Ten Things I Hate About Entourage
Date: Dec 30, 2005
Like many Mac users, I manage my email, calendar, and address book using Entourage, the personal information manager (PIM) component of Microsoft Office 2004. Since I use Entourage extensively throughout the day, every little rough patch or sharp corner that I encounter in the user interface is elevated from mere annoyance to exasperating aggravation.
I’m the first to admit that I can’t program my way out of a paper bag. I have the greatest respect for engineers who can create powerful products such as Entourage, but I have little tolerance for any product that doesn’t work as advertised, or makes me work harder than is necessary. Join me as I recount the top 10 things I hate about Entourage. If you know of any workarounds for my pet peeves, or you’d like to share your own list of things that drive you crazy, please post your comments below.
1: Screwy Sorting
Like almost all Mac programs, Entourage allows you to sort lists by clicking the desired column heading, with a second click reversing the sort order. That’s the way things are supposed to work. However, if you have Address Book contacts that lack first and last names (such as when you’ve entered only a business name), and you click the Name column, Entourage duplicates the display of the business name in both the Name and Company columns (see Figure 1). I’m sure that Microsoft thinks this is a feature, not a bug, but in my book, if a field in a record is empty, it should be displayed as a blank field.
Curiously, if you have contacts that lack business names, and you click the Company column, Entourage doesn’t duplicate the display of the individual’s name in both the Name and Company columns. Not only is the strange sorting behavior wrong, it’s inconsistently applied.
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Figure 1 Why does Microsoft deem it necessary to duplicate the display of the company name, rather than just leave the Name field empty for those contacts without an individual’s first and last name?
Another example of how Entourage’s sorting is screwed up is the inability to set a secondary sort order. Suppose you want to sort contacts by Company, and then by Name, so that all Apple Computer employees are grouped together, and Jonathan Ive comes before Steve Jobs, for example. In Excel, this would be a snap because you could choose Data > Sort, specify that you want to sort by one column (Company), and then by another (Last Name), and even by a third (First Name). But the sort feature in Entourage isn’t nearly as flexible. And you can’t even use the old trick of first sorting by Name, and then sorting by Company to achieve the desired result.
2: Incomplete Clipboard Copying
The pop-up menu that appears next to the postal address blocks in the Address Book’s preview pane has an option for copying the name and address to the Clipboard (see Figure 2). However, it’s too literal. It copies the individual’s name and address, but it omits the company name, even if it’s a work address that’s selected. So when you paste the information from the Clipboard into its desired place, you must manually remember and enter the company name. Thanks a lot, Microsoft, for making a simple operation more complicated than necessary. Why isn’t Entourage smart enough to include the company name when copying a work address and to omit it when copying a home address?
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Figure 2 Don’t forget the company name, because Entourage won’t put in on the Clipboard as it should.
3: Magnified Phone Numbers
To the left of any phone numbers displayed in the Address Book’s preview pane is a tiny magnifying glass icon. If you click this icon, a window opens, displaying the phone number in a very large font (see Figure 3). I’m sure this is helpful to those suffering from poor vision, but it doesn’t make the user’s obvious goal—calling the contact on the phone—any easier to achieve. Even with the giant phone number staring you in the face, you must still pick up the phone and manually dial the number, possibly making expensive long-distance mistakes as you do so.
Almost every other PIM introduced since 1984 has offered the ability to dial by modem, so why doesn’t Entourage? Picture this instead. Replace the magnifying glass icon with a telephone icon that opens a dialog box when clicked. The dialog box displays the local time where you’re calling (a very useful bit of info when calling outside your time zone), and gives you the option to pick up the telephone’s handset to dial the number by using the computer’s internal analog modem. Such a feature would reduce the physical effort needed to dial the phone and eliminate the possibility of misdialing. The needs of sight-impaired users could still be met by allowing them to set the default font size used in the preview pane.
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Figure 3 Jeez, thanks for the magnifying glass, Microsoft. How about actually dialing the phone for me instead?
4: Disastrous Deleting
If you have a folder selected in Mail and you click the Trash icon, an alert asks whether you really want to move the folder to the Deleted Items folder. Click OK and you can always manually drag the folder back out before its contents are permanently destroyed, but you can’t use the standard Mac keyboard shortcut of Command-Z to undo this action. That’s especially odd because if you had selected an individual email message and pressed Command-Delete, the undo feature works as expected.
