"Apple is a small company, we don't have as many resources as Microsoft."
I've had people who work at Apple tell me this, with utter sincerity; often people who have worked at Apple for a long time, especially under Steve Jobs. A small company perched on top of a Matterhorn of cash, I usually reply. But Apple really does see itself as a small company that might die at any minute.
In terms of engineering numbers, Apple is restricted by the amount of office space in Cupertino; even though the new spaceship campus is up and running, Apple hasn't actually closed any of its other offices in the area because it needs them. Not having remote workers and putting almost everything in Cupertino (except for the things like the silicon design done in Austin) does limit how many engineers Apple can physically find room for. If you're all in one town, you must be a small company; after all, you could go see (almost) anyone in the company in just a few minutes, depending on traffic.
But what's really behind the internal self-image is the near-death experience when it was only a $150 million investment from Microsoft that kept the lights on; Apple was weeks away from going bankrupt. If it could get that bad once, says a little voice in the back of long-term employees' heads, it could happen again.
Keep asking why a product doesn't have a feature that it really should do, and you might hear a familiar phrase from Jobs: shipping is a feature. Getting a product out even before it's really finished, because you don't have enough engineers to get all the features done and you can add them in version two and version three, is better than not getting it out on time. There's a touch of the old Microsoft approach in there; the third release is usually the one that has everything the first version should have.
Add in the fact that Apple still sees itself as the scrappy underdog going in a different direction -- focusing on privacy rather than aggregating everyone's information to do better machine learning, say -- and the 'small company' internal narrative is hard to escape from, no matter how much money Apple makes.
Facebook employees honestly believe they're helping society by connecting it. Much of Facebook's story for the last two years comes from the naivety of its founder about the utterly predictable consequences of connecting people with a wide range of viewpoints, from those very new to technology with little experience in assessing the truth of what they are told to people stalking their exes. As long as Facebook views 'being connected' as an unalloyed good, the company is going to struggle with the fact that this is about people and psychology rather than about technology.
The corresponding myth that many Google employees tell themselves is that they're a startup without much impact and if they introduce a new product, change a feature or turn off a service, it won't affect many people. Understanding the scale of the power and responsibility that seems so clear from the outside can be especially hard for Googlers who have been around since the company was a startup and didn't have an out-sized impact on the industry.
As Ember.js creator Yehuda Katz pointed out, when they make a change to a product that has some downsides, Googlers tend to see the ways it helps people first rather than any other consequences. The confusion over whether you're logged in to Gmail or Chrome (which syncs information in ways some users don't like) is because Chrome shows your Gmail login in the browser rather than just on the site. That was done to make it clearer which account is signed in, but it also normalises being signed in to Chrome as well to Google sites.
The other core Google belief is that Google can do more with your information than you can, in ways that will benefit you, so it's the natural home for that information and you should be happy to hand it over because of how much you get out of it, because it's not as if you'll do anything with it yourself. The notion that you don't want anything done with your information is very alien to that way of thinking, because why would you waste what can help you and many others?
When Google leaks data externally, it's taken very seriously at the company; like a serious industrial accident as Yonatan Zunger (who worked on everything from search to user privacy at Google) puts it. But that goes hand-in-hand with the belief that the best and most useful place for your data is inside Google.
Don't be cool
For a long time, the crippling delusion at Microsoft wasn't a delusion at all; it was the impact of the consent decree that followed the epic antitrust case settled in 2001. Even after the decree expired, the habits it inculcated limited how Microsoft saw the world. Say "middleware" (how the court case characterised Internet Explorer) to a veteran Microsoft employee and you'll see a visible shudder -- or at least the hairs on the back of their neck will stand on end. Not doing anything that could put Microsoft back in court became a key part of company culture.
Say it to someone who has only been at Microsoft a few years though and they'll have no idea what you're talking about -- and there are a lot of those newer people, especially working on open source and cloud. Satya Nadella has focused a lot of his efforts on nudging Microsoft employees into a new, healthier attitude towards the company and each other, implementing the One Microsoft idea that Steve Ballmer knew was necessary (and also knew wouldn't be accepted if he was the one pushing it). The system of annual reviews, rewards and incentives gave many Microsofties the viewpoint that, "I'm not paid to fix problems in another division". That internal antagonism is gone; one of Microsoft's key technologies is the Microsoft Graph that connects so many products that divisions can't not work with each other.
Growth mind-set is a cheesy phrase for 'don't assume you know everything' and the work to build a healthier culture at Microsoft has flushed out a lot of those memories from the collective consciousness. But one long-running delusion remains, although Nadella is clearly taking aim at it. 'Don't come to Microsoft to be cool, come to Microsoft to make other people cool by empowering them' is a fantastic message, mixing the humility of knowing you don't know everything with the importance of accessibility and focusing on what people need to get done.
Over and over again, the problem is that Microsoft has started off chasing cool and then given up when what it delivers is useful rather than cool. Kinect was cool, until it wasn't. Windows Phone needed to be seen as cool, because for all the talk of it being a 'dual use' device for home and work, it was pitched as a consumer device people would want at work rather than a work device they'd be happy to take home. Consumer products have to be cool because they're about fashion as much as function.
HoloLens might or might not be cool; it ought to be, since it delivered pretty much everything Magic Leap has finally shipped, only three years earlier -- but it's very much an industrial product because that's where the market for expensive AR headsets is.
Skype wanted to be cool. Skype wanted to keep up with the cool apps likes Instagram and Snap and WhatsApp, even if that meant dropping features Skype users relied on (from being able to make your own custom groups of people to being able to paste conference PIN codes into the dialpad once you're in the conference call).
It's OK not to be cool. It's OK to be reliable. It's OK to be second place in some things. Recently Microsoft has been making a series of pragmatic decisions, from dropping the 'cool' Skype redesign, to Team Foundation Services giving longer support to the 1.1 service pack release because that's what most enterprises wait to adopt, to Windows Defender ATP supporting Windows 7 and 8.1, to extending enterprise support to three years for Windows 10 releases, to supporting Google IDs in the Azure B2C service, to running Logic Apps on premises, and shipping a custom Linux kernel in the secure IoT Azure Sphere devices.
Windows PowerShell development is on the back burner, because PowerShell is cross platform and cross-platform PowerShell is where new features are going. Pick a Microsoft product and you can find a pragmatic decision.
Those pragmatic decisions are a mix of going where the customers are developers and doing the right thing for existing customers. Pragmatic isn't cool; pragmatic is solid and reliable.
The more Microsoft can concentrate on pragmatic over cool the better: but the entire technology industry still values being cool, so the delusion that Microsoft needs to be cool may last for a while longer.
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