The 20 Reasons Why Sensemaking & Critical Thinking Matter

Grey Swan Guild
11 min readOct 26, 2021


Futures & Sensemaking Series #2 — Part 1 of 4

Author: Sean Moffitt, Co-Founder, Grey Swan Guild & Managing Director, Futureproofjng :Next.

Contributors: Mitchell Halpern and Jonathan Powers

W e offer this post up as the second in an ongoing series of advancing “making sense of the world” and a companion piece to our 20 Reasons Why Futurism & Foresight Matter.

The disciplines of sensemaking and critical thinking take us into an area of deeper understanding about our collective current & past states in a world that increasingly has a tough time:

  • understanding the lessons and patterns of history given our shortening fields of view
  • a deficit in evaluative powers for recognizing false news, propaganda, conscious & unconscious biases and polarized perspectives and
  • a frailty at times in recognizing the shifts that are happening all around us, the effects they may be having on us, and our roles within them.

In our tech-fuelled environment of memes, torrents, what’s trending, pundit observations, 15 minute news cycles and fraudulent opinion, we asked, who is actually equipping our minds to find truths, and improve our own cognitive confidence and knowledge synthesis of the world ? We answered — let’s do our part.

Beyond improving the craft of better sensemaking and critical thinking, perhaps most important is ensuring people in positions of influence and tomorrow’s youngest minds have the capacity to sift fact from falsehood… so below we have furnished our “20 Reasons Why Sensemaking and Critical Thinking Matter” for educators & the minds they shape and for power brokers & the minds they influence alike…

In a world of goldfish levels of attention, we hope that we can hold yours,. Rise up, evaluate judiciously and please feel free to comment or add your own reasons to what follows.

The unknown and known worlds of processing and understanding our current & past.


A month back, we discussed amongst sixty curious minds the benefits of sensemaking and critical thinking in Episode #2 of our Futures & Sensemaking Series. It was briskly discussed but probably more than our Futures discussion (Episode #1), participants were largely quizzical on what really is sensemaking? what are its variants? how does critical thinking fit in? Should we settle on a narrow definition of these terms or a larger one? Some answers and bread crumbs below.

What follows is a reaction and summation to that discussion with some noted additions by my esteemed colleagues Jonathan & Mitchell.

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The second episode of our Future & Sensemaking Series:

Join us for our next discussion every other Friday at 1pm ET.

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Let’s get Meta first … Sense our Sensemaking, Critique our Critical Thinking

While building the Guild and recruiting some of the best global change agents and thinkers, we have run across some thought leaders who hold a very prescriptive lens on what constitutes the terms sensemaking and critical thinking.

I suppose if you want to commercialize or standardize the expressions of these terms as disciplines, they may have had merited concerns about our incursion into their thinking. However, for the grand majority of us who are trying to use these as shields against the glut of data, errant beliefs and polarized expressions, these luminaries aren’t helping — by definition, we need to embrace and incorporate more approaches (not less) to make better sense or the world.

There is an inner hive of members of the Grey Swan Guild that are committed to conceptualizing, visualizing, teaching and providing a full taxonomy and lexicon to the many flavours of making sense of the world. We collectively have realized, when comprehending life’s biggest challenges, we don’t always need a hammer; sometimes a drill, an awl, a plane or saw would be more suitable. We have already come up with 70+ distinct approaches in our futures quadrant of tools; we wonder how many will be revealed in our upcoming sensemaking and critical thinking taxonomy work?

