Outlook 2010 New Features and
TWC-MYN Conversion Guide

June 29, 2010 (updated April 28, 2011)

Microsoft® Office Outlook 2010 is out, and the press is abuzz over it and I really like the software. My first observation, however, is this: for users of my MYN productivity system, there are fewer changes from Outlook 2007 than you might expect. That said, there are still quite a few powerful, new features in 2010. So, in this article I will cover the main new features, and more importantly, cover any conversion guidelines for users of my TWC-MYN (Total Workday Control—Manage Your Now) Outlook Productivity system as outlined in my current Outlook book, Total Workday Control Using Microsoft Outlook.


In this article:


First, a note for people who are using my book Total Workday Control Using Microsoft Outlook 2nd Ed. or are using my TWC-MYN Outlook system of e-mail and task management from previous training on Outlook 2007 or earlier. If you are moving to Outlook 2010 from Outlook 2007 there are very few changes in Outlook 2010 that impact TWC-MYN system. So the older (second) edition of my Outlook book, if that's what you have, can still work for you—just follow the Outlook 2007 instructions in that book and see the Conversion Guide below.

That said, there are quite a few changes and it can be tedious to use the conversion guide below, so by all means to make life easier get the third edition of the book. It is out now and covers the 2010 changes and a lot more. It also covers Outlook 2011 for Mac.

Should You Upgrade to Outlook 2010?

So, should you upgrade to Outlook 2010? If you are using Outlook 2003 or earlier, then absolutely yes. There are too many helpful new features in both Outlook 2007 and 2010 that you should be using, and you have put off upgrading too long. This 2010 release is a good reason to make the change.

And, even if you are currently using Outlook 2007, I’d still say “yes” to an upgrade. That’s because there are a number of nice new e-mail features in 2010 that make it worthwhile. For example, the new e-mail feature called Show as Conversations is quite useful and well done. And the new Quick Steps feature will give you time-saving e-mail automation as well (I discuss both of these features below, and have also created a YouTube video about Quick Steps that shows how this feature works).

User Interface Changes

To my mind, the most noticeable changes in Outlook 2010 are mostly cosmetic ones, so let me discuss those first.

New Ribbon Menu

The big change you will notice right away is that Microsoft added its Ribbon menu interface to the main menu system in Outlook 2010. Microsoft had already added a Ribbon to all of its other Office applications as of Office 2007, so it was a bit overdue. Essentially, all the old commands have been moved from various menus and toolbars into the Ribbon, with very few new features added.

Now, inevitably, moving things around like this will create the most love-hate reactions among users when they first start using Outlook 2010. If you are accustomed to where things were in 2007, you'll find the furniture has been completely rearranged, and you'll be growling as you go searching for the same old commands that are in totally new places. I did this immediately (growled) and I struggled at first, but I quickly became accustomed to the new locations and I am now a big fan of the new Ribbon—I like it far better than the old menus. Again though, there are very few new features here, just new locations and occasional twists on old features.

My only complaint with ribbons is that the Ribbon design calls for command icons rather than only command text, and it feels like the designers have sometimes really stretched to convert commands into icons, when simple lists of commands would work better and be easier to read. I give an example of this below when I talk about Task folder view names. But that said, I still like the Ribbon approach better than the older menu and toolbar approach since it eliminates hierarchal submenus and places all like commands together.

Simplified Appearance

The other major change is an extreme simplification of the layout, color usage, and general appearance of the main Outlook window. Apparently, someone told Microsoft that Outlook 2007’s appearance was too busy, and they took it to heart in a big way. They removed many border lines between commands and buttons, eliminated most contrasting colors, and simplified the Navigation Pane on the left and the To-Do Bar on the right. Compared to 2007, everything is now reduced to the same light gray (or optional blue).

The result is a much simpler, even austere, appearance (see above).  I often resist change, so I miss some of the distinctions the extra lines and colors provided—but I am getting used to the new look.

File Menu Leads to Backstage

Another significant user interface change: the File menu is replaced with a File tab in Outlook 2010, and interestingly, it leads to a full-screen command window called the Office Backstage (see image below). It replaces the simple pull-down menu of earlier versions. Think of it as a full-screen version of the Ribbon—one that blocks out the Outlook window completely when opened. I guess Microsoft felt there were just too many File activities to settle for a normal Ribbon. It generally works for me, but, even after weeks of use, it still feels odd when all of Outlook momentarily disappears every time I use it.

