Managing Calendars - GTD Summer Series Part 4 - Episode #309 of CloudFocus Weekly

Machine transcript generated in 2026 from the episode audio (Whisper speech-to-text with automatic speaker separation). Speaker labels are automatic and may be wrong in places. Timestamps shown every few minutes.

00:11 Jason Atwood: This is the 309th episode of CloudFocus Weekly for the last week of the summer, August 2019. This episode is titled Managing Calendars. I'm your host Jason Atwood, joining me co-host for 309 times in a row managing all his life commitments and calendars, Justin Calendar Edelstein.

Justin Edelstein: How you doing Justin? Hey, yeah, I screwed that up, didn't I? Yep, but I caught it. Caught it on the fly. I just fixed it. Well, it's here. It's here that it's messed up. It's right here. See this? Oh, got it. I didn't see that one. It was messed up in two places. That's really great. Yeah, well, that's how good I am 309 times good for you. So what are we talking about calendars here? Huh?

Jason Atwood: So fourth last of our summer series for your Productivity not over though. It's almost nah end of August That's just a date on a calendar soon as football starts summer is over I'll start. It's a crazy, crazy summer, but we'll talk about that on next podcast.

Justin Edelstein: Good thing I have all of the games that I'm attending on my calendar now.

Jason Atwood: Because after our last podcast, we talked about commitments and you captured it. All right. So we kind of started into this last podcast when we started, when we were talking about commitments and we were kind of talking about the GTD side of the non-commitment, the non-time-based commitments. But we did kind of touch on calendars. And, you know, in the GTD world, the calendar actually is really important. I like to use it as my starting point for teaching people about GTD, just giving them the aha moment of, hey, you do this thing all the time. Here's what you do. Here's what it would feel terrible if you didn't do Just do this but with this other tool another tool which is fine and with this other set of stuff and here's how you do it because people are so trained and Through whatever that they know calendars they know to use them.

Jason Atwood: They know what to put on them So we're not going to talk about like how to handle a calendar. We're gonna start we're gonna talk about sort of like

Justin Edelstein: Some do's and don'ts, some best practices, some maybe Well, I think the calendar, in and of itself, is a really useful tool. And I don't necessarily feel there's a wrong way to use a calendar. Oof. It and it's just my feeling on it. I know, I know because you have very strong about by this. What is, you know, what the best part about the calendar is that it does take those time-based commitments and allows you to see them in a way that is super meaningful. So now I'm looking at my calendar, you know, here we are today. You know, the, the end of August. Yeah. I was going to say the, you know, the early part of the week. last week of August. And I can just look at my calendar, very quick scan and, and tell you,

04:18 Jason Atwood: It has a time. It's happening, I One of my favorite things about being good with a calendar, and I consider myself pretty good, again, we'll talk about tips and tricks and things. We can even talk about this family calendar, which is something I wrote a blog post about.

Justin Edelstein: Family calendar is great. Freaking seven years ago or something.

Jason Atwood: But the one thing about being good at calendars is actually being good at commitments. So here's why. Ever had a time, well, I won't make fun. Go on. You may as well go ahead and ask for it. Ever had a time that you ask a friend to do something on a certain date and you're like, yeah, I can do that. And then they go, they say, sure, great, I can do that. And you go, great. And you go, okay. And then, you know. It's terrible, right? You feel like on one side, a friend, like, I'm not going to trust you when you see when you see. the You know in that's why I'm captured that thing. I was like wait.

Justin Edelstein: I'm missing a Large, large number of For us you and I particularly Those a the and a I Those Sundays are sort of committed like that's it and I need to know like ahead of bam Am I gonna be home?

