Classic Outlook: Master Right-Click Options & Email Rules for Peak Productivity (Microsoft 365 Tips)

This content was created by Randy Dean. This content was uploaded by Randy Dean. This is a YouTube tutorial titled "Classic Outlook: Master Right-Click Options & Email Rules for Peak Productivity (Microsoft 365 Tips)" (uploaded 2025-10-28). It’s a single-speaker instructional presentation demonstrating Outlook right-click menu features and how to build rules: making copies vs. labels, quick print, reply/forward etiquette (don’t overuse Reply All), using BCC, favorites/junk handling, reporting phishing, blocking senders, using Ignore, adding labels, moving vs. copying to folders, and creating rules to highlight messages (pop-up alerts and custom .wav sounds) for specific senders or domains (example repeatedly uses “Randy Dean”). The speaker also covers advanced rule conditions (importance flags, subject keywords, sender domains), auto-labeling/auto-forwarding cautions, and practical email etiquette and urgency best practices. The presenter invites viewers to subscribe and provides an email (randy@randydean.com).
Chapters
I'd like to know when this Randy Dean guy's sending me a message. So I'm going to right-click on this email. Now notice I've done a right-click. Look at all these right-click options. Timeout. Let's go through a few of these first. You can make copies of your emails if you wanted to put them in multiple folders. I would argue that's a silly thing to do because you can add multiple labels to the same email as we showed in the last session, thus meaning you can search to find the original email. You don't need to make multiple copies. It is possible though. Here's Quick Print if you wanted to send that thing to PDF or actually print it on paper. Here are your reply and forward options, which you can also do from obviously right here. Stop using reply all, please. Now, what's funny is when I get into my session, I go, you and you and you. I even got in trouble once. One of my clients said that, or one of the attendees, he was yelling at us. I was making a joke, man. Come on. It's funny. Stop using reply all. But, Here's the thing. Um, people way overuse reply all. Let's do a quick little email etiquette tip right here. Did you know you can stop your reply alls if you're about to send and you don't want everybody using reply all? Don't put the whole group distribution in the to field or the CC field. Put that group distribution of all the people in the BCC field. If you put it in the BCC field, Then if the recipients in that field try to hit Reply All, it's only going to go to the names in the To or the CC field. So put your name in the To field, your name and email, all recipients in the BCC field. And if you want to be really snarky, don't put your name and email in the To field. Put your favorite coworker's name and email in the To field. That's a good tip. All right. So fun stuff. Notice here's your Unreads and Flags, which I'm going to say you don't do anymore. Turn them to task, turn them to calendar using the drag and drop in each version of the software as we've already shown. Um, here's your labels. Notice you can right-click on an email to add those labels, and you can go down to all categories and get your entire list and add multiple items in here like streaming programs. Let's add that one too, and Hit OK, and it just added another label. See, look at 2 labels now instead of just 1. Right-click. You can also come down here to Move, and it's going to show you labels that are— I mean, folders you've recently used. But if you want, you can come to Other Folder and get right to the folder that you want. We showed this in the last session, um, but, uh, the one that I really wanted to show you here is I'd like to know when this Randy Dean guy sends me a message. No, wait, wait, I got one more. I gotta show you. Notice down here is your report phishing, report junk. Um, your IT might have a specific way to do this. If they give you a specific way to do it, I would use that specific option. If not, I believe this goes to the Microsoft, uh, people and they will then, if enough people report that same message, hopefully either block that sender from sending future messages, especially if they're phishing, or send them right into your junk mail folder. Now what's interesting, notice I favorited my junk mail folder. Why? Because every once in a while even a real client message ends up in here, and thus I can see the number And if there's anything more than zero, at least once a day I open it to see, did something get in there that shouldn't be? Usually I open it up and just delete what's in there because they are junk. But by having this as a favorite, I can see it and use it better. Um, notice also you can block the sender right here. Block sender, never block sender, never block sender's domain. Right, um, never block group or mailing list. You've got options in here. Wherever you see the little side arrows, always see what they got going on inside those side arrows. Okay, um, the one that I did want to show you before I get into the rules is right here, ignore. And the reason I wanted to get to this one is let me give you the specific example of when I think this is a really helpful tool. You get the group message goes out to everyone. Hey everybody, Betty's birthday today. Make sure you wish her a wonderful day. And unfortunately, the person who sent it did not attend my class, so they put the entire group distribution in the To or the CC field, not BCC, which means everyone's going to hit Reply All. To send their note to Betty. But I want you to be better. Here's what I want you to do. As soon as you get that email telling you it's Betty's birthday, forward the email. Don't hit reply all. Forward to Betty. Write your personal note to Betty. Betty, have the bestest of days for me. Eat some cake for me. Then go back to the original, right-click, and hit ignore. Because if you right-click and hit ignore on that same message, the