At least there are ways to recover email that you accidentally delete. That’s not the case with Address Book contacts. If you’re editing a contact and you click the Trash icon (an easy mistake to make when you really meant to click the Remove icon to delete a phone number, for example), kiss your contact goodbye. There’s absolutely no way to recover your deleted contact and its information. The lack of a functioning undo command for destructive actions is inexcusable, especially since it’s possible to turn off confirmation dialog boxes in Entourage’s preferences (see Figure 4).
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Figure 4 Whatever else you do, don’t deselect the "Require confirmation when deleting" checkbox in the Notification pane of Entourage’s preferences.
5: Troublesome Time Zones
I guess the programmers at Microsoft aren’t allowed to travel beyond their cubicle farms, as only that rule would explain the Calendar’s inability to easily handle events that cross time zones. If you try to enter your departure and arrival times for a flight from Australia to the United States, for example, ostensibly you’ll be landing in the USA before you leave the land down under, which causes Entourage to balk (see Figure 5).
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Figure 5 Don’t you dare try to cross the date line with Entourage.
Not only is it annoying to have Entourage refuse to accept your perfectly valid start and end times, the dialog box is ambiguous because it doesn’t make clear that the program refuses to allow such events. In fact, it seems to tell you it’s okay. Better to alert the user to the potentially odd timing but allow it if that’s what the user wants. At present, the only workaround to this roadblock is to create separate Calendar events for your departure and arrival.
Lest you think I’m just being picky about a specific uncommon instance (international flights across the date line) where events are impossible to enter, Entourage also has trouble dealing with domestic flights. If you book a cross-country flight, the airline gives you the local times for your departure and arrival, so naturally this is the information you would expect to enter in a single calendar event. But when you travel to your destination and update your time zone in Date " Time preferences, Entourage adjusts the times shown in the Calendar to reflect your new time zone. If you forget that Entourage makes this adjustment, you might find yourself showing up for your return flight hours before (or after!) the correct time. If you don’t want Entourage to make these adjustments, the help file says that you should choose a different time zone from the Options icon, but Entourage applies the same time zone to the entire event, so there’s no way to tell it that you’re departing at 6 PM Eastern time and arriving at 9 PM Pacific time. Again, the only solution is to create separate events for a single flight. By the way, why the time zone is hidden in the Options icon instead of immediately to the right of the start and end text fields is beyond me.
6: Forgetful Find
If you choose Edit > Find (Command-F), you’re presented with the "simple" Find dialog box, which is almost always woefully inadequate for locating items of interest, so you click More Options to expand the dialog box into its "advanced" mode (see Figure 6).
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Figure 6 Entourage never remembers the state of the Find dialog, nor any of the search criteria you enter.
Let’s say you want to search for email containing Enter rage in the message body. Just as you click Find, you notice a misspelling in your search criteria, so you abort the search and choose Edit > Find again. Instead of remembering that the last time you chose the Find command you had expanded the dialog box to show more options, Entourage again presents you with the simple version. If that wasn’t annoying enough, your previously entered search criteria are gone, so you must start from scratch. Microsoft could simplify things by combining the Find and Advanced Find items in the Edit menu into a single Find item that remembers its prior state (simple or advanced) when chosen. In the meantime, I recommend using Menu Master to reassign the Command-F shortcut to the Advanced Find item.
While we’re on the subject of things I hate about the Find command, why is it that you must specify the scope first (subject, message body, recipient, etc.), and then the search criteria? If you inadvertently enter the search criteria first and then change the scope, kiss your criteria goodbye. Entourage erases the text field and you have to manually reenter your criteria. This behavior might be acceptable—or at least understandable—if Entourage retained separate criteria for different scopes, but it doesn’t.
Those are just a few of the things I can’t stand about the way Find works, but what really steams me is how unbearably slow it is to search for items. Microsoft, please implement Spotlight searching in Entourage ASAP! Apple got it right; searching should be so fast that there’s no need to waste time specifying detailed criteria to filter your results.
