What Giants Can’t See

The web platform has entered a period of relative stability — HTML5 and similar technologies are here to stay. Internet of Things, Virtual Reality, various blockchain-related techs may be “the future,” but it’s too soon to tell. Everyone is sure that something is coming down the pike. We just don’t know what.

Dare Obasanjo, a long-serving technology executive who leads the advertiser platform team for Bing ads at Microsoft, published a thoughtful article yesterday that discusses why it’s so hard for large tech organizations to change direction. He shared some amazing stories about working on Windows Live, a suite of web services that looked — almost comically — like Windows Desktop. He wrote:

The PC-centric thinking didn’t just manifest in our user interface design but also how we approached building & delivering software. While many tech companies at the time had started to practice what Steve Yegge describes as “good agile” in his epic essay Good Agile, Bad Agile in which teams ship software in a rapid & iterative manner without being primarily driven by fixed launch dates. Windows Live at the time shipped software in waves, every two years or so, to mimic the manner in which PC software like Windows & Office were at the time. In 2016, it’s obvious in hindsight that any app which updates once every 2 years isn’t going to be competitive when users can engage with apps and websites that are updating every week or two.

As Obasanjo notes, Google has a “Design Ethics & Product Philosopher” who pushes back against apps being too addictive. Meanwhile other similarly large organizations are just fine with that addiction. Contrast this with Apple: Apple has come out strongly in favor of letting customers control their own information — while growth at Google and Facebook is coming from relentless mining of petabytes of customer information — the opposite of Apple’s stance.

Apple’s ethics, Obasanjo argues, are going to hold them back.

I appreciate this kind of straightforward statement. Because it lets us ask a different kind of question than “is Apple ethical?” That is an important question—but one with countless answers. Instead we can ask: What would make Apple break from its stance in support of user privacy? What could force Apple to start mining the hell out of its user data? And if (or when) that happens, what does it look like? Are we ready?

Because right now Apple, for all its giant global-corporate issues, is somewhat chill. Imagine if it wasn’t. It would be like someone giving Microsoft in 1997 access to nuclear weapons. And there are tons of scenarios where Apple could decide it needs to treat your personal data the way that Google and Facebook treat it. Which is to say, not that well. Which is to say, rent a bunker.

There’s no simple razor that lets you inventory your own thinking — or that of your own organization — and go “here’s where I’m missing the boat.” What’s even worse is that people faced with change and new ways of doing things will tell you about important things like “software quality,” or “the integrity of the brand,” or “creating a unified ecosystem.” These are important things! Which is what makes this business so frustrating: The things that manage risk are the same things that are going to put you out of business. Our greatest strengths are invariably tremendous weaknesses, simply because we come to believe in them and count on them.