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KF #38. Optimizes Work Processes

1071: Boosting Productivity and Slashing Overwhelm through Timeboxing with Marc Zao-Sanders

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Marc Zao-Sanders reveals the key to breaking the cycle of overwhelm with a power tool that makes a huge difference.

You’ll Learn

  1. How to prune your to-do list effectively
  2. How to use timeboxing to plan your day with intention
  3. The art of choosing breaks

About Marc

Marc Zao-Sanders is the CEO and co-founder of filtered.com, a learning tech company. He regularly writes about algorithms, learning and productivity in Scientific American, Harvard Business Review and MIT Sloan Management Review. He has followed the practice of timeboxing for over ten years. He lives in London.

Resources Mentioned

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Pete Mockaitis
Marc, welcome!

Marc Zao-Sanders
Pete, it’s great to be here. Thanks for having me.

Pete Mockaitis
Oh, thank you. I’m excited to chat and let’s kick it off. I know you have studied productivity, done many experiments, worked it, iterated it. Could you share with us your most surprising discovery you’ve made about us humans and being productive so far?

Marc Zao-Sanders
Most surprising? I mean, maybe it’s just the simple fact that managing your time is so very important and yet it doesn’t get much attention from the public in general, from people at work. If you think about managing time, because time governs everything else, you can adopt a new habit and it might be really good for you. Let’s say it’s exercise or it’s breathing or it’s meditation or whatever, but if you can adopt an exercise, a practice, which is using a time better, then that’s all of the above and many thousands of other things.

So, I find it surprising that, although time management is a thing, if you ask people on the street, what are their systems for managing time, they haven’t thought about it all that much. And yet, that is the entirety of our existence, of our conscious experience of life.

Pete Mockaitis
Oh, yeah. Starting off light, our existence and conscious experience of life.

Marc Zao-Sanders
Straight into philosophy.

Pete Mockaitis
That’s good. Well, yeah, I think that does ring true. We had Demir Bentley on the show who wrote a book called Winning the Week. And he said that this is, indeed, a theme he has observed amongst many of his high-performing clients, is that they all agree, “Oh, yes, planning the week is one of the most important things I could possibly do,” but they don’t do it. And so, almost universally, is the observation there.

So, share with us, what are we missing? Like, why aren’t we doing it? Are we just oblivious to the true benefit? Do we think it’s kind of a nice to have? We haven’t really seen the light, experienced it firsthand? Why are we dragging our feet here?

Marc Zao-Sanders
I think, probably, the main reason is just that life gets in the way. There are so many emails in your inbox, there are tasks to do in a task management system, or communications in Slack or Teams, or whatever it is, our mobile phones now as well. So, there are just so many reasons to not carve out some time for yourself and think about how to spend it well. We’re just hugely, hugely distracted.

So, I’d say that was a big thing with it. And I think, also, with any habit, you need to persevere with it a little bit to feel the benefits. And I think people need to get past that first day or two days to see the benefits of timeboxing or, indeed, another time management technique. Yeah, I think that’s it. And it’s a shame because I think we could, if we all lived more intentional lives, we would be happier. We would be more productive. We would get on better with each other. We’d be better human beings.

Pete Mockaitis
Okay. Well, could you maybe paint a picture for us in terms of an inspiring story of somebody who did just that? They weren’t bothering with the timeboxing approach, and then they adopted it, and what happened for them?

Marc Zao-Sanders
Well, one such person is me. It has worked for me as an individual. And that’s the key thing, I think, for anyone listening to this. You need to think, “Does it work for you as an individual?” There are studies, there’s all sorts of science that says that this works. But the key thing, really, is not whether it works for a bunch of other people, it’s whether it works for you.

So, I mean, my personal story is that I’m 45 years old, about to be 46. And when I started my career 20 something years ago, life was hard. I started in strategy consulting and the pressure was pretty intense.

Pete Mockaitis
Oh, I’ve been there.

Marc Zao-Sanders

I was suffering, frankly. I was a disorganized mess, yeah, the performance issues. I was, but more importantly, I wasn’t feeling very good about the work that I was doing. So, I established a little bit of control by setting up what I called a daily work plan. So, that was just an Excel file. I’d write in the Excel file. These are the things I really need to do today.

This is roughly how long they would take. And I’d check them off. They would sum up then to the productive hours that I’d had that day. That was good. That was much better. And it made me feel better about work, more confident with what I was doing. But it didn’t tell me, at any given moment, what I should be doing. It wasn’t linked to other meetings to my calendar.

So, then, yeah, I saw this article in Harvard Business Review. It’s called why “To-Do Lists Don’t Work.” And it immediately resonated. I changed what I was doing as an individual, overnight. And then, over the next five years, I sort of honed the technique. I made it my own. I wrote my own Harvard Business Review article that became very popular.

And that led to the book, and talking to many, many people over the years about timeboxing and how it can help not just with your, I mean, it’s really not just about your productivity. It’s really mostly about how you feel, the control that you feel as you go through the day, as you’re going through the maelstrom of a knowledge worker’s day. It can be unpleasant a lot of the time, but if you focus on one thing at a time and you’ve planned that out, it feels a lot better.

So, yeah, the case study I would give most of all, first and foremost, that I know and have lived is mine, but, obviously, I’ve heard that story, that kind of story from many, many people, from, I mean, literally, from around the world. That’s, I mean, just one other thing to say about that, that the book’s been, and I’m an unknown author.

I was an unknown author before I started this, and yet the rights were bought up in 33 languages because the story, because this idea of making your life more intentional through, basically, through your digital calendar resonated across cultures, across languages. And there’s also a bunch of case studies at the end of the book as well, stories from individuals that have made timeboxing work for them in their specific situations too.

Pete Mockaitis

Okay. Well, so that’s cool. Works for you, works for them. I actually am curious to hear about the studies. And, in fact, in your Harvard Business Review article, at the very top, it says a recent survey of 100 productivity hacks, timeboxing was ranked the number one most useful. Tell us a bit about that and any other, I guess, researcher evidence saying, “This isn’t just a cool thing Marc likes doing. It’s pretty proven for lots of folks.”

Marc Zao-Sanders
So, that study was done a long, long time ago. I did a lot of the research for it, but this is well before I’d written the book or even had an idea about writing the book. I had no, literally, no affiliation with timeboxing. I mean, I happen to do it myself, but actually a lot of the other techniques on the list, I also happen to do.

So, the way that we conducted that study was to look at lots and lots of thought leadership pieces online and categorized them according to which time management technique, which productivity hack or tip they were, and then just see how common they were. And that gave rise to an ordering, a top 100, and, yeah, like you say, timeboxing came top.

Pete Mockaitis

So, that came about by votes or by most frequently cited amongst industries?

Marc Zao-Sanders
No, exactly, most frequently cited, so how many times they were coming up. And it’s not only that. If you look at a lot of the other entries on that list, and like you say, it’s linked to in the in the book and probably on some articles on my site, you can see that many of the other techniques on the list are very, very similar to timeboxing or, actually, they form a subset of timeboxing.

I’ll give you an example. Just saying no, so just saying no is a thing in business. It’s been encouraged a lot over the last five, ten years. By the way, I think this is more of a nuanced thing. Sometimes people should say yes more than they do. It depends on the person and the context. But sometimes they should say no.

Well, saying no is partly dependent on how busy you are and what you’ve got on. If you timebox, you’re not just saying no or just saying yes, you’re doing so on the basis of what you’ve got on your plate. It’s something that you can point to, point your boss to, or point colleagues to. So, just saying no is, it goes very, very nicely hand in hand with timeboxing, just like so many of the other items on the list.

I’ll give you just one other example as well. “Eat That Frog,” the Brian Tracy idea of, you know, do the most difficult thing at the start of the day. Well, again, it’s not like timeboxing is saying you should do the most difficult thing, but if it suits you as a person, then here’s a system where you can put the most difficult thing at the start of the day, again, just completely, consistently, and to support that system that Brian Tracy came up with or popularized.

But also, if you’re the opposite, if you’re someone who needs to slowly, slowly build momentum through the day and start with some smaller tasks, which suits certain people better than it does the Brian Tracy method, that’s also consistent with timeboxing because here’s a system where you can build up slowly with some easier, smaller tasks at the start.

So, my point is that, yeah, timeboxing is very flexible with, it was number one itself, but it’s also works, so nicely with virtually every other time management technique.

Pete Mockaitis

Okay. Well, so then we say there were timeboxing a lot. Can you lay it on us? What exactly are we talking about here?

Marc Zao-Sanders
Well, I’ve got a definition, but maybe it’s better to describe it in terms of what I do at the start of the day. I’ll come back to a definition after that. So, I wake up, I get dressed, I brush my teeth. And then the very first thing that I do is spend 15 minutes thinking about my day and how I should spend my time. So, those 15 minutes are definitely the most productive of my entire day.

I couldn’t really, now, I can’t really imagine not using them like that. I don’t need more than 15 minutes. I do normally need 15 minutes because sometimes your emails have come in overnight, an idea has occurred to you overnight, and you need to take that into account along with other entries in your calendar. So, it’s a little bit of work, but just 15 minutes.

And then those 15 minutes lead you to have a day where it’s full of what you really wanted to do, what really mattered, what you intended to do. This is what I mean by intentions, giving yourself the space to become aware of what your intentions are, what’s important to you, and then having a system for making sure that they happen. So, that’s what it is, you know, that’s sort of my experience of it. I do that each and every day. I do it in the morning. Some people do it the night before.

But in terms of a definition, which, it’s probably slightly less useful, but I’ll give one anyway. So, I described in terms of what, when, one, enough. What I mean by what is deciding, giving yourself the space to think through what is most important. And then when is deciding when it should start and when it should finish, not being too ambitious, but being ambitious enough with those timings.

One means doing, is single tasking. Just do that one thing in that slot, nothing else. And then enough is doing it to a good-enough level. You’re not aiming for perfection here. Perfection doesn’t really exist for any of us. Do it so that it’s good enough that you can share with others and move things on in your workflow or in your life, whatever the context happens to be. So, yeah, that’s kind of how, that’s the lived experience of it as well as the definition.

Pete Mockaitis
Okay. Well, that seems pretty simple, and yet, in your experience and that of luminaries throughout history – Carl Jung, Albert Einstein, Bill Gates, etc., – it’s revolutionary, you say.

Marc Zao-Sanders
It’s revolutionary in that anyone who wants to achieve a lot and feel good about doing that needs to really use their time well. And I think there’s just something very fundamental about timeboxing. It is working out what’s important, setting a time to do it, not being distracted by anything else, and doing it to a good-enough level.

I mean, it’s very hard, I think, to launch an argument against that. I’m going to invite you to do that, Pete. And, actually, I wanted to ask you if you timebox.

Pete Mockaitis
Well, challenge accepted.

Marc Zao-Sanders

Okay, so go ahead. I mean, which of those elements, which of those four elements of the definition would you say, “Eh, that’s actually not that important”?

Pete Mockaitis
Oh, no. I suppose, I don’t think that it’s not important. I just think we can come up with lots of excuses for why, “Oh, that’s a nice view, Mark, but I don’t think that’ll quite work for me,” or, “Yeah, that sounds cool, but…” so I think there’s a lot of buts that it might be worth our time digging into to a few of those.

Marc Zao-Sanders

Of course. I mean, some people will see that and then not act on it. I mean, of course that happens. It does require a little bit of discipline, and anything that requires even a modicum of discipline can be ignored, and some people will take the path of lesser immediate term resistance.

Pete Mockaitis
“No, Marc, instead, I’m just going to get this cool app. That’s going to fix my time management problems. This fun little app instead.”

Marc Zao-Sanders
So, yeah, I mean, there are some apps that will do some of this for me and for a lot of people. It’s connecting with your intentions and making sure that you’re doing the things that you want to do at the right time, requires a little bit more of yourself. So, yeah, sure, you can have AI just arrange things for you, but then are you going to be happy with the order of them?

And even in the processing of you’re putting these tasks into your calendar, your brain starts to think about, you know, starts to problem-solve. So, you’re making a little bit of progress with each of them, even in the act of doing it. So, yeah, there are apps and there’s AI, and that’s fine for some people. It’s not for me. It’s not the method that I advocate.

I’m a little bit more old school. So, while I advocate having a digital calendar and making that sync with your various devices, rather than a sort of paper-based system, AI is not something that you need for timeboxing. Not in my view.

Pete Mockaitis

Oh, yeah, certainly. Well, so then I suppose, with regard to discipline, for folks who think, “Oh, that sounds cool, Marc, but I just couldn’t even do that because I’m a creative, flexible, fluid kind of a personality. I don’t really do well when I’m tied down,” what do you think of that?

Marc Zao-Sanders
Okay, so I hear this, obviously, sometimes, “They just wouldn’t work for me. Well, it wouldn’t work for me.” Okay, so, I mean, a few things to say. But the first one that occurs to me is like, even if you’re a creative, you’re already timeboxing to some extent because you’ve got meetings in your calendar, right? That’s unavoidable. And however creative or uncreative those meetings are, you’ve got those meetings.

And you have to have some sort of timekeeping system to make sure that you attend those meetings more or less on time. I mean, even if you’re five, 10 minutes late for most of your meetings, as some creatives might be, the meeting is there and it is important and you’re probably annoying some people by being a little bit late.

So, it’s not like this is a brand-new system that I’m suggesting you sort of foist-force into your life. We’re all creative or non-creatives, and also, we’re all creative in some respect. But all of us are using our calendar to spend time specifically, at the very least, with meetings. What I’m saying with timeboxing is let’s extend that a little bit further so that we also do it with some of the work that we do on our own so that we can achieve more and actually, with creativity, specifically, achieve more creatively.

You’re much more likely to achieve the state of flow and get to what Cal Newport and others call deep work, scale the heights of our capability if you remove all of your distractions, if you get to a period of time where you’re just working on one thing. So, I would say that it actually, I mean, genuinely, I think that it supports creativity. It doesn’t stifle it.

Pete Mockaitis
Okay. And then when it comes to discipline, if folks think, “Boy, Marc, I just don’t think I have that level of discipline. That sounds really hardcore. That sounds Navy SEAL-esque to go from thing to next thing, to next thing, to next thing with perfect rigid execution. That sounds beyond my meager willpower capabilities”?

Marc Zao-Sanders
Okay. If someone said that, if you said that, for example, I would say, I mean, first of all, it doesn’t need to be perfect. It doesn’t need to be rigid. It also doesn’t need to be productive thing to productive thing. One of the productive things might well be having a break, might be lying down, might be having a cold shower, might be taking your dog for a walk. It’s just positive, intentional activities that you know, by the end of the day and even actually during the day, are going to be really, really good for you.

The other thing I’d say to such a person or, you, potentially, Pete, is, well, like I said, you’re already doing it to some extent. And then also, well, why don’t you just try it? For tomorrow, you could put into your calendar right now, I mean, actually, if you’re listening to this, or watching this right now, anything you could do to get started is put a 15-minute time box, just an event, into your calendar for tomorrow morning at a time that suits you.

I mean, obviously, you need to be awake. You need to be awake enough to get it done. And in those 15 minutes, plan out some of the rest of your day. I will plan out a lot of the rest of my day because I’ve been doing it for 20 years now. But do it for a couple of hours or three hours or four hours.

And once you’ve tried that for a few days, and I imagine you will achieve some success and you’ll get into a snowball effect, a virtuous circle, you’ll be doing it some more. And if it really doesn’t work for you, well, then stop, but give it a try.

Pete Mockaitis

Yeah, well said. So, we don’t need to start with the entirety of the day that, indeed, could feel intimidating. Understood.

Marc Zao-Sanders

Yeah, don’t let perfection or completion be the enemy of the good here. Get something done. And I’m a big believer in 80-20 and pretty good and doing a decent job of things rather than sort of Navy SEALs perfection, anything like that. I don’t come from that background. I don’t have that in my locker. I’m just a regular guy.

