Announcing the OneNote Smack Down

Just for the heck of it I recently Googled “best outlining software for windows.” I was surprised that OneNote was the consensus opinion on several forums. I like OneNote, and I think its outlining function is reasonable, but the best? I had to put this to the test.

I’ve chosen five other outlining applications for Windows to square off against OneNote. These applications meet the following criteria:

It must be an outliner in the purest sense of the concept

This means that it must facilitate the quick capture of thoughts and ideas. It must make it easy to organize and reorganize those thoughts and ideas in a hierarchy. And it must provide reasonable export of that material to other usable formats, notably RFT and/or Word documents. UPDATE: I am precluding fine applications like UltraRecall and MyInfo, because these applications do not facilitate straight outlining, at least in my view.

It must be a living application

The developer must still be developing and supporting the application, which excludes good outliners such as EccoPro and NoteMap.

So which applications make the cut to challenge OneNote for the title of best outliner for Windows? Here they are:

I’ll explain my selections as I cover each of the contenders in depth in subsequent posts.

Here’s how I’ll be judging them:

Ease of use (40%)

I’ve given this the most weight, because in my view the most important factor in an outliner is how easy it is to forget that you’re using it. That is, it must become transparent as you’re banging out thoughts and ideas. I don’t want to have to stop and think about which key strokes will allow me to move a sub item from topic A to topic B.

Outlining features (15%)

Outlining software generally provides outlining features; that is, automatic line labeling; level styles; cloning; hoisting and others.

Export power (25%)

Few outliners are ends in themselves. They are usually the first stop in the planning or writing process, while your brilliant ideas and glowing prose are on their way to being polished in Word or some other writing program.

Bonus features (10%)

These applications all come with a wealth of features, some of which prove very useful in outlining, among these are inline text notes and various forms of meta-data. Those applications where these features facilitate outlining, will get extra credit.

Overall feel and functionality (10%)

All these criteria are admittedly subjectively rated by me, and this more than the others. Essentially, this could come down to me just thinking how fun and inspiring is this application.

So let’s start with the designated title holder, OneNote.

OneNote – Brash Cassius Clay or Aging Ali?

OneNote, of course, is the information manager from Microsoft Office that uses a notebook metaphor. You organize your information in notebooks, which can have different sections (which are like tabs in a paper notebook). Each section contains pages. On each page you can store notes, images, documents, sound files and more. You can annotate and draw. And you can even create an outline.

Ease of use (40%) = 75 (30 points)

On one hand, OneNote is easy to use as an outliner. Just click on any page, start typing. Select the numbering option off the Home menu. Use it like a type-writer. Indent, outdent and the numbering is altered nicely.

Here are my issues with this, however. Indenting can only occur when the cursor is at the front of the line. Otherwise ON interprets the tab character as you wanting to create a table. (This is a nice feature, but not when reviewing ON as an outliner.) You can drag and drop topics or topic groups to new locations, but there is no keyboard shortcut for doing so.

Additionally, ON does not support extended selection. This is a little crippling in the department of making the application transparent. If you want to select groups of words, you need to carefully place the cursor at the start of the group and drag to the last character of the group. This takes more focus than just double-clicking on the first word of the group and dragging to scoop up whole words — as most word processors including Word operate.

All in all, creating an outline is not hard. It’s just not as easy and fluid as it can be.

Outline features (15%) = 65 (9.75 points)

OneNote does a nice job labeling topics, and adjusting as you move them around. It gives you the option to customize the labels, so they will look any way you want them to; although, I found this feature quite confusing and haven’t yet figure it out.

The program does not offer the ability to customize font style for various levels. So, for example, it won’t automatically make all second level topics bold, underlined. Also, there is no hoisting or cloning capability, and you can’t fold topics or hide subtopics.

Export power (25%) = 85 (21.25 points)

OneNote gets a pretty high score for export functionality. You can export to both .doc and .docx formats. As the screen shot below shows, the .docx export (right) is a bit cleaner. ON also exports to PDF, XPS and web page formats, but I do not count those for this test, as the point is getting the outline out of OneNote and into a writing environment for clean up. Also, it does not export to OPML, which would make it a little easier to import the information into other outliners.

Documents created from OneNote export: .doc export results on the left; .docx export results on the right.

Bonus features (10%) = 85 (8.5 points)

OneNote has some nice bonus features for outliners. Notably, you can set up OneNote to share an outline for collaborating with colleagues. You can also add check boxes to individual topics, along with other meta-data tags.  OneNote also integrates well with Outlook, sharing task and calendar information.

Overall feel and functionality (10%) = 75 (7.5 points)

I think I could get used to using OneNote as an outliner, but it doesn’t have the fluid feel I look for. It works. It gets the job done. But it isn’t inspirational to use. I know that sounds a little hokey. I’m hoping that what I mean by inspirational will come to be clearer as I review. I think it may be a better outliner for use in project planning, especially with its Outlook connection.

Total points = 77

It looks like OneNote gets a solid C-plus rating. Not great for the reigning champion of outliner-dom.

I am hopeful that the results of my test will lead me to another champion in the outliner category (which, I know, makes me a less than objective reviewer).



One of my interests is writing and information management software. Perhaps using the term “interest” is misleading, as I am sort of obsessed with these types of applications, and have been since I got my first computer, one of those early Compaq “portables.” Around 1989, I bought a license for an application called GrandView. GrandView was a DOS program that combined outlining, word processing and task management. It had some features that were cutting edge at the time, some of which remain unmatched in modern software.

