Why Drawing is (Still) Important

It’s day two of orientation at AC4D, and our students are learning how to draw. Matt and Pat are showing them how to sketch lines, boxes, circles, and people; it’s all Expo on whiteboard, and the focus is on fast, loose communication. Given that I’ve been a proponent of moving beyond historic representations of craft in design education (layout, composition, typography, color theory), it might seem strange to have such a focus placed on hand-skills. But there are a few fundamental reasons we’re focusing so much on sketching.

  1. A sketch, sketched publicly, is persuasive. When you draw in front of other people, they get to “go along for the ride”, and this helps them feel some degree of ownership in the output. This means that they’ll be more likely to advocate for your ideas and support them, because they feel a personal connection to the process that spawned the ideas.
  2. “Owning” the whiteboard is one of the fastest ways to gain control of a room. It establishes focus. It forces an agenda (“We’re talking about this and not that, see?”), and more importantly, allows you to deliver on that agenda. Holding the pen is to hold the power of most rooms; it is to hold the definitive source of truth, or the “last word”.
  3. Sketching is the fastest form of visual thinking. I can create a sketch of a complex system in the amount of time it takes Adobe Creative Suite to complain about needing to be upgraded; pen on whiteboard is a medium that allows ideas to be captured before they dissipate, before they have a chance to be judged as “not worth it.”
  4. The ability to sketch what someone else is saying is fundamental to participatory design practice. As we strive to integrate “end users” into our design process through forms of co-design, we often need to act as the output mechanism for people who are too shy or unwilling to be publicly creative. Sketching is a critical part of that process.

Here’s some shots of the work in action.

One and Done: Using an Iterative Process

There’s a particular process hump that design students inevitably encounter: that of quality. This comes after they have learned particular methods, and they realize that they can make a thing. If the student has been taught critique and self-reflection, they’ll also soon realize that their thing isn’t very good, because it’s the first iteration of the idea. Iteration one is a thinking artifact, not a presentation artifact, and for a new designer, the gulf between thinking and presentation is enormous. In the dialogue between maker and material, iteration one establishes boundaries around a problem space but it doesn’t actually solve the problem. That’s because the level of craftsmanship and finish of the artifact is directly related to the quality of the solution, and for all novice designers, their level of craftsmanship and finish is poor.

This learning moment is inevitable, because it’s a place where method and tacit skill collide. Simply, it’s easy to learn a method, because a method is – by definition – procedural. Just follow the steps, and you’ve applied the method. But tacit skill is neither easy nor procedural; it comes through practice over time.

Once a student has produced iteration one, the best thing they can do next is to produce iteration two. And for most students, this is the hardest thing they’ve ever done. Because producing iteration one was so hard, and took so long, and the results are so obviously bad, the student sees only failure. And they give up.

I think, in my teaching experience, this is a critical fork in the road for learning design. Does the student persevere and practice? Does she “play her scales” or “wax the floor”? Or does she cut and run, internalizing various rationalizations for her poor work? I’ve heard “I’m just not meant to be that kind of designer” more often than I care to count, always at this phase in learning. And I’ve also seen students practice through it, giving up their social life, practically living in the studio, and establishing a sense of confidence both with skill and process.

The separation of method and execution is a learning practice, a pedagogical trick for students to learn both. But in practice, there’s no separation. Methodology integrates with craft-based execution over time to form expertise. Once a student has learned method and learned about execution, the rest relies on their passion to practice. There’s no real way to game this system; expertise comes from practice and experience. And that takes time, personal and professional sacrifice, and a disciplined maturity.

The simple truth is that, for a student that’s gotten to this magical moment in learning, they have only one path towards success: practice.

Lipstick on a Pig

Recently, Michael Bierut wrote an article about branding, and our cultural tendency to armchair quarterback design decisions. The first 2700 words (or parts I-IV) poke at populist response to graphic design, during which the piece shifts between sarcastically casting the consumers as a lynch mob to casting designers as arrogant idiots. The last 450 words seem to lament the death of graphic design. That’s part VI, which includes a Vignelli quote that seems to contradict everything in the first chunk.