Pete Mockaitis
All right. Well, so let’s talk about, it sounds like the hardest part of all is we’ve got dozens, hundreds of options, things that have landed in our to-do list with varying levels of seriousness, urgency, importance. How do you begin to decide, “Ah, yes, this is, in fact, the thing that goes on today’s calendar”?

Marc Zao-Sanders

Okay. So, first of all, what you’ve just described is exactly the reason that timeboxing is important. Most of us knowledge workers, at any given moment, could be working on 20, 30, 40, maybe 100 things. They would all be somewhat legitimate. And the existence of so many different things that we could do is stressful in itself. So, you’re doing one thing, and two or three or five or 20 of the other things occur to you. That is so stressful. And that stresses me out every single day.

So, that’s the reason that, the main reason I would say, that timeboxing is important, it kind of pushes all of those other things away and focuses you on a single thing. So, that’s why it’s important. If you have 100 items, though, and how are you going to decide, I’ve got a trick which is very concrete, very tangible, very easy.

So, let’s say you’ve got a to-do list, Pete. You’ve got 100 items on it and you don’t know where to start. Some of those things are going to be very important. Some of them less so. It’s probably accumulated over weeks, months, maybe even years. I would say grab it, put it into a spreadsheet, go down the list, and just score them very roughly on a of an approximation of both urgency and importance. Just sort of, you know, merge the two together, give them a score between zero and 10 every single one.

Now, look, even if you’ve got 100, it’s going to take a little while to do it, but it’s not going to take you more than 10 minutes. This is not a huge, huge task. So, you score them all, zero to 10, and then you sort it on the score that you’ve given it. So, most the highest numbers will go to the top. And then as soon as you’ve done that sort, you will see immediately there’s a group of tasks at the bottom that you really could just delete.

And that is hugely reassuring, gratifying. It’s such a relief to see the list look like that. And then there are tasks at the top that really will be super important because you’ve given them an eight or a nine or a 10. You might want to do some further ordering of those. And that’s also a huge relief because those big important items that you knew were lurking in your to-do list are being surfaced properly. So, they will get your attention.

So those, you know, three, four, five, 10, whatever it is, items that you really had to do are going to make their way into your calendar and get done. And that is so, I mean, it really is about control, like taking control of your life by having a system to understand what is most important, and get it done. This is a specific tactic for dealing with a long to-do list.

And then you can do that even every so often when you’ve only got 20 items, it also works. It sounds, I don’t know, maybe for some people it sounds a little bit much to put into a spreadsheet, but much better that than just leaving it there to gather dust and bother you every so often.

And, occasionally, you’re going to be getting fines because you haven’t dealt with some tax issue or responded to some letter. So, I mean, it’s literally costly, financially costly, to not address it and not address it in some kind of systemic positive, repeatable way.

Pete Mockaitis

Yeah. Well, I love that so much. And you mentioned 80-20 and so much of what you said there, I’m vibing with a ton. And the phrase “somewhat legitimate,” I think is, oh, so perfect for the items that hang out in our to do this.

Marc Zao-Sanders
At the top that we’ve got.

Pete Mockaitis
They are somewhat legitimate and, yet, Vilfredo Pareto would say they are not the vital few of the 80-20 rule.

Marc Zao-Sanders
Yeah, find the vital few. Find the vital few and do those.

Pete Mockaitis
And it is such relief, you’re right, to see a huge list and to see many of them drop off. It’s like the fastest way to get something off of your to-do list is to decide thoughtfully, thoroughly, not to do it, “Hey, that’s off my to-do list and legitimately so.”

Marc Zao-Sanders
Exactly. Yes, it’s basically pruning. And there is no more efficient way of pruning a list than via a spreadsheet. So, the spreadsheet is not officially part of timeboxing. It is a very effective method for, yeah, for getting to the vital few, as you put it.

Pete Mockaitis
So, I would like to hear a little bit about some of those questions by which we might use to determine what is calendar-worthy. And so, vital few, 80-20 type things suggest that vital few activities produce 16 times the output per unit input than trivial many items. So, there’s that. I also love the ONE Thing question. We had Jay Papasan on the show earlier.

What’s the one thing such that, by doing it, everything else will become easier or unnecessary? So, that’s a huge win in terms of a prioritizer. We had Greg McKeown talking essentialism, in terms of like raising your standard, like cleaning out your closet, not from, “Might this someday be useful?” “No, no, low standard,” to, “Does this spark joy?” Marie Kondo style, high standard.

So, any other sort of uber powerful questions that are super handy in the universe of prioritizing?

Marc Zao-Sanders
Yeah, well, the main one for me is actually the emotional response you have to a specific item. So, as you’re going through the list, you will feel stressed or you have some sort of emotional response to some, and to some you just will have the absolute opposite.

What I’m suggesting is that, where you have a stronger emotional response, in general, you’re going to want to action those. So, I think that’s a proxy for importance for what matters to you that comes from your soul, actually. You don’t really need to ask any other questions. It’s just what is your response to this particular item.

Pete Mockaitis
And when you say strong emotional response, is it either positive or negative? Is a go signal for action?

Marc Zao-Sanders
No, definitely. It might well be negative. I mean, look, for example, let’s say a tax return. A tax return, for most people, is not going to be hugely positive, but that doesn’t mean that you leave that and let’s find the good stuff. No. What I’m saying is that any kind of strong response probably means that either, you know, because you really want to want to do it because you’re enthusiastic about it.

In general, we don’t need help with those sorts of tasks. So, it’s actually more the ones where you have some sort of negative response. And to just dwell on that particular example, because that’s something that a lot of people feel when it comes to that time of year, getting something like a tax return back to whoever needs to see it.

The problem with not addressing it is that you just die a thousand deaths instead. You will need to do it in the end, and maybe you incur a fee as well if you go beyond whatever the deadline is. But even if you hit the deadline, if you worry about it 17 times before you submit it, well, why have you done that? Much better to confront it, be front-footed, and get the thing done on your terms proactively.

I use the term. I use the word agency a lot with timeboxing. It’s taking back your agency. You be in control. Don’t let the world happen to you. You decide what needs to happen and when it’s going to happen and get it done.

Pete Mockaitis
Yeah, ooh, die a thousand deaths, or sigh a thousand “Ugh.” Like, “Ugh, maybe tomorrow.”

Marc Zao-Sanders
Or, timebox instead.

Pete Mockaitis
Yeah. Okay. Well, so we got some thoughts on how to choose what goes in on this day’s calendar. Do you have some pro tips on how do I think about how long should that thing take? How long should I work in a bout of work, rest, breaks? What are some of the pro tips to designing a day to be a masterpiece?

Marc Zao-Sanders
Okay. Well, exactly, it is like that. It’s sort of like you’re an architect, you’re designing, you’re like an alchemist of the experience that you’re going to have that day, and the ordering matters. I mean, if you think, let’s say you’ve got to write, I don’t know, a summary of a podcast, right? That’s one of your tasks. And you also want to go to the gym.

Now for some people, it will make a lot of sense to go to the gym first and then do the write-up. And for others, it will be the other way around. It really depends on how your brain works, how your mood is, what energy you have, maybe some of the logistical, the contextual elements of your day, but, really, the order really matters.

So, yeah, build in breaks. Consider that the order matters. I mean, for me, for example, when I’ve got difficult things to think about, I like to have some exercise built in to give me a chance to think about them in a diffusive way. So, I can just be a little bit more relaxed and have sort of answers come to me while I’m doing some hard or semi-hard exercise.

So, yeah, build in some breaks, build in also some slack. If you don’t have any slack and you go, like you were saying earlier, Pete, from thing to thing to thing, if anything breaks or anything takes a tiny bit longer, and you haven’t responded to it, then you can have a cascading, a negative cascading effect. So, build in some slack, build in some breaks.

I mean, to be a little bit more specific, okay, it varies from person to person, but for me, every couple of hours, I will need 10, 15 minutes, normally 15 minutes of a break. And that could be anything. Just get a drink, take the dog for a walk, have a shower, meditate, close my eyes. There are a lot of ways of having a break that aren’t just to default to the canteen or the kitchen and eat something that’s not that healthy for you.

So, with breaks, there’s a bit of an art to it as well. And think a little bit more about what’s going to refresh you and give you energy. But I would say that there’s no hard and fast rules about how much time or how many breaks you should take. It’s really, just coming back to that word intention, what works for you. Think hard about what works for you.

You can take as a guideline, you know, how I spend my day. And in the book, I’ve got some screenshots of how that is, but that won’t necessarily be that way, done that way, it won’t be for everyone. The point is to have a system, like timeboxing, which is super flexible and can accommodate different attitudes to different needs for taking breaks and having slack and what you do in those times.

Pete Mockaitis
Okay, very good. And then when we’re actually doing the calendaring, do you have any pro tips in terms of 15-minute increments, or color coding, or anything that makes this go better?

Marc Zao-Sanders
Both of those, for sure. So, I mean, 15 minutes, so I have three sizes of timebox. And, again, other people can take a different view, and it is flexible to having different denominations. But my denominations are 15 minutes, 30 and 60. It’s nice and easy, there’s only three sizes so I don’t have to spend long thinking, “Is this a 48-minute task or a 17-minute task or whatever?” It’s just, like, a small, medium, large. And I know what small, medium, large are.

They also stack nicely up to an hour. There’s obviously 15s, you know, go into 60, so does 30. And then you asked about color coding. Well, I do color code my calendar, and this is to get a handle on, I mean, quite literally, get a view, a literal view of the balance of my life. So, I have five different areas of my life at the moment. So, there’s one business that I advise, another business that I advise, things that are for me to do with my soul and my wellbeing. And then there’s speculative activities as well.

So, I’ve got a few different categories of my life that I’ve deemed to be important for me right now. Okay, so if I color code the items as they go into the calendar, I can see at a glance at the end of a week, how much time I’ve spent on each of these areas. And, actually, the way that both Google and Microsoft do calendars now, they’ll toss it up for you.

So, they’re telling you, “Well, you’re spending 30% of your time on your…” as I put it, “…soul. Well, is that good or not good?” But if you have the data, then you can make a decision about adjusting it up or down. So, color coding sounds a little bit trivial, I mean, almost absurd, but there’s actually a very good reason for doing it.

I also, Pete, use emojis in my timeboxes. Why do I do that? I mean, probably not for a very good reason. It just gives me, I see timeboxing as sending your future self a message, a little bit of guidance, so that when that future self is distracted and stressed by the inevitable difficulties of a working day, you have that line back to, when you were in a calmer moment, when you were a bit wiser, when things were more still, “Oh, yeah, that’s the thing that I should do.”

How’s that relevant to emojis? Well, it’s a little bit tongue in cheek. It’s a little bit, like, I don’t know, like a wink or a hug. It’s an affectionate message from my former less-stressed self to my later more-stressed self. And so, I put them in. That it definitely is an optional feature of timeboxing.

Pete Mockaitis
That’s fun. And what’s cool about emojis is they can be right in the line of the text as opposed to a separate image thing, which is all weird and complicated and hard to shove into a calendar software.

Marc Zao-Sanders

Yeah, definitely. And it is for me. It’s right before the text that I put it. Yeah.

Pete Mockaitis
I’m also a fan of the Unicode symbol for a checkbox in the calendar. That feels nice. I just have that copy-pasted like, “Oh, and then that happened. Mission accomplished,” because that’s one of the most satisfying things about a to-do list is the checking them off. I can still have that in my calendar too.

Marc Zao-Sanders

Yeah, exactly. So, it sounds, Pete, like you timebox and you are using some of the higher arts of timeboxing, as we speak, as you live.

Pete Mockaitis

Well, yes, higher arts. Well, Marc, tell me, any final things you want to make sure to mention before we hear about some of your favorite things?

Marc Zao-Sanders
Sure. I mean, well, okay, a couple of things that occurred to me. One is just the word time itself. So, this is a not very well-known fact, but time is the most commonly used noun in the whole of the English language, but not just the English language. If you look at Spanish, if you look at German, if you look at Chinese, I think, as well, and many others.

So, it’s super, super common. And it’s not like I was saying at the top, at the start of our conversation. It is surprising that people don’t give it even more time and attention than they do. So, that is just a factor I’ll sort of park with people. The other one I want to say is there’s a, yeah, sometimes you’ve got a plan with someone, like a dinner, and then the dinner gets cancelled.

And there’s nothing nicer than that feeling when you suddenly have some time in your calendar, but it’s very easy to waste, especially with your social media and our phones and what have you. There’s a mnemonic which has really gone down. Well, actually since the book came out. This isn’t even in the book, but it’s Mr. Elf.

So, the M is for meditation, R is for reading, E for exercise, L for learning, F for friends and family. This isn’t an exhaustive list, but it’s a very, very useful list to just run through. If I’ve got a bit of time and I want to use it well, here’s a reminder of some of the things that are probably going to be important, could well be important to me. And why not do that with your time rather than Netflix or Instagram or Snap or whatever it is? So, yeah, I want to get Mr. Elf into the ears of the people that are listening and watching.

Pete Mockaitis

Oh, beautiful. Thank you. Well, now could you share a favorite quote, something you find inspiring?

Marc Zao-Sanders
There’s one from Lady Gaga that I really like and speaks to, I think, what’s the most important about, one of the most important things about life and about this system.

So, the quote is, “I am my own sanctuary and can be reborn as many times as I choose throughout my life.” To me, it’s about agency and hope and truth. And while it’s nice to be quoting Plato and Socrates and Nietzsche in the book, too, it’s also nice to give Lady Gaga some extra attention, too.

Pete Mockaitis
All right. And a favorite study or experiment or piece of research?

Marc Zao-Sanders

There was a study into what’s called implementation intentions. If you just Google implementation intentions, you’ll see. What these basically said was that if you decide when you’re going to do something, what you’re going to do, and when you do it, you’re two and half times more likely to get something done. You’re something like 90% likely to get it done versus 30-something percent.

It’s been replicated more recently in studies. And, of course, that kind of encapsulates exactly what I’m trying to get at with timeboxing. And, actually, when you were asking me earlier, “Well, what about the people that are just aren’t going to do it?” Well, the studies say that you really are two and a half times more likely. So, I probably should have said that back then. It basically says that timeboxing works.

Pete Mockaitis
Okay. And a favorite book?

Marc Zao-Sanders
I mean, the book I’ve read the most frequently is Lord of the Rings because it’s just enjoyable. A book that moved me more recently was The Fountainhead, Ayn Rand. I enjoyed that very much. That felt a lot about freedom and, again, agency. So, that resonated and was enjoyable as well, and it’s quite a different style to Tolkien’s work.

Pete Mockaitis
And a favorite tool?

Marc Zao-Sanders

Well, I mean, in making decisions in business, or in life, actually, the two-by-two matrix is one that I default to pretty frequently. You’ve got an issue, you don’t know how you’re going to resolve it, think about two of the factors involved that are distinct, and then you look at high, low, or yes, no for each of them. You put that onto a two-by-two and, just almost immediately, almost every time, things clarify somewhat. So, yeah, the two-by-two matrix is a really useful one for me. I love the thing.

Pete Mockaitis

And is there a key nugget you share that really seems to resonate with folks, a Marc-original soundbite?

Marc Zao-Sanders
So, this is about, timeboxing is mostly an in-day activity to help you make the most of that day. But the point is if you keep doing it, that adds up to a whole life of intention and purpose and meaning and what have you.

So, the quote is, “The practice of daily intentional activity will eventually yield what almost every human being wants most – a chosen cherished life.” I think that’s very nice and just touches on, like I said, meaning, something that’s sort of deep. Deep and important.

Pete Mockaitis
Yeah. And if folks want to learn more or get in touch, where would you point them?

