Three years ago, I wrote a to-do list for Microsoft to capture everything that I thought Microsoft should be doing to improve its stature in the tech world. Today, I'd like to review that list and grade Microsoft's progress to-date.

When I wrote that blog entry in 2013, I was cautiously optimistic that some of it would be realized. Not because I expected anyone at Microsoft to notice one person's wish-list, but rather because many of the suggestions were simply self-evident improvements.

I didn't anticipate the renaissance that has since taken hold at Microsoft. Starting slightly before the new CEO Satya Nadella took over, Microsoft's is now working much harder to make products that consumers want rather than simply tolerate. And Microsoft has become the tech titan most likely to willingly interoperate with others companies' products and services.

Thanks in large part to that renaissance, my assessment of the current state and the grades I've assigned below are higher than I would otherwise expect.

There are still some significant areas that require attention. And the ever-shifting technology landscape has created new problems that require new solutions. I plan to follow this blog entry up with a new to-do list for 2017 and beyond. But I'll save that for another day.

Now, onto the grading.

The headers below are from the original to-do list.

0. The overall objectives

Grade: B

In 2013, I said:

1. Users need to find Microsoft appealing,
2. Make Windows on the desktop more appealing for content consumption and creation.
3. Stop tolerating mediocrity from hardware partners.
4. Court developers in new ways.
5. Longer-term: Unify the user's computing experience across all devices via continuity of applications. (See PAO.)

Microsoft has made very meaningful progress on all of the shorter-term items (a through d), and made some interesting progress on e as well. Addressing each in turn:

1. Microsoft has worked to improve its image as a software company, as a services company, and as a hardware company. Windows 10 has been generally received positively; services such as Azure are popular, and Microsoft's hardware division is the surprise star thanks to the Surface line-up and HoloLens.
2. Windows 10 returns the desktop computing metaphors that users demanded. In many ways, it's a modern take on Windows 7. And the most recent October 2016 Windows event focused on creation—the next iteration of Windows 10 will even be named the Creators Update.
3. Surface, and the sharing of intellectual property from the Surface division, has improved the quality of hardware from partners. Dell has become a private company once again, which appears to be improving the quality of their work. Meanwhile, new hardware from Lenovo, Razer, and HP is higher quality than what we were seeing a few years ago.
4. Microsoft has been diving head-first into the open source community to court developers. Projects like Visual Studio Code have been successful at getting the Microsoft name back in front of mainstream developers. Similarly, the adoption of Bash into Windows 10 by way of Ubuntu has proven a very popular decision.
5. While PAO—personal application omnipresence—is still just a theoretical computing model, Microsoft has taken some interesting steps toward that goal. Most notably, Continuum on Windows 10 Mobile which puts desktop computing into phone-sized devices. Meanwhile, Universal Windows Platform is effectively a realization of the device-adaptive user interface that I described in the original PAO description. What's missing are device unification and harmony, "singularization" of applications across all devices, and the ability to construct personal private networks, ultimately to disintermediate the cloud.

1. Individuals make technology choices

Grade: A

Focus your server initiatives on being the best at corporate server interoperability across a spectrum of client devices.

Microsoft's new willingness to interoperate with iOS and Android devices basically addresses this. Especially with its cloud services and software products, Microsoft has become very tolerant of other platforms. In short order they have become the tech titan most likely to play well with others.

Convince individuals that Microsoft devices are a Tesla Model S and not a Prius.

The Surface line up, and most recently the Surface Studio, embody this philosophy. I've heard people say things like "I hope my company gets us Surface Books" and "I'm not even a graphic designer but I really need a Surface Studio."

1.1. Stop angering customers

Grade: C

Although Microsoft has worked hard to be seen more positively by consumers, most of that has been "accentuating the positives," so to speak. Microsoft hasn't really dealt with eliminating the negatives as much as they should.

Avoid arbitrary software limitations.

