole. Symphonic thinking is a form of systems thinking in which a person recognizes that the synergy of the whole is greater than its individual parts.  There are often systems within systems as well as overlapping systems that make it difficult to take in the ‘whole’ complex picture at one time; however, doing this kind of thinking often creates synergy where the product is greater than the sum of the pieces. 

Prompts:

1. How is the system perfectly designed to get the results we’re seeing?
2. What are the underlying structures or patterns influencing the behavior I’m seeing? How might I look past the surface event?
3. How might changes in one part of this system create ripple effects elsewhere?
4. What feedback loops (reinforcing or balancing) might be contributing to this problem or outcome?
5. What other interconnected systems overlap with or influence this one?
6. How has this system evolved over time, and what historical dynamics are still at play?
7. Where are the leverage points? Can I name small actions that could create big shifts?
8. Where might the whole be greater than its parts? How might I generate synergy within the system?
9. If someone outside the system examined this situation, what might they notice that I don’t?
10. What unintended consequences might emerge if we intervene in this way?

4. Analytical Thinking

Definition:

Analytical thinking is the ability to break complex problems into smaller, manageable parts in order to systematically evaluate information, recognize nuances, detect and deduce patterns, and draw logical conclusions. It relies on deductive reasoning, clear criteria, and evidence to support thoughtful, well-informed decisions. Analytical thinking is often best leveraged during problem-solving, argumentative debates, and intentional decision-making.

Prompts:

1. What are the component parts of this issue, and how can I break them down for clearer examination?
2. What objective criteria or metrics can I use to evaluate my options?
3. What patterns, inconsistencies, or gaps become visible when I lay out the data?
4. Which pieces of information are most relevant to the decision I need to make? Which are distractions?
5. What logical steps must happen for this conclusion to be valid?
6. Where are the holes in my chain of logic?
7. How would I explain my reasoning to someone who disagrees with me?
8. What evidence most strongly supports or weakens the argument I’m considering?
9. What small ‘test’ might I run to confirm or deny my solution or part of my solution?
10. If I had to rank-order the factors influencing this problem, what rises to the top?

5. Paradoxical Thinking

Definition:

Paradoxical thinking is the capacity to hold two seemingly opposite yet interdependent truths simultaneously, deliberately embracing the productive tension between them rather than rushing to resolve it with either/or thinking. It involves recognizing that contradictory elements (such as vulnerability and strength or compassion and boundaries) can coexist and even enhance one another, enabling more adaptive responses to complex challenges. For example, a team working under tight deadlines may need to honor both efficiency and deep collaboration so that they are moving quickly while still slowing down at key moments for collective sense-making, which ultimately produces higher-quality solutions than favoring only speed or only deliberation. Using a “both/and” mindset and choosing to sit with uncertainty over a quick fix are just two hallmarks of paradoxical thinking.

Prompts:

1. What two truths or priorities seem to be in tension here? How might both truths be valid at the same time?
2. Where can I hold space for “both/and” instead of forcing an either/or decision?
3. How might the strengths of one perspective actually enhance the opposing one?
4. What happens if I sit with discomfort or uncertainty instead of rushing to resolve it?
5. How could embracing the contradiction lead to a more innovative or adaptive solution?
6. In what ways might the “opposite” of what I believe also contain wisdom?
7. How can I honor both urgency and intentionality, or both independence and collaboration, in this situation?
8. What would a balanced, integrative approach look like? What approach would demonstrate I fully value both sides?

6. Self-Awareness & Metacognitive Thinking

Definition:

Self-awareness and metacognitive thinking involve recognizing and understanding one’s own thoughts, emotions, and learning processes, and using that insight to guide more intentional behavior and decision-making. This includes the ability to identify what you know and don’t know, monitor your cognitive strategies, evaluate your biases, and reflect on how your internal experiences influence your actions. This kind of thinking is the most essential for meaningful growth, well-being, and authentic connection with self and others. These kinds of thinking could be separated, however; they are highly interconnected.  I wouldn’t be strong in metacognition without high self-awareness and strong self-awareness takes a deep understanding of one’s emotions, strengths, weaknesses, needs, and drives in such a way that one is neither overly critical nor unrealistically hopeful (Brown, 2025, p.232).  Rather with true self-awareness one is honest with oneself and others in such a way that they are thinking about their thinking constantly and consistently. 

