Designing app-centric sharing for SkyDrive, part 1 of 2: Complexity of “simple”

Designing app-centric sharing for SkyDrive, part 1 of 2: Complexity of “simple”

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A few weeks ago, we released an upgrade to that fundamentally changed the way you can share files and collaborate using SkyDrive. Omar Shahine gave a great overview in his blog post a couple of weeks ago, but I wanted to dive into deeper detail about how our new, simple app-centric sharing for Office documents and photos came about. Tomorrow, David Nichols will publish part 2, which will go into the technical challenges behind these changes.

Here is a quick video Omar made that covers some of the highlights in this post:


What was wrong with the old way?

SkyDrive has been an amazing service from the beginning. To give you some historical perspective: SkyDrive was originally designed for people to share files with other people on the Windows Live network. The first “app” on SkyDrive was a photo sharing experience that shipped in December 2008. Office Client and Web App integration followed in the summer of 2010. The way people share and collaborate has really changed over the past few years. Let’s take a look at some of the user scenarios that grew challenging with our old model:

  • If you want to share files, you need to organize things in a particular way. SkyDrive is about your stuff. And since everyone organizes their stuff their own way, we wanted to create a system that lets you share files no matter where they are on your SkyDrive. With our old model you had to create folders or documents in the root of your SkyDrive and give people permission to view or edit them.
  • Getting started collaborating on a document is challenging. Because the permission granularity was at the folder level, you needed to put your document in a folder, share that folder, and then your friends or colleagues needed to go to the folder and find and open the document. It was just too many steps.
  • You need to know your friend’s Windows Live ID. Our success rates for sharing were low because people have multiple email addresses or will come across a link in Facebook or LinkedIn. For example, I know Joe as, but his Windows Live ID is So in the past, I would share a link with Joe, and he would click on the link and be asked to sign in. He would sign in with his Windows Live ID and not have access to the item!

The challenge of simple vs. powerful

As we worked to design the new model, we really wanted to keep it simple while still providing great features for our power users. Some specific challenges were:

  • Sharing files shouldn’t depend on how they’re organized. While the model worked well enough for photos, it was way too hard to get started collaborating and taking advantage of our amazing Microsoft Office integration. We knew it was critical to separate organization from sharing.
  • Sharing folders works well for collections like photos, but for collaborating on documents you really need single file sharing. The bar here was email attachments. People have been sharing single files forever this way, and we wanted to create a system that was better.
  • Most people don’t understand “ACL math,” so keep it simple. Windows has an incredibly rich Access Control List (ACL) model. It allows you to have conditions that include inheritance of permissions and conditions that break the inheritance of permissions. These rich capabilities can result in complex sharing scenarios that may be desirable in enterprise scenarios, but often add an unhelpful amount of complexity for most people.
  • Optimize for sharing more broadly than just with people in the Windows Live network. People want to share files with another person. More and more, people have several different addresses which added friction to our old sharing model. When you shared a folder with another person using a specific email address, the recipient had to sign in to Windows Live using the matching email address or they couldn’t access the document.
  • We needed a more resilient and transparent sharing notification system, preferably email. Email is the way people have been sharing and collaborating with each other for a long time. That’s the way it should feel like. Power users should have a way to share directly with their social networks or get a link they can use the way they want.

The new SkyDrive sharing experience

SkyDrive lets you store and share your files—but it does more than that. We also provide rich experiences for important file types, specifically Office documents and photos. So when we talk about “app-centric sharing,” we mean that you don’t have to leave the context of what you’re doing or looking at to share.

Sharing single documents

With the new SkyDrive sharing model, you can easily share single documents to start collaborating. If I select any document in my SkyDrive, I can click “Share” and bring up the sharing dialog that Omar talked about in his blog post. But here’s the best part. Let’s say you’re using the Word Web App to write a blog post (!) and you want to send it out to the folks who need to review it. Instead of having to leave the context of Word, you can just click the File menu and choose “Share.” This brings up the—by now familiar—SkyDrive sharing dialog. Just choose the people you want to share with and get back to writing that blog post. Now that’s simple, app-centric sharing!