But it is part V that sparked me to write this response. In Part V – How Many Psychiatrists Does It Take to Change a Lightbulb? – Bierut describes his own experience in redesigning the UPS brand. I appreciate his honesty, because it offers an intimate view into what happens in corporate America. An agency is called in to do some “creative work.” They offer concepts and vision. The work passes through endless meetings and a machine of consensus. If the work is not killed during the process, blanding pops out the other end.

What concerns me is the view of design – and particularly identity design (or branding) – as the hammer, where stagnant consumer growth is the nail, and the need to “change consumer perception” is more important than the need to “change our product offering.” Bierut presents the UPS opportunity as a response to marketing needs. As he describes, “We were hired for a simple reason: surveys kept showing the company was inaccurately perceived as being slower, more inflexible, and less technologically adept than their competition.” Yet there’s nothing simple about this reason, and it begs an even less simple question: if the company was perceived as being slower, more inflexible, and less technologically adept, could it be because they are slower, more inflexible, and less technologically adept?

This is a constant and reoccurring theme in design circles. In the well-publicized Tropicana example that Bierut cites, communications director Jamie Stein initially explained the rebrand: “Our intent was to get people to rediscover the benefits of orange juice.” When UC tried to redesign their identity, the stated goal was to unify the UC system. In the recent American Airlines rebrand, the “new logo and livery are designed to reflect the passion for progress and the soaring spirit…

But a redesigned logo does not make a broken airline better, and a redesigned logo does not make a tired parcel system more flexible. New paint on the outside of a plane does not offer ergonomic support to flyers, who are forced to sit on a “chair” made of metal rods. It does not empower customer service representatives to help confused, tired, or pissed off customers. It does not make right the countless absurdities of random ticketing and return policies, or baggage fees, or headphone fees, or inflight entertainment fees, or change fees. It does not fix the countless broken interactions that occur within the American Airlines service ecosystem, and it will not fix the poor financial state of the company, which is bleeding money.

Similarly, a new logo does not help UPS better respond to the complexities of their customers, who change their mind and need packages re-routed. A new logo doesn’t help educate people about the nutritional benefits of fruit in their diet. And a new logo doesn’t improve the ability for students to register for classes across the UC system, or help them better manage the complexities of course registration and degree completion, or navigate the bureaucracy of the enormous California college system.

We see example after example of branding as band-aid: a new identity will somehow magically transform a company from broken to fixed, from out of touch to empathetic. It won’t. The cited reason for a rebrand, in each example above, should have been addressed by changes to the actual product, service, and business strategy.


I herald design as one of the most powerful forces of change we have for addressing complicated business and social problems. Part of design is selecting tools, methods, techniques, and approaches that make sense in the context of the problem. Design, like any other discipline, is not “one size fits all.” It is not appropriate for “the masses” to critique the aesthetic of the new design in each case mentioned above, and while predictable, it’s particularly disappointing to see the criticism at such shallow and superficial levels (“it looks like a toilet”; “my two year old could do better.”) But it is entirely fair for those same masses to critique the design strategy in each example, for the design strategy in each example was to put lipstick on a pig.



Engagement is about participation. It’s a word relevant in civics, in social and cognitive psychology, and in education. Fundamentally, it’s about autonomy, motivation, and empowerment: you are engaged when you are motivated to purposefully direct your attention.

Attention is about focused concentration. The world is competing for your focus. External events cause your eyes to move, your ears to perk up, and your locus of attention – your single point of sensory awareness – jumps. Imagine sitting at a coffee shop, trying to read a book that just isn’t very good. Someone comes in, you look up. The espresso machine grinds, you look up. Nothing happens, and you look up; your scan of the room searches for something more interesting – more engaging – than the book in your lap. When you aren’t engaged, external events override internal self-talk and self-control, and your eyes, ears, and more importantly, brain, wanders.

Motivation is about understanding value. In learning, the phrase “Cognitive engagement” or the “Cognitive engagement model” describes a way of thinking about education that’s focused less on access to knowledge and more on ability and willingness to process and understand information. This model recognizes that, to be successful, a student must understand the value of what they are learning. Teaching is not simply providing access to content. And to foster this motivated stance, a teacher can utilize several teaching strategies, including:

  • relating the value of the knowledge to the value of something the learner already knows and values,
  • fostering higher-order talk and writing about the subject matter,
  • stating learning strategies explicitly,
  • encouraging active responses that require introspection and synthesis of ideas,
  • and explicitly stating the strategic purpose of the educational activity.