Three boundary stakes in the ground we are prepared to draw in order to provide some parameters to this post:

  • Sensemaking & Critical Thinking are principally past and present-oriented— that’s not to say that there isn’t a certain amount of prospection and casting forward with these two areas but their strength comes in deeply understanding what’s happening now and what can be sensed and felt from the near & far past. They can be antecedents to future action, but unlike futurism and foresights, the sensemaking & critical thinking focal lens are historical and current environments.
  • Sensemaking & Critical Thinking Straddle the Meridians of the Unknown and Known Worlds — although advocates of either school, can dismiss the other for its faults, each purport to do the same thing — make sense of a complex, multi-factored world. It’s just that in sensemaking’s case, it plies its trade in unknown worlds and facets, where no hard and fast rules exist and constant re-evaluation is encouraged (think arts, design, sociology, politics, global pandemic). Whereas critical thinking is best performed in more known worlds and facets where truths, inferences and solutions may be postulated and a level of final conclusiveness is encouraged (think science, programming, medicine, peacetime).
  • Are these disciplines, habits, skills, processes or behaviors — the answer is yes. We’re not even sure it matters as sometimes this is served up as more of a quarrel to dismiss one type of interpretation. In truth, sensemaking and critical thinking are behaviors we all do every day when we cross the street, scan a store shelf or carry on a conversation. Practiced frequently these become habits. Repeated habits become processes. If you study the why and how behind what goes behind a process, it turns into a discipline. And if you are blessed or exert it enough as a muscle. it becomes a skill. Regardless of taxonomic hierarchy , it is something that at all levels, we have seen requires much more exercising than we currently conduct as a global tribe.

Defining “Sensemaking” (aka/related to as Semiotics, Meaning Making, Cognitive Learning, Problem Framing, Ethnography, Social Psychology)

Sensemaking has had a range of academic and organization theory definitions in its recent history dating back to the1960s. Various icons in the field, Brenda Dervin, Daniel Kahenman, Daniel Russell, Dave Snowden, Gary Klein and Karl Weick, have put forward slivers of sensemaking delineations. Common to all of them is that sensemaking presumes there are many possible interpretations for the same event and how we approach our investigation shapes what we will arrive to as conclusions.

With the Grey Swan Guild, we are trying to drag sensemaking out of the shadows of its academic spheres and shape it into something digestible for the real world. The formalized approach to sensemaking has been chewed on and sampled by: organizational behaviorists, marketing/communications types, military planners, designers, economists and technologist domains. However, it has lagged many other approaches in popularity (based on Google Trends, it remains ranked last out of nine popular schools of learning about past, current or future environments).

In the wake of this COVID pandemic, we think its broadest definition summates pretty closely what we are trying to do with our clients, communities and our own interrupted lives — make sense of what’s going on so we can act on it. Time to find the spotlight of society’s stage — sensemaking, your time is now.

Defining “Critical Thinking” (aka/related to Systems Thinking, Logic, Reasoning, Creativity, Design Thinking)

Critical Thinking has had a much longer history of existence dating back to primitive man and codified by Socrates and ancient Greece. Given its age, occasionally we dismiss it as a distinct process or discipline due to its assumed universality of being. Nevertheless, it is an important part of the “making sense” repertoire emphasizing facts, evidence, reason and rationality with the goal of producing knowledge, solution and truths.

More recently, the field of critical thinking has had some internal debate over a broader definition that goes beyond the strict reason and problem-solving calculus to consider other cognitive acts such as: conceptualization, creativity, data visualization, empathy, enlightenment, imagination, intuition, insight, morality, non-sequential and non-traditional modes of reasoning. Critical Thinking is the underpinning of accepted science, progressive societies and new emerging technologies — we should probably tap into it.

The 20 Reasons Why Sensemaking & Critical Thinking Matter:

The Reboot Foundation has studied the effects of society on critical thinking (and vice versa) for the last decade and has surfaced an interesting paradox: ninety-five percent of people affirm that critical thinking skills are important in today’s world, yet 85 percent believe that they are generally lacking in the public.

When queried about the reasons, a number of causes were put under the microscope for the lack of critical thinking skills in society and students in particular , “changing societal norms” took the most blame (and more than in previous years) with 33% of people choosing it. The educational system (24%) modern technology (21%) and lack of parental influence (5% ) all took some of the censure as well..