SkyDrive Sharing in App


Sharing single photos and documents

This also works for photos and albums. If I’m browsing my albums and see one I want to share, in this case some shots I took with my new camera, I can use the new right-click menu on the album cover and share the entire album (folder) from there:

SkyDrive Right-Click Menu

Maybe I want to see who I’ve already shared the album with, so I’ll open the album. Here’s what I see in the info pane:

SkyDrive Sharing Info

I’ve already shared this album with my friends on Facebook, but I want to share it with Omar, so I just start typing his name. All of my Hotmail contact email addresses are available in the “To” line:

SkyDrive Share Email

Note that when Omar clicks on the link, he can immediately view what I shared with him, even if he doesn’t have a Windows Live ID yet.

Quick side trip—Getting everyone’s addresses

SkyDrive sharing (and emailing from Hotmail) will be even more powerful if you connect your social networks to Windows Live. Thanks to some great work by our Connect team, you can connect your social networks to Windows Live by going here. This will ensure that you can share directly with your friends on your connected networks. If you’re connected to LinkedIn, you automatically get those email addresses. For Facebook, you need to do an import by clicking on the Facebook icon after you get connected. Below are the steps you need to follow to import your Facebook email addresses so you can share your files and folders with your friends. Note: You can only import the email addresses of friends that have shared their email address with you.

  1. Connect Facebook to Windows Live by clicking here.
  2. Go to and click the Facebook logo.

SkyDrive Import Contacts Other Services

  • Click the Facebook logo on this dialog box and follow the instructions.

SkyDrive Import Facebook Contacts

Email notifications with links that work

When I click on “Share” in this case, Omar receives an email from me in his inbox. This means that Omar will know that I’m the one who sent him the link. No more fishing through junk mail to find the link. You even get a copy in your “Sent items” folder in Hotmail so you see exactly what you shared and when you shared it.

SkyDrive Email Notification

Also, if for some reason your message doesn’t get through, you can look in your Hotmail “Sent items” folder and see the mail that was sent. You can even forward the mail to other people.

Changing permissions

Now I see that Omar can view the photos:

SkyDrive Sharing View

But I want to let Omar add some of his own photos to this folder, so I’m going to change his permission to “Can edit” using the dropdown.

SkyDrive Sharing Edit

If I want to remove either permission, I just use the ‘delete’ icon to the right of the permission. Overall, this lets you grant and revoke permissions in a granular way.

Straightforward sharing means no “ACL math”

The easiest way to think about SkyDrive permissions is to think about parents and children and the way children inherit certain traits from their parents. Each folder can have a set of permissions (though they are private by default). Each folder can also have “children” (subfolders and files) which inherit permissions from their parent. As you set permissions on things, the action is additive. So let’s say that I shared a folder with Omar, Mike and Dave, and then shared a document in that same folder with Sarah. At that point, Mike, Omar, Dave and Sarah can all see that file. But only Mike, Omar and Dave can see the other files in the folder. We make this clear in the UI by showing where the permission came from, along with a handy link to navigate to the folder where that permission is set so you can easily change the permission.

I’ll go back to my blog post example. I gave Omar permission to my “Blog Posts” folder so he could see all the drafts. I have a subfolder under “Blog Posts” where I keep screen shots for the blog post called, surprisingly, “Screen Shots.” My friend Piero has a fantastic eye, and I want him to take a look at the screen shots before I publish. Omar has permission to the parent folder, and by way of inheritance Omar can automatically also see and edit the contents in the subfolder “Screen Shots.” His permissions to the child folder derived from the parent, “Blog Posts” folder.

SkyDrive Sharing Permissions

The UI shows who can do what for each folder or file that you select, so you always know who can view and edit your stuff.

Our magic links

Earlier I mentioned the email mismatch problem. It used to be hard to share with Omar if I only knew his Microsoft address but not his Windows Live ID. Now, our links sent in email and shared on social networks contain a token to let the recipient view the document, so that it works no matter which email address I send it to, even if the recipient doesn’t have a Windows Live ID. While I can restrict it to a specific email address for really sensitive stuff, the predominant case is that the intended recipient gets the link and clicks on it. David Nichols’ post tomorrow will dive more deeply into how the tokens work.

Other ways to share

Publish to your connected social networks

The sharing dialog also lets you quickly share folders and files with your friends on social networks. Want to share that photo album? Have a Word document with a great recipe you want to share? Need your friends to take a look at your resume on LinkedIn? Now you can.

