Feb 16

Surface Pro and iPad Pro – incomparable

0.12 of a pound less in weight. 0.6 inches more in display area.

That’s all that separates the iPad Pro from the Surface Pro (lightest model of each). Add in the fact that both feature the modifier “Pro” in their name, and that they look kind of similar, and it’s hard to not invite comparisons, right? (Of course, what tablets in 2016 don’t look like tablets?)

Over the past few weeks, several reports have suggested that perhaps Apple’s Tablet Grande and Microsoft’s collection of tablet and tablet-like devices may have affected at holiday quarter sales of tablet-like devices from the other. Given what I’ve said above, I’ve surely even suggested that I might cross-shop one with the other when shopping. But man, that would be a mistake.

I’m not going to throw any more numbers at you to try and explain why the iPad Pro and Surface devices aren’t competitors, and shouldn’t be cross-shopped. Okay, only a few more; but it’ll be a minute. Before I do, let’s take a step back and consider the two product lines we’re dealing with.

The iPad Pro is physically Apple’s largest iOS device, by far. But that’s just it. It runs iOS, not OS X. It does not include a keyboard of any kind. It does not include a stylus of any kind. It can’t be used with an external pointing device, or almost any other traditional PC peripheral. (There are a handful of exceptions.)

The Surface Pro 4 is Microsoft’s most recent tablet. It is considered by many pundits to be a “detachable” tablet, which it is – if you buy the keyboard, which is not included. (As an aside, inventing a category called detachables when the brunt of devices in the category feature removable, but completely optional keyboards seems slightly sketchy to me.) Unlike the iPad Pro, the Surface Pro 4 does include the stylus for the device. You can also connect almost any traditional PC peripheral to a Surface Pro 4 (or Surface 3, or Surface Book.)

Again, at this point, you might say, “See, look how much they have in common. 1) A tablet. 2) A standardized keyboard peripheral. 3) A Stylus.”

Sure. That’s a few similarities, but certainly not enough to say they’re the same thing. A 120 volt light fixture for use in your home and a handheld flashlight also both offer a standard way to have a light source powered by electrical energy. But you wouldn’t jumble the two together as one category, as they aren’t interchangeable at all. You use them to perform completely different tasks.

The iPad Pro can’t run any legacy applications at all. None for Windows (of course), and none for OS X. There is it’s Achilles heel; it’s great at running iOS apps that have been tuned for it. But if the application you want to run isn’t there, or lacks features found in the Windows or OS X desktop variant you’d normally use (glares at you, Microsoft Word), you’re up the creek. (Here’s where someone will helpfully point out VDI, which is a bogus solution to running legacy business-critical applications that you need with any regularity.)

The Surface Pro offers a contrast at this point. It can run universal Windows platform (UWP) applications, AKA Windows Store apps, AKA Modern apps, AKA Metro apps. (Visualize my hand getting slapped here by platform fans for belaboring the name shifts.) And while the Surface Pro may have an even more constrained selection of platform-optimized UWP apps to choose from, if the one you want isn’t available in the Windows Store, you’ve got over two decades worth of Win32 applications that you can turn to.

Anybody who tells you that either the iPad Pro or the Surface Pro are “no compromise” devices is either lying to you, or they just don’t know that they’re lying to you. They’re both great devices for what they try to be. But both come with compromises.

Several people have also said that the iPad Pro is a “companion device”. But it depends upon the use case as to whether that is true or not. If you’re a hard-core Windows power user, then yes, the iPad Pro must be a companion device. If you regularly need features only offered by Outlook, Excel, Access, or similar Win32 apps of old, then the iPad Pro is not the device for you. But if every app you need is either available in the App Store, you can live within the confines of the limited versions of Microsoft Office for Office 365 on the iPad Pro, or your productivity tools are all Web accessible, then the iPad Pro might not only be a good device for you, but it might actually be the only device you need. It all comes down to your own requirements. Some PC using readers at this point will helpfully chime in that the user I’ve identified above doesn’t exist. Not true – they’re just not that user.

If a friend or family member came to me and said, “I’m trying to decide which one to buy – an iPad Pro or Surface Pro.”, I’d step them through several questions:

  1. What do you want to do with it?
  2. How much will you type on it? Will you use it on your lap?
  3. How much will you draw on it? Is this the main thing you see yourself using it for
  4. How important is running older applications to you?
  5. How important is battery life?
  6. Do you ever want to use it with a second monitor?
  7. Do you have old peripherals that you simply can’t live without? (And what are they?)
  8. Have you bought or ripped a lot of audio or video content in formats that Apple won’t let you easily use anymore? (And how important is that to you?)

These questions will each have a wide variety of answers – in particular question 1. (Question 2 is a trap, as the need to use the device as a true laptop will lead most away from either the iPad Pro or the Surface Pro.) But these questions can easily steer the conversation, and their decision, the right direction.

I mentioned that I would throw a few more numbers at you:

  • US$1,028.99 and
  • US$1,067.00

These are the base prices for a Surface Pro 4 (Core m3) and iPad Pro, respectively, equipped with a stylus and keyboard. Just a few cups of Starbucks apart from each other. The Surface Pro 4 can go wildly north of this price, depending upon CPU options (iPad Pro offers none) or storage options (iPad Pro only offers one). The iPad Pro also offers cellular connectivity for an additional charge in the premium storage model (not available in the Surface Pro). My point is, at this base price, they’re close to each other, but that is a matter of convenience. It invites comparisons, but deciding upon these devices based purely on price is a fool’s errand.

The more you want the Surface Pro 4 (or a Surface Book) to act like a workstation PC, the more you will pay. But there is the rub; it can be a workstation too – the iPad Pro can’t ever be. Conversely, the iPad Pro can be a great tablet, where it offers few compromises as a tablet – you could read on it, it has a phenomenal stylus experience for artists, and it’s a great, big, blank canvas for whatever you want to run on it (if you can run it). But it will never run legacy software.

