A brief look at Debrief


Today I want to look at a Windows* PIM application called Debrief. I’ve been intrigued by this software for several years, but its interface is a bit convoluted, and it is missing some key functions, so I’d start to use it then drop it. But I’ve started using Debrief again because I have remained unhappy with all the other business journaling applications I’ve tried. And this time I’m appreciating its many functions more, although I still have my reservations.

*For new readers, you’ll find discussion of both Windows and Mac software here, because I use a Mac as my own personal computer, but my day job requires me to use a PC.

First of all, let me clarify that there are three editions of Debrief (Pro, Standard and Free), and I’m writing today about the Pro version.

Debrief Daily Notepad

The Daily Notepad is at the heart of the Debrief "system."

The basic function of Debrief is creating notes that can be associated with dates, people, todos, references, outline items, projects, etc. You store your notes in folders, which you can create, rename and nest. There is one special folder called Daily Notepad. When you fire up Debrief each morning, it automatically creates a new note that is stored by default in the Daily Notepad folder.

Throughout the day, you can keep all your daily notes in this one document, then, at the end of the day “debrief” it. That is, highlight the various separate notes and transfer them quickly and easily to other folders. Or, you can write new notes throughout the day and categorize them at the time of creation. This in and of itself makes Debrief a nice, functional daily journal.

But there is a lot more to Debrief. I don’t have time to go into all its features, so I’ll just highlight those that standout to me.

Debrief Outline

You can create outlines as separate documents in Debrief.

Instead of a note, you can create an outline document to build hierarchical lists. This isn’t a bad little outliner, either. No, it doesn’t have advance features like hoisting or cloning. But you can add checkboxes and move items around freely. There’s a brainstorm mode, for rapid-fire item creation. And, you can create a note to associate with each of the outline’s items.

You might be thinking, “Any two-pane outliner gives you notes associated with an outline item.” That’s true, but the notes you associate with outline items in Debrief can be further associated in other ways. First, you put them in a folder. But you can also associate the note with a contact or with an action item (another Debrief feature).

Debrief Sarah Association

Associating a note with a contact in Debrief.

This leads me to another feature I like. Debrief shows you all your notes — title, text and date — associated with a specific categorization. So, for instance, choose the calendar view and select a date. All your notes from that date — no matter which folder they are stored in — appear concatenated in the preview pane.

Debrief Calendar Notes

All the notes associated with a single date!

Or, say Sarah Walker calls me. I can select her name from the contact list and all the notes associated with her will show likewise.
Debrief Sarah Notes

This seems to me a very powerful feature, one that will become more and more valuable as my collection of notes grows.

There are a host of other features in Debrief, some more successfully implemented than others. It also has some glaring problems. Glaring to me, at least. First and foremost is that there is no way to import contacts. I had asked about this feature a few years ago and was told that it was planned for a future release. However, responding to a recent inquiry, the developer sort of hemmed and hawed about it, so I can’t say it will be added, and that’s just crazy, in my view. Why make us re-enter our important contact information? Why force us to use two applications for managing contacts?

Another problem is that Debrief does not handle links very nimbly. And it does not appear to have the ability to add attachments to notes. For me, these are not important issues, because I’ve got PersonalBrain to handle documents and links. I use Debrief mostly for managing my own notes.

I’ve also found a couple of bugs — so far nothing information-threatening. And finally, the user interface is highly unintuitive, which, I think, turns off a lot of potential customers.

My purpose in writing about Debrief today isn’t to send people rushing to the web site to download the trial version — although you might enjoy giving it a spin. Debrief, even with its faults, has been built with a vision and with some imagination. I always appreciate that. I just hope it continues to be improved (last update was a few years ago, though the developer told me there was an upgrade in the works). With an interface tune-up and an import feature for contacts, Debrief could be a real killer application.

UPDATE: Using the Index Feature in Debrief

In response to the question in the comments, here’s a screenshot of the Index function in Debrief:

Debrief indes feature

Index works much like a tag. You can create your list of index “tags” or topics and assign as many as you wish to each separate note. When you switch to the Index function, as above, you can select an index topic and see all the notes that have been thus tagged.



  1. Thanks for another excellent debriefing (pun not intended) of an interesting piece of software. Debrief may just be what I’m looking for to keep an activity journal during the day and then classify the interesting bits and pieces to their associated spaces. Within this context, one thing I am not sure of is whether Debrief can use multiple tags to classify notes, or whether its folder logic is of the ‘note only goes to one folder’ kind, which would be quite a limitation.