SkyDrive Sharing Social Network

Get a link (for power users)

The other great way to share is to use our “Get a link” feature. This allows you to create a reusable link that you can include for your own scenario. In addition to standard “view” and “edit” enabled links, you can also make a document public and discoverable. Simply click “Get a link” for any of these types and copy the link.

SkyDrive Get Link

You can revoke these links just like any others you create by clicking the delete icon in the info pane.

SkyDrive Revoke Link

We are really excited about the new sharing model and the powerful collaboration scenarios it unlocks. Be sure to read David Nichols’ post tomorrow for Part 2.

Tony East
Lead Program Manager,

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  • controlz
    145 Posts

    This is off topic, but is that a video call icon in the Hotmail screenshot (next to the words "Tony East")? Is this a Hotmail Wave 5 M3 screenshot?

  • A couple of items:

    This may be a bug: I have a folder that is a couple of levels inside unshared folders. Setting sharing to public provides a link which does not work. The information pane shows the globe and "Everyone". In the main listing under "Shared with" it shows "Just me". Several attempts to reset sharing have not succeeded in getting a public access link and these contradictory indications are restored the next time SkyDrive is accessed (by the owner). The provided "public" link goes to a sign-in page, or, if the recipients are signed in to their SyDrive, shows a "This item might have been deleted ..." bar.

    The default for email sharing has the "Recipient can edit" box checked and the "Recipient must sign in to view" unchecked. A recipient can forward the email message to any number of other folks who get access and can delete the item (the only edit feature for photos that I have seen for this). It would be safer to reverse these default settings.

    "Recipient must sign in to view" is a bit ambiguous, since the recipient must also sign in to have edit access. Maybe the word "view" should be replaces with "access".

  • I forgot another issue, maybe it's a bug:

    When I share a folder with person A without ticking the box "Recipients must sign in to view" and share the same folder with person B (this time) ticking the box "Recipients must sign in to view" person A -who actually should not need to log in-  is also directed to the login page!

  • @Tony East: I have the same issue that metrofan has.

    I think it is not sufficient to forced users to join Windows Live / Skydrive to edit. As you said you need to "optimize for sharing more broadly than just with people in the Windows Live network". In my opinion forcing people to set up an account holds people back from collaborating on skydrive. Nobody wants to set up another account on yet another service just to add - for instance- some fotos to my album. If editing was available to everyone, people could explore skydrive and its great capabilities better and would probably join because of this positive experience.

    Moreover I would like to suggest to make the current situation clearer for skydrive user. Right now you get the impression that everyone who receives a mail or a link with edit permission would in fact be able to edit a file / folder. But this is not the case!

    Other than that I really appreciate your hard work and all the improvements. Keep on working hard!

    (hope we'll see Live Mesh integration and a dropbox like desktop client soon, and maybe even Office 2007 integration)

  • SkyDrive is great sure.

    But I'm missing a feature that would synchronize my files with my PCs. I'm thinking of an integration between Live Mesh and SkyDrive. That would be really great. I mean. I'm lazy as anyone ;) I would use SkyDrive much more in case I could automatically Sync my files as I can do with Live Mesh. SkyDrive is quite an isolated storage for now.

    On the other side Live Mesh isn't perfect too because you can't work with the files over the web browser as you can do with SkyDrive. OK. The beta version of Live Mesh was something close to what I have in my mind.

  • qiziq comment, and Microsoft's response, about seamless Hotmail/Skydrive integration needs to be re-read. When composing a new message in Hotmail. clicking Attachments, Office Docs or Photos opens a file dialog box for items stored on the local hard drive. I'd like to be able to select items from SkyDrive, as well. While I understand the e-mail sharing mechanism is within Skydrive, I believe that for many people it is more natural to share within Hotmail especially if they start by writing an e-mail and need to include multiple documents. This is a different workflow altogether. Curiously Gmail uses the same document sharing concepts - I'd like Microsoft to beat them to it.

    Other than that, Merry Christmas / Happy Holidays!

  • @qiziq - Thanks for the feedback.  Our new sharing features is integrated with your Hotmail contact list.  Also, in Hotmail you can upload directly to SkyDrive while composing a mail.  We are always looking for ways to improve our integration with Hotmail.

    @metrofan - your friends can create their Windows Live ID using any email address.  Then they will have a SkyDrive to use too!

    @controlz - Thanks!!  As for docs at the root of your SkyDrive, we are working on it.  Stay tuned!