Dennis Littky runs a school called The Met. His graduation rate is “consistently above 90 percent, drawing from the same population that is victim of the 66 percent graduation rate in the regular public schools. And 98 percent of the Met’s graduates apply to college, with nearly all being accepted, and most of them are first-generation college students.” [link]

Littky’s method draws directly from the Cognitive engagement model. He identifies a topic that the student wants to learn about, and bases that students’ entire curriculum around that subject matter. Not surprisingly, the students he encounters don’t select typical academic subjects. Instead, they pick things like Hip Hop or, as he describes, dying. He recalls a story of one of his students who wanted to study death. The girl “proceeded to spend the year in and out of funeral homes and cemeteries.” His students are engaged, and so they participate by offering their attention and motivation. And once he has their motivated attention, learning occurs through sensemaking and synthesis.


I encounter the word “engagement” a lot when reading about digital products. It would appear to be the holy grail of social-media: an engaged audience is somehow more valuable to investors and to business owners. Somehow, in this context, the word engagement is always connected to email marketing or spam. Tips from the “pros” describe that “Email providers use a few metrics to determine engagement: opens, clicks, unsubscribes, abuse complaints, and just generally treating email like spam or not-spam.” A good email “re-engagement campaign” should, apparently, ask the question “What is the best way to draw them back in, not push them away?

The director of social business strategy at H&R Block describes that “…engagement and ROI depend on the particular program. For our marketing campaigns, engagement may mean likes, or shares or comments. But then for our educational series, views may be the engagement. The metrics continue to solidify over time, and there is no one answer to all programs.” As you ponder what, if anything, that means, you might also take a minute to ask yourself why H&R Block needs a director of social business strategy. Perhaps the next big thing will be to do your taxes with your friends.


The word engagement, and the marketpreneurs rallying around it, are missing something pretty fundamental. Facebook, pinterest, and instragram are engaging because people want to participate in these services. People are motivated to purposefully direct their attention: they see some form of personal value in the service. Fundamentally, engagement is a question of “value proposition.” In a world where time is the most limited resource we have, ask yourself – why would someone be motivated to direct their valuable attention your way? What’s in it for them?

Designer as Product Owner

There’s a creature in software companies called the “product manager” (almost always referred to as the “product guy”, hammering home the unfortunate fact that nearly all software companies are full of men. For fun, I’ll switch it ’round for the remainder of this post.) The product gal has a strange role, in that her focus is on product-market-fit. This means she’s responsible for determining the features the product offers, for bringing these features to market in a certain sequence and by a certain date, and for making sure the features deliver on the value proposition and promise made to end users and customers.

The reason the role is strange is because it serves two masters. The product gal answers to the needs of the market, and so she must have a strong sense of what competitors are doing and what technological advancements are starting to become the norm. Yet simultaneously, she answers to the needs of users, and so she must have a strong sense of what users want and desire. When these two masters line up, everything is groovy. But frequently, what’s good for the market and what’s good for the users diverge, and so our product gal will have to choose a side.

Most of the product gals I know come from either a tech background (they were coders), or a marketing background. When push comes to shove and the market/user fit diverges, these people double-down on what they know best. This might mean pushing new features, or migrating to a new development stack, or analyzing all hell out of web traffic, or conducting survey after survey. But when the product gal has a background in design, and she sees a divergence between market and user needs, a different thing happens.  She’ll leverage an empathetic lens, and she’ll also double-down on what she knows: user-centered design. She’ll focus on helping users achieve their goals and aspirations. This is distinctly a design perspective on product functionality, and it often means removing features, rather than adding them, and ignoring current site behavior rather than optimizing for it. It’s a maternal voice of usability, and will force a conversation of resource allocation. Perhaps creative and development resources should spend their time refining existing features, rather than producing new ones. It might make more sense to track forward progress based on the outcome of behavioral studies – yes, boring old usability studies – rather than lines of new code shipped or backlog pruning. These are definitively non-sexy places to be as a product owner, but in a strange way, they position usability as a strategic differentiator. For all the talk of experience and engagement as product goals, usability may have found its way back in the limelight as a means of achieving both ends. (This poses a subtle irony to last summer’s bandwagon land grab of the Usability Professionals Association, rebranding as “The User Experience Professionals Association.”)