Jason Atwood: They I I And then you share between the two of you. Then, and you can intermingle it, the best part is you can intermingle it with other calendars, you know, because Google can do that, you can overlay calendars together. And then here's the system. You put into it events that are happening to you in the calendar. You're like, oh, that seems very simple. But it's all about the naming convention. It's all about the subject. And here's the way I do it, and I'll just tell you. So one is, I put the initials, Well, first of all, if I throw something in the calendar and it just has the event, let's call it a vacation in, or let's call it Disney vacation. Yep. Right? Yep. That means to everybody involved, we're all doing it. We glared at it.

08:05 Jason Atwood: We're all doing it. That's the three people in the family,

Justin Edelstein: The wife, the child, and the me. The example I just gave you was on the family calendar and it said Trombone Shorty and it had a location.

Jason Atwood: Tanglewood great. So that's so the first part of the naming convention is if if it's just if it doesn't have anything in front of it It means everybody in the family. So you have three people four people five people you're all going to you're all doing it So if you have three kids everybody's doing it's a vacation is something that everybody's doing it Then you have a what if what if two or three people or two of the family members are doing it or One person's doing it. Then you put your initials at the beginning of the calendar event. So for example I have jma forward slash hja colon camp. That means my daughter and I are going to camp. That means the other person in the house is not going to camp. So when she looks at the calendar, she goes, Oh, he's going to camp.

Jason Atwood: If it's jma colon, you know, drinks with Justin, that means I'm going out with drinks with you. if it's jma forward slash sha colon you know, date night in L.A.C. That means her and I are doing it and the daughter is not. Yep. Right? So it's super simple, but it works because you could quickly scan your calendar and know who's going to what event. Yep. And you don't have to have all these questions. We put in things like workouts, like if I'm going to go for a long run on a Sunday, she's going to go to a class, SHA spin class. We do the same exact JMA long run. It just means that if She wakes up in the morning and I'm not there and gone for an hour and a half. I don't get a text like freaking out.

Jason Atwood: She goes, oh, right. He's going for a long run. Or there's a kind of now and there's the bonus of it that you can set up. Now I called does this is why I stick to iCloud. I worked on your calendar. And it actually does it. It's much better now used to send you an email. It's kind of annoying. But now it just sends you the word on your calendar. So in your on your thing, and it tells you if something's been added,

Justin Edelstein: Or deleted, or changed, you decide how you want that alert show. And it's great.

Jason Atwood: Because then if if someone throws on JMA slash sha, you know, colon Vietnam like you know in December 2020 I'm like oh looks like we're going to Vietnam, right? So and if they change if it's because a lot of times just things that made she's going out for drinks with a friend and then the plans get changed instead of like having that it just I'll get an alert to tell me the plans change we don't have a discussion about it we don't have a text string yeah it just tells me And deleting means it's not happening anymore. in the calendar event, in the name, you can put it at the beginning, you can hold whatever, but the idea is you're telling the other person, hey, I'm not 100% sure on this plan, but I'm putting it so you know it's there so we don't schedule anything around it.

11:21 Jason Atwood: Precisely. That's it. You can put TBD, you can hold, you can put block, whatever you want, but the idea is you're kind of telling the other person it's tentative. Now, you have to be good enough! GTD to go and unremove that because you don't want to have the argument of well you said TBD and then like you whatever you didn't go or you do anything like you should remove the block as soon as you know it's real.

Justin Edelstein: Sometimes we'll like when it's like a there's just two of us so it's very simple it's a J or an S or it's a nothing. Right.

Jason Atwood: That's nothing in front of it. No B? No B. no J slash S B. The cat doesn't get to be involved. No.

Justin Edelstein: He doesn't get a choice. What's that choice? He just knows he's going to the vet. He doesn't have a calendar. He can't read. To my knowledge, he can't read. Oh, but maybe. But what we'll do is use it as a way of like nudging or nudging I guess. where we'll throw something on and instead of saying hold your TBD, we'll just throw like five question marks at the end. It's almost like instead of even asking you, I'm literally throwing it on the calendar. Yes. And this is my way of asking. Yes. Because I really want to do this, but with you, like not alone, not a J, whatever, cause then I'm just. Oh, there's a blank time in the calendar. Good, I'm doing that. It's more of a, we-We're doing this together, maybe if you agree.

