How do you manage your mail?

3 months before I moved out here and started working at Microsoft, a friend of mine told me: "KC, you need a pilot... because you have the organizational Zen, but not the tools required to implement it". Little did I know that I would shortly find that tool, and it would be Outlook. I apparently give off an impression of being on top of the little things, because I recently had a coworker ask me how I kept track of all the things I needed to do and follow up on (that's one of the major focuses of any PM job is following up on things, and a release manager is a sort of PM that does even more tracking and following up on even more things). I'm not a follower of David Allen (at least, not yet - I own "Getting Things Done"  but haven't gotten around to reading it), my system is just something I cobbled together over the years based on what I learned about myself.

Many years ago I read the results of a usability study about Outlook that talked about broad categories of how customers manage email, and at the time there were two main categories - pilers and filers. I am a filer, meaning that I have many folders that are project or topic-based (and are usually organized in some hierarchical fashion), and I sort inbound email into those folders if I might need it later and use search or manually browse to the folder later when I need to retrieve them. In my case, the sibling folders to my Inbox are things like:

  • Mailing Lists: All mass mailing lists go here, including lists like the check-in emails. I do expand the node periodically and glance through the lists, but generally if something is in this folder, it can safely be deleted.
  • News: All of my RSS feeds are stored under here, and I have a couple of search folders that look in a subset of these folders.
  • Email: I send out a weekly email to the Exchange team detailing what's going on in the team and the project. Throughout the week, as I find things that I want to include in my mail, I stick them in this folder. Come thursday evening, I sort through the folder and put together the draft of the mail and then delete the items from this folder.
  • Saved: Everything I want to archive but not remove from my mailbox goes here. This includes a folder for account numbers and confirmation emails for expensive items I want to track, a folder called "Organizational Changes" where I save all of the hello and goodbye emails from everyone (as well as the birth announcements from my coworkers having kids) and other miscellaneous things that I don't refer to often but like to have around. I periodically archive this to a PST that I then leave copies of on several machines.
    • Also under Saved is my kudos folder, which is where I store every email where someone paid me a compliment, big or small. This is a great thing that I find incredibly useful during rough times (or review time, for that matter!). I never archive this folder to a PST because I like looking back on it year after year. For example, when I was a tester in Outlook, I spent a fair amount of time one weekend helping a customer by writing VBA macros to make Outlook's IMAP support use the standard Outlook deletion model (i.e. rather than 'mark items for deletion' and then purge the folder, have a deleted items folder where all the deleted items go and then empty that one at will). The customer was so grateful that they mailed my boss, who forwarded it to his boss, who forwarded it to his boss, all the way up to Steve Sinofsky. I still get a huge kick out of re-reading that thread. The best part was, I had a blast doing it, because it was a project I'd always wanted to do on my own but never got around to it.
  • Seattle Trip: This is a temporary folder. My entire family is coming out to visit us in a few weeks, and I'm keeping all of the email about the trip stored here for easy retrieval.
  • Areas: This is my main subfolder hive. Underneath "Areas", I have 5 subfolders covering the top few projects I'm working on. Each of those 5 has 3-20 subfolders underneath it. One of the 5 folders is Release Management, and I store reference material related to being a release manager there (such as email threads from the internal project managers distribution list with useful info on how other product teams manage software projects, etc).

Pilers are people who tend to keep all of their mail in a single folder (usually the Inbox) and rely heavily on sorting and also search to find the mail. So a piler tends to have many items (I peeked over the shoulder of a coworker once and saw that he had 22,000 unread items in his inbox) in a single folder and is constantly sorting on the from/to/received/size/etc and performing searches in that folder. Pilers also frequently have very large deleted items folders, because they use deleted items as a way of storing things they don't need right now but may in the future.

Here are some of the other strategies I use to stay on top of things:

  • My "create task from email" macro. I use this for items that I need to remember to do, but there's no real deadline. I do set a reminder but only to keep it in my face, not because the due date is really that important.
  • My custom named colored flags. Right now I'm using all 6 flag colors: 3 are project based, two are general work ones (one is "things specific to release management", one is "everything else") and one is for personal/family issues.
  • My search folders. I use a few key search folders such as looking for my name in the body of email sent to mailing lists I read.
  • I try to move items out of my inbox as soon as I'm "done" with them. If I needed to do something based on the email, I usually do whatever I need to do and then delete or file the item. I sometimes flag it for later or keep it marked unread.
  • If I need to do something and there is time pressure, I will put it on my calendar and force myself to not use that time to catch up on email or other issues, but to focus on that to-do.

I'm far from perfect and it's still very possible for something to get lost in my inbox when I get overwhelmed (I really should get around to reading GTD, hey I know what - I'll create a task to remind me to do it!), but for the most part this system works fairly well for me.

