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The Shape of a Technological Window

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    About two weeks ago I released an update to the Commoncog case library beta: a new series of cases around a concept called ‘Technological Windows’. This was the name of a thing first articulated by Steve Jobs in a 1992 talk at the MIT Sloan School of Business; I argued that Jobs took the idea very seriously and that he had built much of his career around it. What was interesting to me was that he seemed to have been remarkably deliberate about chasing the concept to its logical ends — many products and strategies that he undertook over the course of NeXT and his second coming at Apple were applications of the concept over the arc of his life.

    And for good reason. To hear Jobs tell it, ‘technological windows’ happens to be the shape of the game in consumer tech; you had to work out all the implications of that shape if you wanted to win.

    I released this new set of cases for two other, case library development-related reasons. The first one was that I wanted to see if reusing cases made sense: two of the cases (the General Magic and the iPhone Keyboard case) were older ones, originally written for the ‘Idea Maze’ concept, but published as instantiations of ‘Technological Windows’ because they fit into Jobs’s history. But the more important reason was to gather feedback from participants in the beta.

    And that feedback surprised me. To recap a little, the Commoncog case library was my attempt at applying a theory of expertise called Cognitive Flexibility Theory. CFT goes something like this: in ill-structured domains, concepts exist, but the way concepts show up are incredibly variable and highly context-dependent. Business, for instance, is an ill-structured domain — concepts like scale advantages and network effects are real things, but they look very different depending on the specific business, the specific industry, and the specific time period. In other words, if you want to get good at business you’re going to have to get used to the idea that whatever business problems you’ll face are going to be unique to your business, and application of business frameworks will be far messier — with far more variability — than you might have ever imagined.

    CFT explains how experts in ill-structured domains recognise and use concepts when the real world situations they encounter are constantly novel. It tells us that what differentiates experienced businesspeople from less experienced businesspeople is the same thing that differentiates experienced doctors from less experienced doctors: experienced practitioners are not surprised when a particular concept (or medical ailment) shows up in a weird-ass way; they are able to diagnose and respond to concepts in practice because they know that reality is messier and cases are unique in a way that cannot be fully captured in business books (or medical textbooks). In fact, if you’ve ever encountered a situation in business where you say to yourself “crap, the best practices don’t work here”, or “I had no idea a competitor could beat us in this particular way, huh!”, you’ve probably experienced this in action. (For a longer explanation of the theory, and how you might use it your career, read this.)

    The proposed learning approach in that first wave of CFT research was to give learners access a hypertext library of case studies. The intuition behind this idea was that if learners were exposed to a variety of concept instantiations from the get go, they’d be conditioned to recognise that concepts are complex and may show up in very weird ways in reality. In addition, the case library approach would give them enough cases to pattern match and analogise from (the formal term for this was that the case library should hopefully enable learners to develop adaptive expertise). CFT originally came out of research aimed at accelerating medical expertise; the first case library was for cardiovascular diseases.

    So I started wondering: could a case library presenting multiple concept instantiations across a network of cases accelerate business expertise?

    Long term readers would know what happened next: I built a case library of my own. I launched an private alpha test for Commoncog members, and then a publicly available beta test for Commoncog readers, and my answer today is well ... maybe. There continue to be problems. Here is one of them.

    About a month ago I discovered something interesting: about a third of participants found the messiness of the cases disorientating. Initially the feedback went something like “each case is well written, but I don’t know what to pay attention to; there are too many details!” I originally thought that it meant readers weren’t used to messy cases, since the vast majority of business case studies are written with a clear conclusion in mind (thus making them less useful in real life — reality is rarely as clear cut!)

    But about a week ago, after more conversations, I realised that the problem was something simpler: the ability to notice valid cues in a messy narrative is a sign of expertise. Participants who have had similar business experiences were able to process the novelty of each case and zoom in on useful cues. The messiness of the case was no problem for them. But with other participants, I realised that the detail overload was a sign of a bad learning experience for novices. In other words: in order to accelerate expertise, you first need to walk people through the concept instantiation so they are familiar with at least one example.