Marc Zao-Sanders
I’m on LinkedIn. You can just put my name in. I accept requests, generally, there. I also have a website, MarcZaoSanders.com, from which there’s a monthly newsletter, and you can email me and get in touch by just answering, that it’s a Substack.

Pete Mockaitis
All right. And do you have a final challenge or call to action for someone looking to be awesome at their job?

Marc Zao-Sanders

Yeah, don’t just let life and your job just happen to you. Rediscover what you want to do, what your intentions are, and find a way to bring them into being, into your work, into your life.

Pete Mockaitis
Beautiful. Marc, thank you.

Marc Zao-Sanders
Pete, thank you.

1070: An ADHD Strategist’s Pro Tips for Staying Motivated and Productive When You Can’t Focus with Skye Waterson

By Podcasts No Comments

Skye Waterson shares ADHD-friendly approaches to productivity that any professional can apply.

You’ll Learn

  1. The quickest way to shorten your to-do list
  2. How to stop overthinking and make a decision
  3. How to make hard tasks more fun

About Skye

Skye Waterson is an ADHD strategist, coach, and founder of Unconventional Organisation, helping entrepreneurs and executives stay focused, build consistent revenue, and scale—without burnout. With 82K+ engaged professionals following her work, she shares ADHD-friendly strategies for sustainable success.

After her ADHD diagnosis during her PhD, she realized traditional productivity advicedidn’t work for her. So, she developed strategies to help entrepreneurs and executives cut through distractions and focus on what matters, build ADHD-friendly systems for consistency, scale sustainably without exhaustion, and lead with confidence and regain control over their time.

Resources Mentioned

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Pete Mockaitis
Skye, welcome!

Skye Waterson
Hi, it’s great to be here.

Pete Mockaitis
Well, I’m so excited to hear your wisdom. You are an ADHD strategist and coach. That sounds handy. We’ve had over a thousand episodes, but we have not taken a laser shot directly at ADHD before, though it kind of comes up tangentially fairly often. So, could you, first of all, maybe just define, what are we talking about here? What precisely is ADHD? Is it the same thing as ADD? How do I think about this?

Skye Waterson
It’s a good question and it has been changing. So, ADHD is something that, if you wanted to get diagnosed with, you would go to the Diagnostic and Statistical Manual of disorders. Or, more likely, you’d want a psychiatrist to do it for you. And you could be diagnosed in this version, because it has been different in the past, with ADHD, type one, type two, primarily, and type three.

So, it’s primarily inattentive, which is what we used to know of as ADD; primarily hyperactive, which is the ADHD; or combined type, which is what I have. And what we know from this is that, basically, you are somebody who hits a certain criteria, of feeling driven by a motor, struggling to sit down, getting distracted, like all these kinds of things. And it also happens persistently and pervasively, so across different categories of your life and across time as well.

Pete Mockaitis
Okay, so three flavors: inattentive, hyperactive, and combined. And can we hear a little bit of detail for, what does each mean? And how do I distinguish that from just, you know, being a human who has moods and distract-ability and all that?

Skye Waterson
Yeah. Well, you know, and there’s more and more conversation about this idea of subclinical ADHD because I think it’s something that everybody does struggle with. And I will say, about 50% of my clients are undiagnosed. So, they haven’t had the official diagnosis yet. They just think that they might have ADHD.

And so, when we’re talking about this, what, really, we’re talking about is you might be somebody who goes, “Oh, yeah, I get it. On a Friday afternoon, I’m exhausted and very distractible.” But we’re saying, “But what about on a Monday morning? What about on the weekend? What about at home? What about at school? What about at work?” Like, this variety of different environments is the situation that we’re looking at.

And, “Was it happening when you were a child? Is it happening now?” You know, that’s kind of what people will be looking at. And then hyperactive is very much the classic ADHD. If you guys know a person who’s like running three different businesses, two of them on some kind of really strange thing you’ve never heard before, and like always go, go, go, that kind of ADHD.

And then ADD is more of the distractible. So, person who’s looking out the window, distracted, that kind of ADHD. That’s a very generalized version of it. There’s lots of different kinds, but that’s essentially the tropes that people think about.

Pete Mockaitis
And so, then what’s this combined business? Like, someone is go, go, go and inattentive at the same time or, like, back and forth? How does that unfold?

Skye Waterson
Pretty much, yeah. So, somebody who gets distracted and is hyperactive.

Pete Mockaitis
Okay. Now I’d also heard that hyper-focusing can be a part of ADD or ADHD as well, which was a head-scratcher for me. It’s like that kind of sounds like the opposite. What’s going on here?

Skye Waterson
So, what’s happening there is you’ve got something called time blindness. So, people with ADHD, and when I first found out I had it, this was a surprise for me, really struggled with time blindness, seeing how much time is passing. And so, if you’re bored, it feels like, you know, two minutes is like a year.

But if you get into flow, if you’re really focusing, you can actually lose track of time and you can just be fully engaged and fully focused on the task at hand. That hyper focus is specific to ADHD because it’s not that we are necessarily just distractible. It’s more like a wandering attention. So, if your attention gets fixed on something, then we can really dive into it. Sometimes it’s good. Sometimes it’s not good.

Pete Mockaitis
I guess good or not good is based upon what needs doing and what you find yourself hyper-focused upon.

Skye Waterson
Yeah. Did you want to be hyper-focusing on that thing? Sometimes people are like, “I did not have any intention to hyper-focus today, and now I am knee-deep in my closet reorganizing it for the second straight hour. That was not the plan.” So that would be the case.

Pete Mockaitis
Yeah. Okay. So, I guess the way we know if we got it or not is we chat with a psychiatrist who does the DSM. That sounds maybe expensive and intense. Is there a quicker, easier way we can get a pretty good idea, Skye?

Skye Waterson
Well, there are online versions. You can even search the DSM. I think it’s available. But there are online tests that you can take. Some of them, you know, in the NHS and places like that will do a better job of kind of approximating what you would be asked by a psychiatrist. Obviously, if you don’t go to a psychiatrist, they can’t help you rule out whether you have other conditions that might be co-occurring, which happens a lot with ADHD.

But, yeah, it does take a while. It could take a really long time if you try and go public. And if you try and go private, then it’s very expensive. So, for that reason, a lot of people decide to just live with the, you know, they go, “Okay, I’m pretty confident I have it and I need strategies for it,” and they come to me and that’s what I help with.

Pete Mockaitis
Okay. And what’s our best guess for the very rough proportion of professionals, diagnosed or not, who likely have it?

Skye Waterson
It’s about 2.5% of the population of adults. That’s usually the stats.

Pete Mockaitis
Noted. And I’m curious, in terms of, for the 97.5% of listeners who do not have it, are there any particular strategies that work awesomely for people with ADD, ADHD, as well as the rest of folk?

Skye Waterson
Yeah. Well, that’s the greatest thing. I mean, I’ve had the opportunity to work with the New Zealand government on some of their organizations, and I often will teach these strategies, and people will say, “Wait, wouldn’t this be great if everybody was doing it?” And I’m like, “Yes, these are wonderful strategies for anybody who’s struggling with executive functioning or distraction,” which is all of us at some of the time.

Pete Mockaitis
Yeah. Understood. And maybe, just to get the motivations fired up, can you share any transformational tales or research results on just what kind of impact can adopting some of these strategies have?

Skye Waterson
Yeah. Well, there’s a lot of research. One of the things that we do know about ADHD is it’s one of the most treatable conditions. So, it’s very, very treatable. Once you have strategies for it, it’s very helpful. A lot of the problems people have is just that they’ve been taught the wrong systems, and they don’t have a sense of how their brain actually works because no one’s taught them, and so they have no idea.

Pete Mockaitis

So, when you say wrong systems, can you give us some examples of common prescriptions that just aren’t cutting it?

Skye Waterson
So, I would say the biggest thing is that people will be given strategies based on this idea that we have executive functioning when we don’t. So, with ADHD, the biggest struggles we have are working memory, forgetting everything, everything that we’ve recently been told. Time blindness, so not being able to track, estimate, measure time effectively.

Dopamine, so having a struggle with not getting enough of it, not having it processed correctly. And transition time, so not being able to transition between task to task effectively, needing a bit more downtime, needing to chunk things out. Those are really, really important. If somebody says to you, for example, “You should just get started. You’ll feel better,” or, “Why don’t you give yourself a reward once you finish this? That’ll be great.”

Those are the pieces or, “Why don’t you do this just with an hour a day between your meetings?” This is terrible advice for ADHD.

Pete Mockaitis
Right. And I guess I’m saying get the reward was like, “Hey, I got a dopamine situation so maybe that’s not going to cut the mustard there.”

Skye Waterson
Research does not back you up on that one.

Pete Mockaitis
Well, say again?

Skye Waterson

So, there’s research into this, it’s something that I’m very passionate about. It’s called the dopamine transfer deficit theory. So, it came out in 2008, one of my favorite pieces of research, because that’s who I am. And, basically, what it shows is that there seems to be a gap in the type of dopamine boost that you get when you’re ADHD at the beginning of a task.

If you’re neurotypical, you know there’s a reward at the end of the task. Your brain gives you a little thumbs up, a little “Woohoo!” at the beginning because you know that you’re going to get that reward at the end. If you’re ADHD, your brain just kind of goes, “This is lame. Why are we doing this?” And then you do it. And then at the end, you give yourself a reward and your brain goes, “Well, this is nice, but why did we have to do that horrible thing?” The connection is not there.

Pete Mockaitis
Okay. Well, that’s intriguing. And so, that has been shown. When we say neurotypical as opposed to ADD, ADHD, how, and this is based upon they have the diagnosis, or do we have any brain scans, or biomarkers, or I guess we know it because we got the symptoms and the DSM diagnosis? Are there other indicators at the biochemical or level of matter that we can point to?

Skye Waterson
You’re speaking my language. I love a neuroscience paper. So, in terms of, generally overall, you are asking me about, “Do we actually see neurobiological shifts in people who have ADHD and people who don’t?” The answer is yes. There is a lot of neuroscience research. In fact, not just neuroscience.

AI as well, they’ve been looking at AI research and finding that the way people speak with ADHD is a bit different, tend to like jump from point to point, and more likely to interrupt. And so, there is new research coming out that you could actually potentially get to a place where you can tell if someone has ADHD or not, at least at a subclinical screening level using AI.

So, there are lots of different ways, neuroscience and neurobiology are one of them, but it does take a long time because you have to sit in the chair and there’s not that many of them.

Pete Mockaitis
Okay. Understood. So, then help us out, if we do have ADD or are just having a heck of a time focusing, what are your favorite strategies?

Skye Waterson
My first favorite strategy is what I call a two-minute focus formula, because there’s only two minutes. So, I want to give you guys that upfront. You guys can actually DM me at Unconventional Organisation on Instagram. If you want this, just use the word awesome, and I will give it to you because that way I’ll know it came from here.

And, basically, the first thing you need to do is you need to go ahead and you need to write down somewhere you’re going to keep it, not on a random piece of paper. We want it to be something we’ll come back to. You start by writing down everything that you are going to be doing, every single task basically that’s in your head. Don’t look at your email. Don’t look at your other tasks. Let’s just focus on what’s in your head.

And, usually, this is the longest part because it takes people a while. They don’t realize how much stuff is in their head. And then from there, we want to look at everything that’s there, and we want to go ahead and we want to identify “What has to be done tomorrow or there will be a significant negative external consequence?” Significant. It can’t be nothing. It has to be, “There will be a bill that hasn’t been paid,” “You will not be prepared for an event that is happening.”

The kind of stuff that, heaven forbid, if you ended up in a waiting room that day, you still would have to figure out how to do it on your phone, or you’d have to tell somebody that it wasn’t going to happen. That’s urgent. Everything else is not urgent. And the reason I say this is because, often with ADHD, we can really struggle with clarity of thought. And so, this is a very, very clear clarifying indicator. So, that’s step one.

Pete Mockaitis
And you say this only takes two minutes?

Skye Waterson
Yeah.

Pete Mockaitis
Wouldn’t the listing of all the things take a long time?

Skye Waterson
That is true. It depends on how many tasks you have. It might take five. It usually doesn’t take longer than that.

Pete Mockaitis
Okay.

Skye Waterson
But once you’ve done that, basically at this point, what you want to do is you want to go ahead, and this is really, you know, I’ve done this hundreds of times with lots of different professionals, and I’ve never had anybody have more than five tasks that are truly urgent for tomorrow. And this is across work, home, everything.

So, if we’re thinking about this, we’re going, “Okay, I now know what is truly urgent,” let’s look at the rest of the tasks and think about, “Okay, what are the tasks that are on this list that are going to help move me forward? What are the 80-20 tasks, those things that are going to help me with something?” So, that’s the stuff that you really want to highlight.

I usually recommend people highlight it in green, stick it in their calendar, give themselves a dopamine boost to get started. We can talk about that in a second. But these are things you really want to focus on and promote, because a lot of time we actually spend our time doing things that are neither urgent nor important. They’re just easy to take off, and that’s a big problem.

Pete Mockaitis
Okay. So, we have a very clear picture for urgency, which is really nice in terms of getting that level of clarity from, “Well, yeah, there’s a lot of things which would be nice to kind of have done soon-ish,” as opposed to, “If these are not done today, suffering will ensue.” It’s like, “Okay. All right. Bright red line there,” and only five-ish things maybe rise above it.

Skye Waterson
Sometimes none. People are always surprised.

Pete Mockaitis
Hey, good news. So that’s a crystal clarity on the urgency. And, likewise, can we get that with importance? There’s 80-20.

Skye Waterson
One hundred percent.

Pete Mockaitis
Could you tell us how it is done?

Skye Waterson
Yeah, so that’s actually something that, when I work with people, I figure out first. And what we want to understand is we want to understand “What is your 80-20? So, first of all, what is your goal?” And this is where we have a whole conversation about setting goals and how we feel about setting goals, because I’ve never met someone with ADHD who doesn’t have a strong feeling about goals, positive or negative.

But we need to know the direction that you’re going in, in order to understand “What is the 20% thing that you could do that’s going to give you an 80% return to get there?” Because a lot of times, that’s actually something you’re already doing, and you just need to double down on, expand on. It’s not the new shiny thing that could totally work, but has not been tested even once. So, this is kind of what we want to focus on.

And so, usually, when we’re looking at that, what is truly important, it’s what is going to help you reach your goal, what’s the 20% that will give you 80% return on reaching your goal?

Pete Mockaitis
Okay. So, I love the 80-20 Rule, and that’s super. I guess, sometimes, it feels a little unclear, like, “Well, I don’t know, it might be any number of these things.” Do you have any follow-ups, or next-level questions, or prompts, or approaches to zero in on that?

Skye Waterson
Yeah. Usually, if you’re struggling with this because you don’t really know what your goal is. So, that’s what to focus on. So, the first thing I’ll do is I’ll ask people to identify, and this isn’t just me. This is some awesome, you know, I’ve had amazing mentors in my own life. Ask for a 25-year goal. So, we say, “Okay, 25 years from now, what are the five things that you want to have achieved?” And you’re going to be like, “Man, that was great. Like, I am nailing it”?

Because when we take it to 25 years, we’re usually at a position at that point where we are not in fear or we’re like, “Oh, I’ll probably figure it all out about that. What’s the point?” So, we sort of go, “Well, I want to be this.” Most people want, “I want to spend time with my family. I want to travel. I want to be healthy. I want to have money,” or whatever it is they want to do.

And then, at that point, we go in, and we say, “Okay, what is the one thing you could do this year that would make it easier for you to reach your 25-year goal?” That’s really what we’re talking about here. And it could be a financial decision, it could be an organizational decision, maybe it’s a health decision. And then at that point, we’re going, “Okay, now let’s come back into what we have to do, what we have on our task list right now. What is the thing that is helping you get there?” That often is where we get the best clarity.