Justin Edelstein: And it's like, then she'll see it. And she will move the question marks. Or we'll go back and forth and discuss it. We'll delete it. We'll have, she won't just, that's the rules. You don't just go in there and delete it. And those, well, those are the boundaries, right? Yeah. So it's, yeah, you can throw anything you want on the calendar. there. and you can throw holds and question marks and all sorts of things, but if it's a hold or if it's a question mark, we need to discuss whether we're gonna do that like in a timely fashion.

Jason Atwood: I mean, obviously this is with someone, you know, who you are in a relationship with. Yeah, you don't do this with everybody.

Justin Edelstein: This is a personal family calendar. Like I don't even really have my own calendar at this point. I do, I very rarely use it. It's for hidden things. Exactly.

Jason Atwood: That's just about the reason at that point. So you say, how do you put the hidden things? So I have eight, so I do not have, I have one, it's called personal. It's in deep red because it almost never anything goes on it. Yep. Mine's in orange. But I will put things on it that like, like I know actually for my birthday, my wife got me tickets to... Oklahoma. Yeah, and so she literally after giving me the gift she goes, oh and she goes, oh great now I can move it. And so she went into on her phone and then just moved it from one calendar to the next. I've done that too. Like if I get her like a massage or something I'll just, I'll put it in there so I know it's there and then I'll move it to the next calendar when I've given the gift.

Jason Atwood: So a great way, it is a great tip. I will tell you it has saved us from So many fights, so many miscommunications, so many, oh my goodness, you didn't tell me you were doing X. And it gives us a good, it's kind of like the ground. You can say, hey, the calendar is the place you put it. You can have a discussion about it. It's not the end all, it doesn't take over discussions. So it's not like, JMA, Vietnam, three years. It's like, what? Okay, see ya. Oh, I see you're going to Vietnam for three years. That's not a thing. It still has to have a conversation if it needs it. But it is a great way of keeping and knowing where people are. It also is easier when you go to schedule things.

14:52 Jason Atwood: Oh, I see that person is doing that. You know, sometimes I'll say some of the conversations we'll have are, Hey, I see you're like going to concert tomorrow. Then you're going out for drinks with your friend. Then you're going out for dinner the next night. Are you sure you really want to be going out three nights in a row? Aren't you going to be a little tired? because the next day we have to do X. So sometimes it's a little bit of a reminder of Your maybe you know your life partner. You're like, hey, maybe you're kind of over, you know, you're putting too much in there Anyway, that's the family calendar. Let's talk some let's talk some stuff that should go into calendars Okay, so there's a GTD stuff GTD actually says there's three things that should go into calendars.

Jason Atwood: Okay,

Justin Edelstein: I disagree with one of them Okay, what are you let's go through what you disagree with? Well, let's go to the two things that time-based events we just discussed that all day notices. Okay, so those are the I'm gonna be out of the office or just busy today or not around whatever it is. Yes, so for me like with my kids at camp.

Jason Atwood: I have one that spreads the entire summer that's her in camp. It's not I'm not at camp. I just need to know that she's at camp. If you were to go on vacation, I might throw yours or your boss goes on vacation. You might just throw it as an all day event for three weeks, you know, boss on vacation. It's just to remind you that something's happening over a period of time. Yes. Right. And things that are on all day notices like you could put an anniversary or birthdays. Those are things that are trips. So you put us all day. Yeah. So you could see it up there.

Justin Edelstein: You look in the future. Oh, you check that all day thing. So it's not like don't just make it from like 8 a.m. to like 5 p.m. three weeks from now. Please don't do that. Just check the box. This is all day event. Some people do that. I know. And we have. But we just checked the box.