    So I’m going to do an experiment with this post. The current set of cases for Technological Windows may be found here. For the rest of this essay, I’ll tell you what I see in the cases, as a way of priming you to look out for the cues that I think are relevant to the concept instantiation at hand. Feel free to jump back and forth between the cases and this piece; if you’ve already read the cases, my hope is that this essay might cause you to reread your favourite ones in new light. In the future, a post very similar to this one may be inserted in the case library sequence, perhaps after the first or the second case, in order to orient learners on the concept instantiation. That way, they’ll get more out of the cases they read in the sequence.

    (Note that I don’t think my concept instantiation is the absolutely correct one — but it should make it easier for you to come up with your own lessons).

    At the end of this essay, I’ll propose a number of possible applications for the technological windows concept. Of course, I intend to add more cases to the technological windows sequence — as you’ll see in a bit, I’ll reference the stories of various consumer tech products that we haven’t published yet. But let’s get started.

    Exploiting a Technological Window is Extremely Difficult

    First: what is a technological window? I recommend you reading the concept page in full, but I’ll do a quick recap here. In his 1992 talk, Jobs described it as follows:

    I believe you can use the concept of technological windows opening, and eventually closing. And what I mean by that is, enough technology — usually from fairly diverse places — comes together and makes something that’s a quantum leap forward possible. And it doesn’t come out of nowhere. If you poke around the labs, and if you hang around the Media Lab in MIT and other places, you can get a feel for some of those things. And usually they’re not quite possible, but all of a sudden you start to sense things coming together and the planets lining up to where this is now possible, or barely possible. And a window opens up. And it usually takes around — in my experience anyway — around five years to create a commercial product that takes advantage of that technical window opening up.

    The argument that I’m making in the sequence of cases is that pretty much all of Jobs’s most successful products followed the same template that he’d outlined in 1992:

    • Consumer tech is driven by breakthrough products. These breakthrough products are possible when there is a ‘technological window’ — that is, when a number of nascent technical innovations come together to allow you to create a product that is a ‘quantum leap’ forward.
    • You can be too early to a technological window (in which case you pay a high price to push it open), or too late (in which case you lose out). Jobs implies that much of the skill of playing the consumer tech game is to time your technological windows correctly.
    • All breakthrough products that exploit a technological window will spend five-ish years to realise the full potential of the window (which I take to mean multiple product iterations with a high number of innovations), before experiencing five years of ‘exploitation’, where innovation slows and the company makes a ton of profits.
    • The right time to start planning the next breakthrough product is when you hit the exploitation period for the previous breakthrough product.

    But one of the more important things that leapt out at me in Jobs’s talk was the bit where he said “These things are hard. They don’t last because it’s convenient or even because it’s economic. They last because they’re really hard, this is hard stuff to do!”

    My original intention with the Macintosh case and iPhone keyboard cases was to demonstrate some of this difficulty. In the Mac case, Apple took the ideas it saw from Xerox PARC — the graphical user interface and the mouse — and undertook a laborious multi-year process to turn them into finished consumer products. In the iPhone keyboard case, we saw how the entire project hinged on developing a workable touchscreen keyboard, and how Ken Kocienda’s solution took months and a couple dozen prototypes before settling on an acceptable solution. Had Kocienda failed, Apple would’ve cancelled the entire phone product.

    More damningly, both the Macintosh project and the iPhone project culminated in scores of engineers burning out. In the case of the iPhone, engineer Andy Grignon was famous for saying “The iPhone is the reason I’m divorced”, with other engineers confirming his story; one anonymous interviewee told author Brian Merchant, in The One Device:  “Yeah, the iPhone ruined more than a few marriages.”

    Whether or not this horrible set of personnel outcomes could’ve been avoided is a different discussion (there is some evidence that it is possible, as Apple did, decades later, with the AirPods Pro) but the point I’m making here is that Jobs fully understood how hard it was to push open a technological window. He learnt this the hard way from the development of the Mac. (Alas, it seemed like he was never really bothered by the personnel costs.)

    There’s an interesting corollary to this. Notice how, in the stories of the Macintosh, the iPhone, and the iPod, all of the fundamental technological advancements had already been discovered before Apple started work on their devices.