And then if you’re really struggling, I actually do have an entire decision-making ADHD framework because it’s not uncommon to struggle with decision-making, and we go through some of the research behind the significance of tasks, and we talk about the margin of error and that kind of thing to help you figure out, “What is important to really spend time on when it comes to making a decision?”

Pete Mockaitis
Well, this framework is intriguing. Is this discussable in five to 10 minutes?

Skye Waterson
Yes. All of my stuff is very simple because, what I want is to practice. I want it to get, you know, people often say to me, like, “You’re in my head. I can’t get it out now in a good way because it’s, like, helping me understand things.” So, yeah, so basically, at a very, very basic level, and I’m going to mess up some statistics here so I apologize. Apologies for those of you who know what I’m talking about.

We want to talk about this idea of significance. So, even if we’re talking life-saving medication, “Should it be used? Should it be not used?” that kind of thing, there’s a 1% margin of error. So, there’s never something that is truly free from having a chance that it is incorrect.

So, if you think of yourself as all the decisions you make being on a continuum from 1% margin of error, very, very important decision, but still could be wrong to a 50-50 margin of error. You know, it really doesn’t matter. Flip coin, you know, red shirt, green shirt, whatever. It’s fine. Then we need to understand, “What is the margin of error that you are happy to have with the decision that you’re making? What is the amount that you’re happy to have in error?”

So, if somebody’s like, “I don’t know which of these things to focus on this week,” then I ask people, “Okay, well, what is the margin of error on this?” And, usually, people will probably say it’s about 30% because they’re like, “Well, it’s not that important. I don’t want to waste my week, but if I did the wrong thing, it’s not going to be the end of the world.”

And at this point, I will help you assign time to a margin of error. So, if it’s a 50-50 task, it really doesn’t matter what decision you make, then we will go ahead and say, “Okay, you’re just going to take a few minutes to make that decision.” If it’s the 1% margin of error, you could take a year to make that decision. But the most important thing is that you go ahead and you schedule that time to make that decision.

So, if it’s a 30%, 40% decision, which one is more important? I’d say, “Okay, let’s go ahead and we’ll schedule some time later today. Maybe we’ll schedule 20 minutes or 15 minutes. You’re going to sit down, look at all the options, weigh them up, maybe talk to somebody, ‘What do you think I should do?’ And then at the end of that 15 minutes, whatever decision you made at that point is the decision that you’re going to stick with.”

Pete Mockaitis
Now, when you say margin of error in percentage terms, I’m thinking, I’ve always got two different concepts in my head at the same time here. So, one is margin of error, if I’m making an estimate of how much something is going to cost, “Oh, I was off by 5%,” versus a margin of error in terms of thinking about, like, the consequences of error. So, just to make sure I’m conceptually getting this, what does the percent represent in our margin of error here?

Skye Waterson
The percentage that you’re willing to be wrong. So, in a 50% scenario, you’re saying, “I’m happy with a 50% margin of error because the decision I had to make was what are we going to eat tonight. Worst-case scenario, we pick something that I don’t really enjoy, and it’s a new experience for me. It’s totally fine.”

Pete Mockaitis
Oh, I see. It’s like, “How certain must I be to be okay with this decision, such that if I got it, if there was a 50% chance of me getting it wrong, that means it doesn’t matter all that much if I get it wrong,” versus, “There must be 99% certainty of this because, if I mess up, you know, my whole family is dead.”

Skye Waterson
Exactly.

Pete Mockaitis
“Thusly, I’m going to proportionately spend more resources on the actual decision-making research stuff of nailing that decision right.”

Skye Waterson
Exactly, because most of the time, with ADHD as well, we’ll have this thing. And if you have ADHD and you’re listening, you’ll probably be like, “Oh, yeah, I do this all the time,” where you won’t really decide to make the decision, you won’t lock it in as, “I’m going to make a decision.” It’ll just kind of go around in your head. You’ll think about it and you’ll ruminate on it.

But because we have working memory struggles, we’ll lose the thread of the decision we made. We might even talk to somebody and come back and go, “That’s it. That’s what I’m going to do. Oh, I’m glad I figured it out.” Never write it down. Forget that we made that thing and then go and do it again. And so, we can end up in this rumination cycle that is very, takes a lot of mental energy.

Pete Mockaitis
Okay. I dig it. And so then, it seems like a lot of the value here is just getting clear that “What the task is, is making the decision. That is the project that we are embarked upon.”

Skye Waterson
You might even write that down and put it on your filter. That’s a hack for you right there.

Pete Mockaitis
Oh, okay. That is the mission. That is the project, is the making of the decision, as opposed to, you jumping the gun and figuring out all the things, “If I do it and if I don’t do it.” It’s like, “Oh, well, we’re not even there yet.”

Skye Waterson
And then you’re like, “Oh, but what if…?” Yeah.

Pete Mockaitis

Okay. Cool. That’s handy. What else we got?

Skye Waterson
Well, I think the third piece that is often what I get from people is, “Okay, cool. I have made a decision. I now know what I need to do but I don’t want to do it. It’s too boring. It’s too confusing. The last time I did this, somebody yelled at me and I didn’t like it and I don’t want to do it again.” This is something that we don’t talk about enough with ADHD, or even without ADHD.

We often have these experiences, and so you’re going to guess it. I’ve used the research to come up with a strategy to help you do it in about 15 to 20 minutes.

Pete Mockaitis
All right, let’s hear it.

Skye Waterson
Okay. So, I want to ask you, “What is a task that you don’t want to do right now?”

Pete Mockaitis
Oh, let’s just say some tax stuff, yeah.

Skye Waterson
That’s a really good example. That’s a really good example. So, if you’re ADHD, the first thing that we want to do is we want to, and we talked about this before, we want to give you a reward for starting the task. We know the reward at the end is not really going to be attached to the task. It’s not going to be motivating enough to get you to do it. So, we want to give you a reward for starting the task.

And if you’re in a position where it’s tax stuff, we want to give you a really nice reward. So, at this point, people usually say, “Okay, well, Skye, I don’t want to eat piles of chocolate forever.” “That’s okay. We’re not going to do that. We’re going to sensory stack.”

So, if you think about your five senses – touch, taste, smell, sight, sound – what are the different sensory items that we could add to you sitting down at your desk, or sitting down at a coffee shop, or wherever you want to do the taxes? So where are you planning on doing this task?

Pete Mockaitis

In my office here at the computer.

Skye Waterson
Perfect. Okay. So, the reward has to be in your office at your desk. This is very important because of transition times. A lot of people will be on the couch, in front of the TV, being like, “I’m just trying to get the motivation to go do this,” and they’re like, “Why doesn’t this work?” It’s because you’re not doing it in the space.

So, if we think about the different senses, so food, drink, listening to something, watching something, what’s something fun you could do at the beginning of this task? So, it’s not part of the task. It’s just something you’re going to do for 10, 15 minutes.

Pete Mockaitis
Well, what’s funny, because, like, my first thought is, “Ooh, a fun thing I could do in my office at my computer is, like, play a game,” but that’s dangerous because you might get carried away, and do that for hours. Like, “Oh, this is so much. I don’t want to stop.”

Skye Waterson
It does have to be something you will stop. Yeah. It does have to be something you will stop. And so, I will say, over time, people can do things more, like playing a game. Your brain starts to trust you, that you’re going to do this, and it’s not going to be as terrible as it sounds.

But TikTok is never a good idea, so don’t do that one. But is there anything else? Sometimes people like to do Sudoku or a puzzle or a retro game or read a comic or an article or a YouTube video.

Pete Mockaitis
You know, what’s so fun, I’m looking right now in my office. I have this, this is so weird. I think Tim Ferriss talked about these acupressure mats, like Bed of Nails is one of the brand names. And I don’t know why it’s so fun for me to just kind of mush it against my body. Like, it’s kind of like the rush of a cold plunging a little bit, except not messy. It’s not painful, but it’s an intense sensation, which, at least for now, is still kind of novel and interesting. So, I guess we could call that a reward in a weird sense.

Skye Waterson
Yeah, 100%, so we could do that one. Now let’s stack it. So that’s good, but you’ve got to do taxes. So, we want to add something. Is there a cold beverage, a hot beverage, anything like that that you’d like to bring with you to your desk?

Pete Mockaitis
Oh, sure. Well, I’m thinking about GT’s Gingerade Kombucha, or Heineken 0.0, or just straight up Diet Coke, I mean, you know.

Skye Waterson
Okay. Which is the one you want the most?

Pete Mockaitis
Probably the Kombucha right now, yeah.

Skye Waterson
Okay. Perfect. So, we’re adding the Kombucha. It’s very themed. And then let’s go ahead and add some music or something to watch while you do this.

Pete Mockaitis
Wow, watching at the same time as I’m doing a thing, or as I’m doing my acupressure and my beverage?

Skye Waterson
Yeah, as you’re doing your acupressure.

Pete Mockaitis

Oh, man.

Skye Waterson
Because the first thing you’re doing is just something fun. So that’s the first thing you’re doing.

Pete Mockaitis
So, watching, well, if I really go on bonkers on the visuals, I might put on the Oculus Quest 3 and look at some, like, 8K nature videos.

Skye Waterson
That’s cool.

Pete Mockaitis
That’s kind of fun to do in the morning on a cloudy day. It’s kind something I do sometimes.

Skye Waterson
Yeah. Okay.

Pete Mockaitis
Or, I guess watching. I’m thinking about the Fireship YouTube channel. But, again, there’s danger there. YouTube fun, click, click, click, away, away you go. So, watching. What else do people love watching?

Skye Waterson
I mean, you’re right about the whole thing with views. I think some people will put like really cool digital backgrounds on their computers. Some people will just want to watch music videos. That can work, you know, things like that. Personally, I think I’ve got the weird one. I like to watch Twitch streams because I love gaming.

So, if I can’t get some gaming done, and so it gives me like a little piece of that. So, I might choose to do that while I use the mat and have the drink. But, yeah, something like that. Some people listen to music at this point. They don’t want to watch anything. So, they have a couple of pieces. I usually think three is quite nice, especially when you’re doing something that’s particularly difficult, so.

But the question I always want everyone to ask, and this is why we’re doing this live with you is, if you said to yourself, “Okay, forget the task, forget that task. All I’m saying to myself right now is, ‘Will I go and sit at my desk if it comes with a Kombucha, a Shakti Mat, and looking at something nice?’”

Pete Mockaitis
Sure.

Skye Waterson
Yep. Okay. Good. Perfect. Because that’s what we want to know. That’s the most important thing we want to know. So, the second thing that we do is, while we’re doing those things, while we’re giving our brain the boost, the dopamine boost, that we don’t think it’s getting because of the way our brains are currently wired, you want to go ahead and you want to turn off the distractions.

This is a good time to turn off distractions because you’re feeling good. So, who cares about them anyway? What is the stuff that you know is going to distract you when you get down to doing the taxes?

Pete Mockaitis
Well, probably, many open tabs or windows on the computer itself.

Skye Waterson
Exactly. So, we want to turn off the tabs. If you’ve got one of those situations where your brain almost goes ahead and clicks your email before you even think about it, go ahead and remove that bookmark, make it harder to find. If you need to, you can use apps like Freedom to fully remove it. You want to go ahead and remove distractions right now.

The next thing you want to do is you want to dial down the dopamine a little bit. So, maybe at this point, you just switch to music or a podcast or something in the background. Still there. We’re not going to silence just yet, but we’re dialing it down. And then at that point, what you want to do is you actually want to go ahead and write down, on a little Post-it note, a recipe of exactly what you’re going to get done.

So, “I need to open this application. I need to find this form. I need to do this.” And the reason you’re doing that is because you struggle with working memory, right? Too boring, too confusing, too, you know, “I felt bad last time I did it.” So, the too confusing piece, we want to break that right now.

We want to put it on a piece of paper, exactly what you’re going to get done during this period of time, as if you’re writing a recipe for somebody else because that person is probably you. Because if you have ADHD, you’re probably going to get distracted and forget what you were doing and have to come back to that little piece of paper. So, that’s the next piece. Does that make sense?

Pete Mockaitis
Yep.

Skye Waterson
Awesome. And then from there, the last piece we really get to is, “Okay, I’m here. I know what I’m doing. I’m feeling good, but I’m a little bit nervous about actually doing the task. Like, what if it goes badly?” And so, we want to give yourself the opportunity to do a few stretches. When you’re about to do exercise, or artistic endeavors will often stretch or do some practice runs. We don’t really do that with work tasks.

So, we want to just open the application that you’re going to use and tinker around in it a little bit, you know, move some stuff, add some notes, just play in it with no real pressure to get started. And, usually, what’s happened at this point is people have gone ahead and they have found themselves in position where they’re like, “Okay, well, I’ve already opened the application. I know exactly what I’m doing. And I already gave myself a dopamine boost and turned off all distractions.” Inertia starts to go the other way and you go, “Well, I might as well just do it now.”

Pete Mockaitis
Okay. So, that’s really intriguing. So, then the reward is happening before instead of after. And I guess my concern is that I’d be enjoying myself so much, I’m like, “I just want to keep this party going. Now I really don’t want to stop all this fun for the taxes.” Is that not a problem? Or, how does that end up unfolding?

Skye Waterson
It’s a good question. So, what we talk about here is we talk about the idea of the dopamine dial. So, rather than going ahead and just going, “Well, I gave myself a reward at the beginning, and then I turn everything off and we get serious and get to work.” We talk about a dopamine dial. We dial the dopamine down.

So, we don’t just turn it off. We say, “Yeah, the party can keep going. We’re just going to write a list of tasks that need to be done right now.” But let’s just switch it away from the podcasts. What’s the next thing that might work? What about some music? Is that going to work? We still got the drinks. We still got everything there. And your brain’s kind of going like, “This is pretty cool.” Still like, “I’m not panicking yet. We’re not in a dopamine-deprived state yet.”

And then from there, you’re like, “Well, we’re just going to open the application. We’re going to tinker around in it.” What happens for most people at that point is they start to kind of get this situation, which you might’ve found in the past where you go, “This is kind of distracting me now. Like, I know what I’m doing. I know I’ve got to do it. I know it’s on. It’s something that’s on my list, and I need to get it done. And I’m right here and I’m about to do it. This music is kind of distracting me now.”

So, you’ll tend to naturally start to turn those things off, but it’s when you give yourself the pressure of, “Now I’m starting,” that we can get ourselves in that position.

Pete Mockaitis
Okay. Very cool. All right. So, that’s really handy and thoughtful and thorough. Thank you. Any other favorite do’s and don’ts for we don’t want to do the thing, but it’s time to do the thing, how do we proceed?

Skye Waterson

Well, honestly, I think the biggest thing that I would say to everybody is you think that you know how to give yourself a reward for starting a task. You probably don’t. If you’ve sat here and gone, “Yeah, I mean I have a coffee,” this is level one of this, right?

We want to go all the way to level 10. Like, most people that I see who fail to actually get tasks done once they understand the strategy, they fail to get tasks done because of a feeling that, “I ought to be able to just do it. I should just be able to do it. I don’t understand why I can’t do it. Everyone else can do it.”

And that feeling, unfortunately, can hold you back from actually doing the task. So, usually, at this point, I ask people to get really serious about their dopamine. Make a list. Five things for each sense, for each of your different senses, like, combine them in different ways. Like, get serious about this, because this is often the thing that’s really holding you back.

Pete Mockaitis
Well, now I’m thinking about dialing the dopamine up to 10, I mean, well, that invites all sorts of thoughts, like, “Oh, well, let’s crank some, let’s get some alcohol and nicotine and more involved in the party.”

Skye Waterson
That’s exactly what I’m saying. Everyone’s like, “Oh, well, this must be what you’re talking about.” And it’s like, “No, no, there’s many different ways,” you can ask ChatGPT or your favorite AI if you need help. But, like, there’s many different strategies before we get there, right? So, a lot of times people, for example, with the phone, people say, “Okay, well I have my phone. I’m addicted to my phone. What do I do?”