7: Restrictive Editing
It’s an unavoidable fact of life: People often send email with obtuse or blank subject lines, making it almost impossible to tell at a glance what a particular message is about. Unfortunately, Entourage’s editing capabilities do little to ease this common problem. Even if all you want to change is an email message’s subject line, you must first open the message by double-clicking it in the folder list. Then you must choose Message > Edit Message, place the cursor in the subject line, edit as desired, close the message window, and click OK to accept your changes (see Figure 7).
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Figure 7 Editing email in Entourage requires entering a special mode.
Microsoft’s engineers would do well to heed the advice given by interface guru Alan Cooper in his outstanding book, About Face 2.0: The Essentials of Interaction Design (Wiley, 2003): Allow input where you output. In other words, let users directly edit information where it’s displayed; don’t force them to enter a specific editing mode. Why can’t I make changes to the subject line directly in the inbox, or in the preview pane?
This applies to almost all other areas of Entourage, not just email subject lines. For example, if you see a phone number that you’d like to edit in the preview pane of the Address Book, clicking the number highlights it as expected. You can then copy the number to the Clipboard, but you can’t cut, paste, or edit the number. Instead you must click the person icon next to the record’s name, choose Edit this Contact, and then click the tab that relates to where the phone number is stored. (It could be either Work or Home; good luck remembering which.) Only then can you click and edit the phone number. It’s ridiculous to require users to jump through so many hoops to perform basic actions such as editing.
Oh, by the way, altering an HTML message in any way converts the entire email contents into plain text, thereby destroying the HTML formatting. I don’t expect—nor do I want—Entourage to offer full-blown HTML editing, but I should be able to change a message’s subject line without losing the HTML formatting of the message body.
8: Junk Email Protection Doesn’t Learn
Spam is the bane of all heavy email users. It clogs our inboxes with pitches for all manner of offensive products, and wastes our time and computer resources downloading, filtering, and storing the junk email. I’m the first to admit that the Junk E-mail Protection in Microsoft Office 2004 is vastly superior to what was available in the previous version of Office (see Figure 8). But, though it catches a lot of crap, it still misses a ton of stuff because spammers are constantly improving their techniques, while the Office 2004 defenses grow long in the tooth.
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Figure 8 Entourage’s anti-spam features don’t get better over time by learning from tagged messages.
Since email is integral to modern life, Entourage desperately needs anti-spam features smart enough to be trained to thwart the very latest junk email tricks. Currently, if you select a piece of spam and click the Junk icon in the toolbar, Entourage just classifies the email as junk and moves it to the Junk E-mail folder. Instead, Entourage should analyze the message to determine what characteristics distinguish it from legitimate email, and use this knowledge to prevent similar messages from getting by its barriers in the future. And users should have the option to share their spam profiles with Microsoft so that the company can offer its ever-improving anti-spam engine updates to all users.
9: Flawed Filtering
In the Address Book, if the filter pop-up menu is set to "Name contains," Entourage returns all contacts that contain the entered criterion—not only in the Name field, but also in the E-mail Address field (see Figure 9). Look, Microsoft, the pop-up menu is supposed to define the scope of the search. Don’t take it upon yourself to decide that we really should be searching other fields. If that’s a useful feature, allow us to specify those fields by exposing them in the pop-up menu.
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Figure 9 Filtering searches beyond the specified scope. Here Entourage lists a record that contains webb in the email field, but not in the designated name field.
Equally frustrating is that this oddball behavior isn’t consistent. If the filter pop-up menu is set to "Company contains," Entourage doesn’t extend the filter’s scope to the E-mail Address field. If extending the scope makes sense when looking for names, why not also for companies?
10: Toolbars Set in Stone
The toolbars at the top of all the main windows in Entourage are smart enough to hide and expose the text names to the right of the icons if the window is resized (see Figure 10), but what would be really helpful is if users could customize the toolbars. The Tools menus in Excel, PowerPoint, and Word all offer an option to customize toolbars and menus, so why not in Entourage? I never use the Flag or Projects features, but they remain stubbornly taking up space in my toolbar no matter what.
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Figure 10 All other Office components allow you to customize the toolbar, but not Entourage.