E-mail File Folder Strategies for Outlook & Gmail Users

All right.

Well, hello everyone.

Welcome to today's videos. Uh, today I want to get in and talk about the 3 different dominating philosophies about email folder structures, uh, when it comes to getting organized with your email inbox and related folders. Uh, my name is Randy Dean. Uh, people call me the Email Sanity Expert. And obviously I go all around the United States, Canada, and even occasionally Europe, leading and teaching programs on time and email management and the related use of technology. So let's dive in and get in and talk about the 3 different folder structure philosophies that I see out there quite a bit. And we'll sort of talk a little bit about each of those folder structure philosophies and sort of the pros and cons of each. Now, the first one is what I call sophisticated, complicated, and some of you might even add on confusing. And what that folder structure basically does is it's one where you sort of basically sort of look at every single thing that you need and why you'd need a folder for it. And it's the folder structure I've been using for quite a number of years. And I'd like to sort of walk you through sort of what I'm doing with that folder structure. But there's some relatively new beliefs out there that maybe this isn't the best structure for every person. And so what I'd like to do is share with you a much simpler folder structure called the 3 Simple Folder Structure, and, or the KISS, which, you know, probably stands KISS stands for Keep It Simple, Stupid. So we're going to talk about that simple structure. And then the final structure is what email folders? And we'll sort of talk about, you know, the possibility of maybe not even having any folders at all.

And so let's walk through and talk through the pros and cons of each of these.

Now, like I said, I have been using the sophisticated, complicated, somewhat confusing folder structure for a number of years.

I've been using it ever since I started this business 15 years ago, and I used it for about 10 years before that. In the previous companies that I was working for. And in this structure, basically you create a folder for everything you want to keep.

Every client, every project, every activity, event, vendor, coworker, uh, subclients and subprojects within your individual client organizations, individual departments and people, uh, subprojects within each project that you're working on, um, the individual subprojects in your activities, events, etc.

I mean, basically If you want to keep something and you don't think there's a good natural place to put it, you make a folder for it. And what happens is then you'll end up with subfolders in your folder.

So let's take a look at this option.

I'm going to pop right now into my Microsoft Outlook, and as you can see, my inbox is really clean. Why is my inbox so clean? Because I've got my emails in my folders. And notice I have quite a few folders, and in some places I have folders inside of folders, and in some places I even have folders inside of folders inside of folders. Wow. Yeah, I got folders. Now, one important point right here.

I recommend you stop about there.

See how I've gone about 2 to 3 levels deep? I recommend to most people, don't go much deeper than that, because you go more than 2 to 3 levels deep with your folder structure, you're probably gonna not use it. And there's a very simple reason why. Where did I put that thing? You see, the minute you go more than a couple levels deep with your folder structures, it doesn't become sequentially more complicated, it becomes exponentially more complicated. And the more complex you make your structure, the more likely it is you won't trust your own structure because you won't remember where you put your stuff. And if you can't remember where you put your stuff, you're pretty likely to not put your stuff away. You know, this is, by the way, a lesson you could share with your teenager. And so what I want you to do here is build a structure that meets your needs in terms of complexity and sophistication without being so complicated that you're afraid to use it.

Now, I brought this up, I actually got challenged on this a few years ago. I was doing a session for one of my university clients, and one of the people in the room, I believe he was a professor, said, you know, Randy Dean, how many folders do you have? And what was interesting is I had never really counted all my folders and subfolders. I actually counted on the break. I have more than 400 folders in here. But here's the interesting thing. How often do you think I'm using search? Here and then I'm doing, you know, I've got 400+ folders. And what's funny is when I do my live sessions, usually I get a knee-jerk reaction. All the time. I set you up when I do that. The actual answer is maybe a couple times a month. Wait, a couple times a month, but you got 400 folders? Can you please explain? Yeah, let me explain right here. I teach an email management program, and within that program, I basically tell people, you know, if something— if an email is quick, get it done. If it's not quick, it goes onto your calendar task list. Then you either file it or you delete it. And if there's no place to file it, make a place to file and put it there. We're going to come back to that a little bit later. But basically, so what's happening is 75 to 100 times a day, I'm getting emails from different clients, customers, projects, co-workers, vendors, etc. I've got stuff coming in 75 to 120 25 non-junk, non-spam messages on a typical workday would be my estimate, which means 75 to 125 times per day I'm doing that little strategy that I just told you about. And what that means is 75 to 125 times a day I'm taking stuff from here and I'm putting them over in here. And you know what that means? I'm getting really good at knowing where I put my stuff. If you do something 75 to 125 times a day and you don't get good at it, you should probably quit. So, you know, I'm really good at knowing where I put my stuff. However, every once in a while, by the way, you'll, you'll be about ready to drag an email over into a folder. I'll say, whoop, whoa, you go way down to some other weird folder that you weren't expecting to go to. And so what's sort of interesting in that situation, you do— by the way, first notice up here the undo button. Uh, you might want to learn about your undo button or Ctrl+Z, which is the keystroke that can help you and save you with undos every once in a while. But also notice this. If I come up here to hit Search, watch what happens for my Outlook users. And by the way, I'm going to cover some Gmail tips in a minute too. Take a look at this. It doesn't just search the current folder you're in. It could search the entire mailbox, all subfolders, all Outlook items, all mailboxes even, by person, by subject, whether the thing has attachments, by category, etc. So basically you can go in and broaden your search or make your search more specific so that you can find your stuff if you have proper good keywords. And one little tip that I like to share with people, which many people don't think about, let's say you're about to put an email away. You really want to be able to find it. Maybe before you just file that email, consider whether if the email has a pretty poor subject line that doesn't really give you a lot of information, could you forward that email back to yourself, changing the subject line to important keywords like the person or the project or the client or the event that it's related to? Because then when you file it, you'll have an easier way to be able to search and find your emails by setting up a subject line which has better keywords in it. And then of course you can delete the original email because that one has the bad subject line, but the forwarded message has everything you need. So just a little idea right there. And now since I've got this in my Outlook, let's take a look at something else here with the structure, Outlook users.