The iPad Pro may be your ideal device if:

  1. You want a tablet that puts power optimization ahead of everything else
  2. Every application you need is available in the App Store
  3. The are available in an iPad Pro optimized form
  4. The available version of the app has all of the features you need
  5. All of your media content is in Apple formats or available through applications blessed by Apple.

The Surface Pro may be your ideal device if:

  1. You want a tablet that is a traditional Windows PC first and foremost
  2. Enough of the applications you want to run on it as a tablet are available in the Windows Store
  3. They support features like Snap and resizing when the app is running on the desktop
  4. You need to run more full-featured, older, or more power hungry applications, or applications that cannot live within the sandboxed confines of an “app store” platform
  5. You have media content (or apps) that are in formats or categories that Apple will not bless, but will run on Windows.

From the introduction of both devices last year, many people have been comparing and contrasting these two “Pro” devices. I think that doing so is a disservice. In general, a consumer who cross-shops the two devices and buys the wrong one will wind up sorely disappointed. It’s much better to figure out what you really want to do with the device, and buy the right option that will meet your personal requirements.

Aug 15

Continuum vs. Continuity – Seven letters is all they have in common

It’s become apparent that there’s some confusion between Microsoft’s Continuum feature in Windows 10, and Apple’s Continuity feature in OS X. I’ve even heard technical people get them confused.

But to be honest, the letters comprising “Continu” are basically all they have in common. In addition to different (but confusingly similar) names, the two features are platform exclusive to their respective platform, and perform completely different tasks that are interesting to consider in light of how each company makes money.

Apple’s Continuity functionality, which arrived first, on OS X Yosemite late in 2014, allows you to hand off tasks between multiple Apple devices. Start a FaceTime call on your iPhone, finish it on your Mac. Start a Pages document on your Mac, finish it on your iPad. If they’re on the same Wi-Fi network, it “just works”. The Handoff feature that switches between the two devices works by showing an icon for the respective app you were using, that lets you begin using the app on the other device. Switching from iOS to OS X is easy. Going the other way is a pain in the butt, IMHO, largely because of how iOS presents the app icon on the iOS login screen.

Microsoft’s Continuum functionality, which arrived in one form with Windows 10 in July, and will arrive in a different (yet similar) form with Windows 10 Mobile later this year, lets the OS adapt to the use case of the device you’re on. On Windows 10 PC editions, you can switch Tablet Mode off and on, or if the hardware provides it, it can switch automatically if you allow it. Windows 10 in Tablet Mode is strikingly similar to, but different from, Windows 8.1. Tablet mode delivers a full screen Start screen, and full-screen applications by default. Turning tablet mode off results in a Start menu and windowed applications, much like Windows 7.

When Windows 10 Mobile arrives later this year, the included incarnation of Continuum will allow phones that support the feature to connect to external displays in a couple of ways. The user will see an experience that will look like Windows 10 with Tablet mode off, and windowed universal apps. While it won’t run legacy Windows applications, this means a Windows 10 Mobile device could act as a desktop PC for a user that can live within the constraints of the Universal application ecosystem.

Both of these pieces of functionality (I’m somewhat hesitant to call either of them “features”, but I digress) provide strategic value for Apple, and Microsoft, respectively. But the value that they provide is different, as I mentioned earlier.

Continuity is sold as a “convenience” feature. But it’s really a great vehicle for hardware lock-in and upsell. It only works with iOS and OS X devices, so it requires that you use Apple hardware and iCloud. In short: Continuity is intended to help sell you more Apple hardware. Shocker, I know.

Continuum, on the other hand, is designed to be more of a “flexibility” feature. It adds value to the device you’re on, even if that is the only Windows device you own. Yes, it’s designed to be a feature that could help sell PCs and phones too – but the value is delivered independently, on each device you own.

With Windows 8.x, your desktop PC had to have the tablet-based features of the OS, even if they worked against your workflow. Your tablet couldn’t adapt well if you plugged it into an external display and tried to use it as a desktop. Your phone was… well… a phone. Continuum is intended to help users make the most of any individual Windows device, however they use it. Want a phone or tablet to be a desktop and act like it? Sure. Want a desktop to deliver a desktop-like experience and a tablet to deliver a tablet-like experience? No problem. Like Continuity, Continuum is platform-specific, and features like Continuum for Windows 10 Mobile will require all-new hardware. I expect that this Fall’s hardware season will likely continue to bring many new convertibles that automatically switch, helping to make the most of the feature, and could help sell new hardware.

Software vendors made Continuity-like functionality before Apple did it, and that’ll surely continue. We’ll see more and more device to device bridging in Android and Windows. However, Apple has an advantage here, with their premium consumer, and owning their entire hardware and software stack.

People have asked me for years if I see Apple making features that look like Continuum. I don’t. At least not trying to make OS X into iOS. We may see Apple try and bridge the tablet and small laptop market here in a few weeks with an iOS device that can act like a laptop, but arguably that customer wouldn’t be a MacBook (Air) customer anyway. It’ll be interesting to see how the iPad evolves/collides into the low-end laptop market.

Hopefully if you were confused about these two features, that helps clarify what they are – and that they’re actually completely different things, designed to accomplish completely different things.

Dec 14

Mobile devices or cloud as a solution to the enterprise security pandemic? Half right.

This is a response to Steven Sinofsky’s blog post, “Why Sony’s Breach Matters”. While I agree with parts of his thesis – the parts about layers of complexity leaving us where we are, and secured, legacy-free mobile OS’s helping alleviate this on the client side, I’m not sure I agree with his points about the cloud being a path forward – at least in any near term, or to the degree of precision he alludes to.

The bad news is that the Sony breach is not unique. Not by a long shot. It’s not the limit. It’s really the beginning. It’s the shot across the bow for companies that will let them see one example of just how bad this can get. Of course, they should’ve been paying attention to Target, Home Depot, Michaels, and more by this point already.