    With the Macintosh, the fundamental breakthroughs related to the bitmapped graphical user interface and the mouse had already been worked out at Xerox PARC, which meant that the Mac team’s job was to turn the two breakthroughs into a mainstream, polished consumer product. This was no less daunting, to be clear, just difficult in a different way.

    With the iPod, the core technological window that had opened was the tiny Toshiba hard drive that Apple hardware chief Joe Rubinstein discovered on a trip to Japan in late 2000. To quote Brent Schlender’s Becoming Steve Jobs: “Ruby couldn’t believe his eyes. This was the first thing he’d seen that had enough capacity at a small enough size to form the heart of an Apple music player. Unlike the tapes or CDs that you played in Sony’s Walkman or Discman, this hard drive would have enough disk storage to hold copies of perhaps a thousand tracks, rather than just a dozen. And its ‘random access’ capabilities distanced it even more from the likes of a Discman, since it gave you the potential to find a particular song out of that enormous trove almost instantly. In January 2001, Ruby asked some former Newton engineers to begin work in earnest on some sort of portable audio device around the Toshiba micro-drive.” The issue was everything else, of course — designing and building a user interface that could deal with hundreds of songs; putting together software that could give the device sufficient smarts on the go, and making the music syncing process dead simple to use.

    Finally, with the iPhone, the fundamental technology behind multi-touch had already been developed, and there were sufficiently powerful (if barely so!) chips and battery components available on the market. The iPhone team’s job was to pull these disparate technologies together into a coherent, usable whole. On the face of it this seemed simple enough, but the iPhone was potentially as if not more difficult than the Macintosh project — Apple’s engineers needed to invent a new user interface paradigm from scratch. As we’ve already seen with the iPhone keyboard story, this was exceedingly difficult to do.

    I call this out as an important corollary because putting together a compelling consumer product that exploits a bunch of underlying technological breakthroughs is so damn hard, difficult to the degree of destroying marriages — that if the company in question were to attempt to also do fundamental research, my bet is that it’s not likely to work.

    The Initial Solution Stinks

    The second property that Jobs emphasises is the ‘five year realisation, five year exploitation’ property of technological windows. This seems broadly correct if you look at the arc of Jobs’s breakthrough products:

    • The initial Macintosh was not a big success. As we’ve covered in the Mac case study, it was the follow-up Macintosh 512k that cemented the Mac’s reputation as a successful product, and that led to Apple’s early dominance amongst designers and agencies.
    • The initial iPod had a mechanical click wheel, and was launched to rave reviews from the tech press. Unfortunately, it took a long time to become a certifiable cultural hit. In its first quarter, it sold only 150,000 units. Jobs slashed prices by $100 and introduced a new version with a touch-based click wheel a year later. Initially, the iPods only worked with Macs. Jobs reversed that decision two years later with the launch of iTunes for Windows. The company then launched the iPod Mini in 2004, and the flash storage based iPod Nano a year after that. In short, it took multiple product iterations before the iPod became a cultural phenomenon.
    • The first iPhone famously shipped without third party apps, and without copy and paste. Apple changed directions on both within a year — in the case of the apps, they announced a developer SDK within four months of the iPhone’s launch. Worse, the first iPhone shipped exclusively on a telecoms carrier, AT&T, that had terrible cell coverage. Jean-Louis Gassée, formerly of Apple, wrote at the time: “The iPhone was crippled when it first came out.” But he continues: “And then they released the iPhone 3G [the second version, which shipped in July 2008, and had better wireless and a faster microprocessor]. It was only then that the iPhone was truly finished, that it had all its basics, all its organs. It needed to grow, to muscle up, but it was complete as a child is complete.” (Source: Becoming Steve Jobs, Brent Schlender, Rick Tetzeli).