The analytics and data exfiltration capabilities of Windows 10 have earned it a very bad reputation as being spyware in the form of an Operating System. Most, if not all, of the snooping can be turned off in Windows 10 Enterprise Edition, presumably because enterprises won't tolerate that kind of data exfiltration. And we can't blame them.

But come on. Home users shouldn't have to tolerate snooping either. Disallowing the features to be totally disabled is an indication that Microsoft does not appreciate the value of not angering customers.

I am certain I will address this in my upcoming 2017 to-do list, but the obvious solution is to give all Windows users the ability to turn off every single remnant of analytics and snooping. Many Microsoft employees presumably know this is a major PR blunder; and they know how to fix it.

Allow users to make more decisions.

Windows 10 is fairly pleasant out of the box. Appearance wise, in its default state, it's about as appealing to look at as WIndows 7. Different, of course, but quite nice. That said, the degree of customization available in Windows 10 is perhaps the lowest of any Windows version yet. The addition of a (still work-in-progress) dark theme is very welcome, but users should be able to create themes with a diverse color palette.

2. Hardware and network steering

Grade: C

Play to your strength on the desktop.

Windows 10 did this. Desktop computing is still suffering and there are fairly obvious areas where stagnation and cruft need to be cleared. Nevertheless, while the situation could be better, it's definitely a passing grade.

2.1. Immersive desktop computing

Grade: B

Give desktop computing a reason for being in the modern era. Immersive, high-quality desktop computing...

The recent Surface Studio announcement shows how Microsoft is thinking about immersive desktop computing. It's caught the attention of many opinion-makers, and is an immediate object of lust for many a technophile, which just goes to show how much latent desire for compelling desktop computing exists.

Large form-factor high-density displays...

Microsoft has worked fairly hard on the user interface scaling in Windows 10, although there is still more to be done. And the Surface Studio shows the inherent beauty of a high-density display. Meanwhile, the broader market introduced a variety of high-density displays and some large form-factor displays. While I'd personally like to see large, high-density, concave OLED, I understand that's not going to arrive soon.

...don't lose sight of the keyboard and mouse. Continue to play to these strong suits of desktop computing.

Obviously no one at Microsoft has forgotten about keyboards and mice. But one specific failing in Windows 10 gives me pause: the unnecessary difficulty of navigating the login screen using just a keyboard. Be careful with such key user interfaces!

Voice control should be at least as capable as a modern cell phone.

Cortana is now in Microsoft's desktop operating system. That's mostly what I had in mind.

Every time a user consumes or creates on a mobile device while at home or the office, consider this a failure to correct. Ask yourself: why is my user feeling more appeal from a small screen device when they are near a desktop PC?

I believe there is some work-in-progress on this, in the form of better collaboration between portable devices and desktop computers. But a lot remains here.

2.2. High-bandwidth always-on connectivity

Grade: F

As far as I can tell, Microsoft has effectively no initiatives related to this subject. I won't quote the original to-do list, but I recommend re-reading it. I feel the most acute failure in this subject is on the following point:

Extend the idea of a HomeGroup to tunnel through public networks and encompass all personal devices in a peer-to-peer mesh. Every device a user owns should know of and directly interact with all others, with no intermediary third-party services.

HomeGroup, and more importantly the notion it represents—a private network to harmonize a family's devices—has been all but neglected for years. The most glaring oversight is the inability of Windows 10 Mobile devices to work with Windows computers on a local wi-fi network. It is absolutely astonishing that I must connect my phone via USB to copy music onto its SD card. It's as if the year is 2006, not 2016.

2.3. Embrace latent desires for control

Grade: F

Unfortunately, Microsoft has so-far embraced the simple approach of being yet another public cloud data silo. Rather than providing users with a holistic self-hosted option based on Microsoft software and hardware, Microsoft is steering all users to its services. Again, I won't quote the original, but I will reiterate the key warning:

Microsoft should be the only titan promoting a decentralized cloud. Don't allow a start-up to steal this thunder.

