Video: Gmail vs MS Outlook

Gmail is a free, advertising-supported email service provided by Google. Users may access Gmail as secure webmail, as well via POP3 or IMAP protocols. Gmail's spam filtering features a community-driven system: when any user marks an email as spam, this provides information to help the system identify similar future messages for all Gmail users. Google also provides GMail alternative for business - G Suite Mail.
Microsoft Outlook is a personal information manager from Microsoft. It can be used as a stand-alone application, or can work with Microsoft Exchange Server and Microsoft SharePoint Server for multiple users in an organization, such as shared mailboxes and calendars, Exchange public folders, SharePoint lists and meeting schedules. MS Outlook free alternatives are Mozilla Thunderbird, Opera Mail, EssentialPIM.
Face to face in the news:

2016 - Mobile Outlook gets built-in meeting scheduler to compete with GMail

Mobile Outlook now has a new scheduling assistant that helps you find a time that works for everyone. The feature, which is rolling out today to the iOS version of Outlook’s mobile app, will show your coworkers’ availability so you can quickly pick a date and time when everyone can attend the meeting. To use the new scheduling assistant, you’ll first create an event from the app’s included calendar, then add the coworkers to the People field. You then tap on the date picker, and the app will automatically show you the times that work best, as color-coded suggestions.

2011 - Kinect + GMail Motion : use gestures to manage your inbox - a new advantage over MS Outlook

On the 1st of April Google kinda joked - introduced the new feature - GMail Motion - the ability to control emails and even enter text in the GMail mailbox using gestures (see video). But some people don't understand jokes. The guys from Southern California University took Kinect, connected it to GMail using the plug-in and turn into reality the technology that Google showed in the promotional video. Here's how it works:

2010 - Google rolls back innovations in search of revenue

GMail threads
Google has created a lot of innovative products, including GMail and Google Apps. Almost all progressive people enjoy and use them. But unfortunately, most office workers who use the paid versions of these applications - can hardly be called progressive. They are doing their job and want that mail and other business applications work in a traditional way and not to change. That is why, we see strange (but logical) things: Google rolls back innovations in order to please this paying majority. For example, GMail. Last year Google resolved the global problem with tags (because this paying majority got used to folders in Outlook). GMail tags began working like folders - with tree view, drag and drop feature. Today GMail adds an option to switch off the threaded view - that is, to remove the most convenient GMail feature. The similar process is taking place in the Google Docs:

GMail labels
Remember, Google completely changed the upper menu in Google Docs and made it like in Word 2007? And now they made the "Track Changes" feature like in Word - with red text, line-through corrections and right-side panel with the versions list.

Google Docs editing
So, the startups that develop business applications can take a lesson from this: If you want to sell more - learn your (paying) users better, maybe they are not ready for your innovations. BUT! add innovations as options.

2010 - Microsoft adds Facebook and Windows Live Messenger to Outlook. GMail should better react

Outlook Social Connector
Microsoft has updated its social Outlook plug-in - Outlook Social Connector, which can now can fetch the contact's data from Facebook and Windows Live Messenger (formerly the plug-in by default only supported LinkedIn, MySpace and Sharepoint). The Outlook Social Connector is intended to provide users with the actual information about a contact to better understand his mood and interests, which is very important when communicating with customers. The plug-in can display only publicly-available information from the profiles in social networks. Meanwhile it can only receive data but doesn't allow to post messages or statuses to the social networks. Microsoft says that soon the plug-in will be integrated with some local social networks.

2010 - Socialwok uses Gmail and Outlook as its clients

Socialwok (known as the "social layer for Google Apps") like the online organizer Producteev, shows us the new meaning of "cross-platform" definition. Realizing that users most of time spend in email clients (such as Outlook and GMail), Socialwok simply decided to get inside these email clients. Socialwok was one of the first services to use the new GMail API and has created the gadget that can be expanded on the entire GMail workspace (see screenshot) and allows to post messages to microblogs, share Google Docs files, images, Youtube videos and events from Google Calendar, search for Google Docs, post to Twitter or Facebook right from your GMail interface.

The next step was inside MS Outlook. Socialwok has released the Outlook plug-in that can be downloaded and installed. This plug-in works with Outlook Social Connector and allows you to view contact's social profile, its latest messages in microblogs, email-threads, attachments and shared events. The plugin also creates the Socialwok contacts folder in Outlook and syncs contacts with Socialwok account. Interesting,  that to log in the Outlook plugin (as well as to the online Socialwok account) you use Google Apps or GMail credentials.

Currently Socialwok - is absolutely free. And at the same time, it's continually innovating and adding new features. Probably this service will repeat the fate of Etherpad and Docverse - i.e. will be acquired by Google.

2010 - Harmony - a lot of pleasure for Outlook and Google Docs users
Harmony, the new plug-in for MS Outlook by Mainsoft gave us a lot of positive emotions, which we want to share. First, is its video presentation, which is really cool. Secondly, Harmony - is really useful tool that allows to access and collaborate with documents stored in Google Docs or MS Sharepoint, without leaving MS Outlook. In particular, you can open and edit office documents directly in Outlook, search in docs content and share documents with co-workers instead of sending them back and forth. And it's not necessary that your co-workers have this plug-in installed and have Google Docs account - they just click the link in the email and the document will be shared to them automatically (for viewing or editing).

Besides, the plug-in is absolutely free and the Mainsoft CEO, Yaacov Cohen, sais that it will remain free forever. The future versions that will include functionality that IT departments want (granular control, permissioning, central admin etc) will potentially be paid. But it seems the company has a good chance to sell the startup to Microsoft or Google.