Task System Changes Are Minimal

As you know, I emphasize using the tasks features in Outlook, and these are essentially unchanged in Outlook 2010 compared to 2007. However, there have been a number of minor tweaks; most I like and a few I do not.

One I like is they removed the close box from the upper right corner of the To-Do Bar. This I highly applaud. It was a huge source of confusion in 2007—people kept wiping out the whole To-Do Bar when they just meant to minimize it. Now only a new simplified minimize button is present on the To-Do Bar as shown at left (though, to fully close the To-Do Bar, you can still use the Ribbon commands under the View tab).

Another good one: when you click on a task in the To-Do Bar, you now see an extensive list of “Task Tools” in the Ribbon menu—commands you had to right-click to see before (see below). It is nice to have these more readily visible and available.

Icon-Based View Selector in Ribbon. One change I do not like is the new icon-based view selector in the Ribbon, shown in the figure below. I liked the old 2007 Tasks folder view because you could select views from a nice list of all task view names right in the middle of the Navigation Pane on the left. Those have now been moved to a smaller area up in the Ribbon, one that you need to expand to see fully—so one extra click is needed (somehow I'll survive that). But more significantly, following the guidelines I mentioned above, they have switched from a list format to an icon format for these view names (see below), and I miss the list format—this is one case where large icons just seem inappropriate; if the view names are long (as many custom view names are—see the ClearContext views for example), you cannot read them. I do see how putting them in the Ribbon is more consistent, and I applaud the overall design effort. Still, I think an option for small icons with longer text to the right would be a good design choice. Note, as a fallback, you can still get to a list format by choosing Manage Views... at the bottom of the icons.

Advanced Instant Search Interface Change

One Ribbon-inspired change is the Instant Search interface. The 2007 chevron that led to a dropdown set of advanced Instant Search criteria is gone. Instead, clicking in the Search Box leads to opening a contextual tab in the Ribbon called Search Tools—here you will see a set of search tools in the form of icons.

The good: I like that Microsoft combined the Scope controls into the left side of the Ribbon along with the other search tools. Outlook 2007’s placement of those Scope controls in the Navigation Pane was confusing. Also, the designers have highlighted the main search criteria as easy-to-see icons in that Ribbon group.

The bad: Maybe I just need to get used to it, but I prefer the “fields” approach of the old interface. My reasons? Well, when using the new icons, as I click them, I have to enter any parameter information inside the text query string (see the bottom of the image above), and I am not used to looking there for that. And, as these query elements build up, they can get hard to read and can disappear in the search field’s narrow width. Overall, it feels harder to get a quick gist of what the search is, and harder to edit parts of it.

But no worries, if you prefer the field approach, simply click the More button in the lower-right corner of the Refine group (see above), and you can get the 2007 field approach back.

E-Mail Changes: The Main Reason to Upgrade

E-mail is where the real juice is in the Outlook 2010 change set. The two new features: improved Conversation views and the Quick Steps functionality are, I think, the main reasons to upgrade to Outlook 2010.

Show as Conversations

If you have used Gmail before, you are familiar with the conversation-view possibilities in e-mail; the Gmail mail list view is, by default, arranged by conversations—that’s the only way to see mail there. Conversations, of course, are replies to replies to replies—“threads” of mail so to speak. And conversation views are mail list views that group all linked conversation mail items together and allow you to expand and collapse those groups.

Even though Outlook has not defaulted to conversation views in the past, it has included the option of such a view for a decade or more. However, in older versions, it was not very smart. For example, using the conversation arrangement in 2007 resulted in creating large titled groups for every message (whether it had conversation threads attached or not); it was ugly and clearly an inefficient use of space. As a result, few people used it.

In Outlook 2010, that has all changed. Conversations now appear in a lightweight and very smart way. To activate (or deactivate) them, just click (or clear) the Show as Conversation checkbox in the View Ribbon as shown below.

Once activated, the Show in Conversation layout is quit elegant and functional, and it’s implemented in a way that saves space and cuts down on the amount of e-mail you need to see.

