Daniel Kahneman is something of a sage. He is a psychologist, yet he has won the Nobel Prize for Economics. Why? Because he’s demonstrated through experiment and argument that humans are not entirely rational creatures. In fact, we’re often quite irrational, making decisions that aren’t in our best interest, acting on impulse and blinded by unseen bias, and taking actions that aren’t, to say the least, well evaluated. He recently put his several lifetimes of insight into a book that anyone with an interest in his or her consciousness should read, Thinking, Fast and Slow, a text to be savored and lived with and returned to. Your authors hope to have a quarter of that effect.

It is no surprise that wise people go to him for wisdom. One such occasion involved Legg Mason chief investment strategist Michael J. Mauboussin, who now tells the story with the distance of years. When they met, Mauboussin asked Kahneman what the one best way was for him to improve his decision making. The psychologist’s reply was to buy a notebook.

The nearest composition notebook will do. What’s it for? This is now your decision notebook, Mauboussin explained to the Motley Fool, the investment website:¹

Whenever you’re making a consequential decision . . . just take a moment to think, write down what you expect to happen, why you expect it to happen and then actually, and this is optional but probably a great idea, write down how you feel about the situation, both physically and even emotionally. Just, how do you feel?

What do you get from such a pen and paper practice? This mapping out of your decisions, Mauboussin explains, is a way of alleviating the hampering effects of hindsight bias, the nearly universal tendency to view past events with a favorable tilt toward our noble selves. This has short-term benefits: it feels good to think that you were right all along. But there are long-term negatives: if you make all your decisions in an unexamined fashion, you won’t learn from them very quickly.

What the notebook acts as, then, is a record of your decisions. As you map decision after decision—and perhaps find yourself making mistake after mistake—you’ll begin to recognize the elements of your identity, your various strategies, and the assets you’re drawing upon for a given decision. Then, once you make the mistake—which will happen if you’re stretching yourself in any way—you can go back to see where the misapprehension was. This is a very honest form of feedback that helps us spot our patterns of behavior and (in)decision and is the kind of practice that helps us become better acquainted with the parts of ourselves that we don’t or can’t acknowledge during the bustle of the decision-making time. But let us make ourselves clear: the point is not to never make mistakes; the point is to grow. By stretching ourselves and having the courage to make difficult decisions, we may make mistaken decisions—and anything that helps us to see the blind spots, the false assumptions that led to the mistaken decision, will accelerate our understanding.

This is also where we connect with Chapter 8, where we took a broad approach to bringing as wide a range of experiences—and thus ideas—into our lives as possible. However, as we stated just a few pages ago, ideas are just the beginning of strategy. What are you to do once you’ve had an insight that could launch a company? As we’ll see with the story of the start-up Orchestra, it’s a matter of making informed decisions about strategy. We need to test that strategy, to bring that idea a little closer to reality. We can do that by examining the interdependent causes that will need to be brought together for an idea to find its home in the world. By mapping our decision-making process, we can see what our assumptions are and where they might go wrong, and when they go wrong, we can find the incongruence between our perception of reality and the way it actually is. That mapping of the decision process is the center of this chapter: here we explore the art and craft of blueprinting.

MEETING THE BLUEPRINT

This mapping of decisions is not entirely new in the business world. In the literature and white papers and the rest you might find mentions of technology architecture, process architecture, and other decision-making taxonomies; though they are useful to a point, these things function as schematics of systems. It’s like knowing all about your digestive or endocrine system, which is great if you have a problem or solution particular to those domains. However, if you’re acting with your whole body—as organizations tend to do with big-time decisions—you need a map that takes into account not just one or two of your organ groups but all of them and the way they interrelate. This is the premise of the enterprise blueprint: to draw lines around and between the different factors that contribute (or don’t contribute) to the success of an idea as it moves into the world.

What this is, then, is a diagram of an action, and the body that’s moving has many parts.

IDENTITY

Whether deliberately designed or not, every organization has an identity, both tangibly—that is, in the design and feel of the products and services it brings into the world—and intangibly—in the way people relate emotionally to the organization. This takes form in a number of ways; when we talk about branding, positioning, and differentiation, we’re discussing organizational identity.

