How does a design strategist think?

How Does a Design Strategist Think?

Some forms of design are easy to judge. I can look at a website, judge the aesthetics of the site, and then form an opinion about it (and I can also judge the talent of the team that worked on it).

I can do the same thing with interaction design, walking through an interface and evaluating the flows and usability, and by extrapolation, the designers and their abilities. Most of us are good at criticizing things we can see or touch, as we’ve established a clear personal taste for things and are good at comparing what we see to what we think is good.

But design strategy isn’t a thing you can see, or touch, or hold. It’s not something that can easily be judged at a surface level, or even at a behavioral level. I can’t “use” a strategy and then reflect on my experience using it, like I can a physical product.

And making strategy even more difficult to assess is that most of us don’t have a good pattern language for determining what makes a good design strategy at all. We haven’t developed strong taste and don’t have educated opinions about design strategy, and so even when we see evidence of that strategy, it’s hard to know what to think about it.

But there are things that make better or worse design strategies, and those often come from better or worse design strategists. There is evidence of this “better and worseness”, and over time, we can build up a taste for judging and evaluating that evidence.

Learning to judge design strategy work and building up that taste means understanding how a design strategist thinks.

In computer science culture – at companies like Google or Facebook – the “job interview question” is a traditional way to judge how people think. The questions are often brainteasers, sometimes with no actual solutions, and the intent is to see how people solve problems. At my first job, one steeped in engineering culture, one of my many interviewers asked me this brainteaser:

We have 12 identical bottles of beer; each bottle contains 12 ounces. Except one bottle only has 11 ounces. You have a scale, but you can only use it once. How do you find the lighter bottle?

The quiz is intended to see the process I use to work towards a solution. Is my process rigorous? Is it logical? Is it methodical? Is it creative? Are there multiple solutions? How do I judge if a solution is good or bad?

These quizzes are dumb, and I don’t think they really test much except to prove that the interviewer, who has the answer, is smarter than the candidate. But the specifics aside, one part of that type of questioning is to judge someone’s technical thought process, not their technical skills. This is “how do they solve problems”, not “how do they author code.” And frequently, the way they solve problems is through a rigorous and logical thinking process. As they work through a problem on a whiteboard, their logical strategies become clear and overt.

In the same way that developers are often characterized (and judged) by their logical, deductive thinking, design strategists are characterized by a series of unique thinking strategies and tendencies. These thinking strategies include making inferences through leaps in logic, introducing provocations into ideas to see them in a new way, integrating new ideas into existing ideas through synthesis, and sketching as a way of exploring experiences over time.

Inferential leaps

Design strategists make inferential leaps about human behavior, and feel comfortable making those leaps. These inferential leaps aren’t “logical” in a traditional sense. They aren’t deductive (or even inductive), but instead are “abductive”. This is a fancy way of saying “the argument from best explanation based on experience.” It’s a hypothesis: it’s a way of observing behavior or cultural phenomenon, and then proposing why that phenomenon is happening. For a design strategist, what’s unique about that hypothesis is that it then becomes the basis for structuring a plan. The insight that emerges from an inferential leap provokes action.

Recently, the Modernist team spent time with college students researching their experiences with college debt. During the research, students struggled to describe even the basics of their debt commitments. One student didn’t know he was already paying compounding interest on his loan, and only found out because we looked at the paperwork together during the research. Another student had stacks of unopened debt notices. Still another described how he received his loan check, and spent the money on food and beer. He figured that the amount he owed was becoming so large that it didn’t matter if he tried to be responsible, because it was impossible to ever pay back – so why not live it up?

We don’t have, and can’t find, logical causality for why these students are doing what they are doing,  and we don’t have a statistically significant sample size to make sweeping claims about all students. But an inferential leap will attempt to prescribe causality, and we’ll make those leaps from a small, non-random sample to all students. A design strategist may identify the common action between these participants is a sense of resigned avoidance. Then, based on their observations, their own experiences, and their knowledge of the world, they can propose a reason for this resigned avoidance.

They can make the assertion that “students have a resigned avoidance to their student loans because they are unable to see how a short term decision has long term consequences” or “students have resigned avoidance to their student loans because practical skills, like financial management, are elbowed out of the way of a high school curriculum in favor of more academic, but less applicable, skills like chemistry or physics.”

Or, they may make the assertion that “students have a resigned avoidance to their student loans because they didn’t eat enough fiber growing up“, or “students have a resigned avoidance to their student loans because they don’t own pets.”

Objectively, all of these are as likely to be right or as wrong as any other, because we just don’t know. But clearly, the first pair is more plausible than the second – the second two ideas are realistically (but not necessarily logically) ridiculous.

A good design strategist feels comfortable making plausible inferences without concrete evidence, with only realistic evidence. And, they have become really, really good at making inferences that end up to be more or less accurate: they have honed in on making those “first pair” style of inferences that hone in on the causality of human behavior.

Divergent and lateral thinking

Lateral thinking is about looking at old things in new ways, often sparked by a purposefully strange or unfamiliar provocation. We all know that a car has a transmission with a gear system, a person driving it, and four wheels. Except when it’s a Segway with two wheels, a Tesla with no gears, or an autonomous vehicle with no driver. “What is a car without gears?” seems obvious to us now that we’ve seen the Tesla – it’s clearly one with instant torque, powered by electricity. But it’s only obvious in retrospect. Before the Tesla existed, the phrase “a car without gears” seemed silly. It challenged our established views of what things are and should be, and was easily dismissed as being unrealistic, naive, or just plain dumb.