For a designer looking to move into product ownership roles, this has several implications. First, she’ll need to become extremely interested in the competitive product landscape, understanding how market dynamics are shaping alternative approaches to the same value proposition. Next, she’ll need to become aware of more strategic approaches to design, thinking about how a combination of feature decisions, timing, and delivery models contribute to a user’s perception of value in her product. Finally, she’ll need to dust off those old, fundamental skills of think-aloud usability testing, and constantly beat a drum of simplicity and reduction. A designer in a product role is about as far from a pixel queen as one can get; strategic design is about usability, not beauty.

Iteration and Variation

Two of the most basic principles of design process are iteration and variation. They aren’t the same, but they are related. Iteration is making informed changes to an existing design. These changes may be provoked by user testing or critique. Commonly, these changes are provoked simply through the act of making the previous iteration; this is the pursuit of perfection, and can be endless (which drives some project managers crazy). When designing software or services, I’ve found that I gain a “sweeping sense” of design ideas, but I can’t keep all of the details of that sense in my head at once. Iteration is the process that allows me to infuse this sense into the work and overcome the limitations of my own memory. The first pass is a “broad stroke”, intended to get the essence of the idea out. For a service, this typically includes a view of the touchpoints, the people involved, the handoffs, and a few key details. In software, this is typically the “hero path”: the main push through the interface, helping a user achieve a single primary goal. The input for this broad stroke is imagination, and the bottleneck is the ability to remember.

Once this broad stroke has been created (drawn, wireframed, coded, etc), further iterations assume the basic framework as fact. The initial iteration acts as a constraint, and becomes rigid: I’ll refine details and extremities, review and change aspects of the idea, but the idea itself has come to life. That’s good, because it serves as a creative anchor. It’s bad, because I now have a subjective sense of ownership over it, and I’ll become unwilling to let it go even when a better idea presents itself. Each further iteration serves to solidify details, and they become taken for granted: they become facts.

Variation is a way of adding a sense of objectivity to design exploration. Variation is an exploration of alternatives. In my own design process, I’ve found that I’ll avoid variations unless explicitly prompted to make them, and sometimes I need to prompt myself. Where an iteration moves an idea forward (or backwards), a variation moves an idea left or right, and is not productive in a typical engineering sense: the expectation is that all of the variations (except one) will be rejected. But variations act as provocations for what-if scenarios. When I’m urging other designers to produce variations, I advocate what my friend Bob Fee calls the A-B-C-Q approach to variation. This is the idea of creating several expected variants, changing minor details (A leads to B, B leads to C), and then creating a wild or surprising jump (Q). These later “Q” jumps will ignore or purposefully reject constraints, or established precedent, or social norms, and it is from these “Q” jumps that more risky but exciting innovations emerge.

F. Scott Fitzgerald describes that “the test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.” I usually can’t hold opposed ideas in my mind, but I can visualize them one at a time on paper or in code, and process them at once after-the-fact. Developers are starting to embrace iteration through methods like “agile.” This is useful, because it treats designed (and developed) artifacts as less precious and more malleable. It is useful to also introduce variation into a development process, in order to explore multiple ways of solving a given problem, and it is extremely beneficial to allocate development cycles to the exploration of both iteration and variation. It’s not a “waste of time”; it’s how design works.

Scale and Social Entrepreneurship: Is Bigger Better?

Kriss Deiglmeier, Executive Director of Stanford’s Center for Social Innovation, recently wrote a blog post on the nature of scale. She’s pondering the urgency of growth, as described in nearly every entrepreneurship competition, pitch-fest, or best practice. She specifically hones in on the role of locally-specific, effective, but un-scalable solutions. She asks, “It is well known that social issues are interconnected; health, education, environment, and economic development are all intertwined. This is particularly evident across the world in low-income communities. Challenges such as hunger, poor health and poverty impact a child’s ability to learn or engage in education. Thus, there is evidence and research that supports the need for comprehensive solutions –– which are often too complex to be “cookie cutter” scalable. Yet are they not also worthy of funding?”