    @ma7mgte - we hear that feedback frequently.  Nothing more to say now.

    @windowslivefan - Thansk for the report.  For #1, unfortunately you can't have a OneNote file with the same name as a folder.  OneNote is special  -  we show it as a file but behind the scenes it is really a thicket of folders and files.  Sorry about that.  For #2, that's the way it currently works.  We hear the feedback so stay tuned.  As for Android, no comment.

  • Are there any plans for SkyDrive App for Android ?

  • I have to bugs to report...

    1. while using skydrive, i created onenote file with the name TechResources and later I tried to create a folder onto skydrive with the same name. It didn't allowed me to create. I believe this a bug.

    2. The search on the skydrive is not working properly. It only searches Word/Excel/Power point files. It is not searching folders or onenote files.

    I hope this will be resolved in upcoming release.

  • ma7mgte
    4 Posts

    Is the 100MB limit going away?  Why is it even there?

  • controlz
    145 Posts

    This is kind of off-topic, but when will we be able to move files created in the root of SkyDrive before the Wave 5 M2 update? I know docs created in the root of SkyDrive since the update can be moved, but docs created before can't.

  • controlz
    145 Posts

    SkyDrive just gets better and better... Google Docs is nothing compared to it now.

  • I cannot see the video because of doctype switches IE to IE8 rendering mode. Please change doctype to <!DOCTYPE html>.

  • These are fantastic features. I love how you can right click on everything just like native apps.

    But, when you share a document with a person with an email address other than Hotmail, he/she can only view that document, and can't edit it even if you set the permission to View and Edit. It asks for a Hotmail login when he/she tries to open the file.

  • qiziq
    23 Posts

    Unless I am totally missing something, the Skydrive/Hotmail experience is still not as seamless as it could be.  If I create a document in Office to share for collaboration, it seems that it is stored only in Skydrive, not Explorer.  Hnotmail then should have an "insert from Skydrive" tab, just as it has an "insert from Bing" tab.  At the very least, the Skydrive share functionality should be integrated with my contact list in Hotmail.

  • @j00v if you share something, and move it, the permissions will follow the item into the new location. The exception is that it will also inherit any permissions from the parent folder that are more permissive. For example if you move something into the "Public" folder it will inherit public permissions in addition to any permissions on the items being moved.

  • j00v - links are resource ID based and so you can move the folders and not break existing sharing links.  The Office applications use DAV links to documents which are path based.  These links will change if you move the doc so your "recent" list in Office won't work.

    Markiz - we definitely hear feedback on the links.  Stay tuned.

  • markiz
    40 Posts

    I only wish links were nicer. like, desriptive.

  • markiz
    40 Posts

    @Sir Peter

    Yeah, that is true, BUT!

    Well, there is a BUT, but i just realized that what i had in mind is facebook's issue and can not be done. Nevermind than.

    In any case, the new sharing features are a vast improvement from the user friendliness perspective.

  • Sir Peter
    11 Posts

    @markiz – I've just checked – you are able to share files with your contact's groups.

    If you have eg. group called "Family" in SkyDrive share window in address (To:) field type word Family – et voila all members of this group will be added. It's so easy.

  • j00v
    1 Posts

    Now that sharing has been separated from organizing, what is the impact of reorganizing files that I have previously shared?  I have several photo album folders that are currently shared on blog posts (created using Windows Live Writer or Windows Live Photo Gallery).  These are currently stored in the root directory of SkyDrive.  If I decide to move the Photo album folders to the "My Pictures" folder now (which is set to private), will the link break and cause the reorganized photo album folders to no longer be shared?

    According to the post, it seems that the rearranged sub folders should still be shareable even though the permissions on the parent folder are private.

    The other question really is does rearranging the files and folders within the SkyDrive folder heirarchy cause the path to those files and folders to change?

  • markiz
    40 Posts

    Until it is possible to share with a certain group of people easiliy, every one of these ways has disadvantages.

    For example, If among my htomail contacts i have groups, like familiy, coworkers etc, why is it not possible to simply share with them only?

    As it is, i can share a photo album with the whole facebook (which i don't want,) or by spaming inboxes of people i do want to share that album with.

    While i am at it, it should be possible to "hide" some facebook contacts from hotmail contacts. It should not be all or nothing.