Instead, the Sony breach is emblematic of the security breaking point that has become increasingly visible over the last 2 years. It would be the limit if the industry turned a corner tomorrow and treated security like their first objective. But it won’t. I believe what I’ve said before – the poor security practices demonstrated by Sony aren’t unique. They’re typical  of how too many organizations treat security. Instead of trying to secure systems, they grease the skids just well enough to meet their compliance bar, turning an eye to security that’s just “too hard”.


While the FBI has been making the Sony attack sound rather unique, the only unique aspect of this one, IMHO, is the scale of success it appears to have achieved. This same attack could be replayed pretty easily. A dab of social engineering… a selection of well-chosen exploits (they’re not that hard to get), and Windows’ own management infrastructure appears to have been used to distribute it.


I don’t necessarily see cloud computing yet as the holy grail that you do. Mobile? Perhaps.


The personal examples you discussed were all interesting examples, but indeed were indicative of more of a duct-tape approach, similar to what we had to do with some things in Windows XP during the security push that led up to XPSP2 after XPSP1 failed to fill the holes in the hull of the ship. A lot of really key efforts, like run as non-admin just couldn’t have been done in a short timeframe to work with XP – had to be pushed to Vista (where they honestly still hurt users) or Windows 7 where the effort could be taken to really make them work for users from the ground up. But again, much of this was building foundations around the Win32 legacy, which was getting a bit sickly in a world with ubiquitous networking and everyone running as admin.


I completely agree as well that we’re long past adding speed bumps. It is immediately apparent, based upon almost every breach I can recall over the past year, that management complexity as a security vector played a significant part in the breach.

If you can’t manage it, you can’t secure it. No matter how many compliance regs the government or your industry throws at you. It’s quite the Gordian knot. Fun stuff.



I think we also completely agree about how the surface area exposed by today’s systems is to blame for where we are today as well. See my recent Twitter posts. As I mentioned, “systems inherently grow to become so complex nobody understands them.” – whether you’re talking about programmers, PMs, sysadmins, or compliance auditors.



I’m inclined to agree with your point about social and the vulnerabilities of layer 8, and yet we also do live in a world where most adults know not to stick a fork into an AC outlet. (Children are another matter.)

Technology needs to be more resilient to user-error or malignant exploitation, until we can actually solve the dancing pigs problem where it begins. Mobile solves part of that problem.


When Microsoft was building UAC during Longhorn -> Vista, Mark Russinovich and I were both frustrated that Microsoft wasn’t really doing anything with Vista to really nail security down, and so we built a whitelisting app at Winternals to do this for Windows moving forward. (Unfortunately, Protection Manager was crushed for parts after our acquisition, and AppLocker was/is too cumbersome to accomplish this for Win32. Outside of the longshot of ditching the Intel processor architecture completely, whitelisting is the only thing that can save Win32 from the security mayhem it is experiencing at the moment.


I do agree that moving to hosted IaaS really does nothing for an organization, except perhaps drive them to reduce costs in a way that on-premises hosting can’t.

But I guess if there was one statement in particular that I would call out in your blog as something I heartily disagree with, it’s this part:


“Everyone has moved up the stack and as a result the surface area dramatically reduced and complexity removed. It is also a reality that the cloud companies are going to be security first in terms of everything they do and in their ability to hire and maintain the most sophisticated cyber security groups. With these companies, security is an existential quality of the whole company and that is felt by every single person in the entire company.”


This is a wonderful goal, and it’ll be great for startups that have no legacy codebase (and don’t bring in hundreds of open-source or shared libraries that none of their dev team understands down to the bottom of the stack). But most existing companies can’t do what they should, and cut back the overgrowth in their systems.

I believe pretty firmly that what I’ve seen in the industry over the last decade since I left Microsoft is also, unfortunately, the norm – that management – as demonstrated by Sony’s leadership in that interview, will all too often let costs win over security.


For organizations that can redesign for a PaaS world, the promise offered by Azure was indeed what you’ve suggested – that designing new services and new applications for a Web-first world can lead to much more well-designed, refined, manageable, and securable applications and systems overall. But the problem is that that model only works well for new applications – not applications that stack refinement over legacy goo that nobody understands. So really, clean room apps only.

The slow uptake of Azure’s PaaS offerings unfortunately demonstrates that this is the exception, and an ideal, not necessarily anything that we can expect to see become the norm in the near future.


Also, while Web developers may not be integrating random bits of executable code into their applications, the amount of code reuse across the Web threatens to do the same, although the security perimeter is winnowed down to the browser and PII shared within it. Web developers can and do grab shared .js libraries off the Web in a heartbeat.

Do they understand the perimeter of these files? Absolutely not. No way.

Are the risks here as big as those posed by an unsecured Win32 perimeter? Absolutely not – but I wouldn’t trivialize them either.

There are no more OS hooks, but I’m terrified about how JS is evolving to mimic many of the worst behaviors that Win32 picked up over the years. The surface has changed, as you said – but the risks – loss of personal information, loss of data, phishing, DDOS, are so strikingly similar, especially as we move to a “thicker”, more app-centric Web.


Overall, I think we are in for some changes, and I agree with what I believe you’ve said both in your blog and on Twitter, that modern mobile OS’s with a perimeter designed in them are the only safe path forward. The path towards a secure Web application perimeter seems less clear, far less immediate, and perhaps less explicit than your post seemed to allude to.


There is much that organizations can learn from the Sony breach.


But will they?


Nov 14

Is Office for mobile devices free?

As soon as I saw today’s news, I thought that there would be confusion about what “Office for tablets and smartphones going free” would mean. There certainly has been.

Office for iOS and Android smartphones and tablets is indeed free, within certain bounds. I’m going to attempt to succinctly delinate the cases under which it is, and is not, free.