Western and Eastern psychological traditions make a distinction between the individual ego and the social ego. The individual ego is the way we think about ourselves, how we relate to ourselves, the self-talk that tends to chatter in our mind as we go through our days. Then there’s the social ego, which is what other people think of us, how they regard us, and the feelings we leave with them. If we extend this to an organization, the individual ego graphs effectively to the organizational culture—the way people relate to one another in the organization and especially to the idea of the organization itself, that is, the way the employee regards the brand of the organization she’s working for.

We can see this intangible identity by evaluating the way we regard some of the major brands. The difference in emotional connotation between a laptop made by Apple and one made by Dell is staggering: the former is sleek, understated, and emotionally aware, and the latter is vaguely robust and haplessly utilitarian. That cuts into high-end goods as well: Ferrari and Tesla both make cars that you might kill for, but only Tesla gives you the feeling that it’s making the world better to live in. Identity rests in locations as well: Starbucks has a complex social ego, for it is more upmarket than a deli and more downmarket than a posh café, and its ubiquity lends it an array of properties—extremely hip people may not wish to associate with something so common, but the chain’s pervasive penetration lends it a comforting familiarity. Your authors can’t be the only ones who have regarded a Starbucks in an unfamiliar city as having a markedly maternal presence. This social identity, of course, is most palpable in cases in which you’re interacting with people who represent the brand—Trader Joe’s, the widely beloved grocer, makes a point of hiring creative, outgoing employees and pays them well—a kind of practice we’ve argued for throughout this book. One of the positive outcomes of that prosocial behavior of the organization is the prosocial interactions its employees have with customers, which is very, very good for the company’s brand, its social identity, and its overall blueprint. 

Strategy, then, is the struggle of taking this identity to market, a process we’ll examine with one in-depth case study. 

REINVENTING THE MAILBOX

Have you ever had an insight that made you want to quit your job? What if you actually did it? Gentry Underwood has—to sizeable start-up success. But the path of fruition was not a straight line: as we’ll see, the route from epiphany to acquisition is not a straight line—it is bent with unseen assumptions.²

Underwood is a prototypical example of a broadly experienced person. As we discussed in Chapter 8, broad experiences allow you to find grand or subtle insights; in the case of Underwood, he may have streamlined one of our most basic electronic interactions. Within 30 seconds of conversation with the man, you can tell he’s quick-witted, sympathetic, and blessed with fast-firing synapses. Now getting deeper into his thirties, Underwood, with a certain flabbergasted amusement, tells of Stanford letting him in for his undergraduate studies by virtue of his coding ability. There he would study symbolic systems, a field at the intersection of philosophy, psychology, linguistics, and computer science. He talks of having a lifelong yearning to change things, which led him after his undergrad to begin work as a therapist, though he’d soon pursue a PhD in social change at Vanderbilt. There he would discover dissatisfaction with academic life, which he found was too abstracted from the actual solving of problems. Around this time he learned that Ideo, the design thinking consultancy, was looking to fill out its human factors team and was seeking people with a mixture of social science and design skills, people who had developed the ability to study social groups but had enough of a design background to be a part of the design process. “My crazy mixed background of software design and sociology and ethnography was perfect for them,” he says. He’d be there from summer 2006 until fall 2010, leading an internal team that designed and deployed an intranet system that, interestingly enough, would anticipate products such as Yammer, and then he started to consult with other companies on designing their own intranet systems. But that was still not direct enough of an experience. As a consultant, he says, it’s the difference between hitting balls at a driving range and playing a proper round of golf: you may get to tee off, but you don’t get to make the final putt.

With that yearning for direct doing still simmering inside of him, he had a life-changing realization with Scott Cannon, who was then a team leader at Apple. During a Skype conversation, Underwood recalled the following:

The thing that got us to leave our jobs was the realization that people use email as a terrible to-do list. Everyone has stuff they need to do trapped in their inboxes, they feel overwhelmed, balls get dropped; it’s a big mess. [There’s] a lot of opportunity to make it a better experience. We said, “What if we built a to-do list with the communication baked right into it? Can we skip that email step and help people to send tasks more directly?” Then people can free themselves of their inboxes.

After that insight, Underwood and Cannon would cofound Orchestra in January 2011. Their arriving at that insight evidences the process of ideation we’ve discussed throughout this book: unexamined connections lie latent between fields, and when we find those connections between things—such as the psychological experience of using email on a mobile device and the mismatch that most mobile software has for that use—extreme amounts of value can be uncovered, though not always immediately.