I wrote a little more about this in Wicked Problems – where my emphasis was on the generalizability of the solution itself. This is a relevant issue when scaling is attempted across cultures, as if proving the efficacy of a solution in Vietnam implies that it will work successfully in Cambodia.

A design solution always begins with a local insight. For many designers, this is taken to an extreme, as it’s an insight about themselves or their personal surrounding. It’s a personal process, one made only slightly more sociable by participatory design or other forms of co-design. Scale is an external force that’s applied or encouraged, often through manufacturing, operationalization, or the amplification effect of digital technology. The externality of scale is artificial: the design solution works and exists independent of the number of people served.

So why an emphasis on serving a large number of people?

For many, it’s a question of ethics, or “goodness”. I once encountered this argument from an extremely wealthy woman, one who gives a great deal of her money to important social causes. She viewed her giving as a selfish act: she was working to improve the quality of the world around her so that she and her children would have a better place to live. As such, she took great pains to research and understand the recipients of any money she provided, and took a self-declared “rational approach to giving” so that her money would “benefit the most people possible.” She thought about it like this: if I’m going to act to help people, I need to be aware of the cost/benefit tradeoff of my actions. Most of us have a practical limit on resources like money; in her case, the scarce resource was her time. And so she based her philanthropic giving on the rationality of maximizing her scarce resource. If it takes 100 hours to evaluate a potential grant recipient, she wanted the most social return on her investment – the most people helped, per hour invested.

The ethical question can be turned around by examining breadth of impact in respect to depth of impact. Pretend we have $100,000 to give to the broad cause of “literacy in the developing world,” and consider this simplistic argument.

Vietnam has approximately 7 million students enrolled in primary and lower secondary schools [pdf link] , and government expenditures per primary school student are an abysmal $23 [pdf link – worth reading in its entirety]. We could take our $100,000 and spend $1 to provide some basic materials to 100,000 students, thus increasing the expenditure per student, for 1.5% of all students, by a small amount. They may purchase books, pencils, or other basic supplies with this money.

Or we can spend $20 to provide more materials, or materials of a higher quality, to 5,000 students, having a more powerful impact but on a limited scale. $20 will appear significant to the students, parents, and teachers, as it represents a doubling of their current resources. This might buy chairs, desks, chalkboards, textbooks, basic electronics, teacher training, benches, more teachers (and therefore more classes – consider that “In Vietnam, more than 90 percent of children in rural areas attend schools with two or more shifts, resulting in an average class time of only 3 hours and 10 minutes per day” [pdf link]).

An ethical argument can be made, successfully, for either of these investments. But I don’t think the ethical conversation happens at the funding level (although I know it happens in excruciating detail at the execution/program level). I think the first investment is broadly assumed to be the best because it touches more lives. It is probably the best in the case of commodity solutions, such as medicine. I don’t think that’s true for most conceptual, qualitative, subjective issues, such as education.

I think scale is also a question of fame and positive press. While the internet has made it possible for massive awareness of an extremely narrowly focused campaign (Kony, for better or worse, provides an example), typical foundation thinking around PR seems to be conservative: a press release describing the massive financial scale of a grant, with the number of people helped as a byline. I’m not smart enough to do the mental arithmetic to figure out what $10B to save more than 8 million children by 2020 means; I also would typically not research child deaths in developing countries to see if 8 million people is a lot or a little (turns out it’s about how many children die each year in the world). Instead, I would marvel at the large numbers, because millions and billions are indeed large numbers, and that would shape my casual view of the effort as extremely positive.

Deiglmeier points out that she hears “… over and over again the frustrations of community driven organizations because funders immediately want to know the ‘scaling’ model of such organizations –– and that funders dismiss them if they cannot provide it.” I hear that, too, and I’ve seen extremely impressive solutions ignored because of their perceived lack of scalability. I would like to see more of a conversation around the need to scale – particularly from the big name funding agencies and foundations – and more questioning of the assumptions around bigger, broader, and more. Design-driven social entrepreneurship can push deep impact, and can provoke meaningful change, without necessarily touching thousands or millions of lives.