And my favorite aspect of the new Show as Conversations is this: it will optionally pull e-mail in from other places (like the Sent Items folder or even filed mail) to ensure that a full conversation is displayed. This is a really cool feature. Here’s how it works:

Once you turn on Show as Conversations in the View Ribbon, all e-mail conversations are indicated by a small black triangle to the left (see above); otherwise nothing looks different. By default, only the latest message is shown and older messages in the thread are hidden. When you click the triangle, the line expands to show all mail in that conversation. It starts out only showing conversation mail in the current folder (say the Inbox). However, if you click the triangle again, the conversation group expands even further and shows related mail from the Sent Items folder (or even filed messages) in their proper place in the conversation. There is even a small notation in the Received column indicating what folder it was borrowed from (see image above).

Clicking on individual messages at this point shows a small dotted line pointing to the message being replied to inside the thread (see the thin line linking messages at the left side in the image above). The design and implementation of all this is overwhelmingly excellent—it works just right.

Furthermore, if you right-click the message and choose Clean Up Conversation, Outlook will automatically delete (or file) all redundant messages—anything that has content duplicated in the more recent items. And it does this smartly—if there is an attachment in an e-mail that is, say, in the middle of the conversation, and the attachment did not make it into later replies, Outlook will retain that middle item too.

I do have one minor complaint, and that is this: since Outlook simply matches the e-mail title (the subject field) to determine whether an e-mail is part of a conversation, I get a lot of “false conversations” indicated. For example, if you think of any automated notification message or newsletter that is consistently sent with the same title, you will know what I mean—these all get grouped together as if in a conversation—which they are not. That said, I do admit that once these are collapsed, it does allow for a more compact Inbox. But for those of us that don’t want this, it seems to me a way to prevent it—to turn it off—should be provided.

But, that quibble aside, Microsoft really got it right with this new implementation of conversations. It is a powerful new feature and worthy of an upgrade. When you do upgrade, I encourage you to be sure to fully explore and use this feature.

Quick Steps and My New YouTube Video

New in Outlook 2010 are Quick Steps—command shortcuts that save you time on repeated e-mail actions. Examples of Quick Steps are one-click to reply to and delete a message, and one-click to create a message to your whole team. You can see the Quick Step buttons in the middle of the Ribbon on the Home tab.

Shortcuts like those I just listed are standard when you install Outlook 2010. However, none of these standard ones really excite me. Luckily, deleting these and creating new ones that do excite me is pretty easy, and I quickly created a few that help automate some important actions in the Total Workday Control system. With that, I am now convinced this feature is quite worthwhile.

YouTube Video. I've even made a four-minute YouTube video all about Quick Steps, showing you what they are and how to create them—take a look at that now (below) if you want to learn more.

Command Shortcuts Compared. How powerful are Quick Steps and how hard are they to create? And aren't there other ways to do this? Yes, there are actually four other ways to automate commands in Outlook. And, in terms of power and ease of use, Quick Steps nicely fills a gap in the middle of the four other ways.

In order of increasing power and difficulty here are the five ways you can add custom commands to Outlook:

  1. Custom Quick Access Toolbar items (the small set of buttons in the upper left corner of the Outlook window) – Yes, you can add to those. Click the small down-arrow to the right of them. This is what it looks like:
  2. Custom Ribbon buttons – Yes, you can add more Ribbon buttons. Just right-click anywhere on a Ribbon and choose Customize the Ribbon...
  3. Quick Steps – New to Outlook 2010, see the video above.
  4. Outlook Rules (use the Home tab Rules button) – Very useful but somewhat difficult to create.
  5. Visual Basic Macros – Very powerful and very difficult to create.

So, Quick Steps sits right in the middle of these in terms of the power/difficulty trade-off. Since Quick Steps allow multiple steps, they are more useful than simply adding a toolbar or Ribbon item, and they are much easier to create than rules or macros. Again, check out my new YouTube video, above, in which I show you how they work and how to create one to automate conversion of e-mail to tasks in Outlook 2010.