    The common attribute across the Mac, the iPod and the iPhone was that the form of the version one product was ‘correct’ — it had the bones of a compelling product, and turned out to be a solid foundation on which to iterate on. But I found it striking that all three products shipped with glaring flaws, and demanded its creators to change positions rapidly in response to market feedback:

    • The Macintosh’s early product market fit was surprising: it found a niche amongst designers and agency owners, and quickly developed a reputation as being ‘the computer for creative work’. Apple leaned into this early market, and eventually consolidated its hold with subsequent iterations of the Mac that took this key constituency into account.
    • Likewise, Apple took a few years to learn that iPod sales drove Mac sales. When Jobs learnt this, he shifted $75 million of the Mac’s ad spend to iPod ads instead. Jobs also took two years before he reversed course on an early decision: in 2003, Apple finally released iTunes for Windows, making the iPod available to PC users.
    • Finally, Jobs’s reluctance to allow third party app developers onto the iPhone is the stuff of tech history legend. It’s impossible to imagine Apple’s iPhone dominance today without the App Store, but both the iOS developer SDK and the App Store ecosystem took several product iterations to get right.

    You could say that Jobs’s ‘five year realisation’ comment captures this rapid course correction. But in all three cases, the products settled into familiar shapes by the end of their first decades. I was too young to live through the Mac’s evolution, but I distinctively remember the iPod’s innovations tapering off over the course of 10 years; today, we live in the twilight years of the iPhone’s maturity curve, 15 years after it was first introduced.

    Strategy and Org Structure

    Let’s say that you’re Steve Jobs, and let’s say that you took the ‘technological windows’ concept that you articulated in 1992 very seriously. What might some of the implications of this concept be on your work?

    Well, one implication is that you’d be honest with yourself: you’d recognise that the path to winning in the consumer technology space is to structure your business strategy around the exploitation of technology windows. We highlighted this with the ‘Jobs’s Second Act’ case:

    In the summer of 1998, I got an opportunity to talk with Jobs again. I said, “Steve, this turnaround at Apple has been impressive. But everything we know about the PC business says that Apple cannot really push beyond a small niche position. The network effects are just too strong to upset the Wintel standard. So what are you trying to do in the longer term? What is the strategy?”

    He did not attack my argument. He didn’t agree with it, either. He just smiled and said, “I am going to wait for the next big thing.”

    Another implication might be that you’d structure your company to be on the lookout of potential technological windows. From Becoming Steve Jobs, on the projects that led to the iPhone:

    Apple did not have a formal research and development unit per se. Steve didn’t like the idea of relegating all forward-looking tinkering to a separate area that somehow wasn’t beholden to the people leading his most important product development efforts. Instead, research projects flowered in pockets all around the company, many of them without Steve’s blessing or even awareness. They’d come to Steve’s attention only if one of his key managers decided that the project or technology showed real potential. In that case, Steve would check it out, and the information he’d glean would go into the learning machine that was his brain (emphasis added). Sometimes that’s where it would sit, and nothing would happen. Sometimes, on the other hand, he’d concoct a way to combine it with something else he’d seen, or perhaps to twist it in a way to benefit an entirely different project altogether (emphasis added). This was one of his great talents, the ability to synthesize separate developments and technologies into something previously unimaginable. It’s a talent that he would call on to decide what came next.

    Two projects had been launched with the intention of exploring the possibilities for creating a new kind of cellphone. Steve himself had asked the folks who developed Apple’s Airport Wi-Fi networking product line to do some early research on cellular phone technology. This decision made some on his team just shake their heads—Wi-Fi data-networking technology has very little to do with the cellular radio technology behind wireless phone networks. But there was another, much more immediate project in the works. Beginning in the fall of 2003, several members of Steve’s executive team, including Eddy Cue, the mastermind behind the iTunes Music Store, had been engrossed in finding a way to build iTunes-compatible music players and iTunes Music Store accessibility right into cellphone handsets.

    “Everybody carried two devices. A cellphone and an iPod,” Cue recalls, patting both front pockets of his jeans. “We knew you could add iTunes to a phone and it would be almost like an iPod. It was mostly a software problem. We looked around at the industry, and in early 2004 we settled on working with Motorola, which at the time completely dominated the handset business with its RAZR flip phone. Everybody had one.”

    (...) Ironically, two other projects that started out having nothing to do with cellphones would come to have the greatest impact on Steve’s decision about what Apple would pursue next. One of these was called Project Purple. It was a skunkworks effort Steve had ordered up to devise a new approach to what was proving to be an elusive “form factor” for personal computing: an ultralight, portable device that resembled a tablet or a clipboard, with an interactive touch screen. The concept had thwarted Microsoft’s best researchers and engineers for years, but Steve believed that his guys could make headway where others had failed. There simply had to be a more direct and intuitive way for users to interact with a computer than a keyboard and a mouse. Preferably it would be something he could use anywhere, even when sitting on the toilet.

