Business Insight Zone

Step 1: get a sharp knife.

Just kidding — but you DO need to sharpen your readiness to delete & file old e-mail in double time.

WHAT YOU’RE ABOUT TO DO: Clear out your Outlook “Sent Items” box.

WHAT YOU’RE GOING TO END UP WITH:

1. An empty “Sent Items” box, for whatever that may be worth.
2. A list of things — or a clutch of e-mails representing a list of things — for your follow-up.
3. A deep sense of inner calm? (Maybe — YMMV.)

HOW TO DO IT STEP BY STEP:

1. Go to your “Sent Items” file.
2. Sort by message type. That’s this icon:



3. Go to one end or the other of the mailbox (use the “Home” or “End” buttons) when it’s sorted like this, and you’ll find all your Outlook meeting responses — the messages sent automatically when you hit “Accept” on a meeting invitation. Once you’re there, delete all of them. This has no effect on your calendar — these messages are just sitting there taking up visual space.
4. Re-sort by date. Click on this . . .

   

   . . . until it shows the newest messages first. Make an Outlook folder called something like “Old Sent Mail” and move every sent-mail message older than, say, two months to that file. That way you still have it if you need it, but it’s not blocking your field of view.

5. Start at one end or the other of the timeline — I like to start with the most recent messages — tossing trivia as you go. Just use the “Delete” key wantonly here. Crucial concept: don’t open messages at this point. Today I threw away seven messages from last week that bore the subject line “Lunch?” Even though I didn’t open them, I’m positive none of them held the secret to a Grand Unified Theory of anything. Sometimes it’s most useful to go through the entire “Sent Items” this way, just trashing obvious junk so you can cut down on the clutter.
6. As you travel through time in your “Sent Items” box, pause when you come to a particular topic (2009 Budget, the new marketing campaign) or a particular correspondent (your friend Liz, your mom, Bill from IT), then toggle on “To” or “Subject” as appropriate to find all the messages in the box with that subject or from that person.

   

   Then take ALL of these messages — everything on the 2009 Budget or from Liz or from Bill in IT — and file it in one Outlook folder or another. If it’s a delimited project like the budget, make a dedicated “2009 Budget” folder if you haven’t already. If Liz only writes you notes as your friend, not as your colleague, drop them all in a “Friends” folder. Bill’s messages can go in an “IT issues” folder. It doesn’t have to be perfect — folders are easily to merge or split later.

7. As you do this, some projects will be easy to file. “Oh, we submitted the budget,” you’ll say to yourself, and you’ll be able to file the whole lot with no mental friction. But for other things — current projects, ongoing conversations — you’ll realize there’s more to do. When you have this realization, open up that thread of conversation, starting from the most recent messages (i.e. the messages that are likeliest to contain the backstory of prior messages).
8. As you look through each message, figure out if there’s anything pending, and figure out if there’s anything you need to do about it.
9. If you need to take action on it, file it in a folder labeled “#Action.” (This is my version of David Allen’s “@Action”; putting a hashmark or at-sign at the front will force the folder up to the top of the file alphabetization order.) You don’t have to do anything about it now — just file it where you’ll see it later. THIS, by the way, is the step that has saved me from embarrassment many times, because it is here that I figure out when I’ve dropped the ball and need to pick it up again.
10. If someone else needs to take action on something, file the e-mail in a folder labeled “#Pending” or “#Waiting-for.” This file could become your new best friend: you can just check it as often as needed — twice weekly or whatever — prompted by an Outlook reminder, and you’ll amaze everyone with your ability to keep up with everything.
    Key distinction: if the person you’re waiting on is still within limits for doing the thing you’re waiting on, leave them alone. But if it’s been a while, send them a reminder now: when you have the e-mail open, just hit “Reply All” so that it will address them and include the prior conversation; delete every other recipient (including yourself); and write a one-line ping at the top of the new message: “Hey, Tom — just curious where we are with this. Can I help?” Once you’ve sent it, don’t forget to file the original message in the “#Pending” file so you can follow up again if need be.
11. Repeat steps 6 through 10, singly or in rotation, until you’ve gone through all the messages in your “Sent Items” folder. This should mean that you’ve flushed out any hidden items that either you or someone else should be working on but might have forgotten.
12. Set a recurring Outlook notification to remind you to sweep “Sent Items” again in a week. It gets much easier if you do it regularly — and you stay even more solidly on top of your projects.
13. EXTRA CREDIT: Spend some time going through the “Old Sent Mail” file you created and dividing its contents among appropriate files. Doing this sometimes lets you uncover older, completed projects that you could politely follow up on with vendors, freelancers, or colleagues in other offices. When you reach this point, sweeping “Sent Items” extends beyond personal project management into the care and feeding of your professional network.

BENEFICIAL SIDE EFFECTS: If you stay alert while you do this, you might gain insights into, among other things:

• How well (or poorly) you use e-mail to talk about and track projects, and how you might do it better.
• The e-mail habits of your colleagues, with a better sense of who needs more contact, who needs less, and what kinds of messages they respond best to.
• Your overall e-mail management system, including how you use and organize folders (or fail to) and how well you delete cruft.
• Your overall approach to tasks and projects. Do you work better in bursts, one or two projects per day? Or when you touch each project every day / week / month? Are you bad about putting things off? What works to jog you toward prompt action? The list of questions like this is endless, and working with the actual facts of your project communication, message by message, is a great way to gather data for your ongoing research on how you work best.

HOW OFTEN YOU SHOULD DO THIS: As often as you find it useful. I’ve gone through spells when I’ve done it once a week; this is incredibly useful when you have a lot of competing projects on tap. At other times, I’ll go a month between cleanouts. It’s up to you, and there’s not a wrong way to do it. The point is to give yourself a productivity boost using a method that will have your “Sent Items” cleared out in half an hour.

So, once you’ve tried this . . . did it work? What did you uncover? And what tricks do you you use to stay on top of your projects?

~

(Knives photo by kompressor.)