Jason Atwood: We checked the box. We checked the box. But GT and then there's block time that goes into calendar So sometimes you want to block something you a want someone else not to take your time That's a whole nother discussion about allowing people to take your time I don't allow people to steal in this society, but whatever but if you if One of the techniques that we like to do is if someone says to you. Hey, I got some time for you next week Yeah, how about Tuesday at three? Wednesday at four or Monday at five, I will then go most likely and put those events hold and I'll put the name of the person because I want to make sure someone else doesn't, you know, I don't I or I forget they don't get back to me.

Jason Atwood: So sometimes I'll block sometimes we have like all day people coming in for interviews like tomorrow or months ago. I'll just throw a block just to know that that's what's happening and then I'll put all the things in it as it comes up. Those are all great, right? The one that he, the one that they will say is things that need to be done on a specific day. That's the one that I disagree with because I think that's where you have a better tool for that. You don't need to put specific day things on a calendar because it doesn't scale well. It doesn't scale well because you might have 30 things due on that one specific day. Then your calendar, you look at the top of this just like covered in all these little things.

17:56 Jason Atwood: Two, they're not connected to what the thing they should be connected to. They should be connected to the larger outcome. In the calendar, they're not connected to the larger outcome. So therefore it's kind of failing. You should have a to that connects your things that are due to your watch our outcomes, right? And it's also, it's hard, it's hard to renegotiate those. Like what are you going to do? Drag and drop them all to the next day. Like what are you going to do? Delete them when you do them. It doesn't make sense. So I think day specific tasks, that's still in your task land. So that's why that's an actually disagree with the GTD methodology.

Justin Edelstein: There is a satisfaction. Two crossing things off, right? There's a real response. It makes you happy to accomplish the things. It's like it's not that hard. Like sometimes things are just not that hard. You just have to break them down to the smallest possible thing that's the next action. Those things going on a calendar you don't really get the satisfaction of crossing the thing off. And then defining the next thing that you have to do, which is very satisfying and gratifying, and it moves the needle. It gives you that perspective of, I am moving this project forward. This is not that hard and hairy. I'm just taking it.

Jason Atwood: Action at a time and I'm gonna get there. It also then also doesn't allow you to get It's really when people didn't have really good, yeah, good tools because because that again, I think in

Justin Edelstein: The OmniFocus episode, I said I live in the forecast view because it pulls my calendar in. Yep. So I've got my tasks and I've got my calendar. I've got all the things I need to see. for that day and I can scroll through and look at the next day and scroll and look at the next day or I could just click today and just see today. All the things I need to do today are on my calendar and in my task manager and that's it. It's just great. Drag and drop it to another day. Sure. Oh, you know what? I don't need to do this right now. I can do this in a week That's right. I want to do this thing with you. Do we need to do that today? Well, no. Let me ask him about it next week.

Justin Edelstein: Right. It's not, it's not that important or it is truly important. I must ask, but why is that on a calendar? Like not until we say, okay, we're doing that thing. When are we doing that thing on this day? Great. Then it goes on the calendar. So let's talk about some best practices of calendar events.

Jason Atwood: Sure. Let's do it. Calendaring and managing calendars. First of all, I would suggest that you almost always, always ask to put things on someone else's calendar. I know we live in a world where you. You can just throw people. People things events and just throw counter events at them. I don't think that's a good practice. I think no matter what you should have an agreement in advance. Hey, is this time work for you? And it takes a little bit extra time to write that out and to email them or text them or whatever, but I think it's a better practice. I think it's better to ask somebody for their time than just to throw some random thing on their calendar and not express it. So what I would suggest is the best practice. Spend the time.

21:25 Jason Atwood: And if it's important enough to have an actual meeting, then spend the time to actually figure out when someone can be and get their buy-in and not just have it show up as a meeting invite they click on. One, two, the format of the calendar invite is important. Putting in, you know, meeting in the subject line and no agenda and no dial-in is terrible. You should always provide something in the subject that when I'm looking at my calendar, it makes sense. Who and what who is in this? Company names people and what what is this about remember these things are searchable these days Yeah, throw the who and the what in the subject so we can understand so anybody can see it and go whatever it's about and what it's about in the subject.