    The other effort was something that developed far from Steve’s purview. In 2002, Apple researchers Greg Christie and Bas Ording started looking into a user-interface technology that had been stuck in the mud for years. Christie and Ording decided to reconsider the possibilities of a touch-screen monitor, which allowed people to use a fingertip to activate an icon or button displayed on a video screen.

    (...) Apple’s Greg Christie had been one of the key designers and software engineers of the ill-fated Newton. He had gotten over his romance with pen computing, but he had steadily followed all the multi-touch research efforts in academia and the tech industry. He hoped that partnering with Ording, who had joined Apple in 1998 and who had worked on the iPod’s scroll-wheel user interface as well as on OS X, might lead the way to make multi-touch the distinguishing technology for a serious new computer. They believed it might serve as the basis for a whole new kind of user interface.

    (...) Having five different projects sprout up around similar technological possibilities wasn’t unusual at Apple (emphasis added). Steve didn’t issue a “Let there be the iPad” command one day, and wake up the next to find the whole enterprise devoting itself to his single wish. Instead, the place was always bubbling with possibilities. His most important job was to sort through them and imagine how they could point the way to something entirely new.

    How Is This Useful?

    Given the shape of the concept that I’ve laid out, and assuming that you believe Jobs took this simple idea very seriously — I think one useful thing you could do is to take technological windows as a concept and turn your attention to more modern breakthroughs.

    So, for instance:

    1. Is the technological window for generative AI open?
    2. Is the technological window for Virtual Reality open? Can we say that Meta is making a good bet with its Oculus headsets and its metaverse software?
    3. Is the technological window for Augmented Reality open? Bear in mind that rumours about Apple’s AR headset have been rife for years now, possibly indicating that some team within the company is exploring a technological window.

    The nice thing about Jobs’s articulation is that you can now ground these questions in some more specific ones:

    • Is the shape of a compelling solution clear yet?
    • Has all the basic research been completed? Are all the necessary basic technological breakthroughs done? (Recall: even if it is completed, there’s still a shit ton of work to do to get to a compelling product).
    • If you believe the window is open, are we in the pre-exploitation phase, or the post-exploitation phase?

    And so on.

    I think there are obvious caveats to this concept. For instance, Jobs may have built his companies around the exploitation of technological windows, but despite his remarkable track record, even he didn’t have an unblemished history of product successes. We know from various Apple engineers — Ken Kocienda included — that Apple has killed many internal projects before launch; sometimes exploration of a technological window reveals that the window isn’t quite open yet. We also know that Apple has had several dud products on its books that it did launch. So the concept is useful, but not foolproof. In the end, the test of a compelling solution is within the market.

    Another obvious caveat is that the concept applies most cleanly to consumer electronics. This makes sense: Jobs built his career in personal computing and consumer tech; Apple was never very successful in other domains. We may talk about technological windows when we’re talking about Walkmans, MP3 players, ebook readers, smart phones, VR headsets, and personal computers. It’s unclear to me that the concept extends to consumer products that are purely software (Facebook, Instagram, TikTok), or even to hybrid consumer products that depend on some combination of software capability and real world coordination (Uber, AirBnB). Are fundamental technological breakthroughs as important to these product categories as it is with consumer tech? Is there really a five-ish year realisation/exploitation phase in these categories? I’m leaving this as an exercise to the alert reader.

    My point, though, is this: technological windows was the shape of the game of consumer tech as Jobs saw it. I think it remains an uncannily accurate accounting of just about every major consumer tech product we’ve had over the past 30 years — Apple product or no. As with all concepts in an ill-structured domain, I can think of several potential exceptions (the Kindle; the Walkman) that do not fit as neatly with Jobs’s articulation, that I intend to cover in future cases. But as it is, Jobs’s concept of technological windows seems useful if you want to evaluate (or exploit!) coming trends.

    I hope you’ll read the cases and come to your own conclusions. These are mine. Hopefully it’ll make it easier for you to come up with yours.

    Originally published , last updated .

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