2.4. Encourage hardware innovation

Grade: A

Ideas are abundant; what Microsoft needs to do is invest in ideas with conviction.

Although I do not agree with every idea that Microsoft has pushed to market since I created my to-do list, I recognize that it has definitely acted with conviction.

2.5. Shore up Nokia

Grade: C

Since writing my to-do list, Microsoft both acquired Nokia (yay!) and then allowed it to stagnate to the point of laying off tons of staff (boo!). So I give this a C. It's still a passing grade because whatever pain and suffering came through the Nokia acquisition and layoffs, the net is that we now know Microsoft will make its own phones—it won't rely exclusively on unpredictable partners.

I'm looking forward to the Surface Phone, and will address that in my 2017 to-do list follow-up.

2.6. Pursue the ultra high-end

Grade: B

I feel Microsoft deserves a passing grade here because initiatives such as Surface Studio and HoloLens are clearly pursuing the high-end. There's no doubt there. But what I am not seeing is pursuit of the ultra high-end. Remember, the following examples?

1. Mainstream deep color.
2. Aim for lossless compression within the next 10 years.
3. Eradicate synchronization from multi-device life.

And these are just examples. I am sure Microsoft's engineers have a bunch of ideas of ultra high-end technology.

3.1. Get Surface 2 out as soon as possible

Grade: A

Well, that heading really dates the original to-do list, doesn't it? Since it was written, Microsoft has released three generations of Surface.

You should have known better on the naming.

Sure enough, new product names have been better. Surface 2 Pro, Surface 3, Surface 3 Pro, Surface 4 Pro, Surface Book, Surface Studio. Keep it up. I'm a little bothered by "Surface Book i7 with Performance Base." Ugh.

Microsoft should no longer tolerate low DPI in new devices. Low DPI is legacy.

I'm very happy that Microsoft seems to agree that low DPI is legacy.

4.1. Retain the desktop

Grade: B

I still feel Microsoft should have paid off the chumps who claimed ownership of the word "Metro." In the time between my to-do list and today, others eventually adopted a variation of the Metro design motif and called it something else. The graphic design industry even coined the term "flat design," which is a truly awful choice of words. Once again, Microsoft should have owned that claim to fame: We were the first with Metro design. But they couldn't even call it Metro because some of some trademark silliness. So hardly anyone even remembers that Microsoft Metro as such.

In my to-do list, I pointed out the need to unify the look and feel of desktop applications and used Windows Media Player as an example of an application that looked tragically outdated—back in 2013, mind you. The good news is that Groove replaced Media Player and it looks great. The bad news is that many other Windows applications and accessories still exist in their original form.

Allow users to pull Metro applications onto the desktop...

This was done in Windows 10. What are now called Universal Windows applications can indeed be resized on the desktop just like any other application.

4.2. Window management

Grade: C

Review the window managers available for Linux desktops. Plunder good ideas without remorse.

Windows 10 has virtual desktops built-in, so some plundering did in fact occur.

Easily and optionally snap windows to a grid and/or nearby window edges, both in positioning and sizing.

But there's still no easy to use a grid or snap-to-neighbor features.

Don't allow windows to steal focus. Ever. Build a notification system if you must.

There is now a notification system! But application windows can still steal focus. That absolutely must be prevented, especially with users increasingly alarmed about security. Some people consider preventing windows from stealing focus the single most important feature of a window manager.

4.3. Own the command prompt

Grade: B

Okay, on this one, I will concede that I was too harsh on PowerShell in my 2013 to-do list. But putting that aside, Windows 10 has seen a couple nice improvements to its console emulator and, more importantly, the Linux subsystem for Windows 10 achieves some of the things I suggested without having to implement a lot of new new code. Ultimately, that was probably the best course of action.

Render cygwin unnecessary by providing similar functionality out of the box.