Other New Features in Outlook 2010

There are lots of other new features in Outlook 2010 that I won't go into detail on now, but are worthy of mention. Here's the list:

  • A better ability to combine multiple e-mail accounts, calendars, and address books and manage them from a single, centralized view.
  • A new popup Contact Card (accessible within an e-mail) that shows the availability of people addressed in the e-mail, and that also gives you quick links into multiple ways to reach that person (see below).
  • The new Outlook Social Connector that combines various sources of information feeds about a person into one view, and creates new connections to Facebook and Twitter (see below).
  • A new Schedule View that allows you to mix calendars from various people and online sources in a “streamlined horizontal display” (see below).
  • Quick View. When you receive a meeting request, Quick View helps you better understand how a meeting request affects your calendar. When you create or respond to a meeting request, a calendar snapshot appears in the meeting request.
  • A new Screenshot command that allows you to select all or any part of your computer screen and include a snapshot of it in a message.
  • The browser version of Outlook, previously called Outlook Web Access, is now called Outlook Web App. The 2010 version includes significant upgrades such as its own Conversation view, multiple browser support, single-page scrolling of message lists, and more. See a full list of its features here. Note that along with this new web version of Outlook, Microsoft just released a full set of free web-based versions of Word, Excel, PowerPoint, and OneNote. And that you can store and share files for these programs, and for the full version of Office 2010, on Microsoft’s version of a cloud (called Skydrive—it’s free). Reviews such as this indicate that these applications and this cloud approach are comparable to Google’s free web-based applications and web storage.

Note that many of the features in the above bulleted list depend on your having Microsoft Exchange Server 2010 as your mail server, and, in some cases, also having access to Microsoft Office Communications Server 2007.

Conversion Guide: Changes in Outlook 2010 to Consider When Using the Book Total Workday Control Using Microsoft Outlook, 2nd Ed.

Okay, you now have an overview of Outlook 2010 and how it has changed compared with 2007. What about the TWC-MYN system? As I said in the introduction, that system is only moderately affected by the changes. The new third edition of the book covers all of those (and a lot more new material).

That said, if you have the older edition of the book (the second edition), there are some changes you should note, particularly in Lesson 3 where I show you how to configure Outlook tasks. You see, Microsoft changed a few menu and button names and that may distract you as you work through that lesson.

But, here’s the good news—if you upgrade from a TWC-configured 2007 to 2010, there is a good chance the 2010 installation process will pick up all or most of your TWC-MYN configurations. I have not tested this fully, so it may not work in all situations, but be open to being pleasantly surprised. If it does not pick them up, you'll need to do the Lesson 3 configurations again, and yes, some name changes have occurred in menus that you will want to be aware of; I list those below.

2010 Menu and Dialog Box Changes Affecting TWC-MYN Configurations in Book's 2nd Edition

Here is a list of the few, but key, Outlook 2010 menu and dialog box name changes that will affect your TWC configurations if you are using the older second edition. Most are pretty obvious, but if you are configuring an Outlook 2010 version using Lesson 3, take a look at this table first. You may even want to first scan through all of Lesson 3 and pencil-in the few changes indicated below (there are a number of places to do that between pages 49 and 56, especially for the first item in the table below).

Also, per page 59 of Lesson 3, Task Reminders are turned off by default, so there is no need to change them, just like 2007. But if you do want to change them, in 2010 you access that command on the File tab, then the Options entry on the left, then the Tasks entry on the left.

Lessons 8, 11, and 12 also have a few configuration instructions that are affected by the name changes above, so, as you follow any of the 2007 instructions there, glance back at the table above.

Also, in those chapters, wherever I show you how to create a new view, there is another change to be aware of that is due to the new 2010 Ribbon menu. This affects pages 169, 227, 274, 295, 297, and 300. When using any view creation instructions on these pages, the first steps always have you use the Advanced toolbar and the Define Views command. However, in Outlook 2010, that toolbar and command no longer exist, so you should now create these views as follows: go to the View tab of the Ribbon, select Change View, and then select Manage Views. Then follow the rest of the steps in the book.

And that brings up one more point. With the new Ribbon replacing nearly all menu and toolbar commands in Outlook 2010, there are many other references scattered throughout the book to menu commands that have now moved into the Ribbon in 2010. It does not make sense for me to list them all here as I think you will have no trouble locating their new Ribbon locations. However, if something stumps you, drop a note to support@michaellinenberger.com and we'll get an answer right out to you. Good luck!

ClearContext Software. Discussions in the second edition of the book about the add-in software ClearContext are dated since they cover a previous version (v4), and v5 is now out. The new book covers most of those, and check my website for more. Just know, if you want to use ClearContext with Outlook 2010, you'll need that new version, v5.

To Sum It All Up

Outlook 2010 has brought a long list of new and very useful features to this venerable e-mail and personal information management software. The best new features are all about e-mail. And since the tasks features have changed little, MYN users will have no trouble advancing to the new version from Outlook 2007.