Like, before phones, we used to have, I don’t know if you’ve ever were in an office before phones, but, like, we had a ton of things. It was like the little thing that you like to throw a basketball into, and the Sudoku, and the weird little like water thing that you pressed and little hoops went into it.

Pete Mockaitis
Oh, yeah.

Skye Waterson
You know what I mean? There’s like a whole thing.

Pete Mockaitis
Severance had that one.

Skye Waterson
Exactly. So, go in that direction and then think about, during the week when you’re at the supermarket, what is a new cold drink that you’ve never tried before? Grab that off the shelf. Leave that for when you’re going to get started off on that next task. Those are the things that you would be surprised make a huge difference.

And, you know, obviously, we can always talk about the hardcore negative sources of dopamine, but that conversation is actually why we end up in that situation where everyone’s, like, we’re either dopamine deprived. And if you’re ADHD, you’re already dopamine deprived. So, it’s not really a helpful conversation a lot of the time.

Pete Mockaitis
Well, for funsies, could you give us just a quick rundown of a few of your favorite tidbits? Because, yeah, I think you’re right. Once we really let the creative juices flow, I mean, sometimes I have a feeling, it probably gets pretty, like, weird and uniquely custom for your own proclivity.

Skye Waterson
Oh, yeah.

Pete Mockaitis
Like, I actually do have, now you mentioned, a Tupperware vessel of water in the refrigerator that I will shove my face into. And so, the mammalian dive reflex is a real thing. It reduces heart rate, etc. And it just feels kind of fun. And so, I guess, if we’re pushing our own buttons, then that could take all kinds of interesting flavors. Can you share a few things with us?

Skye Waterson
Yeah, I love that because people often, you know, this level one dopamine is, like, “I’ll get coffee and then I’ll do this.” And level 10 is like, “On Wednesdays, at 7:00, if I do this in this light, this is great.” People get very specific. My favorites, I mean, I love all kinds of different carbonated drinks, is my favorite. So, I’ll go for different kinds of those ones.

I, like I said, will watch Twitch. I will also watch YouTube. I know not everyone can do that. They’ll get distracted. I am lucky enough not to do that. I have, the Spotify AI guy now has me pretty well dialed in. So, if I play the DJ, it usually knows exactly what kind of music I want to listen to because it’s got me based on time of day.

Yeah, those are kind of the biggest ones that I do. In terms of physical touch, I have a lot of fidgets. And if all else fails, I’ll usually go to a coffee shop and I’ll go there with no ability to plug my computer in, and I’ll order something really nice, and that’ll kind of get me through.

Pete Mockaitis
All right. Well, tell me, any final things, tips, tricks, things you want to make sure to mention before we hear about some of your favorite things?

Skye Waterson
I think, usually, what I like to tell people is just your systems are probably broken, not your brain. I think it’s really important for people to understand that because so often we people will find themselves sort of slamming up against a wall again and again and again.

That’s what leads to burnout. I’ve done it many, many times before I figured out I had ADHD. And being able to work with different systems makes it a lot more fun. It’s not just better for you and what you do, but it’s also a lot more fun.

Pete Mockaitis
All right. Well, now could you share a favorite quote?

Skye Waterson
Yeah, my favorite quote is, “We rise by lifting others.”

Pete Mockaitis
All right. And a favorite book?

Skye Waterson
At the moment, I am reading most things by Naval Ravikant. So that’s kind of the area I’m in right now.

Pete Mockaitis
And a favorite tool?

Skye Waterson
It’s split between Notion and Miro.

Pete Mockaitis
Okay. And a favorite habit?

Skye Waterson

Dopamine. Starting with dopamine, for sure.

Pete Mockaitis
All right. And is there a key nugget or Skye-original sound bite that is quoted often?

Skye Waterson
I think a lot of people, to come back to the dopamine thing, will just be like, you know, that people tend to say like, “You have to take your dopamine seriously. You have to take having fun as seriously as working if you have ADHD.”

Pete Mockaitis
Okay. And if folks want to learn more or get in touch, where would you point them?

Skye Waterson
You can find me at Unconventional Organisation on Instagram. Like I said, you can just DM me there and I will give you the two-unit folks formula. And you can also find me at Unconventional Organisation on the internet. I have a podcast, The ADHD Skills Lab, where I talk about a lot more of this research. And if you want to join my program, I work with executives and entrepreneurs who have ADHD who want focused, balanced growth.

Pete Mockaitis
All right. And do you have a final challenge or call to action for someone looking to be awesome at their job?

Skye Waterson
Probably, stop trying so hard and start thinking about ways to do things differently.

Pete Mockaitis

All right. Skye, thank you.

Skye Waterson

No worries. Great to be here.

1039: How to Stop Wasting Time on Email with Randall Dean

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Randall Dean shares practical tips for taming an overwhelming inbox.

You’ll Learn

  1. The best time-saving investment you can make
  2. How to keep unread emails from flooding your inbox
  3. The inbox shortcuts that’ll save you hours

About Randy

Randy Dean, The E-mail Sanity Expert®, author of Amazon bestseller Taming the E-mail Beast, is an expert on time & e-mail management and the related use of technology. For 25+ years his humorous and engaging programs have given attendees key strategies on better managing their time, e-mail, apps & technology.

Resources Mentioned

Thank You, Sponsors!

Pete Mockaitis
Randy, welcome!

Randall Dean
It’s great to be here.

Pete Mockaitis
I’m so excited. We’re talking email. You are the Email Sanity Expert, registered trademark. So, I’d love to start by hearing a little bit in working with so many people and their email, is there anything that’s particularly surprising to you that you’ve learned about us professionals and doing email?

Randall Dean
Well, you know what’s interesting, I’ve been leading programs on this topic for 20 years now, started my company all the way back in 2004, and what I’ve learned over all this time is that not only are people spending, I think, the average that I saw in a published study was a little bit more than two hours per day, but at a lot of the conference events, conventions, places that I speak, I’m getting people answering anywhere from three to six hours a day just on their inbox.

The interesting contrarian fact and statistic that I’ve discovered, I ask people at these programs, I go, “How many of you have had prior training?” And if it’s an audience that I haven’t spoken with before, it’s less than 5%. Less than 5%, not just here in the United States, Canada, Mexico. I’ve spoken in Europe several times on this. And in all of those places almost no one has had strategic or technical training on how to be more efficient with their email on a tool that’s taking 25% to 50% or more of their workday. It’s crazy.

Pete Mockaitis
That’s what’s funny is I think we have a sense, or I have a sense, and I think I’m getting the vibe from other professionals, that we’re spending “too much time” on meetings and emails. Well, first, I just want to check that assertion for validity, because I guess it’s conceivably possible that even if you are spending six hours on email a day, if most of these messages are thoughtful works of written craftsmanship in which you are casting a vision and offering clear guidance, and wisdom, and leadership, and insight, and clarification, and coordination that that might be okay.

Like, you’re doing work. You’re doing knowledge work at a high level. You’re spending six hours on email but those six hours are well-spent in these communications. Tell, Randy, how often is that the case? Or, is, in fact, our assertion correct, that that’s too darn much?

Randall Dean
I would actually say for the vast majority of people, they’re not doing what you just described.

Pete Mockaitis
Okay.

Randall Dean
They’re dealing with 200 emails a day, and they’re trying, in a mass flurry, to get through them as fast as they possibly can, and they’re not writing terribly high-quality and high-level communications. They’re just trying to get through the flood of information that’s coming in at them. It’s funny because I actually talk about email etiquette sometimes and I’m actually of the point, like, make the subject line sort of say what is in the email.

If there’s tasks inside the email, make sure people, right up front, know who’s got what tasks. And if you can’t get down to bullet points, it’s almost the exact opposite of what you just said in terms of crafting really nicely crafted communications. And I actually even mentioned that, if you are going to write something that’s sort of wordy and requires extra time and effort to go through it, you should probably turn that into an actual document, like a Word doc or a PDF so that you attach it to the email, so people slow down and read it more carefully.

Because one of the problems that they have is if it’s sort of a long email in terms of message length and density, a lot of people are just scanning over the top of them and not getting into them because they’ve got too many coming in.

Pete Mockaitis
Oh, Randy, you’re bringing back a fun memory of my first kind of grown-up internship was at Eaton Corporation in Pittsburgh, and I was part of this program, and the one coordinating the program, her name was Amber. And it was funny, her email signature had “Thank you for your attention to this communication,” like in all of her emails.

And it was so funny, I don’t know if this is what she was going for, but it caused me, an insecure 19-, 20- year-old intern to say, “Oh, shucks, I didn’t actually spend much attention on your communication. I better read it again.”

Randall Dean
Yeah, and the thing is, I always tell people, “If somebody’s getting 150-200 emails a day, and you’re barraging them with a 14-paragraph soliloquy, and they miss something, is that really their fault for missing something? Maybe it’s your fault for not getting to the point, you know? So, yeah. Now that doesn’t mean you throw out all rules for appropriate grammar and etiquette.

But I also am a believer that email is best used when communications are simple, obvious, and straightforward. And the minute they start getting complex or confusing, it might be time to pick up the phone or go find the person.

Pete Mockaitis
Yeah, or, I guess, we’ll talk alternatives and tools. I personally love the Loom video, if we’re remote and asynchronous, in terms of, “Hey, these are my thoughts on this matter and some detail. So, you can see my face, hear my voice, see the document, or whatever we’re talking about at the same time.” So, okay, understood.

It sounds like it’s quite rare that email time is time brilliantly spent, and we may, even if we do need to craft a beautiful something, it might be better off in a document. And so, the Tim Cook’s up early in the morning, emailing the day’s leadership wisdom for each of his key team members, it sounds like that’s not what most of emailing is.

Randall Dean
That’s really funny because, I mean, if you’re at Tim Cook’s level and his senior leadership team’s level, then maybe what you described at the start of this conversation might work. Most of the people that are coming into my audiences are administrative professionals, mid-level to low-senior level managers and directors, and they’re just dealing with a barrage of messages, and they’re trying to figure out what they need to get done within these messages, who they need to follow up with from these messages, and how to then turn that into a work day.

And so, a big part of what I’m doing is like, “Okay, here’s how you go through this stuff to figure out what’s important, what’s urgent and what’s not.” So, I think that that’s been a big part of the struggle.

Pete Mockaitis
Yes, I hear you. So, that’s kind of the email vibe we’re talking about here is tons of incoming things, kind of unprocessed, unsorted, that need to be gotten through. And I’m thinking we had Cal Newport, we talked about A World Without Email on the show, and he used the phrase, just haunting, “In some corporate environments, we are human network routers.”

Randall Dean
That’s a good way to put it. I like that a lot.

Pete Mockaitis
In terms of, “Okay, here’s a message that’s coming to me. Okay, I can do this thing. I can forward it. No, it doesn’t belong to me, it belongs over here, forward there.” So, for many of us, it’s about processing large volumes, and having help is awesome. Shout out to my producers. I just forward all my pitches to them and they know what to do. It’s like, “Read all of these thoughtfully and tell me which ones are fantastic finalists.” And so, I don’t read 90% of the pitches in my email, and that’s awesome that they do that for me. I greatly appreciate them.

Randall Dean
And that’s a perfect delegation right there, that not enough people, I think, are doing. And so, I always tell people, “If you’re more of a senior level in your management chain and you feel like you’re spending way too much time, especially on low-level emails, that’s a mismatch because you’re getting paid to do higher-level work than low-level emails.”

So, you got to find a way to sort of fix that a little bit. And it’s probably going to require a reallocation of some of the messaging so that you’ve got somebody else helping you with screening a bit. I think that’s a really good way to put it.

Pete Mockaitis
Okay. Well, I am tempted to jump into tips and tactics, but, first, maybe, can you orient us to, you mentioned, okay, almost none of us get training in this. Can you give us a glimmer of hope or inspiration? What’s on the other side of this? Let’s say we do get some training from this insightful conversation with Randy or more, what’s possible? In terms of when we’ve got our email game optimized, what’s the before-after transformation look like?

Randall Dean
I think email is what you could call a necessary nuisance. It’s something you have to deal with and we’re not going to get rid of it. I don’t see anywhere on the horizon where email is going to completely go away. But when you think about what it is, the vast majority of what’s coming in are what I basically say are a whole bunch of hungry squirrels with the occasional big angry dog, right?

And so, basically, you’re trying to figure out, “Which one of these is the big angry dog that’s barking? And how do I reduce the distraction of all these hungry little squirrels?” And so, when you say “What’s on the other side?” I think having a logical triage mentality with processing your emails that requires some new habits.

But if you get into the habits, and you do it well, you will look at your emails less times per email, you might look at your inbox less times per day in total, you will be able to better identify what’s really important or urgent, and you’ll end up without such a big cluttered mess so that it’s not a distraction in and of itself.

You know, I would bet almost every program I’m into, maybe 15-20% of the audience has more than a thousand emails in their inbox that haven’t even been filed or deleted. And I mean that’s common. So, if you’re in that boat, you’ve got a lot of company. But I can also tell you, I know that when you’ve got just got pages and pages and pages of email streaming in your inbox, some marked unread, some flagged, some starred, most of them not, and you don’t know what is most important, that’s stress. I mean, I just think that’s the definition of stress, and it doesn’t have to be that way.

Pete Mockaitis
Okay, yeah. As you described that scene, I could actually feel my heart rate ticking up a bit. So, okay, less stress, fewer times, fewer total minutes there. Could you ballpark it for us? I mean, I’m sure it varies a lot based on roles and responsibilities and email volume. But in terms of untrained to email Jedi Master, what kind of email time savings might we realize?

Randall Dean
Well, it’s interesting. I had one of my university clients at one time, they had to sort of justify the expense of bringing me in to do the program. They did an ROI justification. And what they did was really cool. They actually asked people about a week or two after the program how much time they thought they were saving from the tips they learned in the program, and how confident they were, they were saving that much time.

And, now, the average person was basically saying they were saving more than two hours a week with a good number of them as much as four to six hours per week. Now, I know that may not sound like a lot, but if you could get a half day to three quarters of a day of additional productivity time every week, I think you’d be pretty happy with that.

Pete Mockaitis
Absolutely. And my mind just leaps to running the spreadsheet. So, two hours a week times 50 work weeks a year, 100 hours. What’s that annual rate for those employees? And now that time spent more valuably. So, Randall, unless your workshops cost a quarter million dollars, I’m pretty sure they got their money’s worth.

Randall Dean
Yeah, I mean, I think it’s easy, low-hanging fruit return on investment. I believe that we figured out that if you extrapolate those findings across all users in the room, that the first year ROI in and of itself was over 2,000%.

Pete Mockaitis
Okay. That’s what I like to hear.

Randall Dean
Because, like I said, it would be a different math if half the people or more already had this training, but if it’s literally 5% or less, it’s almost impossible not to see a significant productivity improvement.

Pete Mockaitis
All right. Well, we’re fired up, Randy. Lay it on us, what do we do to realize these gains?

Randall Dean
Well, when I teach my programs, I’m mostly speaking to professionals using tools like Microsoft Outlook or Gmail, and one of the first things you have to do is just understand how software works. Most people don’t know what the software can actually do. And one of my first tips to anybody is, if you’re using a piece of software frequently, daily, multiple hours per day, there may be no better use of your time if you want to be more efficient to spend a little bit of time at least every week learning another new tip.

Because, by learning that extra tip or two over time, you’re just going to get so much more efficient and so much more time back just by understanding how the software works.

And the one example, really interesting thing, because most people are self-taught, I’m going to play a scenario out for you that happens super frequently for a lot of people. They get an email, they open it, they read it far enough to go, “I don’t have time for this right now,” and then they mark it unread or they flag it or they star it. Okay, now right there, let me share with you the statistic that I believe comes from that behavior right there.