How to Use a Concept Map to Get Your Way

Most professionals will, at some point, find themselves in positions of selling: of persuading a skeptical audience that their vision of the future is a good one, and is worth pursuing. Most professionals do this poorly, attempting to use words to appeal to logic, as if the best argument is the most rational. Whether that should be the case is debatable; it certainly isn’t the case in most organizations. Instead, a successful argument for a future state is usually made through a combination of emotion and narrative, and appeals to the heart and soul. I’ve previously talked about one way of making this case, by connecting design research to value. And I’ve also talked a great deal about sensemaking, as the way people understand and form relationships with new ideas. Concept maps are a way of persuading an audience, while at the same time, educating them: helping them to see the world from a new perspective (yours!), and giving them a mechanism through which they can make sense of the new future you are proposing.

This is a step by step guide on how to make a concept map. My point here is not to show how to make one, but instead, how to use one. A concept map is overwhelming when it is first presented. It was an extremely effective tool for the person who made it. It becomes a point of confusion for the person who has to read it, and this is where a concept map crashes and burns: it’s a manifestation of the expert blindspot. In creating a concept map, you’ve learned new things and you see the world in a new way. It’s tempting to present the finished artifact as proof of this new vision. But the audience wasn’t along for the ride. They didn’t learn what you learned, they don’t see the world the way you do, and because the map is visually complex (as was your learning), they’ll be intimidated.

And so I recommend that you use a concept map for organizational change over a period of months, strategically, socially, and with a goal of manipulating the trajectory of your company by helping colleagues view the world as you do.

First, you’ll need to have an end-vision, a target for your organization. This may be a new role for your product, a new delivery mechanism, a platform change, a strategic acquisition, a re-org, and so-on. Over time, as you figure out what this end-game is, a concept map becomes a useful tool to represent the vision – to you. Use it as a selfish tool. For example, if I was pushing a healthy-eating rock up-hill at McDonalds, I might arrive at a big concept map, with a small portion that looks like this:

My intent is to show that the only way healthy eating will survive in a fast-food setting is if it is introduced by corporate, pushed to suppliers, and manifested through massive large-scale discounts, negotiated at the same level as corn. It’s complicated, hard to understand, and while it makes perfect sense to me, it’s of no use to anyone else. There’s no story being told; I literally need to explain it with words, or people won’t understand it or use it.

So, I might start by introducing this:

It seems dumb: it’s so simple. It doesn’t really say much. But it stakes out a view of the world with three major constituents. This is, potentially, not how people in the organization currently view the world – commonly, people in big organizations view the world through the lens of an org chart. This challenges that, albeit it extremely subtly.

I would put this in my presentations, email it to a few people, print it out and hang it on my cube.

And then, over time, I would start to replace it with this one:

I would start to describe how our franchise owners are fairly apathetic about what products are actually served in the stores, and instead, care about minimizing change, conflict, and cost.

After a few weeks, a version like this would start to show up:

Over time, the map is introduced into the organization, and at each step, there’s no announcement, unveiling, or massive production associated with it; it’s not a design artifact in a finished sense. Instead, it’s “released” through one on one meetings, in presentations, in conversations. And over time, it gets traction, because it begins to stand for things. The diagram itself starts to act as a placeholder for the conversations you’ve had, the vision of the future you see, and even the roles and responsibilities of individual people or entire business units. One way of thinking about a concept map, released in this style, is that it challenges the org chart: it’s a way of affecting change in a bottom-up fashion, rather than an autocratic manner.

And one day, you’ll be sitting in a meeting, and someone you don’t know, from an area of the business you’ve never had influence in, will present your diagram back to you, as if they made it. That’s an amazing feeling: your design work has shaped the tenor of the organizational dialogue.

Sometimes, you’ll need to introduce the map slowly – taking weeks or even months – until all of the various constituents have accepted it as a common language. We did just this in a client project at frog for an extraordinarily large client (hundreds of thousands of employees). We offered an initial view of a service landscape through a concept map. It was simple, just a few circles and some words – so simple that, at first glance, someone might say “that’s it?” And the map began showing up in various presentations, and posters, and emails. Over time, the map become more complicated – and was still “infused” into decks and emails. And it became part of the organization language; it became the way people talked about the future. This type of strategic introduction of new design language is extremely powerful. Organizational change can occur through design proxy – slowly, methodically, and purposefully.