Prompts:

1. What am I thinking or feeling at this moment, and how do I know?
2. What patterns do I notice in how I typically respond to situations like this?
3. Which of my assumptions, biases, or fears might be shaping my interpretation?
4. What do I genuinely know here, and what do I only think I know? 
5. How effectively am I using my current strategies, and what might I need to adapt?
6. Where am I resisting feedback, and why?
7. How do my internal experiences (emotions, beliefs, expectations) influence my external behaviors?
8. What would my wisest, most grounded self say about this situation?
9. The last time I thought this way, how did it work out? 
10. How is my current thinking similar to or different from my thinking in the past? What other kinds of thinking might I draw upon here?

7. Creative & Design Thinking

Definition:

Creative thinking is the ability to generate original, unconventional, and meaningful ideas by engaging in curiosity-driven exploration, divergent thinking, experimentation, and reflection. Creative thinking also often plays in abstract spaces or brings complex ideas forward visually through graphic representation and interpretation to incite human-centered design and conversation. It requires challenging existing norms, seeing things others don’t see, looking “out of the box,” looking with new perspectives, combining the unusual, and creating the psychological safety necessary for people to take risks, share unpolished ideas, and embrace the uncertainty inherent in innovation.  Design thinking extends critical thinking by putting people at the center over process or product. In both creative thinking and design thinking, the skill of flexibility plays a key role. 

Prompts:

1. What if I completely reimagined this problem from a different angle? What would I notice?
2. What unconventional or “wild” ideas could I brainstorm without judging them?
3. How might I combine two unrelated concepts to spark a new possibility?
4. What constraints, if loosened or inverted, could open up more imaginative solutions?
5. What assumptions about “how things are done” could I challenge right now?
6. If I asked a child, an artist, or an inventor to approach this problem, what might they see?
7. Where can I take a small creative risk to discover something new?
8. What unpolished or half-formed ideas am I willing to share to spark collaboration?
9. If I am designing for people, what matters most here?

8. Intuitive Thinking

Definition:

Intuitive thinking is the rapid, subconscious ability to reach conclusions or make decisions based on pattern recognition, lived experience, and gut instinct rather than step-by-step analytical reasoning. It is most effective when grounded in a strong base of knowledge, data, and prior practice, allowing the mind to draw on deeply internalized cues in high-stakes or time-sensitive situations. As Brené Brown notes, intuition is not a single way of knowing but the capacity to hold space for uncertainty while trusting the many forms of insight we develop over time—including instinct, experience, faith, and reason (Johnson, 2018).

Prompts:

1. What is my gut telling me right now and what past experiences might be informing that instinct?
2. What does my body feel when I imagine choosing Option A versus Option B?
3. If I quiet the noise and listen inwardly, what direction feels most aligned?
4. Where do I feel a sense of “knowing” even if I can’t fully explain why?
5. What patterns, seen or unseen, does my mind seem to be recognizing?
6. How has intuition served me well in similar situations in the past?
7. What uncertainty am I being asked to tolerate, and what inner wisdom can guide me through it?
8. What would I decide if I trusted both my instinct and my reasoning equally?

Conclusion

Ultimately, the goal is not to master one kind of thinking and elevate it above all others, but to become more aware, more intentional, and more adaptive in how we think across different situations. Each kind of thinking named here offers something important. Each one can sharpen our judgment, deepen our understanding, and expand our capacity to lead, learn, and respond well in a complex world. At the same time, each one has limits when used in isolation or without reflection. That is why the invitation is not simply to think more, but to think with greater discernment, humility, and wholeness.