Lateral thinking is about purposefully instigating these unrealistic, naive, and often dumb provocations. What is a car without doors? How about a car that floats or a car that does your dishes or a car that can paint? For many people, these are increasingly obtuse non-sequiturs, phrases that don’t connect properly. And for many analytical people, thinking about the phrases is a waste of time because they appear inane – it’s a fool’s errand to try to understand what a painting-car is. But a design strategy focused on innovation requires the ability to craft or hear a sentence like a car that can paint and consider it as an acceptable potential future, something as viable as a car with or without wheels.

A painting car may really be a painting drone, sold by Behr paint or Home Depot. Or it may be a small robot that can re-tar your driveway. Or it may be half a dozen other things that we never would dream of without that lateral provocation.

Lateral thinking isn’t just about throwing out crazy ideas to spark new innovations. A lateral approach to products and services can also recast a static thing into something that fosters experience. For example, if I asked you to imagine a coffee cup, you would probably imagine something that’s pretty familiar – a thing that holds liquid, probably roundish, and with a handle. But if I asked you to imagine a way to enjoy coffee, things change. We start to imagine things that happen over time (enjoyment is a process), and that changes what we expect from the world: it’s a way to laterally traverse the idea space of coffee.

Design strategists are comfortable in this land of reimagination, where new ideas are driven by (often bizarre) provocation. They feel at ease thinking about how things could be, temporarily suspending the realities of technical feasibility, business value, and social precedent.

Integrative synthesis

During the creation of a strategy, problems are often framed as “this or that.” Two options are provided, often as extreme opposites, and teams debate which path is the right one. This simplifies decision making, because the overwhelming idea of “all of the things we can do” becomes “which of these two things should we do.” A sea of possibilities becomes tractable. Many teams don’t even realizing this is happening – the urge to simplify decision making is so strong that we end up reducing our solution set to two almost innately.


But in an effort to simplify decision making, our reduction shortchanges strategy development by removing an opportunity for synthesis. This is not unique to design strategy: this is true for all strategy work.

Roger Martin, Dean of the Rotman School of Management, describes a process of integrative thinking that he’s discovered as common across industry leaders. “Over the past six years, I have interviewed more than 50 such leaders, some for as long as eight hours, and found that most of them share a somewhat unusual trait: They have the predisposition and the capacity to hold in their heads two opposing ideas at once. And then, without panicking or simply settling for one alternative or the other, they’re able to creatively resolve the tension between those two ideas by generating a new one that contains elements of the others but is superior to both.”

What Martin is describing is called integrative thinking, and it’s a form of synthesis – of making sense of complexity by combining things that aren’t obviously combinable. I wrote a whole book on this because I was trying to understand where insights come from. Part of developing insight is in hearing and being aware of multiple perspectives on a topic. Another part of finding insight is in the ability to hold multiple ideas in the mind at once, without capitulating to one or the other: to give the ideas time to marinate, and rejecting knee-jerk or impulsive decisions. And another part of insight development, the most important part, is the ability to find connective tissue to act as glue for ideas: to produce a whole out of parts.

Design strategists are comfortable looking at problems from lots of different ways. They’ve learned to “hang around” in the space of ambiguity, rather than finding comfort in making a decision. And then, when they are prepared to make decisions, those decisions are informed by many different sources of ideas, some of which initially appear contradictory to one-another.

Generative reasoning

One of the most fundamental things that separates design from any other field is that design ideas are represented visually, through sketching. Sketches help people see what ideas look and feel like and are often used to communicate decisions that have already been made. But sketching is also used as a way of figuring things out, not just communicating things that have already been figured out. Designers use sketching as a way of working through problems. They draw sketches for themselves, incomplete or quick gestures, investigating and exploring different ways to solve a problem or visualize a new idea. One of the most well-known examples of this form of visual thinking is Leonardo da Vinci’s sketchbooks. These books were filled with small thumbnails that show what he was pondering.

da Vinci

Just like da Vinci drew sketch after sketch of birds to understand how flying works, a strategist sketches an experience over and over to understand how that experience “works.” Design strategists work through strategy problems with generative reasoning, too. But their sketches typically aren’t “things” like toasters, posters, or website wireframes. Their sketches are sketches of stories. They draw experiences that occur over time, as comic strips or diagrams. These aren’t “deliverables” that are intended to be shown to other people.

Design strategists are comfortable drawing things that happen over time, and aren’t concerned that what they draw don’t look photorealistic: they draw ideas to understand.

Thinking strategically

All of these approaches are about crafting futures in the face of uncertainty. They are unique ways to explore how people will interact with one-another and with the world, mediated by technology, products, and services. The thinking styles I’ve described above – inferential leaps, divergent and lateral thinking, integrative synthesis, and generative reasoning – aren’t unique to design strategists. Historically, these methods are established ways of thinking in all other parts of design. Designers who make shoes and chairs and toasters have long been leveraging these styles of thought. We’re just now learning how to point these approaches in the direction of strategy, but as the importance of a design strategy increases, these ways of considering the world will become more and more important. We’ll be able to better think through, and around, problems of human experience.

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Jon Kolko

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