Office is free for you to use on your smartphone or tablet if, and only if:

  1. You are not using it for commercial purposes
  2. You are not performing “advanced editing“.

If you want to use the advanced editing features of Office for your smartphone or tablet as defined in the link above, you need one of the following:

  • An Office 365 Personal or Home subscription
  • A commercial Office 365 subscription which includes Office 365 ProPlus (the desktop suite.)*

If you’re using Office on your smartphone or tablet for any commercial purpose, you need the following:

  • A commercial Office 365 subscription which includes Office 365 ProPlus (the desktop suite.)*

For consumers, this change is great, and convenient. You’ll be able to use Office for basic edits on almost any mobile device for free. For commercial organizations, I’m concerned about how they can prevent this becoming a large license compliance issue when employees bring their own iPads in to work.

For your reference, here are the license agreements for Excel for iOSPowerPoint for iOS, and Word for iOS.

*I wanted to add a footnote here to clarify one vagary. The new “Business” Office 365 plans don’t technically include Office 365 ProPlus – they are more akin to “Office 365 Standard”, but appears to have no overarching branding. Regardless, if you have Office 365 Business or Office 365 Business Premium, which include the desktop suite, you also have rights to the Office mobile applications.

Learn more about how to properly license Office for smartphones and tablets at a Directions on Microsoft Licensing Boot Camp. Next event is Seattle, on Dec. 8-9, 2014. We’ll cover the latest info on Office 365, Windows Per User licensing, and much more.

Sep 14

On the death of files and folders

As I write this, I’m on a plane at 30,000+ feet, headed to Chicago. Seatmates include a couple from Toronto headed home from a cruise to Alaska. The husband and I talk technology a bit, and he mentions that his wife particularly enjoys sending letters as they travel. He and I both smile as we consider the novelty in 2014 of taking a piece of paper, writing thoughts to friends and family, and putting it in an envelope to travel around the world to be warmly received by the recipient.

Both Windows and Mac computers today are centered around the classic files and folders nomenclature we’ve all worked with for decades. From the beginning of the computer, mankind has struggled to insert metaphors from the physical world into our digital environments. The desktop, the briefcase, files that look like paper, folders that look like hanging file folders. Even today as the use of removable media decreases, we hang on to the floppy diskette icon, a symbol that means nothing to pre-teens of today, to command an application to “write” data to physical storage.


It’s time to stop using metaphors from the physical world – or at least to stop sending “files” to collaborators in order to have them receive work we deign to share with them.

Writing this post involves me eating a bit of crow – but only a bit. Prior to me leaving Microsoft in 2004, I had a rather… heated… conversation with a member of the WinFS team about a topic that is remarkably close to this. WinFS was an attempt to take files as we knew them and treat them as “objects”. In short, WinFS would take the legacy .ppt files as you knew them, and deserialize (decompose) them into a giant central data store within Windows based upon SQL Server, allowing you to search, organize, and move them in an easier manner. But a fundamental question I could never get answered by that team (the core of my heated conversation) was how that data would be shared with people external to your computer. WinFS would always have to serialize the data back out into a .ppt file (or some other “container”) in order to be sent to someone else. The WinFS team sought to convert everything on your system into a URL, as well – so you would have navigated the local file system almost as if your local machine was a Web server rather than using the local file and folder hierarchy that we had all become used to since the earliest versions of Windows or the Mac.

So as I look back on WinFS, some of the ideas were right, but in classic Microsoft form, at best it may have been a bit of premature innovation, and at worst it may have been nerd porn relatively disconnected from actual user scenarios and use cases.

From the dawn of the iPhone, power users have complained that iOS lacked something as simple as a file explorer/file picker. This wasn’t an error on Apple’s part; a significant percentage of Apple’s ease of use (largely aped by Android and Windows (at least with WinRT and Windows Phone applications) is by abstracting away the legacy file and folder bird’s nest of Windows, the Mac, etc.

As we enter the fall cavalcade of consumer devices ahead of the holiday, one truth appears plainly clear; that standalone “cloud storage” as we know it is largely headed for the economic off-ramp. The three main platform players have now put cloud storage in as a platform pillar, not an opportunity to be filled by partners. Apple (iCloud Drive), Google (Google Drive), and Microsoft (OneDrive and OneDrive for Business – their consumer and business offerings, respectively), have all been placed firmly in as a part of their respective platform. Lock-in now isn’t just a part of the device or the OS, it’s about where your files live, as that can help create a platform network effect (AT&T Friends and Family, but in the cloud). I know for me, my entire family is iOS based. I can send a link from iCloud drive files to any member of my family and know they can see the photo I took or the words I wrote.

But that’s just it. Regardless of how my file is stored in Apple’s, Google’s, or Microsoft’s hosted storage, I share it through a link. Every “document” envelope as we knew it in the past is now a URL, with applications on each device capable of opening their file content.

Moreover, today’s worker generally wants their work:

  1. Saved automatically
  2. Backed up to the cloud automatically (within reason, and protected accordingly)
  3. Versioned and revertible
  4. Accessible anywhere
  5. Coauthoring capable (work with one or more colleagues concurrently without needing to save and exchange a “file”)
  6. As these sorts of features become ubiquitous across productivity tools, the line between a “file” and a “URL” becomes increasingly blurred, and the more, well, the more our computers start acting just like the WinFS team wanted them to over a decade ago.

    If you look at the typical user’s desktop, it’s a dumping ground of documents. It’s a mess. So are their favorites/bookmarks, music, videos, and any other “file type” they have.

    On the Mac, iTunes (music metadata), iPhoto (face/EXIF, and date info), and now the finder itself (properties and now tags) are a complete mess of metadata. A colleague in the Longhorn Client Product Management Group was responsible for owning the photo experience for WinFS. Even then I think I crushed his spirit by pointing out what a pain in the ass it was going to be to enter in all of the metadata for photos as users returned for trips, in order to make the photos be anything more than a digital shoebox that sits under the bed.

    I’m going to tell all the nerds in the world a secret. Ready? Users don’t screw around entering metadata. So anything you build that is metadata-centric that doesn’t populate the metadata for the user is… largely unused.