original, now everyone hitting reply all to send their little wishes to Betty, they don't come into here. They go right into your trash can. You're welcome. Booyah! When you get included on a list that you don't need to be part of, of any future conversations, you can set up an ignore and they won't even come into your inbox. You're welcome. That's not the tip. I want to know when this Randy Dean guy sending me an email. Let's go down here to rules and notice always move messages from Randall Dean or to Randall Dean. They're giving me an option to make sure that those always go into where that place is. I don't want to do that though. That's an auto file. Um, I need to see the messages from this guy because sometimes I have tasks and if they get auto-filed, I might not see them at all. Right here's what I want you to go to: Create Rule. Because when you create rule, and I'm going to show you the different version for new and web here in a minute because it's a little bit different. Um, here's the rule wizard and this is the top screen of the rule wizard. Notice down here is advanced options, but right from the top screen, I'd really like to know when this Randy Dean guy sends me a message. So what I can do is say, well, if it's from Randy Dean, notice you can also do it on does it have certain words in the subject line? If it's from Randy Dean or has certain words in the subject line, and it doesn't have to be the entire, the entire subject line, let's say you just want to have just the word Copilot. If you see it says Copilot, you want that to pop. Or be auto-deleted or be auto-filed. We're going to show you all these. Auto-labeled. Okay. But you can do it by just specific words. I'm going to turn that one off though. I want to know when Randy Dean sends me an email. Right here, I can display in the new item alert window. Timeout. I believe we mentioned the Microsoft Department of Not Terribly Intuitive in the last program, but if I did not, this is a point where the Microsoft Department of Not Terribly Intuitive decided to jump in once again and, uh, do something to their software that makes it a little bit hard for people to understand. And, and I'm a firm believer Microsoft, when they are about ready to launch a piece of software, uh, out of their headquarters out there in near Seattle, before it gets released to the public, has to go through review in the Department of Not Terribly Intuitive. And if the department are not terribly intuitive, says, this is too easy for people to understand. We can't do this. Um, we really need to make this a little bit more tricky. They'll add in something. Here's one of them right here. Display in the new item alert window. What's a new item alert window? It's a popup. Microsoft. Every other human on planet Earth that uses a computer calls these things pop-ups. Call it a pop-up so we all know that it's making a pop-up. You can have a pop-up when Randy Dean sends you an email. Nice. And see, if you do that for all of your most important people, as well as all emails that have certain subject line words, those will pop up on your screen. Notice this: Play Selected Sound. Oh, right now it's Windows Notify. I think I got my sounds turned on. Let's see if this comes into the recording. If you didn't hear it, doo doo doo doo, that you've been hearing for years and years. However, notice I could come over here and hit Browse and it should go right into your C drive on your PC. PC's media folder. And if you go into the media folder on your C drive and you page down, you'll start to see a whole bunch of little .wav sound files. This is Alarm 6. So let's right-click on this one, because if you right-click on it, it gives you the option to play with Media Player. So now you can sample some of these and hear what the sounds are. So let's see what this one does. It's going to load up the media player in Windows. That's not a bad one. So you could take this one if you heard it was— dun dun dun dun dun dun dun dun dun. Nice. For some reason now I got dun dun dun dun dun dun dun in my head, but I digress. You could set this as the standard sound So I'll hit open. Now when this guy sends me it, I'm not getting the doo doo doo doo. I'm getting the doo doo doo doo doo doo doo doo. You could set these up so that when this special person or this special email comes in, you get a pop-up from that on your screen and you hear a unique sound. I would say set them both up because You— what if you're not there when the unique sound plays, but you have the pop-up? You left your desk, you come back, you went to the bathroom, went and grabbed a cup of coffee, you come back, still got the pop-up. You know, oop, got the message from Randy, better look. Cool. That's what you do for your most important people, most important messages. But wait, there's more. Let me turn these off. By the way, little funny thing. If you have your own little sound recorder, Voice recorder, you could create your own little sounds. As long as they're .wav output, you could load them in, put them in your media folder, load them in. So instead of that you've been hearing for years and years, you can put this one in for your boss. Don, don, don, don, don. Now I'm going to tell you something. If you're working in the same office, it's funny. But every time they send an email, that sound goes off. At some point they're going to figure that out. So, you know, use a little caution. But that is fun. Let's go to advanced. I'm going to turn these off. So it's from Randy Dean's, my condition selected. I'm going to go to advanced. Let's dive into this a little bit more with nuance. Let's say your boss watched this video too, and they're an enlightened supervisor. She watched the video and she goes, This right here is a good idea. I'm going to share this with the team. Some of my emails are more important and urgent, but not all. Some of my messages are just normal messages, and if they get to them when they get to them, that's fine too. Well, look at this