Orchestra, Underwood says, was formed with a founding promise: “to make tools that people actually want to use as opposed to tools that people are forced to use.” And so they soon launched Orchestra To-Do, a gorgeous app that allowed you to send and receive tasks from your contacts. It was a service that Underwood and the team hoped would help people manage their tasks more directly and more socially, freeing people from their inboxes.

The app was launched in September 2011 and earned immediate accolades, as the productivity blog Lifehacker named it the best to-do app for the iPhone and Apple named it the productivity app of the year. But then it all fizzled out.

Underwood realized why when he was walking down the street in Palo Alto: his wife was supremely excited about the prospect of winning an auction on eBay, and she, who clearly had a vested interest in the success of Orchestra, emailed him the listing rather than sending it via her husband’s app.

“Even our hardest-core users still had tons of tasks trapped in their inbox,” Underwood said. “We hand-waved over a fundamental problem to our solution—unless the whole world made this switch, best case, you’re going to be managing two in-boxes now. You weren’t really going to be solving the problem.”

In other words, Underwood and his team had found the right idea and identified the right problem: people were using email as a terrible to-do list. On an abstract level, they had discovered a suitable solution: a productivity app with sharing built directly into the experience. But they had also made a mistake that sprang from a blind spot. When they looked back at how they built the original Orchestra app, they suffered from a lack of context: that is, the way that their product would have to fit into users’ lives if the app was going to have ongoing engagement. It’s sort of like having an amazing pair of bright orange shoes (which, full disclosure, at least one of your authors has): they can be colorfully wonderful, but if they don’t blend into your life, if they don’t integrate into your preexisting behavioral patterns, they won’t become part of your life. But after the fruitful failure of To-Do, Underwood and the Orchestra team set out to get to the heart of the task-email problem. To refine their answer, they would have to reframe their question.

“What would happen if we turned it on its head?” Underwood recalls asking. “What if instead of building a to-do list with the communication-like capabilities of email, what if we just transformed the inbox in which those tasks were already living into something with significantly better organization—a delightful experience. Could we build an inbox that gave people a different relationship with their mail?”

It was a question that felt insane at the time: to essentially have all of your email be dumped into something like Orchestra To-Do, and you could then manage those embedded tasks with aplomb. But then another realization emerged.

“This seemed like an insane idea, building a to-do list that sucked in every email,” he said, “and then we realized what we were really talking about was a rethinking of the email client itself.” Then their initial solution would be turned on its head. “Instead of building a to-do list that worked like email,” Underwood says, “we needed to transform your inbox, where all those tasks that are trapped in email live.”

The result of that transformation opened up to the public in February 2013: Mailbox, a gesture-oriented email client built to fit the way people already dealt with email on their phones, as triage. In the same way an emergency room physician takes the most pressing cases first, when we open up our phones to check our mail, we’re usually looking to see if there are any fires to be put out: what needs to be acted on now, what can be stored for later, what can be delegated. After studying this use case, Underwood and his team realized that the vocabulary of potential actions for mobile email was incomplete. If you wanted to act immediately on something, you could reply; if you needed to delegate a task, you could forward the message; if you could simply get rid of the unwanted message, you could delete or archive it. However, a piece had been left incomplete: the situation in which you encounter a message that you don’t want to deal with right now but know you’ll have to tackle when you get back to your desk or later that night or the next morning or the next week—what you would call deferment, an organizational practice systematized (in an analog fashion) by David Allen and the Getting Things Done school of task management. In Getting Things Done, the solution was to make separate buckets (often physical) for tasks to be taken care of in those respective blocks of time. But managing all that analog organization is anxiety-provoking for people who have not built those organizational discipline skill sets, including at least one of your authors. Therefore, as a good designer does, Underwood saw the opportunity to smooth out a rough edge: swipe your finger across a message to the left and you’re prompted with eight forms of “snoozing” the message as you would an alarm clock so that you can address it in a few hours, in the evening, the next morning, or over the weekend—removing the need to build that organizational skill set. In this way, the app becomes like a personal assistant, an extension of yourself that you trust implicitly.

“We began to ask ourselves,” Underwood said, “how could we create a service that is reliable like the alarm clock is reliable, that didn’t overpromise and didn’t get cute, but instead simply began to establish a relationship with the user where more and more of those things that might have been living in their own head as unfinished loops are handed off, and in being handed off, could be forgotten about until the time that it was appropriate for it to be dealt with came, and then they could be handled. That’s the heart of this system, setting up that relationship.”