    1. Hi, Alexander.

      Thanks for the nice comment. To answer your question, it does not appear that you can organize a note in more than one subject folder. You can associate it with with a person and/or a task. But there is also another way to give it multiple associations. That is using the Index function, which acts like tags. You can mark any note with multiple index tags, and then view all like associations. Admittedly, this is not the most elegant use of “tagging” but it seems to work pretty well.

  2. Steve, Thanks very much for such a detailed review. Debrief has an elegant design and is a very tempting proposition for veteran CRIMPERS.

    But as someone trying to extract myself from another neat journal program – iDaily Diary (FREE) – my first action was to see whether DB provides ways of exporting one’s entries, whether for a defined period or in totol. iDD has no such function (I should have paid more attention), although the paid version does. It looks as though Debrief’s “Reports” might provide the sort of export function I am after. Is that so?

    I noticed on outlinersoftware.com you mentioned Zoot 5 as another possible diary/journalling option. Do you have any more views on how best to set this up, given the limits on numbers of folders for version 5?

    1. Hi, Derek,

      I’m not at the office, where I use Debrief, so I’ll have to answer your question on Monday. As for Zoot 5 and folders, one thing to keep in mind about Zoot is you don’t need standing folders. You can just create a smart folder as you need it. For example, you could just have one main folder for keeping all your notes. You can add columns for specifying important meta-data, such as what projects each note might be related to, people involved etc. Then create smart folders as needed, which scan your notes for specific meta-data (or even just text). When you’re done reviewing the data in the smart folder, you can just delete the folder.

      You can also keep all your day notes in one database, but create smart folders that send copies to other databases based on criteria. So you could have one large “day book” type journal database, but also have databases for individual projects, if you feel the need for them.

      Does this answer your question? Also, if you purchase Zoot 5, I believe you are entitled to a free upgrade to Zoot 6 — which no longer has a folder limitation.

      Thank you for reading my blog and commenting!

    2. Hi, Derek,

      I just took a closer look at exporting from Debrief. It’s a little rigid, but you can get plain text or RTF documents from your notes fairly easily. Using the Reports function, as you surmised, generates output based on selective criteria. The caveat is that it all goes into one document. So, if you want to import the material into another application, you’ll have to figure out how to parse it. There is also a “Save Current Material to File on Disk” function, which is clever in this way: Which ever notes you have selected, get combined together into one file, but you can select notes as you prefer using the ctrl-click method. If you want and need your notes exported as individual documents, you will need to separately export each one, but this is certainly doable.

      1. Hi Steve,
        Thanks very much for the advice, and apologies for the delay in responding. I got caught up in a lengthy exploration of the pros and cons of using Ecco Pro for my purposes. I missed out on Ecco when it first came out as I was using Lotus Agenda together with Grandview. I gradually weaned myself from Agenda on to Zoot when I moved to Windows, but have continued to use GV for outlining. But I have always wanted to use Ecco for something, now that it free and so well supported by its users. Hence the delay.

        re Zoot: it’s a funny thing but I started to use Zoot in quite complex ways but have gradually simplified them as my work changed. Over the last ten years or so I have been using Zoot as a three-pane outliner for planning the arguments and contents of books and articles (along the lines of Jim Fallows’ methods), but probably with less use of smart folders. So I was very grateful for your reminder that Zoot is a lot more powerful than that. I’ll have a hard think about your ideas.

        I have been closely following the development of Zoot6, but with mixed feelings. I understand that PIMs have to keep up with developments on the web, but I have been disappointed that more attenion has not been paid to new ways of manipulating and organizing information – e.g. , (i) given that individual items can be displayed in their own windows, why not provide a way of moving them around and arranging them into a corkboard-like display; and (2) why is no outlining available within item notes. Both ( and I guess I am thinking of Scrivener here) would help the creative process along.

        Mainly, though, it’s the time this has inevitably taken. I am really satisfied with Zoot5. All I really wanted was for item and folder limits to be lifted (Apparently Ecco has its own limitations, too). I wasn’t interested in rtf editors, browsers, mailing fr0m Zoot, nor did I like the new icons that appeared with Zoot 5 and now 6, and which compromised its original plain-text elegance). Which is to say that I am holding off on moving to v6 until I have an overwhelming need to do so.

        Thanks also for confirming Debrief’s exporting options. Though not as powerful as Ecco’s, it means that they could if necessary be imported into Zoot with suitable delimiters. I’ll have to approach the developer to see if he is willing to extend my trial, which ran out before I could do much exploring. I must say, though, that your review of Debrief has really got my Crimping juices going.

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