Let's sort of just sort of see what I got going on here.

Notice first, look what I did here with these exclamation points before the name.

By using a special character.

That little trick, by the way, works in Google too, in the Gmail folders.

If you put a special character in front of the name when you name the folder, it supersedes alphabetization and it moves those things to the top. So you can get your most used or most important folders right at the top of your structure.

Additionally, as an Outlook user, watch what else you can do. You can do a right-click on any folder you have and Add to Favorites, which means it will be added to this very short list of popular folders up here.

So that's two ways you can get to your most used, most frequent folders more quickly. And let's take a look at this structure. Notice this exclamation point boss. That one of course is for my wife. There's my video programs, my book on Taming the Email Beast, my webinar programs, clients, competitors, consultants, email software applications and articles, marketing PR activities, prospects for the business, website activities and projects, speaker services and bureaus, vendors. I got a lot of folders here, big buckets. And then second level, individual clients, individual vendors, individual marketing PR activities, individual PR activities. Third level folders, individual departments within same said client, individual departments within same said vendor, subprojects within the main marketing PR projects or website projects.

And I stop about there.

So as you can see, what this does is this means it's a complex structure. It's a sophisticated structure, but it matches my work very specifically.

And because it does so naturally match my work, I know where I'm putting my stuff.

Okay, now that's the Outlook version. Let's pop into Gmail real quick because I want to show you something in Gmail here. This is interesting. There was a bad crash on US 127. I'm gonna get rid of that one, but I want to show you something else here. Take a look at this. Inside of my folder structures, if I page down, I can have a whole lot of folders. Notice there's more folders than this. Let's go to more and watch this. Look at— I've got the folders I'm using the most. It looks like what Gmail's doing is sorting those so that the ones that I'm using the most are near the top. But now if I page down, take a look at this. You can now have folders inside of folders inside of folders, even in Gmail, which by the way are labels, which are folders. Wait, what? Watch this.

This is—

especially if you haven't used Gmail in the past, this could drive you a little bit crazy when you first start using it. But I think it's crazy genius, actually. And it's actually something I like about Gmail a little bit better.

Watch this.

If I click on the message, now I get a whole series of potential options of things I can do with my Gmail items. And one of them is to label this email. Now notice here's the names of my labels, and down here I can hit Create New. And if I hit Create New, I can create a new label. But look at this, Nest Label Under. That's how you can make subfolders. See, here's where you're creating subfolders and sublabels. But now watch this. Look at the names of the labels: Anna Soccer, Taming Email Webinar, Speaker Match. Now watch this, folders: Anna Soccer, Taming Email Webinar, Speaker Match. Folders in Gmail are the same as labels in Gmail. Labels in Gmail are the same as folders in Gmail. If you move something into one of these folders, it gets this label. But here's the genius part of this. If you go to labels, let's say you want to put this one message in Anna Soccer Speaker Match and Taming Email Webinar and hit apply. This one email is now going to be in all 3 of those folders. And if you come over here in Archive, after you put it in multiple labels, it leaves the inbox. It's not gone, but it's in all 3 folders. And the reason that's genius is what they're basically doing is they're making it to where you can move emails into multiple folders and find it in any one of those folders. You ever had an email where you're like, what folder should I put it in? It could go into one, it could go into the project folder, the client folder, and the vendor folder. In Gmail, you can put it in all three. And see, what's happening in Outlook, what they do instead is when you have a message, you can come up here and categorize it. But these categories that you can create by hitting All Categories and, you know, basically renaming these color codes are completely separate entities from the folders. And so you could put something in a folder and it could have a couple different categories, and you could search by category but you can't go to all of these categories to find the email per se. You're gonna have to use that as a search capability in order to get your stuff. And so I actually think this capability where they're making folders and labels about the same, pretty darn cool actually. All right, so, so remember, as many folders as you need, dropping down a couple levels if you need to, to the level of sophistication and complexity that makes sense for you, but not so deep that you're afraid to use your folders because you can't find your stuff.