If you’ve interacted with the app, you know that it is a beautiful experience, a “euphoric inbox” as Underwood would say. The app is very simple, but as the trend tends to be, these obvious-after-you-meet-them solutions spring from uncommon discernment. Underwood’s journey as a human led him to become an entrepreneur, and his journey as an entrepreneur fulfilled, at least from our vantage point, part of his journey as a human: to fulfill his lifelong need to directly fix problems. Although Mailbox isn’t the solution to email, it makes beautiful what was once ugly, makes resonant what was once repulsive. But that came only after a long train of personal experiences on Underwood’s part—we didn’t even touch on the time he spent doing field research as an ethnographer—that formed a multifaceted understanding of the way people work, which then informed the creation of Mailbox.

At its core, Mailbox represents a deep insight; we’re tempted to call it “app as poetry.” As you would imagine, an app coming from someone with a deep involvement in human factors is deeply empathic: as our discussion has suggested, the greatest insights occur at intrapersonal and interpersonal levels. It’s a matter of thinking with high degrees of contextual awareness. By joining an understanding of both the ecosystem surrounding email and the system of email itself with a deep comprehension of the way people interact with those systems when they’re on their phones, Underwood and the Mailbox team were able to fulfill the founding promise of Orchestra: to create a tool that people wanted to use rather than had to use.

There’s a happy ending, too: a month after Mailbox’s launch, Orchestra was acquired by Dropbox for an estimated $100 million.³ Such is the power of executing and then reexecuting an idea sprung from seeing how everything connects.

As Mailbox suggests, much of process and planning consists of the strange and serendipitous occurrences that happen as an idea finds its form in the world. We can have a penetrating understanding of how people handle one of their primary modes of communication, but with the intense unknowability of a volatile world such as ours, we’re going to miss out on some aspect of the value that we’re trying to create. Strangely enough, a great proportion of planning—especially if we’re opting for long-term growth over short-term profits—requires a deep appreciation for how much we don’t know (and how much we don’t know we don’t know). It’s like Adam Pisoni, the Yammer CTO, likes to say with a laugh: we can safely assume that everything we think is right today will be wrong tomorrow.

CONCERNING ASSETS

When we’re mapping out our decisions, we need to think of the what involved that will get us to the value we’re trying to create. These are, in their many forms, our assets, the organs that form the body of an organization.

Implicit within any decision is the question, What do we need to get this done? Put in businessese, the question is, What core competencies do we need in order to execute?

Blueprinting, then, is a sort of diagnostic of assumptions. We’re trying to measure the inputs we need to get the outcomes we want. And the more granular we can be with that description, the more easily we can see our inaccuracies and learn to spot them.

The greatest asset will always be people. Corporate culture might call us human capital or talent or human resources, but we can just go with people or, if you’re feeling fancy, persons. No product or service is made without a range of people. And the user, consumer, or customer on the other end is a person too. Therefore, when we consider any decision, we need to make sure we have the right people involved to make a plan reach its fruition—which will always be, in some way, connecting with people. This is why, as we noted before, a leader must be a curator of talent: we want to hire the right people who fit our culture and create spaces for them to find the right solutions to create value for all the humans involved. When we’re blueprinting a major decision, we should think of the group of people involved that will make it as amazing as possible, possibly using the cluster approach we proposed earlier in the book.

The next asset is insight. It’s become a truism that entrepreneurs solve problems, but to solve a problem, you need to be able to spot it; before you can supply a useful answer, you need to supply the right question. The dustbin of history is filled with organizations that were answering the wrong questions—“Customers want a physical storage medium for movies, right?”—so much of the work in any project involves asking the right question, which is a subtle sort of knowledge. This is why we want to continually amass understanding: finding the questions the world needs answered is an emergent process, and so we need to be always exposing ourselves to the opportunity to recognize our gaps in knowledge, as we discussed at length in Chapter 8. The right insight can be powerful. The realization that people used email as a terrible to-do list motivated Gentry Underwood to start his own company, though that insight didn’t find its fulfillment until the company moved on from Orchestra To-Do to Mailbox. After all those long hours, Orchestra became an overnight success.