The average professional email user tends to look at each and every email they receive, on average, three to seven times before they finally take a smart action with that item. And I think a big part of the reason that’s happening is because they read it, they go, “I don’t have time,” they mark it unread, they flag it, they star it. It stays in the inbox. This is where your inbox mess is coming from too. And then what happens is you’ve just guaranteed you’ve got to go back and look at it again later.

And so, you’re not doing anything. I mean, you’re really not doing anything with that input, but you are giving it time that is basically worthless time that you’re throwing away. And so, one of the things that I share with the people is a little triage method, sort of based a little bit on the work of David Allen, who wrote the book Getting Things Done. I took training from him all the way back in the early ‘90s. And one of the things that I learned from him is, if something is quick, you do it right now.

Pete Mockaitis
Two-minute rule.

Randall Dean
Yeah. If it’s quick, you do it right now, and don’t you dare keep it for later. I love this. Somebody said, “Let’s go to Ohio. OHIO, only handle it once,” right? So, that should be your philosophy when you run into something quick. And I always challenge people in my programs, “If you’re looking at an email, you figure out what you need to do, and it’s only going to take you a couple minutes, and you don’t have time to do that? Why are you looking at your email? Shouldn’t you just keep working on what’s on fire? Why are you looking at your messages if you don’t have time to handle a quick little thing?” So, keep your focus.

But then, when I talked about what’s inside the software, both Outlook, classic Outlook, new Outlook, as well as Gmail have internal capabilities to take an email and quickly convert it into a related task or calendar item.

And so, I say take a few more seconds to get to the point where you know what you need to do next and then turn that item into a task or calendar item. And then once you’ve done that, if you haven’t got it done, but you got it on your task list or calendar, get it out of your inbox. Because, I mean, you’re done for now. It’s time to either file it for later reference or delete it if you don’t need it. And if you don’t have a good place to put it, make one and put it there. Not really rocket science.

I, sometimes, am surprised I get away with this as a living because, really, it’s sort of advanced common sense, but people just don’t think it all the way through, and they’re very inconsistent with how they’re triaging these messages.

Pete Mockaitis
Well, yeah, what’s interesting is, I think the reason you are getting away with it is because there’s some psychological things at play here.

Randall Dean

Absolutely.

Pete Mockaitis

Because whenever you go to the email, it’s like, “Ooh, here’s new interesting things. Oh, and some of it’s really important and urgent. I better handle it right away.” So, we’re almost never in the mind space like, “Okay, fire up Outlook, fire up Gmail. Hey, you know what? I wonder what all this software is capable of?” Like, we’re not in that headspace to do that.

And those functions, I guess, we’re not as accustomed to them, as well as thinking about the GTD, Getting Things Done, David Allen kind of philosophies of the inbox is merely a temporary repository by which it means, “Hey, you haven’t looked at me yet. Process me out of here in one way or another.” As opposed to, “Let me be the long-term storage facility for messaging.”

Randall Dean

Far too many people are using their inbox for three things. One is to receive and process new items. Two, is their de facto, but very dirty and highly disorganized task list. And, three, is their Uber storage for all things that haven’t left that inbox. And my strong belief, especially with my background understanding some of the GTD-type philosophies is the only one of those three that’s valid is processing new items. That’s what your inbox should be for is processing new items.

If you can deal with it quickly, you get it done. If you can’t deal with it quickly, it then becomes part of your task list or calendar because there, in your task list and calendar, once you understand those tools, you’ll be able to say, “What is the best use of my time right now? Where should I be putting my focus?” And you can’t really do that easily in a big messy cluttered inbox with 200 things marked unread and flagged. It’s just not going to work well.

And then, of course, once you’ve either got it done, got it on your task list, got it on your calendar, get it out of there. You don’t need it in there anymore.

Pete Mockaitis

Yeah. So, help us out, if we’re worried, like, “Okay, I read a message and I realize, hmm, this is going to take some more thought and attention, and it is not to be dealt with now. I’m not leaving it in my inbox. So, what am I doing with it? And how do I make sure I don’t forget about it and lose it if it’s not in my inbox?”

Randall Dean

Now, simultaneously, when I teach the tip about putting it especially into your task list, I also show in both programs how you can turn on reminders. And then, so what will happen is that task will pop back up on your screen at a time when it’s better for you to see it. Not the email, the task, although the email text is typically inside the task that’s been created.

And so, that way you can say, “Okay, I’ve identified what needs to be done. It’s going to come back and find me when I need to see it. I don’t need to leave it where I have it right now. I can put this thing away if I need to keep it for later, or get rid of it if I don’t need it.” And, I think, by utilizing the reminders that are available in both task and calendar, you can relieve some of that stress.

Of course, now I’m going to say this, I regularly get my inbox down to close to zero every day, which makes a lot of sense because I’m teaching people how to work their inbox. But because of that, what I’m trying to teach people is, once you get that inbox down to close to zero, that’s when you shift your focus to your task list and your calendar by habit.”

“If there’s nothing on my calendar right now, no meetings or blocked time for anything, then I work my task list until it’s time to go back and check my email again, or go to my next meeting.” And so, you just sort of get into this habit of where you’re surfing across those three tools throughout the day, balancing your needs to get your critical focused work done with your needs to periodically get back to people.

And I think if you can get yourself into that habit, that flow, you can both reduce the distraction of your email, reduce the time spent on your email, and potentially increase the time you’re spending on your more important stuff, which is the goal of all this anyway.

Pete Mockaitis

Okay. Well, let’s say we’ve scheduled a time, we’re going to spend 30 minutes or so processing this email, and just rocking through it. How do you recommend we execute this step by step? You mentioned triage.

Randall Dean

Yeah. Well, like I said, I think if you’re going to open an email, you look at it once. If you look at it, what do I need to do with it? If it’s quick, deal with it now. OHIO, only handle it once. If it’s not quick, it goes on to your task list or calendar, and then you either file it for later reference or you delete it. And if you don’t have a good place to file it, make one and put it there.

And I will say this, nobody’s perfect at this. I’m not perfect at this. But the closer I get to following that triage mentality when it comes to processing new inputs, especially at the start of the day, but maybe a few more times throughout the day, the more efficient I feel myself getting at dealing with this, once again, necessary nuisance, and keeping the squirrels under control.

So, that’s sort of the goal is, “I want to keep these squirrels from taking over. I want to be in control of this input stream.” And the way to be in control of that is by having a good consistent strategy, habit, routine on how you deal with them and try to stick as close to it as you possibly can.

How much time would you save over a year if you went from looking at the typical email three to seven times, down to once maybe twice max? How much time would that give you in a year?

Pete Mockaitis

Well, it sounds like perhaps 100 plus hours.

Randall Dean

I would think so.

Pete Mockaitis

Well, so you mentioned, learn the software. And I remember there was a day, and I was. I was just goofing around in Gmail, and I think in the settings, I saw enable shortcut keys.

Randall Dean

Yeah, yeah, I show that in my Gmail sessions. I actually go in the settings and I click on the link that says keyboard shortcuts. And, I mean, like that’s a classic example. It’s right there in your settings. You click on it, it opens up. It says shortcuts for computer, for Android, for iPad, right? And I’m like, “My gosh.” And then it’s got like 14 categories of ways you can use the shortcuts; each one is its own drop menu with a whole list of potential shortcuts.

And I tell people, I go in there and I show it, and I say, “Now look at this. This is a classic example. Print that. Print it onto a sheet of paper, set it right next to your computer, highlight two, three, four of these things that you want to get really good at, and then practice them for the next week or so. And then once you feel like you got those ones down, cross those out, highlight two, three, four more.

Once you get those done, then go back to the next drop panel and print that one and do the same thing. And if you just did that, picked up two, three of these keyboard shortcuts a week over the next year, you’d be like a maestro. I mean, you would be fantastic and so much more efficient at just doing the normal little stuff on your computer because now you don’t have to move your mouse to do it.

Pete Mockaitis

Absolutely. When I made the discovery, I was astonished at so many levels. One, I thought, “How is it that these have been here the whole time and I was not aware?” Two, “Why were these not just automatically turned on as the default setting?” because I guess it was not at the time. Maybe it still is not. And, three, “How come none of my friends, who know I love productivity, ever felt the need to share this with me,” probably because they assumed I already knew it, and it would be insulting to bring it up to me.

Randall Dean

I’m going to give you a different assumption.

Pete Mockaitis

All right.

Randall Dean

They don’t know about them either, because nobody has the time to go take a look. That’s why I said, especially if you’re using Gmail, just in the last week, I saw two things that have changed. They’re constantly working on things behind the scenes. One of them was really minor. They moved it from the little three dots at the top of the screen to the little three dots over to the side of the screen.

And so, I was doing a live program, and I go where it’s always been, and I’m like, “Uh-oh, it’s not there anymore.” And then, just out of nature, I went over to the one, “Oh, there it is. They moved it.” And they’re doing that kind of stuff constantly. And so, I think when you’re using a tool like Gmail, as well as maybe the new and Web Outlook because those are sort of Cloud-based, real-time being updated type tools, you want to go in and look into your toolkit quite frequently because there’s new stuff showing up all the time.

Pete Mockaitis

Yeah, that’s telling. And you’re right, and doesn’t take a lot of shortcut knowledge. The ones I use all the time is J for next message and E for archive message.  And you can do a lot of damage if you just say, that’s how I like to triage, I go, “What are the emails I can archive without even really reading? Like, I can just know these can disappear in under three seconds.”

And I go J-E, J-E, J-J-E, E, J-J-J. And it’s just like, boom, flying through it. And it does feel like you’re a maestro. It’s cool. Can you share with us, what are some other software discoveries that are eye-opening and game-changing for people?

Randall Dean

Well, I think one of the biggest ones that most people don’t realize, both Outlook and Gmail, you can actually utilize the Signatures tool as an automated response template manager. So, basically, like let’s say there are certain messages you’re sending all the time, and the same question keeps coming up over and over again. You go into your Sent folder to find the last time you sent it so you can forward it again until the next time you need to send it again.

And every time you’re doing that, you’re spending, I don’t know, a minute, two, three looking for this thing in your sent folder. You could just copy and paste the text of that message. Go into your Signatures tool in both Outlook and Gmail, create a new signature, give it a name, paste that text into the copy field with your signature at the bottom and hit OK. And now from this point forward, that message reply is push button.

So, as soon as somebody sends you the message, you just copy their email address, you go up to your signature, you pop that into the message, put their name in the Send field, personalize the “Hi, Joe” and then, boom, in like five seconds, you’re sending that message. Not two minutes. Five seconds. And so, that’s like a great example of a way that once you learn the way the software works and what it can do. I always tell people get the word signatures out of your head, replace it with automated email sender, and use that three to five times a day, that you just got half an hour right there.

Pete Mockaitis

Lovely. Well, boy, there is so much we could cover. So, Randy, I’ll just leave it to you to curate. Could you give us maybe the top three transformational tips or practices in terms of this takes very few minutes but it will yield you very many hours?

Randall Dean

One of the things, and this is a little bit of a technical tip, so I’ll describe it, but it always gets the oohs and aahs when I’m doing my program. Did you know that you can just highlight a piece of text in Outlook, Word, Excel, PowerPoint, Google Docs? You can highlight it, release the click, then pick it up and move it to a different place.

And here’s the thing, it’s like almost like a shortcut to copy and paste, cut and paste. And the thing is that it works on all of these tools – Outlook, Word, Excel, PowerPoint, OneNote, Microsoft Teams, Google Docs, Google Slides, even on a lot of web forms it works. And if you can get really good at this, it’s like this quick little thing that you can do to allow you to take a piece of information that’s in the wrong place in your document or file, and quickly move it to the right place in your document or file.

And little tips like that, I think, can, you know, I will say, you know, when I show that to people and they’re all going like, “I didn’t know that I could do that.” I go, “Ah, I just gave you three days this year. There’s your three days.”

Pete Mockaitis

Yeah, I guess we’re saving the Command X and the Command V steps in doing that. Okay.

Randall Dean

And, I mean, it’s literally going to save you a second or two every time, but that second or two, multiplied by 40,000 times a year, it’s going to add up. The other one that I love is that a lot of people don’t realize this. When you’re creating folders, that you can use a special character, like an exclamation point, or even a number, and that will allow your folders to supersede alphabetization. So, what you can do is identify the folders you use the most or that are most important, and move them to the top of your folders list.

And that’s another one that is just like a no-brainer, super time saver, because now, instead of having to go all the way through the alphabet, you’re truncating that, and you can get to the folders you use most frequently right there at the top of your list. And that works not just in your email. It works in both Outlook and Gmail, but it also works in tools like OneDrive and Google Drive with your folders for your documents and files. You can actually move up your most used folders to the top and save a ton of time there, too.

Pete Mockaitis

Nifty. Okay. What else have you got?

Randall Dean

The other one that I really love is to get into the settings, you might need to go into rules in Outlook. You can also do this in New Outlook. You might have to go into Settings, Mail, Notifications. So, they’ve sort of moved it just a little bit. And in Gmail, you might have to go in and set up a filter to do this to make it all work.

But the basic tip is this, identify who your most important senders are. You know how I talked about the big angry dog? You want to identify, “Who sends me emails that are my big angry dogs?” Because what you can do in these tools is you can then go in and tell Outlook and Gmail, “These are my most important people. So, when they send me a message, I would like a pop-up or I would like a unique sound.”

And that means that you don’t necessarily have to get distracted by every squirrel, but when it’s one of those most important people, you certainly can. You can be, “Okay, boom! You know what? I’ll make a different sound, ‘Dun-da-dun-dun’ instead of ‘Doo-doo-doo-doon,’” you’ve been here for years and years, you’ll hear the “Duh-duh-duh-duh-duh.” “Oh, I got to stop for a second, I got to see what this one is.”

And so, that way you don’t feel like you have to look at everything coming in right now because you know that the really important things are going to probably jump up and get you, which means that actually, you might feel a little bit more comfortable keeping your focus on things, knowing that it’s going to tell you when the big angry dogs bark.

And I’ll even add one little micro thing about this. That same capability of setting up those rules can also allow you to set rules to auto-delete things that you don’t want to see at all. So, not only can it help you know when your most important people are trying to get a hold of you. It can also get rid of a bunch of the junk and spam automatically so it’s not even taking two seconds of your time.

Pete Mockaitis

Cool.

Randall Dean

So, it’s both sides. It helps on both sides of this. One last thing I’ll say is Outlook, specifically, will even allow you to set a priority level. So, like, I want to know when I get an email from my boss that is marked important. See, and it will only make the special sound when it’s from my boss marked important.

In that way if you’ve got an enlightened boss, who’s also taken my program, they’re going to learn that they should only mark emails important when they want faster action. Everything else can just be processed in normal strategy. And I always make the joke, “If every email you send is marked urgent or important, none of your emails are truly urgent or important.”

Pete Mockaitis

Understood. Well, tell me, Randy, any final things you want to mention before we hear about some of your favorite things?

Randall Dean

Once you get this efficiency regained, then you can actually take advantage of some of the other tools in in the suite – calendar, contacts, tasks, notes, maybe tools like OneNote or Google Keep, Teams, Drive, Planner – to get significantly more prioritized and strategic with that extra time you’ve now created.

And if you can get to where, you know, you get that email under control, it’s not taking quite as much of your day, you’re getting some of these efficiencies in time, then maybe you can actually step your game up to be a little bit more prioritized, more strategic, more effective, because now you’ve got this new necessary nuisance under control a bit.

Pete Mockaitis

Well, thank you. Well, now could you share a favorite quote, something you find inspiring?

Randall Dean

Well, it’s funny. I put it in my book. The quote is from Gandhi. It’s, “Be the change you wish to see in the world.” But I then put right under it, “Be the change you wish to see in your inbox.” 