There's no "right" way, each system has its ups and downs and not all systems work for all people as there's a heavy human element in any organizational zen. On that note, I really enjoyed this story from an anonymous associate of mine who is an Exchange administrator:

A few years ago I was moving a big wig's mailbox to another server. When I opened his mailbox to spot check it, I was horrified to find the inbox completely empty. I did find everything, but it was all in his deleted items, something like 2 years worth of stuff. I figured it was some weird glitch, so I moved it all back up to his inbox. After he logged in, he called me on the phone and asked me why I screwed up his "system" of keeping all his important emails in deleted items.

Comments (17)

  1. Nicole says:

    I would never use "deleted" as a folder to keep important mails – because "delete it when closing" is a default I have run into one to many times.

    I use folders for some special things I can sort in there (like announcements, or mails regarding a special topic), rest goes into "ablage" which is the "to much effort to sort out more".

    Most of my mails can be sorted out into year.pst because they are done after a usual year.

  2. Mike Griggs says:

    LookOut is your friend! It’s an absolutely essential product. I no longer have to waste time sorting things into separate folders.

    The biggest issue that I found with the "lots of folders" approach is what to do when a given e-mail spans two or more different categories. Then you end up wasting time digging through a folder that you *think* it should be in, but in fact you filed it somewhere else as it could equally belong there. Finally you end up using search functionality anyway.

  3. Shrink says:

    Great post KC.

    I am planning to reorg my mail folders as your recommendation. I invite you to see my post


    "Writing good email" (

    I hope you will have few good comments to make.


  4. Peter says:

    I love the story about keeping the mail in the Deleted Items folder.

    It reminded me of a coworker who never had anything in his Inbox either. I noticed unusual messages in his Sent Items folder. I asked him about it and he told me he manually moved all his incoming items from the Inbox to the Sent Items as he was done with them.

    He was under the impression the Sent Items folder was for items sent TO him.

    I was never able to convince him otherwise and he continues to work that way.

  5. KC Lemson says:

    Mike: I use lookout, and i still find separate folders useful. For me, I don’t see search entirely replacing sorting. That’s why gmail drives me nuts. The truth is that i’m quite good at sorting and i almost always find what I want without having to search.

  6. Tommy says:


    Would you be able to point a reference to the VBA IMAP macro you described? I gave up on using Outlook for email at work because of the IMAP mark-purge behavior.

    Thanks for all your insights into what you do!


  7. Jonathan Payne says:

    It would be nice if each folder had an option to trigger the new mail notification or not. For example, something that is filtered into a mailing list or spam folder shouldn’t put a new mail icon in the task bar (as it is unlikely to require timely attention) while unfiltered should cause a notification.

    This would really help with the way I use(d) Outlook as there is some mail I like to read right away and some that can wait a while.

    Perhaps this is already possible?

  8. KC Lemson says:

    Tommy: I have long since forgotten or deleted the code (and it wasn’t that good anyway). Basically it did things like changed the views to hide items marked for deletion, changed the delete button to do a delete and a copy to a server-side Trash folder, added an ’empty trash folder’ button that purged deleted items, etc. I didn’t get too fancy and do things like trap the delete key, it was a proof of concept.

    Jonathan: In Outlook 2003, the desktop alert is far more configurable than that annoying little envelope icon. You can use rules to say which items should and shouldn’t display the notification for example.

  9. Cindy Winegarden says:

    Have you discovered any way (such as Search folders) to combine POP3 and IMAP messages into one Inbox? Not being able to combine them prevents me from making better use of my IMAP accounts.

  10. Ed Hobbs says:

    My biggest headache has always been the Send Items folder. The option require you to either keep a copy of all sent items or none. I would like an option to prompt me, after sending a message, if I would like to keep a copy in Sent Items.


  11. tom says:

    Out of interest, what mailbox limits do you have at MS?

  12. KC Lemson says:

    Cindy: Well, you could have a rule to move items you download via POP to your IMAP inbox…

    Ed: It’s possible to specify this on a per-message basis in the Options dialog when you’re writing a message.

    Tom: I currently have a 500mb limit, but that is higher than most employees, the Exchange team is in a separate forest and has slightly different rules compared to most MS employees.

  13. Steve says:

    One of the problems that we have is that, especially with OL2003 and the new PST file size cap (20gb), is how we are going to back up these monstrous files. We actually have a desktop backup solution provided by Veritas, but it cannot handle the PST files (even though it does block level backups). Would it make sense to provide some sort of standardized API when installing Office (ala how the backup API gets changed with the install of Exchange) to allow for incremental backups of PST files or is there a better way to go about it?

  14. Weinan Hu says:

    Nice job, KC!

    I really want to know the difference between LookOut and the search feature in Outlook 2003, which in my opinion is good enough for me to find every mail I am looking for.

  15. Stewart Whaley says:

    Weinan: LookOut is all about SPEED. It can quickly find any text in your e-mail (or Contact, etc.). It’s a LOT faster then Outlook’s search feature

  16. Weinan Hu says:

    Thanks Stewart! I will definitely try that then.

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