    I mention this because, as we move towards vendor-centered repositories of our documents, it becomes an opportunity for vendors to do much of what WinFS wanted to do, and help users catalog and organize their data; but it has to be done almost automatically for them. I’m somewhat excited about Microsoft’s Delve (nee Oslo) primarily because if it is done right (and if/when Google offers a similar feature), users will be able to discover content across the enterprise that can help them with their job. Written word will in so many ways become a properly archived, searchable, and collaboration-ready tool for businesses (and users themselves, ideally).

    Part of the direction I think we need to see is tools that become better about organizing and cataloging our information as we create it, and keeping track of the lineage of written word and digital information. Create a file using a given template? That should be easily visible. Take a trip with family members? Photos should be easily stitched together into a searchable family album.

    Power users, of course, want to feel a sense of control over the files and folders on their computing devices (some of them even enjoy filling in metadata fields). These are the same users who complained loudly that iOS didn’t have a Finder or traditional file picker, and who persuaded Microsoft to add a file explorer of sorts to Windows Phone, as Windows 8 and Microsoft’s OneDrive and OneDrive for Business services began blurring out the legacy Windows File Explorer. There’s a good likelihood that next year’s release of Windows 9 could see the legacy Win32 desktop disappear on touch-centric Windows devices (much like Windows Phone 8.x, where Win32 still technically exists, but is kept out of view. I firmly expect this move will (to say it gently) irk Windows power users. These are the same type of users who freaked out when Apple removed the save functionality from Pages/Numbers/Keynote. Yet that approach is now commonplace for the productivity suites of all of the “big 3” productivity players (Microsoft, Google, and Apple), where real-time coauthoring requires an abstraction of the traditional “Save” verb we all became used to since the 1980’s. For Windows to succeed as a novice-approachable touch environment as iOS is, it means jettisoning a visible Win32 and the File Explorer. With this, OneDrive and the simplified file pickers in Windows become the centerpiece of how users will interact with local files.

    I’m not saying that files and folders will disappear tomorrow, or that they’ll really ever disappear entirely at all. But increasingly, especially in collaboration-based use cases, the file and folder metaphors will largely move to the wayside, replaced by Web-based experiences and the use of URLs with dedicated platform-specific local, mobile or online apps interacting with them.

Dec 13

Siri, Topsy, and the Web – Context is everything

Last night, my youngest child and I were talking, and I wound up telling her about the scene from 2001: A Space Odyssey where the HAL 9000 computer, as he is being disassembled, sings the old song Daisy to Dave Bowman. My child loves music, and didn’t see the irony in immediately asking me, “How does the song go?” So I taught her – she hadn’t ever heard it before. At the time I didn’t get the irony in doing that either – not until I woke up this morning.

Think about that line right before Dave tells HAL to sing him the song:

“My instructor was Mr. Langley, and he taught me to sing a song. If you’d like to hear it I can sing it for you.”

Topsy is Siri’s Mr. Langley.

A little over two years ago I wrote about how Siri was the start of Apple escaping the Web, and escaping Google search. In that piece, I discussed how important context was for Siri. Over the last few years, Siri has been improved as Apple has connected it to (often very contextually specific) sources, such as sports and movie information, and demonstrated them at WWDC.

However, Siri had, and continues to have, rather large holes in her knowledge set. What we think of as very simple questions, Siri cannot answer. The child of mine I mentioned earlier is fascinated with technology, and Siri in particular. Periodically, she will come up with random obscure queries and throw them at Siri. While the Siri system often can’t answer them, sometimes it can.

Twitter is amazing because it can provide insight into the zeitgeist (the Web’s short-term memory), but it also has such knowledge of long-term events along a timeline as they happened. In many ways, Twitter is a bit of a knowledge mechanical turk, where Twitter users mine the Web and real-time events and surface their knowledge in discrete snippets of information. Topsy was uniquely situated to surface Twitter’s knowledge in an API-driven way, and is ideally situated for Apple to integrate into Siri (since Siri doesn’t really learn anything, it just connects into other systems.

Many people have said Topsy was acquired to enhance advertising or iTunes content. Both are tangentially right. But ads have never appeared to be a primary focus for Apple – which makes sense, because the customer they build their hardware, software, and services for usually isn’t a fan of ads. That said, the analytics from Topsy Pro could well wind up integrated into iAds. We’ll see in time. As for content discovery? Sure, that’ll happen too, and people will buy content as a result of their searches. But I don’t believe that this is what this acquisition was about.

People expect Siri to be able to answer their queries, and if it can’t, they disengage from the service, and potentially from Apple’s platform, if they don’t find that it just works the way they expect. That’s why I believe Topsy has everything to do with Siri, and that’s where the team will end up, and how we’ll see the technology demonstrated at WWDC next summer.

A few pundits have also made the association to Siri, but most analysis I’ve seen seems to focus on real-time search, not mentioning the (relative) long-term knowledge that Topsy surfaces from Twitter, and how that can only grow over time. Just as importantly, as I understood it Topsy had created an algorithm that enabled tweets to be sorted geographically. This is invaluable to Apple, as it then gives Siri location-based context, and will let the system help users find resources near you that others are discussing in near real-time through the Twitter firehose. I think the acquisition of Topsy by Apple is good news for Apple and their customers, as well as Twitter itself and Twitter users. I think it’s really bad news for Google.

Oct 13

How to kill your business

I’ve been tidying up my media subscriptions of late. Although I’ve subscribed to many paper and online publications over the years, I’ve found that there are only a few which give me an adequate mix of content to the price they’re willing to charge and the time I have available to give to consuming them.

I know it costs a lot to create a publication, but it’s astonishing to see how much some media companies value their product – more than their consumers, and charge accordingly.

Within the past year and a half, I’ve had two experiences with publications which, like Hollywood, try economic games in order to try and keep customers they already have, instead of just offering competitive prices to begin with for new subscribers, or offering existing subscribers a logical extension of the initial rate they paid.

Like I said – I understand that it costs money to make a publication. I also understand that often, costs increase annually, or at least on a semi-regular basis.