Mission accomplished, yeah?

Borders, colors, gradients, shading, transparency, common controls (progress indicators, prompts), multiple terminals, automatic re-layout on sizing.

There has been more progress here than I would have expected. For example, 24-bit color in the console.

Provide a secure remote shell

I understand that Windows has "Remote Management," but I was very happy to read that SSH is coming to Windows.

4.4. Holistic review of configuration

Grade: C

It is clear that this is a work in progress. Windows 10 gradually is replacing legacy applications and control panels with a new, unified configuration user interface.

A quick warning, however: do not allow functionality to be lost in the conversion. The new implementations must provide feature parity and ideally would provide even more customization and control.

4.5. Rename and unshackle Windows RT

Grade: B

Again, this shows the age of the original to-do list. Remember Windows RT?

The grade is fairly high because RT was essentially just allowed to fade away. Seems like a reasonable approach, all things considered.

4.6. Expand the Microsoft Signature program

Grade: ?

I'm not sure what Microsoft has done here. The Signature program is still a good idea. I suspect it has already improved matters for a lot of people. But I've not personally interacted with a non-Microsoft or non-whitebox Windows device in quite some time. So I'm not sure how widespread the elimination of the awful "bloatware" experience has been.

5. Server operating systems

Grade: F

Microsoft is not seizing the opportunity to demystify servers and bring serving to the masses.

It's the flip-side of consuming. Be the decentralized cloud company by giving everyday people the tools to serve.

It's a shame, since the spirit of Windows 10 Creators Update demonstrates Microsoft understands the value of treating users as more than consumers. Go the next step of people total control of what they create.

Disintermediate the cloud.

This is eventually going to happen, and Microsoft can be the company to do it.

5.1. and 5.2 Hobbyist licenses, home servers

Grade: F

As each year passes, it seems less likely that anyone will use Windows to manage their personal/home network. If anything, Windows Server keeps moving further up-market, seemingly happy to cede the hobbyist and personal space to Linux.

Consider making it just plain free to use Windows Server in a hobbyist capacity.

Ah, the dream.

5.3. Home application hosts

Grade: D

See Sandstorm and similar open source projects starting to stake their claim to this space. Eventually this will be where AI agents should exist. Maybe Microsoft is doing something in this space, but I see no evidence of it.

Consider personal application omnipresence as a long-term goal.

I'm giving this subject a D only because Continuum and Universal Windows Platform are both incremental steps toward a PAO computing model.

6.1. Grow open source initiatives

Grade: A

Massively double-down on existing open source initiatives.

I think it's fair to say that Microsoft's open source footprint has grown immensely since I wrote the above three years ago. It's surprising and awesome.

6.2. Provide full Hyper-V on all Windows versions

Grade: B

Hyper-V is in Windows 10 Professional. It really should be available in Windows 10 Home as well, but so be it.

6.3. Cut MSDN pricing massively

Grade: C

MSDN pricing is still very high. However, in the time since I wrote my to-do list, Microsoft has added options for developing for Windows that are free. So although MSDN should be cheaper still, the existence of free options makes this a passing grade.

7. Email

Grade: F Microsoft should become a principal corporate sponsor of the GPG project and bring quality GPG user interfaces to mainstream e-mail platforms...

All of the recent high-profile email leaks reinforce the need for e-mail encryption. All e-mail should be end-to-end encrypted. As part of a renewed emphasis on privacy (which I will mention at length in my 2017 to-do list follow-up), Microsoft should make it a mission to make end-to-end e-mail encryption available to average people. Obviously this is not an easy challenge, which is why a tech titan should tackle it.

Conclusion

As I said at the top of this report card, I am impressed at how many of my wish-list items Microsoft accomplished in just over three years. The new leadership and positive culture have changed this large company. I hope the momentum keeps building and as Microsoft evolves, the company becomes ever more a leader and innovator.

Coming soon: a follow to-do list for 2017!