As we grow in our ability to recognize these different ways of thinking, we also grow in our ability to make wiser decisions, ask better questions, and engage more meaningfully with others. We become more capable of slowing down when needed, noticing what is missing, challenging what feels automatic, and drawing on the kind of thinking a moment truly requires. This kind of awareness is not about perfection. It is about practice. It is about becoming more honest with ourselves, more thoughtful with others, and more responsive to the complexity around us.

My hope is that this resource does more than name a few kinds of thinking. I hope it helps you become more conscious of your own patterns, more curious about the perspectives and approaches you may be underusing, and more open to the possibility that growth begins with noticing. If this reflection leads you to pause, question, reframe, or try something differently, then it has done meaningful work. In the end, how we think shapes how we live, how we lead, and how we show up for one another. That alone makes this work worth returning to again and again.

Disclaimers*

• These are not the ONLY kinds of thinking that exist.  These are just some that have challenged, assisted, and even limited me in my lived experience. I also believe that Systems & Symphonic Thinking; Self-Awareness & Metacognitive Thinking; Creative & Design Thinking are actually separate, different kinds of thinking but didn’t want the article to be too long.  
• The 8 kinds of thinking are not in any value or rank order.  
• Along with my extensive reading, research, and discussion with others, ChatGPT, Gemini.ai, and Claude.ai were used in the refinement process and to assist in the creation of this document. 

This blog was originally posted on Michigan Virtual. View that posting here.

Dr. Tovah Sheldon is the Michigan Virtual School Design Strategist. For more than 20 years, Dr. Tovah Sheldon has served education as a teacher, professor, administrator, researcher, leadership coach, and consultant across PK-12 and higher education. She has a passion to cultivate constructive relationships, bring innovation to spaces that are managing complex change, and support implementation of evidence-based practices that promote equity and opportunity for all. Her demonstrated expertise ranges from curriculum, instruction, and assessment to professional development, capacity building, strategic planning, and system iteration for growth and sustainability. Dr. Sheldon has also served on various boards within her community of Jackson and across the state of Michigan. Dr. Sheldon earned her Ph.D. from Michigan State University in Curriculum, Instruction, and Teacher Education.