In almost any business, finance usually likes to see revenue go up while expenses go down. But there are only two real ways to do that. Say I have 200 customers I sell my widget to, and I rely upon annual sales of that widget at $10/each in order to keep my business going. I either

  1. Find additional customers to buy my widgets (good idea).
  2. Charge my existing customers more for the replacement widgets when they come back (bad idea – causes churn).

There’s this warped psychology that says you can shaft an existing customer and they’ll just gleefully take it. They will – for a bit. But in today’s economic climate, when you take a publication that costs less than US$30/yr for a first year weekly subscription, and you offer a “discounted” renewal for more than US$150, all I can say is, “You’re high.”

That’s not even close to sustainable. Either you’re not charging customers enough in year one and your little loss-leader for that year is actually a stupid idea, or you’re charging too much for years after that. Usually this is trying to pass along costs due to dwindling subscriptions to those who have stayed behind and renewed – which is not viable. I’ve seen far too many friends on Facebook complain about a handful of well-known US newspapers that have been jacking up their prices at rates that are so ridiculous they don’t risk churn, but instead guarantee churn.

I’ll give you a hint – you can only pass the pain of your financially stressed business model to customers for so long before they will cease being customers – and trust me, they will. There are far too many sources of information today – consumers are simply overloaded. Where you may have once thought your news was special and exclusive, you’re largely incorporating newswire feeds that consumers are seeing over Twitter, Facebook, and countless news channels that cost less than you or are free. You either add unique value, or figure out how to make your subscribers happy at a non-extortionistic renewal rate.

Which brings me to my second point. A long time ago, I used to read the NY Times quite often. Then came the paywall. Then I became a “tenner”. I’d read the ten allotted articles per month, and unless I bumped into an article syndicated through Twitter, I wouldn’t read it again until next month.

On a sidenote, I fear for local newspapers that have been inspired by the NYTimes’ ability to keep the paywall up (unlike Slate, where we tried a paywall, but it failed rather brutally). Local newspapers – especially those not in major cities – that are putting up paywalls in order to access the small amount of unique content they have (and the large amount of syndicated content people can find elsewhere) are really taking a risk. I don’t see that being sustainable and will hurt in the long run.

As for the NYTimes, I do value the unique content they provide. But their subscription rate and the amount of value I get out of it given the time I have/other sources of news I have are simply incompatible. Recently, I did decide to subscribe to the NYTimes because I earnestly wound up finding several articles I wanted to read but couldn’t because my monthly 10 were burned. So I did. The NYTimes of course does the same thing I talked about earlier… US$.99 for the first month, and then every model of subscription is US$15 per month or more after that. While I found I did use the site more for a few days, I just found that I wasn’t using it enough to justify US$180/yr – the value just isn’t there for me. I’m sure it is for some people, but wasn’t in my case.

But this is where it gets fun. Or not. Did you know that, in order to cancel a NYTimes subscription in 2013, you have to call an 800 number? Yes. That’s right. No email cancellation. No Web form. A phone call. And you know why, of course… because the hard sell is really hard to do through electronic media. While the site says, IIRC, you can “quickly and easily” cancel your subscription, the result of a phone call wasn’t quite that. I had to stay on hold for a few minutes, and then got the usual result.

The call went like this:

  • I calmly told the operator something to the effect of “I don’t have the time to get the value out of the content that it will cost me when my trial is up, and want to close my account.”
  • She proceeded to tell me about features of the site that can help you ensure you’re seeing the most appropriate content to you.
  • I restated my request, verbatim.
  • She volleyed back with more site hints.
  • I restated my request, verbatim, again.
  • She paused, changed angles, and proceeded to offer me a discounted renewal (for a year, IIRC).
  • I repeated it yet again…
  • She paused again, and volleyed back with an even more steeply discounted renewal.
  • I said it again, for the fifth time.
  • She gave me the warning that my account would close on such and such a date, and then finally closed it.

And in the end, this was just like the magazine (although the magazine wasn’t so obnoxious about me not renewing, and just lets the subscription lapse). Initial loss-leader trial, followed by a massive ramp-up on renewal (where hopefully the subscriber has stopped paying attention to the line-item on their credit card). But if you complain enough or threaten to quit, they drop the price. Offer the reduced price to at-risk subscribers, and shaft your loyal ones. Brilliant.

Charge people a fair rate out of the gate, and keep that rate. If you have to raise the costs passed along to your subscribers, fine – do it – but understand that you can’t do it significantly, or you will get churn. If you keep doing it, you won’t have churn, you will have priced yourself out of existence, and your business will not be long for this earth. Frankly, I feel the same about the tendency for free or nearly free in-app purchase (IAP) apps on iOS like games where there are bull***t line items available for purchase for insane costs like US$99 for “200,000 coins” or some virtual bunk like that. In time, I think people will realize how idiotic it is to pay that much for a game or an app on their phone, and that model will flop as well. I hope.

As I wrote this, I had to contemplate how much magazine publishers wanted Apple to pass along subscriber details to them, and how much Apple resisted. In the end, the subscriber got to select whether or not their personal information was actually visible to the publisher. Also, as far as I am aware, there is also only one price available for subscriptions – it doesn’t matter whether you’re a first year or fifth year subscriber, magazines can’t use the loss-leader model to get you in, and in the end, you can easily cancel your subscription through iTunes. No phone call, no hard sell. I love that.

This post talked primarily about media publications – but I’m seeing the same thing happen with many software vendors. Regular price increases passed along to largely loyal customers, in order to keep revenue numbers going the right way – which is also not sustainable in the long run. Loyalty and lock-in will only take you so far.

I’ve said it before, I’ll say it again. You need to focus on delighting your customers first. Don’t nickel and dime them, or they won’t come back – they’re your lifeblood – and often your best opportunity to find new customers, through word of mouth.

Sep 13

No, that new application you’re hearing about won’t replace Microsoft Office.