little, little micro tip. What if it's from Randy Dean marked as importance? Now, notice wherever it looks like it's a little bit of a web link, it's not really a web link when it's here in Outlook. You click on it and it gives you the ability to specify the level. Let's say your boss sends something that's marked high importance and you hit OK, right? And then you go to next. Then what you can do is play the unique sound. And let's see, I think it's down here. Low display, new item alert window. You try the desktop alert also, see what that is. So they give you a couple of— now remember, these are way down at the bottom, but you see what you can do here. You could set it up so that if it's from your boss marked high importance, those are the ones that give you the special notifier. Everything else from your boss just goes in and it gets handled with normal email processing. Timeout. Would that be a good discussion point in an upcoming staff team workgroup meeting? Hey everybody, some of our emails are more important or more urgent than others. What if we set up rules in Outlook so that when we are sending to each other high importance emails, Those are the ones that have the pop-ups and sounds. Everything else just goes into inbox properly. And I have to get on my soapbox here. Listen closely. If every email you send is marked important, none of your emails are important. You're welcome. Seriously, don't overuse it. Use some discretion. Only mark them important when they're truly important. Now let's go back because there's another wrinkle to this. Notice this: specific words in message header. This might be where you could put in, for like urgency and criticality, like ASAP or urgent. And you could make an agreement with everybody on your team. Hey, if it's got ASAP at the front of the subject line or urgent at the front of the subject line, Why don't you put in like both the pop-up but also a very different sound so you know, ooh, this one's hot. But I'm going to tell you this, I'm a big believer you really shouldn't rely on email for super urgent messages. If it's truly urgent, you can definitely hit send on that urgent email. But man, I would immediately be picking up the phone or walking over and finding the person too. Because the problem with sending emails that are super urgent is what if they're not there looking at the screen and it's got to be done in 10 minutes and they're not there, they're physically not looking at their email. It can't be their fault in 10 minutes when it doesn't get done because they're not looking, they're not there. They're stuck in traffic out on the highway. You got to follow up with a second form of two-way communication. Not just emails, a one-way communication until they hit reply. And if something gets messed up before they see it, I'm a firm believer that's the fault and responsibility of the sender for not closing the loop in an urgent situation. All right. Didn't think you were going to get into email etiquette stuff here, but I hope you see that all of this is an effort to Help the most important stuff pop, be seen, be acted on more quickly, but not having to look at all of everything to see if it's one of those most important things. Reducing the distraction. Now wait, there's even more. Let's say you're working for a critical client organization, one of your most important clients, or a critical vendor working with you very in-depth on a major project. And you don't want to just have it be by this one person, look what you could do. You could turn that off, come down here, specific words in sender's address, and then put in the @domainname.com for your client's company and/or the vendor company. And then what you can do is if it's from the client company or the vendor company, maybe you turn off the importance. Every email they send will have a popup and sound, even if it's not your lead primary contact. Yes. Can you do it for your lead primary contact too? Absolutely. But this way you'll know if it's anybody from that same organization. But wait, there's more. What if that organization is a spammer or that person is a spammer? Next. Did you see it? Permanently delete. You can also delete. If you do delete, it goes into your deleted folder. If you use permanently delete, it's gone. It won't even be in deleted items. Now notice this auto label. You can set up auto labels like if it's one of your key clients, Every email they send, you could automatically label it client. Um, notice this, uh, you can do auto-forwarding. Be careful with that. Um, you can also— now notice this— move copy to specified folder. Let me tell you what this one's for. Let's say there's a person that 95 times out of 100 They're sending you the monthly e-newsletter or monthly internal weekly update, but 5 times out of 100, they send you a real email that you actually need to respond to, attend to, deal with. You don't want to automatically move that one into your e-newsletter folder. What I would recommend is move copy to specified folder. So everything that from that party is going to go into that specified folder. But it'll also come into your inbox. Now, if it's the newsletter, you can just delete it because you know the copy is in the folder, but that way you won't miss the one from the person who's sending you a legitimate email, not just the newsletter this time. Now, of course, there's a second option. You could do it based off subject line and move to specified folder, especially if every time it comes in, it has the same certain words, timely tips. At the somewhere in the subject line. Well, those could auto-file into the Timely Tips folder and then you block time on your calendar maybe once a week to go review Timely Tips. That's my e-news. Send me an email, Randy@randydean.com. Hit subscribe. Wow. I hope you see all of these options and I would recommend coming in here and looking and seeing and playing around with some of these. Um, now let's get out of here.
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