Citations

• American Psychological Association. (n.d.). Systemic thinking. In APA dictionary of psychology. Retrieved November 19, 2025, fromhttps://dictionary.apa.org/systemic-thinking
• Arnold, R. D., & Wade, J. P. (2015). A definition of systems thinking: A systems approach. Procedia Computer Science, 44, 669–678.https://doi.org/10.1016/j.procs.2015.03.050
• Bonn, I. (2001). Developing strategic thinking as a core competency. Management Decision, 39(1), 63–71.https://doi.org/10.1108/EUM0000000005408
• Brown, B. (2010). The gifts of imperfection: Let go of who you think you’re supposed to be and embrace who you are. Hazelden.
• Brown, B. (2018). Dare to lead: Brave work. Tough conversations. Whole hearts. Random House.
• Brown, B. (2021, January 13). Brené on words, actions, dehumanization, and accountability. Unlocking Us with Brené Brown [Podcast]. Brené Brown Education and Research Group.https://brenebrown.com/podcast/brene-on-words-actions-dehumanization-and-accountability/
• Brown, B. (2025). Strong Ground: The Lessons of Daring Leadership, the Tenacity of Paradox, and the Wisdom of the Human Spirit. Random House Publishing Group. 
• Brown, T. (2008). Design thinking. Harvard Business Review, 86(6), 84–92.
• Brown University School of Professional Studies. (2024, February 2). Four steps to thinking more strategically.https://professional.brown.edu/news/2024-02-02/thinking-more-strategically
• Cambridge International Education. (n.d.). Metacognition. Retrieved November 19, 2025, fromhttps://www.cambridgeinternational.org/Images/272307-metacognition.pdf
• Center for Assessment. (2024, February 21). Assessing students’ creative thinking. National Center for the Improvement of Educational Assessment.https://www.nciea.org/blog/assessing-creative-thinking
• Center for Assessment. (2025). Analytical thinking as a 21st century skill [Blog post]. National Center for the Improvement of Educational Assessment.https://www.nciea.org/blog/analytical-thinking-as-a-21st-century-skill/
• Dwyer, C. P. (2023). An evaluative review of barriers to critical thinking in educational and real-world settings. Journal of Intelligence, 11(6), Article 105. https://doi.org/10.3390/jintelligence11060105 
• EBSCO. (n.d.). Systems thinking [Research Starters]. EBSCO Information Services. Retrieved November 19, 2025, fromhttps://www.ebsco.com/research-starters/social-sciences-and-humanities/systems-thinking
• Facione, P. A. (1990). Critical thinking: A statement of expert consensus for purposes of educational assessment and instruction (The Delphi report). American Philosophical Association.https://stearnscenter.gmu.edu/wp-content/uploads/12-The-Delphi-Report-on-Critical-Thinking.pdf
• Fitchburg State University. (2020). Creative thinking [PDF]. Fitchburg State University.https://www.fitchburgstate.edu/media/5704
• Flavell, J. H. (1979). Metacognition and cognitive monitoring: A new area of cognitive–developmental inquiry. American Psychologist, 34(10), 906–911.https://doi.org/10.1037/0003-066X.34.10.906
• Johnson, S. (2018). Farsighted. Penguin Audio.
• Liedtka, J. M. (1998). Strategic thinking: Can it be taught? Long Range Planning, 31(1), 120–129.https://doi.org/10.1016/S0024-6301(97)00098-8
• Martin, R. L. (2007). How successful leaders think. Harvard Business Review, 85(6), 60–67.
• Mattone, J. (2015, August 11). 6 thinking patterns to embrace for better leadership. John Mattone Global.https://johnmattone.com/blog/6-thinking-patterns-to-embrace-for-better-leadership/
• Miron-Spektor, E., Ingram, A., Keller, J., Smith, W. K., Lewis, M. W., & DeVaughn, M. L. (2018). Microfoundations of organizational paradox: The problem is how we think about the problem. Academy of Management Journal, 61(1), 26–45.https://doi.org/10.5465/amj.2016.0594
• Penn Career Services. (2022, August 11). What is creative thinking? Definition and examples. University of Pennsylvania.https://careerservices.upenn.edu/blog/2022/08/11/what-is-creative-thinking-definition-and-examples/
• Purdue University. (2024, April 15). The paradox mindset—Both/and thinking. Steps to Leaps, Purdue University.https://www.purdue.edu/stepstoleaps/new/featured/well-being-tips/2024_0415.php
• Senge, P. M. (1990). The fifth discipline: The art and practice of the learning organization. Doubleday/Currency.
• Senge, P. M., Kleiner, A., Roberts, C., Ross, R., Roth, G., & Smith, B. (1994). The fifth discipline fieldbook: Strategies and tools for building a learning organization. Doubleday.
• Skillsoft. (2025, February 25). Analytical thinking is the No. 1 core skill employers want—Here’s why. Skillsoft Blog.https://www.skillsoft.com/blog/analytical-thinking
• Smith, W. K., & Lewis, M. W. (2011). Toward a theory of paradox: A dynamic equilibrium model of organizing. Academy of Management Review, 36(2), 381–403.https://doi.org/10.5465/amr.2011.59330958
• Torrance, E. P. (1966). Torrance tests of creative thinking—Norms–technical manual (Research ed.). Personnel Press.
• University of Louisville Ideas to Action. (n.d.). What is critical thinking? University of Louisville. Retrieved November 19, 2025, fromhttps://louisville.edu/ideastoaction/about/criticalthinking/what
• University of Phoenix. (2024, April 29). What is systems thinking? University of Phoenix.https://www.phoenix.edu/articles/business/what-is-systems-thinking.html
• Wang, M., Mohd Matore, M. E. E., & Rosli, R. (2025). A systematic literature review on analytical thinking development in mathematics education: Trends across time and countries. Frontiers in Psychology, 16, Article 1523836. https://doi.org/10.3389/fpsyg.2025.1523836