Then there’s capital. It takes money to make money, they say. Although it is not something to be worshipped, capital allows us to move with alacrity, provide security to the people on our teams, and build the infrastructure we need to grow rapidly. As we have seen, organizing our lives and our organizations around capital undermines the long-term potential of both; however, when used elegantly, capital can help us absorb difficulties, take risks, and press forward. We can apply the psychologist Stephen Porges’s point from Chapter 1: if you’re going to be bold, you need security. Capital is a source of security, so if we use it wisely, we can be thoughtfully bold. But be wary: outside capital will come in exchange for one’s autonomy, a phenomenon one of your authors knows quite well. But if you don’t have enough capital for a long enough time, you don’t have an organization.

An organization’s plumbing and central heating is its infrastructure: the system of roots by which decisions are made and distributed among its people. This can take the form of software—any range of enterprise systems can be included—or simply the way decisions bubble up from data collected along the front lines or are mandated from leadership way above. It takes a lot of mindfulness to see how the organizational system will affect execution. This is another incentive for having an experimental approach to organizational structure: if we try different clusters and other arrangements over time, we can begin to gain a sense of which form suits which project.

Last is the ecosystem. Just as any sort of value creation is contingent on the people who are involved in its creation, any value is contingent on its context: if the world isn’t ready for your genius idea, your genius idea isn’t going to catch on. Perhaps it’s a matter of consumer taste: the Segway, hyped as a world changer, has found its home among well-poised police officers and awkwardly balanced tourists. Or it could be a matter of broader infrastructure: one of the reasons the electric car (initially) had such a tough time catching on was the dearth of power stations. That is precisely why Tesla’s determined instillation of charging stations, though still in its infancy, is as great an innovation as its Model S and potentially more world-changing: Tesla is forming the substrate of the electric car’s ecosystem.

THE BORDERS OF THE BLUEPRINT

When people say that “timing is everything,” they really mean that the circumstances that allow a plan to reach fruition are out of our control or unseen. When those unseen causes aid your action, you’re deemed a success. But this doesn’t always happen, as da Vinci’s life evidences: though he made many major works during his lifetime—this we know from the few that survive—he left many of his works incomplete. We cannot know why he never finished his Battle of Anghiari, a landscape of war whose studies were so powerful that every young Italian artist worth his paint came to see it. Bramly, the biographer, contends that da Vinci made some mistake that his painting technique would not allow him to correct as he went along, though we cannot say for certain.

The greatest example of how da Vinci’s work fell apart (or, more accurately, melted) was the Cavallo, the gigantic equestrian statue that Ludovico Sforza, the duke of Milan, commissioned him to create. It was to be the largest equestrian statue in the world and a testament to the duke’s father, Francesco. Da Vinci put immense effort into the project, starting, stopping, and returning, and according to the records, its model was shown in honor of the betrothal of Bianca Maria Sforza in November 1493—at over seven meters tall. He spent nearly two years researching how to cast the bronze monument. Da Vinci was at his creative height, right in line to make one of the finest statues the world has ever seen, and then something nonlinear happened: Charles VIII, the king of France and commander of Europe’s largest army, decided to invade Italy. As Bramly notes, the French had high-end artillery technology, prompting Italian technological advancement, which would require materials such as the bronze for a horse, the metal for which would become unavailable in late 1494.⁴

Could da Vinci have completed the horse if he had blueprinted his process? All we can assert is a firm maybe. Although Milan was prosperous at the time, peace was a fleeting thing in Europe, and the French were always on the other side of the Alps. If he’d considered that volatility a bit more—a theme we’ve discussed at length—perhaps he would have completed the project with greater urgency. As Steve Jobs loved to say, real artists ship. Blueprinting, then, is a way of ensuring that the shipping happens.

We need not be angst-ridden Renaissance masters to incorporate such lessons into our personal and organizational lives: whenever making a major decision, we need only to sketch out the assets we need in order to execute. At a personal level, we’d do well to note our emotional state, too, since anger primes people to make aggressive decisions and fear prompts timid ones. Still, there is the question of what we don’t know and how to deal with that ignorance: how could we possibly prepare for the French on the other side of the Alps?

We’ve spent a lot of time sketching out possible practices to aid our ignorance. One of them is meditation, since it makes us more familiar with the movement of our minds; another is the bond of partnership, since close friends and colleagues can see things about us and the world that we would never see alone. Another is to allow ourselves to have a continuous dialogue with our present and future selves. Yet another is what we offer to you here: the diagramming of a decision we call blueprinting. By noting our assets and our assumptions, we may grow more intimate, more nuanced, and more rigorous in our approach to making decisions.