Okay?

So that's sophisticated complicated.

Now, let's go back and take a look at this. What about just 3 simple folders? And I call this the, the simple stupid strategy. Whoops. I jumped forward a slide. This, the simple stupid strategy is this. And, and, you know, I think that, like, David Allen and a few other thought leaders out there have, have have sort of posited that maybe this is a better strategy for some of the people that are out there. Let's go in and show you what I'm talking about when I say this. Watch this. Instead of all these dropdowns, what if you just had 3 simple folders? Take a look right here. Exclamation point active. That's for any email that moves into your task list or your calendar. You know, whatever needs to be done, it's going to be done in the future. And it's going to happen when you see it on your task list or your calendar. It's still active. !toarchive. That's for any email that you did whatever you needed to do with it. It's done, but you want to keep it for later reference. !tod delete. Pretty sure I don't need this one, but maybe I should keep it a couple days just in case. And that's where you move the stuff that you're hanging on to for a couple days just to make sure it doesn't pop back up again. But I mean, think about it, pretty much every, every email you have could go into one of these three folders. If it's on your Tasks or Calendar, it's still active. If you're done with it, but you want to keep it for later, it's archived. And if it's, you know, something that you're pretty sure you can delete, but you want to hang on to it for a couple days just in case, to delete. Pretty simple little folder structure. Now, of course, if you're going to put it into this simple folder structure, then you're going to use search or possibly even sort to find your stuff. Now, what sort? Let me show you something here real quick. I'm going to pop into my sent folder now. This is my backup sent folder, so it's very small. So I'm doing this to sort of protect, you know, privacy for people. But notice that you can sort by name by clicking on the From field, and it'll sort all of the ones with the same name. You can sort it by subject line. Now watch, that puts them in alpha order, but what that means is that every email that would have had "send" in it would all be right next to it because "send" was the first words in the subject line. And you can also sort it by size. So this time it does top, and if I click it again, it's going to put the smallest to the largest. You could find the emails with the largest attachments. And this capability of both search in Microsoft Outlook and sort in Microsoft Outlook make it pretty easy to find groups of messages. And what that means is you can find all the messages from a particular sender or on a particular topic or of a certain size. And you can find your stuff more quickly. And that's what you would use in here is both the sort capabilities and the search capabilities to find your stuff when you need it.

You only have 3 folders.

You don't have all these dropdowns.

You just have 3 folders.

Now that's interesting. Let's go back over here to Gmail real quick because what's interesting about Gmail is you do something slightly different. If you want to find a whole big group of stuff, you come into your settings and take a look at this. You actually click on Settings, and now what I'm going to do while I'm in my Settings here is I'm going to go and make a filter. And with the filter, now what you can do is create a new filter. And now watch this. I'm going to say I'd like, just like to see all the emails from me to me, and I'm going to hit Search. Now notice it doesn't just have to be from, it could be by who it's to, what's in the subject line, sort of the same as the sorting I just showed you in Outlook. By the way. Now watch what happens when I hit search. Watch the background.

There they are. All of the emails from me to me just popped up.

Isn't that pretty cool? So I can find all of those emails. And then of course, what I could do potentially is, you know, I could tag those to move them into labels and/or, um, you know, archive them if I want them out of my inbox. We're gonna talk about that more in the next video. So, so you've got a whole lot of this that's going on here that will help you with managing this stuff just a little bit better. And I wanted you to take a look at this kind of stuff because what it does is it gives you an option to do something much more simple. So instead of having all of these dropdowns, you could instead just have those 3 folders we talked about.

As a matter of fact, I could even see an argument for just one folder.

One folder. Yes. Let me give you this one folder option item that you might want to consider, which is this. What if you just had a folder called exclamation point done for now? Because think about this, if you got done what needed to be done with that email right now, aren't you done for now? And if you added it to your task list or your calendar to look at it and work on it later, aren't you done for now? I would argue that once you do any one of those three things, get done with it, get it on your task list or get it on your calendar.

You're done for now. And that means every single email after you do one of those three things can move out of your inbox into your Done for Now folder.

And then you'd use search or you'd use sort to find what you need when you need it. And by the way, little bonus thing, take a look at this.

If you do a right-click on a message in Outlook, Look at this right here, find related. So that means you've got another way to find the related emails to the one that you either sent or received or replied to or forwarded.