For two weeks straight, I’ve seen prognostications that <application> from <competitor> will replace Microsoft Office.

No. Nothing will ever replace Microsoft Office – at least for the time being for a huge chunk of business users. I know, I know… strong words – but let me explain.

While a single user who needs to simply compose their thoughts for personal use, or sometimes share them with one or two other users might be able to do so with a third-party Office document editor. Whether they save or export as an Office document, or insist that the recipients simply read it in a proprietary format (including OpenDocument), as soon as you have multiple users exchanging documents, embedding additional Office documents, using reviewing/track changes, or other complex Office features, these documents begin to fray and fall apart at the seams.

I typically see three use cases for Microsoft Office in a multiuser office setting:

  1. Simple Office document exchange between two or more users.
  2. Complex Office document exchange (use of “deep features” in Office).
  3. Custom Office document workflow between two or more users.

Even I have said in the press that the lack of Microsoft Office on the iPad has created an opportunity. However, that opportunity isn’t explicitly an opportunity for competitors. More often than not, it’s created an opportunity for the user in the sense that they haven’t had Office for the entire time they’ve had an iPad, so either they’ve simply “gone without” Office, or found alternative tools (most likely either a Web-based productivity suite or a productivity suite for their device that doesn’t include feature parity with Office for Windows or the Mac).

The users who have likely had the most “success” (using the term loosely) with replacing Office are likely the individual users I mentioned early on who are simply using Office documents as containers, not using any Office specific features to much depth, and can likely survive just using the document export features in Google Docs, iWork, or any other Web/mobile productivity suite not from Microsoft. Admittedly, Microsoft surely sees this scenario, and as such has made the Office Web Apps for consumers freely available and interconnected with SkyDrive.

For users who are simply throwing documents back and forth, but not relying either on deep features in Office document formats or the Office applications, there’s a possibility that they can switch to Google Docs, iWork, or another Office suite. But if an organization has been using Office for some time, odds are there are documents and document templates they rely upon that require actual Microsoft Office applications or even require applications that interoperate with Office, but have no direct competitor on non-Windows platforms or the Web (see Access, Visio, or InfoPath).

You’ll often hear “document fidelity” discussed when the topic of Microsoft Office comes up. This is an important thing to understand. If I give you a complex Word format document (doc or docx) to edit, and ask you to use track changes to send it back, I’m going to be a bit upset if you a) send it back to me with the changes inline because your alternative word processor doesn’t support track changes, b) mangle the document because some formatting I had wasn’t understood by your alternative word processor or c) send it back to me in a .garble document or some other document format that Word doesn’t understand. Microsoft Office documents – both the original formats and the new xml-based documents – are the lingua franca of office productivity. Third-party tools may be able to open them. What they do with them from that point on is anybody’s guess.

Surely at some point, you’ve found a Web page that was interesting to you but was in a foreign language. If you translated it using Bing or Google, you got a result that was close to, but not an exact match for, the actual translated text as a human would have performed. More importantly, if you translate the result back to the source language, the result isn’t the same as the source text was to begin with. This is the same thing that happens with Microsoft Office documents (or WordPerfect documents among some professional fields – even today). If you want to tick people off or annoy them to the point of generating passive-aggressive behavior from them, screw up the formatting or the document type of an Office document that you’re supposed to look at and hand back to them.

For many organizations today, Office isn’t something they can just swap out – they depend on features and formatting capabilities buried in the Office applications – features that sometimes it even seems like Microsoft forgets are there (like Word outlining). When you must send Office documents back and forth between users and have the formatting and document type remain consistent, there are few choices other than… Office. I’ve tried numerous third party Web and mobile Office suites, and not really found one that doesn’t break documents here or there (often in undetectable ways), or only support <feature x> if you convert it into some other proprietary format.

The final scenario for Office users is that third case. In this case, you’re talking actual server-side code (SharePoint or other) or custom Office code that reads the Office document and could actually break if a document is incorrectly formatted or submitted as the wrong document type. Much like a user who is expecting a well-formatted document to be returned from review, applications centered around client or server-side consumption of Office documents don’t handle bad formatting or incorrect documents types well (though they respond logically, rather than emotionally as many users would).

I think Office, like Windows, is at an interesting inflection point. While some consumers and a smaller percentage of businesses may want to consider (and a small amount may actually be able to consider) not using Microsoft Office, their ability to do so will be directly in relation to how broadly they use Office documents today, and how deeply into the document format and type the features they depend upon are. In addition, many Web-apps are a no-op for truly mobile users as they need the ability to work completely offline – something that Office 365, being a streamed, but completely installed version of Office 2013, can do quite well. For most organizations, replacing Office with <application> is about as likely in the short term as replacing Windows with a Mac, an iPad, or a Chromebook. It’s possible, but you may be looking at ripping out deeply embedded line-of-business applications the organization has depended upon for years just to say you got rid of Office. You’re also usually then buying into someone else’s locked in hardware ecosystem or subscription-based software ecosystem.

I think there is opportunity for someone to do an Office suite better. But I don’t think most vendors so far are focused on that. Instead, most seem to be largely aping Office with locally installed or mobile apps, or aping Office with light-featured Web apps. Nobody is really pushing the boundaries, and making collaboration better – they’re largely reimagining what we’ve been working with for 20 years. So what eventually replaces Office? I’m not sure yet – but I don’t think it looks like envelopes of text sent from one user to another, or individual silos stored in a proprietary collaboration storage bin.

Jul 13

What’s the deal with OWA for iOS?

Earlier in July, Microsoft announced OWA for iPad and OWA for iPhone. Available only for Office 365 subscribers for now (available for Exchange 2013 at an undisclosed point in the future), OWA for iOS originally left me a bit confused.

You see, at a glance, there’s really nothing that OWA for iOS does that you can’t do with the built in mail app on iOS. The one benefit I arrived at upfront was that with Exchange’s autodiscover, configuration for novice users might be easier – it’s just a matter of entering in their username and password to configure it. It also seemed the app might be more comfortable for users who really enjoy the Windows Phone/Windows 8 design aesthetic (why those users would have an iOS device instead is a good question).