Jason Atwood: Because again, that shows up in me in the calendar in the top level. It also shows up in your mail so you can go back and search on it. So find it. Search is important. Two, put agenda. Put something in the counter event that indicates. So I get the big level. Can I just stop? Oh yeah, just for a second. He just gave me hand signals. Well, yeah, I just wanted to stop you there.

Justin Edelstein: Well, for one, just for one second. Yeah. We're talking about, now the naming goes across life. Even family calendars, we're talking about the naming convention was important. Very important. But I don't ever really put an agenda in a family calendar item. Okay, so let me just make that very clear that you are talking about work right now. Now through this course of this summer series, we've been talking about work life integration. And this calendar is a big part of it because of the overlays that you're allowed to that you can do right with Google Calendar And you can just bring you can subscribe to calendars bring them in and see them on top of each other So that you're not just looking at your work calendar when someone asks you if you can meet well You might have a dentist appointment, right?

Justin Edelstein: Which you may not want on your work calendar because who needs to know that you're going to the dentist You might just throw a three hour block block not available, but you might not right So that's the point is to be able to see them both now what you're talking about It's really a work calendar thing so that when you're working internally or externally with you know, your your Your co-workers or maybe your clients or maybe vendor of yours whatever it is That it the expectations are clear when the meeting is accepted that there is a purpose and there's a desired outcome of that meeting. And if it's not understood why that meeting exists, you really shouldn't go. You shouldn't have a habit. Well, it's just don't even bother. Like respond back and say, hey,

Jason Atwood: What are we talking about? It serves two purposes. One is when you get the meeting invite, you can quickly scan it to see what it's about. What's in this? The second is the invite could be a week from now. When I get to the meeting, you're gonna forget and I click on it on a Friday and I'm doing America review and I'm scanning my calendar. Like I should be able to look at any calendar event and know what it is about. That's why I don't have to put an agenda in my family one because it's kind of already there. Pretty easy in the name. Right, but I'll tell you the more difficult it is like when When my wife travels and she throws her flights in the calendar, she puts in more information. She puts in the flight information.

24:52 Jason Atwood: She puts in the confirmation number, right? She puts in stuff that makes it easier for her to click on and for me to click on. If I want to track the flight, make sure it gets in, whatever, whatever. So it's just really putting better information into the calendar event. and more. If it's a big meeting with lots of involved stuff, it should have a huge, it should have a lot of time put into it. We were talking about the GDD Summit. The amount of information that was put for this two-day meeting was tremendous. Huge, day-by-day breakdown things, speaker bios, whatever. Right. They didn't just send out a meeting invite for two days called summit and enjoy. There's a huge website and then a collaborative document built on top of it.

Justin Edelstein: So allow you to see what was going on with the event. A 15 minute check-in call, quick subject,

Jason Atwood: Dial in number, check in on project. Cause you just do it, right? You scale it to the size of the thing. So... Put in the meeting invite, put the way we're meeting. Is it a call? Is it a s Google Hangout? Is it a, like there's too many meetings that I get that just don't have you. Then you click on it, you know, you're five minutes before the meeting, like getting ready. I okay. Let me go. Oh, there's nothing in because someone provided the dial into this call. Come on. Like seriously, people grow up, put something in there. a--, Get these groups to just the people to a

Justin Edelstein: And the Sure, you want to listen to all the people But at the time, the chances relenting to a consensus among are way lower than the two people agreeing on a thing and moving forward. And remember to remember,

29:03 Jason Atwood: Right now. Here's my go-to meeting. Let's I do it. Like, let's just do it. Let's just say it's just saying intentional and sometimes it's. Sometimes the best not a meeting. There's so many other solutions that the other thing is like sometimes it- When people do work, they do it by themselves, right? People don't do work together. In most services industries, yes, if you're a builder, two people are holding a ladder up you. don't have two, They're weird. Or even writing the same trigger at the same time. They might be writing different parts of the trigger or a class and like a test class or a front end and a back end, but generally they're writing separately because you can't,,, And then work is done apart. You bring the work together and it creates the outcome.