So you've got ability to find your stuff. And here's the whole argument, that means you can put your stuff away.

Now let's go back though. Wait, there's one more option here.

What about this?

What about no folders at all?

Warning, warning, Warning, Will Robinson.

Sorry about that very old reference right there.

But let me tell you about this.

I've actually run into quite a few people, they don't have folders. They just leave everything in their inbox. Let me tell you why I'm sort of against that for the vast majority of email users. The statistics have shown that the vast majority of people that leave messages in their inbox, even if they've already done what they need to do with that message, they are very likely to open it up and read it again at a later date because they can't remember if they did it or not.

Doesn't that sound a bit crazy?

I mean, that's pretty much the definition of insane. That's why I don't want you to do that. I'd want you to— I don't care if you do the sophisticated, complicated folder structure or the very simple folder structure that we've already discussed. But I do want you probably to have a folder structure of some sort so that you can move the emails out of your inbox once you're done for now. Now, wait a minute though. There's always an exception to every rule. I'm doing one of my client sessions. I'm in Las Vegas a couple years ago. I get stopped by a woman after I lead my session on email management at the conference. She goes, Randy, 'Got a question for you. What's the biggest number of emails you've ever seen in an inbox?' And I thought I had her. I said, '132,000,' which, by the way, that's a lot of emails in an inbox. She goes, 'Oh, I got that easy.' And then she shows me her iPhone, and the little icon on her mailbox on her iPhone says 248,000. I went, 'Whoa, you win clearly.' She goes, 'Yeah, but you want to hear the weird thing?' I don't think I need to change what I'm doing after attending your session. And I go, well, explain to me what you're doing. She goes, well, here's the thing. I've been just leaving them all in there. I've been using this account for like 15 years. I don't delete a thing. But here's what I'm doing. If I open the email and it's something I can either reply to or forward or take an action, I do that right now. If I can't do that, I put it on my paper task list. She ran— she made a paper task list every day. And/or it goes onto my calendar. So it sounds like I'm sort of doing what you want me to do. And I go, well, yeah, but one critical question: are you opening and rereading those messages again? She goes, no, once I've looked at it once, I know I've looked at it. I don't look at it again. I wait till the next message. And I thought about it for a second. I go, you don't need to change a thing. That'll work. She wasn't rereading her messages over and over again. She wasn't doing that critical flaw that so many people do She was just using her inbox basically as old email storage. I said, you know, from a productivity management perspective, I think what you're doing is fine. Now, you might run into a problem at some point where your email provider tells you that your email file size is too large and you need to, to move some stuff out just so that your account is reasonable. But from my perspective, if your email's running fast enough for you, keep doing what you're doing. She goes, I thought so. So Remember, there's always an exception to every rule, but I want you to consider the different folder strike types that are here. Once again, you can build it the way you wanna build it. I'm a pragmatist. I want you to use whatever's gonna work for you. If you think the sophisticated, complicated folders with dropdowns is gonna work for you, build it. You think a simple folder structure using search and sort will work for you, use it. You think you can leave 'em in your inbox and not read 'em a second time or third time or fifth time, by the way, Average person looks at their emails 3 to 7 times each. See, I really want you to watch yourself to make sure you're not doing that. And the easiest way to not do that is once you either get it done or get it on your task list or get it in your calendar, you get it out of your inbox. Out of sight, out of mind. All right.

All right. So we've covered a lot here. What I want to do now is finish this thing up. Now, this is a two-part video series that I'm doing today. This is the first part, is how to build your folder structures. And hopefully this gives you something that you want to, maybe even some motivation to go and start cleaning up your mailbox a little bit. But here's the interesting thing. My next video that I'm going to do is how to clean up a messy inbox fairly quickly. And I'm going to post both of these today. I want to do them as two separate videos covering once again, both Outlook and Gmail strategies on how you can clean up stuff quickly. If you'd like to find out a little bit more about me, um, go out to my website where you can find information about my programs and my speaking engagements, but also about some of my streaming full-length webinar programs and email programs. And just go to my website, randaldean.com. If you'd like to get a whole series of additional bonus PDF articles, look down here at the bottom, randy@randaldean.com, and put YouTube PDF in the subject line. You'll get a whole series of bonus PDF articles and tip sheets on time management, email management, you know, Outlook usage, Google usage, smartphone/tablet usage. And I'll send those to you by automated email. Imagine that. And of course, if you found today's tip pretty good, uh, excuse the little background dog barking that just occurred at the very end of the video, um, go ahead and subscribe to my channel. And, um, I'll be posting these videos every month or two, and you can get more tips on how to be more productive on a more regular basis. And once again, look in the links below, because in the links below I am going to give you the link to the video about how to clean up your mailbox more efficiently. Thanks. Bye now.