OWA for iOS is effectively the Outlook Web App (OWA) component of Exchange 2013/Exchange Online, wrapped in an iOS-native wrapper. Since OWA can run offline as of Exchange 2013, this is a neat sort of parlor trick that enables a unique Office app experience without requiring a massive amount of new code. The native wrapper then enables push notifications, voice-command (that I couldn’t get working very well), as well as a few other bells and whistles not available with OWA normally.

But then outside of this easier configuration and/or Modern-friendly experience, what’s the benefit to OWA for iOS? I didn’t get it initially. But last week I started wrapping up work on a SharePoint 2013/SharePoint Online evaluation guide for work, and something hit me.

What else can OWA (or Outlook 2013) do that the mail app on iOS can’t? It can run Apps for Office. Formerly called “Agaves”, Apps for Office are Web-based add-ins for many of the Office 2013 applications (including Outlook 2013 and Outlook Web App on Exchange 2013) that extend applications with additional functionality. Though the Apps for Office are not really widely embraced yet,  there are a handful of Apps for Office available today for use with Outlook. I have installed an App for Office in Outlook 2013 in my Office 365 account, and sure enough, it was available in OWA for iOS – though the design was hardly optimized correctly (surely the designer of the app didn’t have running on an iPhone in mind while designing it) it worked.

In the future, Microsoft’s own Dynamics applications – as well as other Web-based apps that need to hook into email content – could  be made available through OWA for iOS and integrate into the Exchange mail content there.

Many people criticized the fact that Microsoft made OWA for iOS first, rather than a Windows client. Frankly a lot of the same features are available if you pin your Exchange 2013/Exchange Online OWA page to the Start screen, although notifications aren’t available that way (perhaps in the future). More importantly, when Windows RT 8.1 ships this fall, Windows users have Outlook available across the board – largely negating the need for OWA for Windows RT.

Though I don’t think the Apps for Office were the main reason for OWA for iOS to be delivered, I do think they’re an interesting value-add that you can’t get with the iOS mail client.

Jul 13

Friction-free commerce? Hold on to your wallet.

I’ll admit it. I have a problem. It’s an iTunes problem. Apple doesn’t think I have a problem, they’re quite happy with me. My wife has the same problem, but it’s with Amazon, not Apple.

You see, online commerce has been pushing us all farther and farther down the road of “frictionless commerce”, where we can buy things without dealing with the pesky nuisance of actual cash. I’ve recently started contemplating how frictionless online commerce works, and I’ve begun referring to it also as “unconscious commerce”. It’s the same problem that has existed for years – and crushed many a consumer under its weight – with credit cards.

By not shopping with actual cash, we often cannot tangible assign psychological cost to the things we buy. For me, it’s a $1.99 app here, a $3.99 app there… a book, some music… eventually, it actually adds up to real money.

Amazon began removing friction from online commerce long ago with one-click buying. Throw in a Prime subscription, and it’s a Pavlovian experiment gone wild. Add something to your cart, quickly check out without entering any payment info, and salivate while you wait for your free delivery. I have many friends who have, use, and love Prime because it’s so convenient. I don’t – and don’t want my wife to, because I think it’s actually somewhat dangerous to our budget.

When it comes down to iTunes, the process is just as bad. One click rewarding.

I’ve mentioned before that I briefly sold cars after college. There’s something you have to understand about the car business. It’s built entirely to take advantage of the fact that car buying is an emotional process; that falling for a car will make you swoon and the typical tire-kicker will turn into a puddle of mush over a car when they fall for it. Think about the typical process… looking at cars, car Web sites and brochures, going for the test drive or two… it becomes an exercise in emotion, not an exercise in logic. There’s a reason why the icky part of car buying (Finance & Insurance, usually shortened to F&I) is saved to the end. The typical consumer is so head over heels that they’ll check boxes and sign things without reading them – much to their detriment when they come to several months later, and realize the financial obligation they just signed on to (See also: the mortgage crisis).

Too many of our commerce transactions are becoming frictionless. While frictionless online commerce sounds like a great thing, and it’s a great usability boon to consumers, it is innately geared to the benefit of the seller rather than the consumer. I’ve often debated with people why it is that Apple doesn’t have trials, and instead leaves developers to either:

  1. Build an app that is compelling enough, and a good enough value, that people just buy it.
  2. Build two versions of an app – a free version with some limitation, and a paid version that removes the limitation
  3. Build one app that behaves as the free version, with an In-App Purchase (IAP) to turn it into an unlimited paid version.

There are a couple of other options, but those are the main ones. In all of those cases, you’ve got some version of the app installed on your system. I’ve never talked to anyone at Apple, nor do I expect they’d ever discuss this on the record – but I believe that they don’t offer actual trials of paid apps because doing so could rattle the volume that comes in due to path 1 above, where consumers just say, “Screw it. The reviews look good, and it’s only $4. I’ll buy it.” Let consumers kick tires beforehand, and you’ve removed the emotion from the point of purchase. It’s actually funny to look back at how iTunes has moved from being a clone of a Website, with a basket and checkout, and now lets you one-click your heart out, bundling up multiple purchases in a receipt that is rolled up to you later. There’s a few really interesting results when you search the Web for how to turn off one-click purchasing in iTunes. Answer? You can’t. Either don’t have a credit/debit card stored, or be good about your purchases.

Back when online commerce sites were hard to browse, it was sketchy to trust purveyors, and items took time to receive, there were plenty of barriers that popped up along the way and may have tripped you on your way to checkout. Those barriers are rapidly disappearing, and it’s quite easy to get the shins kicked in your budget without ever noticing it. As frictionless commerce becomes the norm online, and it becomes more and more distant from the tangibility of our hard-earned paychecks, it is easy to get lost and spend more than you should. Think every time you check out. Add a little bit of mental friction to your emotional purchases.