Pete Mockaitis

All right. And a favorite study or experiment or bit of research?

Randall Dean

It’s more than 20 years old now, it was by the group called Basics. And they actually did a study where they got permission to go into a whole bunch of different organizations, have their researchers stand around just waiting and watching for people getting unexpectedly interrupted, and they tracked what happened.

And they found an interesting thing, that people that get unexpectedly interrupted in the workplace, after that interruption has been handled, they answered the question, they had the conversation, they get off the phone call. The interruption is now over. If they’re not ready for that interruption when it first occurred, they will then spend an additional four to 15 minutes each and every time before they get back to what they were working on, because they lost their place and they forgot what they were doing.

And so, the little micro tip that I share is, if somebody interrupts you, you can just go, “One second, please,” grab a sticky note and write down exactly what it is you need to do next on whatever you’re working on, put that right on your computer screen. And the goal of that is so that you’re basically leaving yourself bookmarks throughout the day, “Oh, yeah, that’s what I was doing.”

So, the interruptions can still happen, and I even say, I think it will help your communication quality because if you don’t do that, what are you very often doing the whole time you’re talking to that person?

Pete Mockaitis

To remember you’re still doing the thing, yeah.

Randall Dean

Trying to remember where you’re at, which means what are you not doing, listening? And that is where mistakes and errors of omission creep in, too. So, I think that’s just a classic little study that can then morph into it. And I always conflate that, you know, four to fifteen minutes per, and then I will ask my audience, I’ll go, “What do you think, 10 to 25 a day, 10 to 25 unexpected phone calls, stop-bys, interruptions, text messages?” And people give me the head nod.

I go, “If I’m right on this, that means you’re losing 45 minutes to as much as two hours a day just because you’re getting distracted that many times per day. And if you can get it down to where you have a strategy for that, that could create another hour or two, daily.”

Pete Mockaitis

Yeah. And a favorite book?

Randall Dean

It’s called Clutter’s Last Stand by Don Aslett.

Pete Mockaitis

All right. And a favorite habit?

Randall Dean

Don’t start your day in your inbox. Start your day in your calendar for a few minutes. Not just looking at today, but looking forward to see if there’s anything coming you need to get ready for. Are there any blocks of time that you could block for more strategic use on your key projects or activities? And then build a short, focused task list for today that matches your key projects and responsibilities, but also your available time.

If you’re doing that right, that should only take you three to five minutes at the start of the day. But you want to do that before you even dare open your inbox. Because if you open your inbox first, it’s basically like going over the door of the office, opening the door, and saying, “Come on in, squirrels! Take over,” right?

So, I want you to get into your time, your projects, and your tasks for a few minutes before opening your email so that you put that email into perspective. And then if the email fully takes over, it probably should. It probably is the most important thing. But if you’re not looking at your calendar and your projects and tasks first, how do you know? You’re just guessing.

Pete Mockaitis

All right. And if folks want to learn more or get in touch, where would you point them?

Randall Dean

I would just say go out and check out my website, RandallDean.com, pretty easy. That’s Randall, R-A-N-D-A-L-L. And if you go out to RandallDean.com, I’m also on LinkedIn. I would say search “Randy Dean” to find me. And I have a popular and growing YouTube channel too, and I think you could just type in Randy Dean, email, and it’ll probably, something of mine’s going to pop up right near the top of the list, so, yeah.

Pete Mockaitis

All right. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Randall Dean

Rome wasn’t built in a day. Pick two, three, four pieces of low-hanging fruit, do those first, baby steps. You don’t have to become an expert overnight, but find those really good nuggets wherever you find them and try to integrate those right away, and then build your system from there.

Pete Mockaitis

All right. Randy, this is fun. Thank you.

Randall Dean

Yeah, I had a good time.

2024 GREATS: 950: Cal Newport: Slowing Down to Boost Productivity and Ease Stress

By Podcasts No Comments

 

Cal Newport shows how to achieve more by doing less.

You’ll Learn:

  1. Why we’re measuring productivity all wrong
  2. The surprising math showing how doing less means achieving more
  3. The trick to eliminating tasks that don’t serve you

About Cal

Cal Newport is a professor of computer science at Georgetown University and a founding member of the Center for Digital Ethics. In addition to his academic work, Newport is a New York Times bestselling author who writes for a general audience about the intersection of technology, productivity, and culture. He is also a contributor to The New Yorker and hosts the popular Deep Questions podcast.

Resources Mentioned

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Pete Mockaitis
Cal, welcome back.

Cal Newport
Well, thanks for having me. It’s always a pleasure to chat.

Pete Mockaitis
Oh, I have been loving your book Slow Productivity, and I would like it if you could kick us off with any particularly, strikingly, fascinatingly counterintuitive discoveries you made while putting this one together.

Cal Newport
The importance of doing fewer things is something that I think proved to be a pretty rich vein. So, I have this principle that’s in the book, it’s one of the three principles of Slow Productivity is do fewer things. And when most people encounter that for the first time, what they think I’m probably saying is like, “Look, it’s stressful to do a lot of things. You need to go easy on yourself. Stop trying to be so productive. Like, do fewer things and you’re just going to be happier.” But that it’s a sacrifice, right? You’re going to produce less, but you need to because it’s for your own sanity and psychological health.

As I really looked into this, though, one of the big surprises is, “Oh, wait a second. Doing too many things is like this endemic productivity poison. Like, it’s not just making people miserable, it’s an incredibly terrible strategy for trying to produce valuable stuff with your brain. And when you commit to doing fewer things, it doesn’t actually lead you to accomplish fewer things, and these are somehow separate.” And this was a pretty exciting discovery because I was ready for it to be like, “Look, we got to just reconfigure what we think reasonable amount of work is,” and this ended up to be one of these sorts of win-win situations.

Working on fewer things at a once not only makes your life much more sustainable, you’re going to produce more. Like, over the long term, you’re producing more. You’re finishing stuff faster. You’re producing better work. You’ll actually be better at your job in any sort of observable, measurable way if you’re doing fewer things right now.

Pete Mockaitis
So, doing fewer things in a zone of time, like a week or a month, results in more total things done over a longer arc of a year plus.

Cal Newport
Yeah. So, here’s the math on that, and really, let’s think about doing fewer things at once, like concurrently, “What is my count of commitments that I’m actively working on?” That’s the number that I want to reduce. Here’s the math of why this leads to more accomplishment, is that in knowledge work in particular, when you agree to a commitment, especially if it’s a non-trivial sized thing, like a project, it brings with it administrative overhead, like, “I have to send and receive emails about this project. I have to attend meetings about this project.” So, everything you say yes to has administrative overhead that is necessary to support the work, but it’s not the actual work itself.

So, what happens is when you’ve said yes to too many things, the quantity of administrative overhead goes past a threshold where it’s really sustainable, and now what you have is a lot of your day is now dedicated to talking about projects, like the talking to the collaborators, having meetings, sending emails, and these are fragmenting your day as well. So, it’s not just like, “Let’s do our administrative overhead hour this morning and then get to work.” No, no, no. These emails and meetings are spread out throughout your day, which means you really never have any ability to give something a long period of uninterrupted time to really give it your full concentration.

So, now you have a fragmented schedule, a small fraction of which can actually be spent working with real concentration on the actual projects, the rate at which you’re finishing things goes down. And so, by having, let’s say, ten things on your plate at once, the rate at which you’re finishing things is very slow. Like, most of what you’re doing is being in meetings and sending email. If you instead had three things on your plate, you’re going to actually finish those three things real fast because you have huge swaths of your day to actually work on them. And what happens after finish one of these three things? You can bring another thing on.

And so, if you work through this scenario, “How long will it take me to finish ten things if I work on them all at once versus if I just do three of them at a time?” That second scenario, it’s going to take much less overall time to get through those ten things than the first, and it seems counterintuitive because we’re used to thinking of ourselves like a computer or a robot, “This thing takes this much time, that’s just it. Ten things take ten units of time, that’s just it.” But it’s not like that. The overhead matters. So, doing fewer things at once actually moves things through faster and at a higher level of quality.

Pete Mockaitis
That’s beautiful. And not only that, so there’s the administrative overhead situation fragmenting our time and our attention and our energy, and there’s also the psychological factor of, “Oh, hey, I’ve made some great progress today,” or, “Oh, hey, celebrate. That whole thing is done. Feel good.” And then there’s just the market responding.

Like, I remember when I was land-lording, because if I had a unit that was almost ready to go, it did not produce rent. It’s like, “Oh, no, it’s really close!” I could maybe have someone come tour and say, “Now just imagine this, this, and this will be different when you move in.” And that didn’t really work for them, in terms of like, “Yeah, no, I’m ready to go with another option, because that place already looks done and beautiful, and maybe I can imagine what it would look like done but it’s not done now, and it’s not visually appealing,” that’s why they stage homes, you know, all that stuff. So, there’s benefits on numerous dimensions psychologically, and then starting to reap the rewards of what you have sown.

Cal Newport
Well, it’s important to remember busyness doesn’t create revenue. So, just like you don’t get rent for the days you spent painting and working on a unit you owned. You have to do that stuff, but it generates no money. And if you spend more time painting and spend more time rearranging, it doesn’t generate more money. You have to actually rent it. The same thing is true in knowledge work. Emailing about a project doesn’t generate revenue, attending a meeting about the project doesn’t give you revenue. Finishing the project does, right?

And so, what we should care about is, “How quickly am I completing projects? How good are they?” because that’s what actually generates revenue. But in knowledge work, more so than in like renting buildings, it’s also obfuscated and complicated because, “Well, I was working on this but also this, and I have seven different things I kind of do, and other people are involved, and no one really knows what I did.”

In that obfuscation, we get a lot of the problems with modern knowledge work because it’s hard to just say, “You produced nine this year, and last year you produced six and you’re doing better.” Because it’s hard to say that, we tend to fall back on what I call pseudo productivity, which is, “Well, let me just focus on this high granularity activity that’s highly visible, emails, meetings.” I just see you doing stuff and so I assume you’re productive. Like, that’s the core of the knowledge work dilemma, is we’re focusing on visible activity in the moment as opposed to quality accomplishment over time. From that fatal mistake comes like almost everything negative about the current knowledge work experience.

Pete Mockaitis
Cal, this is beautifully articulated. Thank you. We love actionable wisdom here, but let’s go meta and slow down, and say I would love for you to take us through that whole journey of history, philosophy, perspective, principles on this very concept of pseudo-productivity, knowledge, work, and how we have found ourselves in this current state that is kind of jacked up.

Cal Newport
Yeah, I mean, it’s a fascinating story. It’s what the first part of my book delves completely into, is just understanding how we got where we are. Because this is, by the way, just as an aside, it’s a big part of my approach is because I’m also a professor and a founding member of the Center for Digital Ethics at Georgetown. I think a lot about culture, society, and technology and their interactions from the sort of removed of, “How do these systems work?” I think the systems matter.

And there’s a fascinating story when we look at what’s happening in knowledge work that spans from basically Adam Smith to Slack. Okay, so here’s what we get. Before knowledge work emerges as a major economic sector, which is really the mid-20th century, the term “knowledge work” is coined in 1959. Before that occurred, we had a pretty good handle on what we meant by productivity. It goes, “An economic concept that we could measure pretty accurately within specific organizations.” It goes all the way back to Adam Smith.

So, we first get good with measuring productivity in agriculture, and it’s a ratio, “How many bushels of wheat do I produce per acres of land I have under cultivation?” It’s a single number. And we also had in agriculture well-defined production systems, “Here is how I rotate my crops. If I change how I do this, and that number goes up, then I say, ‘Oh, this is a more productive way of doing it.’ And so, what we get here is sort of rapid innovation in cultivation of crops and planting systems because we have a number we can track.

Okay, we go to mills and factories. We could do the same thing, “Now I’m going to measure how many Model Ts are we producing per labor hour I’m paying for,” and that’s a number. And we have a very clearly defined production system, “And if I change something in that, we can see if that number improves.” This is what happened with automobile manufacturing. Henry Ford innovates the continuous motion assembly line with interchangeable parts and that number went up by a factor of 10. They’re like, “Oh, great, this is a much better way to build cars.”

And this sort of quantitative productivity journey was massively successful. The industrial sector, the wealth created by the industrial sector, grew at a staggering rate from the 1800s into the 1900s. Some economists would say, essentially, all of the capital in which the modern Western world was built came from the productivity miracle of being able to measure these ratios, adjust systems, see how those numbers got better.

Then we get knowledge work. None of this works anymore because we’re not producing Model Ts, and we’re not just producing wheat on acres of land. It’s a complicated position where I could be working on a lot of different things that shifts over time. It’s different than what the person right next to me is working on. How we do this work is highly personal. There is no production system we can tweak as an organization. Everyone manages their own work and time internally however they want to do it. So, we have no systems to tweak, no numbers to measure, and this was really a big issue because, “How are we going to manage knowledge workers without these numbers?”

What we introduced was pseudo productivity. A crude heuristic that says, “We can use visible activity as a proxy for useful effort.” So, I see you doing stuff that’s better than not. So, let’s all come to offices where we can have bosses. So, let’s make sure that you’re working all day. And if we really need to get ahead, let’s come in earlier and stay later. We can just increase the window of visible activity. So, we use this crude heuristic.

What happens where this goes awry is when we get to the front office digital IT revolution. So, we introduced computers and networks and then mobile computing and ubiquitous internet. And now suddenly, you can demonstrate visible activity, the thing that pseudo-productivity demands. You can demonstrate this at a very fine granularity, like sending individual email messages anytime, anyplace, and this is where pseudo-productivity begins to go off the rails.

Once I can be engaged in pseudo-productivity and measure pseudo productively anywhere at any time, and it has to be at this really fast, fine-grained granularity where it’s not just, “You saw me in my office during this hour,” but, “How many emails did you send to that hour? How quick were you to reply? How many things are you saying yes or no to?” It’s spun off the rails.

And we see this sharp discontinuity, if you study knowledge work, study how people talk about productivity in knowledge work, study how people talk about what’s good and bad about knowledge work, you get to the early 2000s, there’s a sharp discontinuity where suddenly we become unhappy. Just as email and laptops and then smartphones arrive, we suddenly begin to get much less happy.

Pete Mockaitis
Intriguing. And, Cal, what is the measure of that and what’s our approximate year when we start seeing that go, “Boom,” downhill?

Cal Newport
Well, you can see it in survey data, but where I like to look for this is actually in the tone of productivity books, because I’m a collector of business productivity. Look at the business productivity books from the ‘80s and ‘90s, like what are the big players here? It’s like Stephen Covey.

Pete Mockaitis
Getting Things Done, yeah.

Cal Newport
The 7 Habits of Highly Effective People, First Things First, you know, Eat That Frog. These are very optimistic books. Like, Stephen Covey’s whole thing is, if you’re careful in identifying what’s important to you and what’s urgent and what’s not urgent, you can figure out what to do with your day with the goal of actualizing all of your deepest desires and dreams as like a human, “We’re going to self-actualize you.” What’s the first big business productivity book of the 2000s? David Allen, Getting Things Done.

Pete Mockaitis
Oh, that was 2000, okay.

Cal Newport
And if you look at that, the tone is drastically different.

Pete Mockaitis
We’re overwhelmed. We’re drowning. We need help.

Cal Newport
We’re drowning, yes. I profiled him for The New Yorker. I really went deep on David Allen. It is a nihilistic book. Getting Things Done is like, okay, forget Stephen Covey trying to self-actualize our deepest goals as a human being. What is the goal of Getting Things Done? Can we find a few moments of Zen-like peace amid the chaos of the day?

Pete Mockaitis
After your weekly review, you can, Cal, and then it’ll pass.