If you like thinking about concept maps, check out Hugh Dubberly’s great archive at www.dubberly.com/concept-maps.

The Long Haul – Thoughts on Acceleration

There’s a lot of startup-hype dealing with speed. Go faster! Accelerate your product! Always releasing, always testing, always honing, always in beta! There’s an implicit idea that for an entrepreneur, faster is better.

When driven by venture capital, there’s an expectation of a massive exit within approximately five years (so investors in the fund can enjoy large returns, and liquidate some of their gains). Entrepreneurs who have taken VC money commonly describe a huge sense of urgency for the company, the drive to launch and scale quickly. I know I felt it at the startups I worked at; there was some large and mythical scary force looming right behind us, and we had to hurry, lest it “won”. Through all of this, tech bloggers and breaking news announcements have created a sense of overnight success and failure. Instagram was just bought for a billion dollars! Just like that – it happened so fast!

The thing is, when you talk to the entrepreneurs who have the amazing success stories of wealth through buy-out or IPO, they constantly talk about a long, slow slog through multiple and unsuccessful versions, flavors, and iterations. While there’s usually a single “moment of success”, most describe the process as more of a constant and ongoing climb up-hill.

In 2011, Foursquare created (and TechCrunch published) an infographic showing the massive growth of the service in a short time – growing from 0 users to 100,000 people in six months, and then to 10,000,000 members in a little over two years. But Dennis Crowley created a service called Dodgeball years before founding Foursquare, and “began toying more than five years ago with ideas about connecting cell-phone users through social networking software” – said in 2006, indicating that he had been pondering location-based check-in services since 2001. Toying and pondering are strange words, words I don’t think we give enough value. These describe a head-in-the-clouds awareness of how things are progressing, how the world is changing, and this feeling becomes tacit. It becomes a frame, a way of viewing the world. It becomes a form of expertise.

The story of Instagram is equally both long and short. The short story goes like this: a billion dollars, after two days of meetings with Facebook. But the reality is harder and longer, as Kevin Systrom describes working on Instragram as Burbn, and his peers in college recall that “As early as 2005… Mr. Systrom had his eyes on mobile phones as the wave of the future.” The quote seems so cliché – the wave of the future – but I think it’s a gesture to the same sort of reflective incubation I see in entrepreneurs. It seems to happen in the valley purely around technology, but it happens around other things too, like health and wellness, education, politics, and so-on. It’s the constant and low-level buzz of viewing the world through a lens and forming a long-term opinion about how things should be.

Facebook didn’t become a giant brand overnight. Zuckerberg started Facemash in 2003, Thefacebook in 2004, and a private, closed network called Facebook in 2005. Google has a similarly long and strange history. The story of Netscape founder James H. Clark, told by Michael Lewis in The New New Thing, is a similar tale of long, arduous, stay-the-course, subtle and reflective thinking.

The drive for speed, the need to always be launching and pivoting and hurrying and moving just doesn’t have a historic grounding in reality. It seems to be a distraction, and I think it’s harmful. I think it encourages a half-cocked form of product thinking, a defeatist attitude towards design and planning and a rejection of quality. You learn from failure, no doubt, but the idea of pursuing failure as a mechanism to short-circuit product incubation just doesn’t work.

Many people feel that there’s a certain window of opportunity for a “product/market” fit, during which a product will achieve the most traction and success. This window of opportunity is theoretically shaped by platform adoption, by familiarity with technology, and by perceived wants and needs of consumers. It’s also shaped by the competitive landscape. As competitors make strategic investments and react to market changes, there’s a sense of looming takeover: a feeling that the next big thing is always steps away from your innovation, ready to grab your market share. But this window of opportunity is just out of your control: it’s a result of all of culture coming together into a blend of technological adoption. The serendipity of product/market fit comes from being in the right place at the right time; it’s luck. But it’s not entirely luck, because you can hedge: you can increase your odds of success through the long-term, nose-to-the-grind refinement of a design, and a careful eye to trends and culture.

Design is not about speed, and design-led entrepreneurship isn’t about speed, either. There is no day where suddenly your product is irrelevant, or your competition has “won”. It happens gradually and amorphously. There are mechanistic (and real) reasons to hurry (your investors will bail on you, you need to pay your bills). But those are externalities to the idea of product/market fit. And if you don’t have those issues, there’s no real need to force such an extreme hurry.