In this entry to Welcome to Sherwood, I want to explore my favorite features of GrandView, because many people have never had the chance to see GV work. So let’s begin:

On its face, GV is a basic single-pane outliner. That is, you can view all of your information in a single window. (Outlook, for example is generally a three-pane outliner, in which you have your list of folders in the tall, slender left pane, your list of e-mail headers in the upper right pane, and the content of any single e-mail message in the lower right pane.)

Here is a screen shot of a basic outline created in GrandView (I’m running it on VM Fusion on my MacBook — thus the status bar along the bottom of the screen):

Basic Outline in GrandView

Basic Outline in GrandView

Notice that headlines I.A, II.A.1, and II.A.2 have little down-pointing arrows at the end. This indicates that there is a document associated with those headlines. We can view those documents in a dedicated document window:

Dedicated document window in GrandView

Dedicated document window in GrandView

Document view is essentially a hoist to view just the text of the document. (Note that the odd cursor blocks in this and other screen shots are relics of using GrandView in emulation mode in Windows XP running on my MacBook.) I always liked this feature of GV, because it is like switching to a dedicated word processor to work on this one section of your outline. But one of the most powerful features of GrandView is the ability to see the text of your document inline with the rest of your outline:

Document text viewed "inline" in the GrandView outline

Document text viewed "inline" in the GrandView outline

An important point here is that this text is not a separate headline or node. It is directly associated with a headline and can be viewed inline (as above), in its own window (as in the second screen shot), or collapsed and not visible in the outline (as in the first screen shot) This visual flexibility is a powerful feature for writers, because it allows you to switch from a focussed view of your writing to the big picture. You can work on getting each section of the text right, then make sure the entire work flows smoothly with appropriate transitions. Two-pane outliners (such as MyInfo and Ultra Recall, for example), force you to keep your writing in separate, discrete blocks. To this day, no other application has matched GrandView for providing this combination of powerful outlining tools AND single-pane, inline text.

But GrandView had other impressive features, ones ahead of their time. First of all, it had all the outlining tools you could ask for, including hoisting, collapsing, mark and gather, and others:

GrandView provides a host of outlining tools

GrandView provides a host of outlining tools

It also provided advanced meta-data capability to help you organize your work. Here’s a basic list of tasks:

Task list created in GrandView

Task list created in GrandView

But now I want to organize this random list. I’ll start by turning on the Category Display (see the bottom of the screen):

GrandView with Category on

GrandView with Category on

Date and Priority are default categories that automatically attach to each headline. I created the category “Role” in order to separate my tasks into my three roles: Work, Home and MIC (the latter being a nonprofit organization I volunteer with). I can now fill in the due date, priority and role for each of my tasks. But to help me with this, I can have GrandView automatically assign a Role category based on a rule. Here I’ve created a rule to assign any headline with the text “MI” to the Role MIC.

You can have GrandView automatically assign categories

You can have GrandView automatically assign categories

Once I’ve assigned data to all the categories of each headline, I can now quickly filter those categories in the Category View:

GrandView filtering all headlines with Priority category set to High

GrandView filtering all headlines with Priority category set to High

GrandView showing me all the headlines with the category Role set to MIC

GrandView showing me all the headlines with the category Role set to MIC

Those of you into the GTD method of managing your day, can instantly see how GV would be an excellent way to manage your daily tasks.

Switching to Calendar View, I can now view tasks based upon the day they are due:

GrandView in Calendar View

GrandView in Calendar View

And when I want to get an overview of the date, priority and role for all my tasks at the same time, I can turn Columns on. Category data for each headline is then displayed in columns (which I can select) on the right:

GrandView with Column View turned on

GrandView with Column View turned on

It shouldn’t take too much imagination to see that GrandView’s incredible flexibility made it an exceptional tool for all kinds of work. When I was using it daily (up to about 15 years ago), I created an outline I called Mission Control. Here I kept a list of my major projects, daily tasks, and reminders. I created individual outlines for each of the projects, and used GV’s linking ability (common now, but pretty radical for DOS) to create hot links from my Mission Control to the project outlines. Some projects were task/milestone heavy, some were writing heavy. I could manage it all in GrandView.

GrandView was abandoned by Symantec at the dawn of the Windows age, and has yet to be matched. EccoPro by NetManage had outlining with powerful meta-data, but did not have GrandView’s document view nor its powerful outlining controls. And, it too has been abandoned (though it still has a dedicated group of users). Scrivener on Mac has its scrivenings view, which allows you to combine separate documents into one long view and edit them. But Scrivener has a weak outliner, and no customization of meta-data fields. NoteMap was a fairly powerful single-pane outliner, but it didn’t offer document view or meta-data or true inline text — plus it appears that development has ended on this application, as well. OmniOutliner has user-definable meta-data and columns, as well as “inline text” but this latter feature is very weak. You could manage tasks very well in OO, but I don’t think you’d ever try writing anything of any length.

Of course, GrandView had its deficits. It was only developed for about five or six years. It never had the advantage of being a Windows application, and existed before anyone had ever heard of the Internet or e-mail. All I can do is imagine how terrific this application would be if developed today with the same imagination, consideration for the end user, and innovation.