This post represents one of the first planks in our campaign to make a holistic sensemaking & critical thinking taxonomy, pedagogy and landscape maps helpful for the lives of corporate and civic leaders, societal causes, not-for-profits, teens & children, and for the craft itself. As we can see the from the recent World Economic Forum’s Future of Jobs Report top skills of the future, your future livelihood may depend on it:

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Why Sensemaking & Critical Thinking Matter #1. — Emphasizes Learning vs. Knowing, Providing for Adaptation to Uncertainties

For most of human history, the greatest gains accrued to societies that were successful in accumulating and transmitting (with minimal loss) knowledge. The birth of language gave us tradition — the passing down of knowledge from generation to generation. With the invention of writing, knowledge could be recorded and transmitted far beyond family lines, and could accumulate in the form of scrolls and books.

The printing press again reorganized human knowing, making it possible for a much larger group of people to put book knowledge to more varied uses. The internet, in turn, has made it necessary to rethink what knowledge is, because so many of us now could learn so many different things so easily. Knowledge, in short, has become a commodity, while the skill of learning — and the wisdom and insight it promises — has become the passport into the new forms of culture on the horizon.

What you knew used to form the core of every professional’s capacity to work. As long as you had this knowledge/skill, it didn’t matter how you had learned it. Now all professionals need a suite of skills — and a dynamic, growing suite at that.

By 2030, according to the a recent McKinsey Global Institute report, Jobs lost, jobs gained: Workforce transitions in a time of automation, as many as 375 million workers — or roughly 14 percent of the global workforce — may need to switch occupational categories as digitization, automation, and advances in artificial intelligence disrupt the world of work into those jobs of learning, sensemaking and critical thinking.

Sensemaking and Critical Thinking are the new luxuries of talent in our era. We can no longer afford to learn slowly, poorly, awkwardly. The future already belongs to those who learn best. It’s time to join them.

#2. Provides a Better Grasp of Shifting Environments

In a recent Future of Jobs report, the World Economic Forum surfaced the biggest socio-economic and demographic swing factor facing us is the changing nature of work and flexible work environments. The Toronto Skills Centre has suggested that that over half the Canadian workforce will need to reskill within the next five years due to the disruption of the pandemic and accelerated technological automation.

Our workplaces are changing, our homes are changing, our values are changing and our climate is changing. Oftentimes, in zig zagging lines.

According to Deborah Ancona in her Harvard Business review article “In Praise of the Incomplete Leader” the two top predictors of leadership effectiveness in this era are– making sense of complex issues and innovation. Whether it is as individuals of teams, the ability to process our environments and come to consensus is key.

Sensemaking & Critical Thinking are the deflector screens and sails that stand against increasing faster & unpredictable societal headwinds & tailwinds.

See our following posts over the next month:

Part II — Why Sensemaking & Critical Thinking Matter — Reasons #3–8

Part III —Why Sensemaking & Critical Thinking Matter — Reasons #9–14

Part IV — Why Sensemaking & Critical Thinking Matter — Reasons #15–20

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This post represents the second of a series of long form posts entitled The Futures & Sensemaking Series. We have canvassed a leading group of passionate and talented people who think a lot about the “why” and the “how” about our current and future state. We hope you enjoy our outputs and decide to join our Guild to participate, collaborate and contribute.

The Grey Swan Guild — Get Involved :

Sean Moffitt is the co-founder of Grey Swan Guild — Making Sense of the World’s Biggest Challenges and Future Grey Swans , Managing Director & Author, Futureproofing ; Next Innovation You Can Take to the Bank . Sean spends equal amounts of time navigating the now, and getting ahead of the future. A great majority of his efforts are spent building out global networks of leading thinkers & doers, fielding foresight ventures, authoring reports on the future, hosting innovation masterclasses, conducting futureproofing sprints, producing change workshops and providing strategic & innovation counsel for corporations & scale-ups. His new book Futureproofing ; Next — The Future Beyond Innovation launches this Fall. Feel comfortable getting in touch with Sean and his team here.



Grey Swan Guild

Making Sense of the World’s Biggest Challenges & Next Grey Swans — curating and creating knowledge through observation, informed futurism, and analysis🦢