Jason Atwood: So meetings aren't about doing work. They're about reviewing and making decisions about what work should be done. make sure not to wait into that meeting to get the work done. Don't make a meeting out in five days to review something you could reviewed yesterday.

Justin Edelstein: I could go on forever. So You're actually using my quote. Oh you rate you made that one wasn't this guy Tom no good for you that's a great one. I just me back to myself back to you just one the podcast one the five.

Jason Atwood: Six nine times winner winner chicken dinner anyway.

Justin Edelstein: It is the weaving. watch me do this. That is work getting done in a meeting. But that is not high level, highfalutin thinking, like what needs to happen, that can't really get to the bottom of all that. You can't get to the doing. Yeah. You're meeting about a thing.

32:33 Jason Atwood: The use calendars as... Thanks, that's a good one. Steal that. They steal it. Borrow it. Most people use these meetings as crutches. They use them as ways of deferring things. They use those ways of... of not getting things done, I, really, like people to start to use meetings for just what they're meant for and realize that the work happens, the work, the actual work happens in those blank spaces of your calendar not in the ones where you have the back-up meetings. So, one other trick or tip of calendar management is confirmations, so here's a trick for you. For anybody. The role you. Yeah, the role you. If you have people in your life, clients, customers, people, bosses, family members, who are the overwhelmed ones, the stressful ones, they don't know, they're overcommitted, they have the 17th, they have the email, the calendar pounded full of stuff.

Jason Atwood: They're the ones who almost always cancel at the last minute. it. Like. Learn to check in your GTD. Here's a thing you, do you looking your calendar weeks in advance? I check in I have friends who are like this I have a few of them who you make a plan and then it's like, you know The two days before the plan and you say hey we still want for Tuesday Because you know, they're the kind of person like oh actually go So you have those other people in the professional world that you know are just kind of flaky, so I suggest you adapt to them and you check in with them. So if I know this is super flaky, I check in on them a week in advance. Hey, we got the calendar event next Friday.

Jason Atwood: We're going to meet? Yep. Yep. We're on. Then I check in on them Monday. Hey, it's Monday. Still on Friday. Yep. We're still on Friday, Thursday, day before. Tomorrow we're meeting at nine o'clock. Are we all good to go? Sure are. And maybe if I'm super crazy, it'll be on the Friday morning. Hey, meeting a couple hours because honestly I don't, you know, if they're going to cancel, I'd rather them. I'd rather them cancel in advance so I can free up my time. Anyway. All right. So meetings the best it's ever been.

Justin Edelstein: Justin quoted me. That was the best. I really enjoyed that quote. Good, I'm good for you man. You came up with that like on the spot while you were like listening to that guy talk. Yeah. There's another one in there. It's very good.

Jason Atwood: Anyway, all right. Well, that's it for our summer of series. You've been GTD'd. You've been GTD'd. You've been done.

Justin Edelstein: We'll be back in the next- Done, done, done, done. I really want that.

Jason Atwood: In a couple weeks, we'll be back. We'll probably hit some more news, catch up on anything else sales forsy that happened in the summer that we didn't discuss. But until then, and we'll come back with our picks and all that. It's the least notes. Dreamforce is coming. I'll send November's to Dreamforce. Yeah, it's coming though. Yeah, it's coming. It's coming. I think Winter 20 is probably the least answer. They're all coming. Alright. Then we're back with all that stuff. Until then, and as always, it's Justin and Jason saying, enjoy those cloudy... days.