Inspiration and Khan Academy

I’ve been thinking a great deal about the work of Khan Academy. I’ve felt uncomfortable with the success of Khan, and uncomfortable with my discomfort: why do I have a strong, negative, and emotional reaction to something that’s receiving so much praise and respect?

I thought, for a long time, that it was the lecture format.

I now think it’s something else: the assumption of motivation. Lectures (both in person and online) assume that the viewer wants to learn. Baked into this assumption is a more subtle idea: that the viewer wants to integrate the new material into their existing view of the world.

I think, broadly, that’s false.

Educational scientists use words like active and passive to describe the nature of learning. Active can then be described with more nuance: compare collaborative learning (where students work together to solve a problem), cooperative learning (where students work together but ultimately solve a problem on their own), and problem-based learning (where actual examples are introduced and then solved over the course of learning). (pdf link) Cases – the norm in business school – come to life as problem-based learning through skilled delivery from a master teacher. Projects are the basis of most design and architecture education, and typically include collaborative, cooperative, and problem-based learning. While engineering is typically taught as a private endeavor, paired programming is gaining recognition as an effective form of learning for both lower and higher level topics of computer science. The “Socratic method” – a form of systematic questioning – forces students to think critically and then construct a compelling argument to substantiate a point; it’s a common way of learning law.

All of these examples show how teaching can encourage sensemaking. Sensemaking is a complicated name for a process of integration: it’s how we take new ideas and meld them with our existing world-view.

My interest in sensemaking began as I examined how designers explored new topics quickly. Each time a designer gets a new project – say, to redesign a shipping website, or to create an iphone app for banking – they need to rapidly understand enough about the subject matter to propose beneficial changes. This process happens most effectively through apprentice-based learning in context. Sensemaking, for designers, is about working alongside an expert, asking them questions as they work, trying things, and building models that illustrate existing and optimal approaches. A designer making a banking app would benefit from working alongside a banking teller to serve customers, from standing in line with a customer as they fill out a deposit slip, from sitting with a loan officer as they formulate mortgage agreements, and so-on.

The larger idea of sensemaking, outside of the discipline of design, recognizes that learning happens through conversation. I don’t necessarily mean a literal conversation, although that’s how Karl Weick describes it. I also mean a “conversation” with a model as it is being built, as described by Daniel Russell.  All of the various perspectives of Sensemaking acknowledge that it’s an active process, and there’s two salient points here. First, learning has to be active in order for Sensemaking to occur. Second, the active part of a learning experience occurs inside of the learner. Put an apathetic thirteen year old in the middle of the most active and vivid chemistry experiment in the world, and if they aren’t interested, they won’t learn a thing.

Consider that, for many of you, you just heard the work “Sensemaking” for the first time; it’s a new idea. It won’t be meaningful to you until you find a way to integrate it with your existing view of the world. You might find this blog post inspiring enough that you reflect on your existing learning style, consider how Sensemaking works, and then come to a new conclusion of your own. But I bet you won’t, because being interested is exhausting. It takes effort. It usually takes a human as a support structure. It’s one reason why we have therapists, coaches, and consultants. It’s why we have TED and PopTech. It’s the only real reason why we have teachers.

The missing part of Khan Academy, and the missing part of online learning, and the missing part of blended, or flipped, or hybrid learning, is the passion. Passion can come from inside. For lots of people, it comes from outside. It comes from heros, and inspirational talks, and stories of failure and success, and through competition and collaboration. It comes through hundreds of different forms for hundreds of different people. For some people, it does come through online learning. But my guess is that it’s a very small amount of people, people who are extremely introverted, and thoughtful, and reflective, and self-motivated. Further, I bet there’s a correlation between those people and people who excel at engineering. Khan Academy is being built by a team of extraordinarily bright engineers who are building for people just like them.

Online tools have the potential to be inspirational and drive the type of passion described above. Facebook has illustrated how engaged we can be with digital. The medium is not the problem. But a digital medium, in the context of learning, can’t yet adapt to individual passion drivers: it can’t learn to inspire.