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:
- UV Outliner
- Inspiration
ScrivenerNatara Bonsai- Noteliner
- ConnectedText
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).