Cal Newport
He’s trying to reduce work to this agnostic widget polling, like at least we can find some peace. It’s a very nihilistic book. But what changed between 1994 and 2003? Email. So, we see it. It’s just a change. And then what are all the biggest business productivity books of 2010s? We got Essentialism, The ONE Thing, my own book, Deep Work. All of these are books that are about, “How do we push back against the overload? How do we resist this? How do we find the things that really matter?”

I mean, it’s a complete tone shift where overload, having too much to do, being stressed out, becomes the defining feature of knowledge work once we get to the early 2000s. You don’t pick that up at all in the ’90s, in the ’80s, in the ’70s, and in the ’60s. So, the technology had this huge discontinuity in our experience of this sector.

Pete Mockaitis
Okay. Understood. And so then, when it comes to the measurement has broken down, what is to be done there in terms of like there are, I think in your book you said, we’ve tried some really stupid things, like, “How many lines of code have you written?” or, “How many words have you produced?” And it’s like, “Well, I mean, were those lines of code brilliantly efficient? Were those words tremendously insightful?” or, “Are they kind of like bloated and lame and blah?” So, it’s like those might have a purpose of, “Kind of, if I can constrain them with a quality-paired metric as well.” It’s a real tricky beast, Cal. What is to be done here?

Cal Newport
Well, as long as you’re in the pseudo-productivity mindset, all the solutions are going to be like that. It’s going to be, if activity is what matters, my biggest concern, if I’m a manager, is you’re taking breaks from activities. So, I want to make sure, like, what was the big concern of managers about remote work? It’s like, “Well, what if there’s periods of the day in which the person is not doing things? That’s taking away the bottom line,” because we imagine knowledge workers like they’re on an assembly line, “Hey, if you stop putting the steering wheels on the Model T for an hour, we can’t produce Model Ts for an hour.”  It’s just this very direct.

So, what is the solution? We have to move away from this activity-based notion of productivity towards something that’s more outcome-based. And that allows for a much slower definition of productivity that has a lot more variation, a lot more idiosyncrasies, and is a lot more sustainable and meaningful for the people involved.

Pete Mockaitis
All right. Can you give us some cool examples, or stories, or metrics, or numbers we might use when we talk about outcome-based? I’m thinking, in some fields it seems pretty straightforward, like sales. Like, okay, there’s revenue or gross profit generated from the sales that you’ve made. And that could look very different in terms of you were cultivating a relationship with a multimillion-dollar account for months or years, and you landed it, and we can measure that, and it’s way bigger than you hustling with your cold-calling, your cold-emailing to get dozens of smaller clients. So, there’s one outcome.

Cal Newport
And sales is an interesting example because I just met a salesman from a big tech company at a book event talking about Slow Productivity. And you know what he said? He said, “Look, in our company,” because sales is clear, unlike almost every other knowledge work, you have these metrics, like, “What did you bring in?” And so, it’s an interesting natural experiment. If we take a knowledge worker where there is a clear metric of success, do we see a drift away from pseudo productivity? And we do.

This is what the salesman told me. He said, “Yeah, in our company, the sales staff doesn’t have to go to meetings. Everyone else does. Everyone else. You got to go to meetings. If someone invites you, whatever, everyone in these more ambiguous jobs, yes. But the sales staff, all meetings are optional because they have this number and they want that number to be better. And the sales staff is like, ‘That number is worse if I’m going to meetings.’”

Pete Mockaitis
That’s true, “What you do is so important, we’re not even going to put that at risk for anything.”

Cal Newport
Which shows how important were those meetings in the first place, right? Another place where we’ve seen innovation, like this actually is in software development, because software development, it’s knowledge work in the sense that it’s all your brain, but it’s pretty closely aligned with industrial manufacturing because you’re producing products. So, there’s much more of this notion of, like, “We’re shipping something. How long did it take to ship?” Like, it’s more measurable than other types of knowledge work.

We’ve seen tons of innovation, tons of innovation in software development that try to get away from just this completely generic activity base, because they learn, like, “I don’t care if you’re busy. What I care about is do we get these features added quickly? What’s our turnaround cycle on updates to the software?” Like, they have things to measure. So, what do you see in software development? You see a move towards these agile methodologies where, A, workload management is transparent and centralized. It’s not just, “I have a bunch of junk on my plate.” It’s, “No, no, it’s all on the wall, and this is what you’re working on, and it’s just this one thing.”

You see things like sprinting in software development, “We want you to do nothing but work on this feature until it’s done, and then we’ll talk to you again tomorrow,” because, again, whenever we begin to see adjacency, the actual measurable outcome, all of these tropes of pseudo-productivity that are really killing us in digital age knowledge work, they all begin to shatter and fall away. So, it’s like we have to take that mindset from sales and software development, and we need to move this into more types of jobs, we’d be clear about the workload management, work on fewer things at a time.

Just measuring performance at the scale of the year makes a big difference, “What did you produce this year?” Because when you’re talking at the scale of the year, you don’t talk about meetings or emails or small things you did. You talk about things you finished. So, just having like an annual perspective for thinking about productivity, that makes a difference. So, all of these types of things, we see it in software, we see it in sales, we need to move that to many more jobs.

Pete Mockaitis
I like that a lot, the thought associated with, “What is the time horizon we’re looking at?” Because if it is a day, and I’m looking at, “How many emails did you send?” or, “How many hours were you logged on?” it’s like that tells me very little. If I look at a year, that could tell me a whole lot. And then, I guess, in a way, there’s some art and science right there in terms of evaluating, “What’s the ideal period by which we should be looking at and thinking about these things?” Do you have some perspectives there?

Cal Newport
Well, even allowing people to figure this out on their own can be really effective. Like, you say, “Okay, I want you just to make your pitch to me as your boss, like what you did that was valuable this last quarter or this last year.” Like, you can kind of figure out the timeframe when you write about it, just allowing the individual to report like, “Okay, here’s what I’ve been working on. I completed this and this, and we’re working on this big project, and we made this much progress on it. And I think this is all really important.”

Like, letting someone just describe why they’re valuable, because it’s not going to work if I ask you to describe why you’re valuable. You said, “Look, I just looked up my statistics. I’ve been sending 150 emails a day. I’ve been logging seven hours a day in Teams meetings. I’ve been in a lot of meetings.” Like, it sounds absurd when someone’s asking, “Quantify why you’re valuable.” You think about the big things. You think about it at a bigger time scale.

There are organizations that do this super explicitly. I profiled these in The New Yorker a few years ago, these organizations that had a very hardcore way of doing this, called ROWE, results only workplace environment, where it was all that matters is results, including when you show up to work, when you don’t, what days you don’t work. Everything is up to you, but they’re really, in these environments, they’re really hardcore about what are your results.

And because of this, it really banishes pseudo-productivity culture. If you’re like, “Hey, come to all my meetings,” you’re like, “No, because in the end, I’m going to be measured by these things I’m producing, and that’s going to hurt me. So, no, you’ve got to convince me to come to your meeting. And if it’s not going to be worth the time, I’m not going to do it, because all people care about is what I have produced.”

And they’re really interesting to study because, you see on the positive side, these hardcore results only environments, a lot of pseudo-productivity falls away. On the negative side, it is really difficult for a lot of people to leave the comfort blanket of all the obfuscation you could generate by just sending lots of emails and meetings because you can’t hide anymore. You produce or you don’t.

And there is, I think, a certain segment of knowledge workers, and it should be acknowledged, that do find some comfort or peace in being able to be much more obfuscated about their work, like, “It’s not really clear what I’m doing, but I answer my emails a lot, and I’m in a lot of meetings, and I sort of just, I’m around, and so it feels like I’m being productive.” When that goes away, it gets exciting for a lot of people, but it gets scary for some people as well.

Pete Mockaitis
Yeah, I’ve heard that in particular about the culture at Netflix, in terms of, like, it’s exciting and terrifying for this very reason. I think ROWE could also have some potential downsides with regard to collaboration and team camaraderie culture. It’s like, “I’m out to get my results. Period. So, get out of my way.”

Cal Newport
“Get out of my face.”

Pete Mockaitis
So, it’s tricky to get all the pros without the cons. Well, the security blanket, you might feel secure in the moment, but I would venture to say, “If you’re not clearly creating value in excess of your salary and payroll costs, your security is quite slim come lay-off time.”

Cal Newport
I think that’s right. In the good times, where no one needs to be fired, it prevents you from being noticed in a negative light. Like, “Yeah, I’m not thinking about Pete. Like, I see him a lot. I’m sure that’s why I’m not thinking about them.” But you’re right. When times get tight, “All right, now we have to start reducing staff,” that’s suddenly when people shift their thoughts to not, “Are you doing something bad?” to, “What good are you bringing?” And, right, that’s when things get to be dangerous for you.

So, when times are good, you can just be really active and you’re not going to draw any attention. But when times are bad, ultimately people are going to wonder, “Hey, what do you do? What’s the value? Like, what would happen?”

Pete Mockaitis
“Like, what is it you do here?”

Cal Newport
I would say people, by the way, so my column for The New Yorker during the pandemic was named Office Space, in part because of exactly that reference that there was a lot of people in the pandemic, especially when they were forced to do all their work from home, and they could see like their partners and what their partners were doing for their jobs, and I think a lot of people in knowledge work had that same reaction of like, “What would you say I actually do here? Is it “I’m a professional Zoom meeting attender?” Like, is this really a good use of my graduate degree?” I think a lot of people had that crisis.

But, yeah, back to your point. If you’re producing stuff that’s valuable, not only does that give you security, it begins to give you leverage to slow down your definition of productivity. Because the more you can point towards, “I do this and I do this really well, but that’s also why I’m not just sending emails all day and a bunch of meetings. Hold me accountable for this. But in exchange for that accountability, you’ve got to give me more autonomy.” Like, that’s a fundamental exchange of trying to negotiate for a more sustainable, slower definition of productivity.

Pete Mockaitis
That’s good. And when it comes to this notion of doing fewer things, you mentioned the book The ONE Thing, which I love. And it’s so funny, when I read it, also with Greg McKeown’s Essentialism, it’s so calming to me, and I guess I like productivity books or non-fiction business-y books. But I think it’s also just like, “Oh, I don’t have to do everything. Okay, okay, that’s nice.” So, it’s just sort of reassuring.

But I’d love your perspective on, “How do we really select from a noisy world of thousands of options? What are those few things I’m going to do?” And the number you suggest is it, “It’s probably going to be more than one, but hopefully is less than five?” Is that the range you are shooting for?

Cal Newport
Yeah, for major projects. Yeah.

Pete Mockaitis
Okay. And so, how do I pick and choose, like of hundreds of potentially good things, what really, really, really deserves my one to five?

Cal Newport
Well, there’s two environments here. So, one is you work for someone. So, if you’re in an organization, what really seems to matter is just add constraints, and then you will see pretty naturally like what makes the cut. So, for example, one of the things I recommend if you work within an organization, where you can’t just directly say no to a lot of things, what you do instead is saying, “I’m going to keep a two-tier list of what I’m working on. Tier one is actively working on. Tier two is queued up for me to work on next. And as I finish something in the active tier, I pull in the next thing from the waiting tier, and that becomes something I’m actively working on.”

So, you artificially constrain the number of things you’re actively working on. And the rule is why this works is you say, “Okay, administrative overhead can exist for the things I’m actively working on. If it’s in my queue, then I don’t do administrative overhead. So, if you give me something to do and I put it on my queue, and I make this public, and you can look at it, and it’s a shared document, you can watch it. I can tell you, ‘Watch this march up my queue until it gets to my active work tier.’ Once it’s there, email me about it. We can have meetings about it. You can ask me how it’s going. But until it’s there, the answer is ‘I’m not working on it yet.’ And where is it in my list? You can look at it yourself.”

So, now you’ve restricted the administrative overhead that’s being generated to only a small number of the things that you ultimately have committed to. Once you have those constraints, it leads to better selection because other people are now involved. So, a boss comes in and says, “This thing, I want you to do this thing.” You say, “Great. It’s on my queue, it’s back here.” They’re like, “No, no, I need this. This is way more urgent.”

Well, now you can involve the boss, and be like, “Great. Well, which of these three things that I’m working on now should I swap out?” And now they’re kind of involved. Like, “Actually, you know what? Stop working on that thing. I don’t think that’s as important as I thought it was when we first thought about it. Move this in here instead. And now that I’m looking at your queue, take out these four things as well. That’s not where the priority is.” So, once you have constraints, you begin to get wisdom.

So, another, this is an example from the book, but another place where this began to happen was a division within a large research lab where they had a lot of projects coming at them. And what they did is they centralized this, they said, “Okay, we’ll put every project we want to work on, on an index card and we’re going to put it on the wall under this certain column. These are all things we want to work on. And then here next to it are the ones we’re actively working on now, and we label it with who’s working on it. And so, when someone finishes something, we pull something else in here, we decide together what to do next.”

And they have this heuristic that arose over time, “If something’s been on that left side of the wall for a while, and we keep pulling other things in but we’ve been leaving that alone, that’s probably not that important. You know, let’s take it down.” Like, if you’re on the wall too long and it never moved over to, like, “Let’s work on it actively next,” that was their cue of, “This was exciting when we thought of it, but it’s not that important.” So, once you have constraints, wisdom about what’s important and what’s not, it begins to emerge because you’re thinking about this in a way that you don’t, when all you’re doing is just saying yes to things and trying to keep up with everything at the same time.

Pete Mockaitis
So, if you have the constraints, it’s almost like a forcing mechanism such that it’s not so much like, “Oh, there’s a magical measurement, there’s a magical question, or a magical metric by which we use to measure that answers this question for us.” It sounds like you’re saying, “Yeah, that doesn’t really exist across all industries and types of work but, rather, put the constraints in and you’ll feel the tension, and you’ll see what just really, really has to get done soon and what can wait.”

Cal Newport
Yeah, just being forced to continually make the question of “What next?” forces a lot of wisdom. And I keep having to say, “Okay, what am I going to pull in next? What am I going to pull in next?” And making that decision again and again, what emerges from it is, like, a better understanding of, “Oh, this is the type of stuff that’s important to me. And this stuff I keep leaving over here, and moving other stuff ahead, oh, I guess that’s not really that important to me.” And it’s a lesson that comes out from people who use these two-tier pole systems.

It’s something I talk about often. You build up the muscle of understanding over time what matters and what doesn’t, because you keep making these decisions and keep getting feedback on what stays and what moves. And, then over time, you stop adding the stuff to your “to-work-on-next” list that you know, like that’s never going to be pulled off. And then you become much better at being like, “No, we don’t do that anymore,” because you’re like, “I’ve seen too many things like that type of project that we put on this list or we put on the wall and it sits there for two months that we finally take it down. I have now learned, I’ve gained wisdom, this is not the type of thing that we really need to be working on.”

So, you become much more self-aware of what you can actually do with your limited time and what’s worth doing with your limited time when you’re explicitly and consciously having to make these decisions again and again.

Pete Mockaitis
And when you say “explicitly and consciously,” that reminds me of some of the interviews we’ve had about decision-making with Annie Duke and others who suggest having a decision journal. And I think the practice perhaps of writing out, “What is the rationale by which I’m using to place this in the top tier or not?” And then having that written enables you to kind of reflect on it and say, “Oh, yeah. Well, that was true at the time, but things have shifted,” or, “Yes, this is the pattern I see over and over and over again. Like, it’s really important to a really big client. Okay, that seems to be a prioritization principle that we keep going back to again and again.”

Cal Newport
I love that technique. By the way, yeah, I know Annie talks about it. My friend Dave Epstein from “Range” and “The Sports Gene,” he was on the show recently, and he was telling me about how he does this as well. And part of the reason why I think this technique, like a decision journal, is effective in knowledge work is that we don’t otherwise have clearly defined processes.

One of the defining features of knowledge work is that organizational strategies, processes, how I figure out what to work on or not, how I figure out how to manage my day, all of this is informal and personal, and most people just wing it, it’s like, “Oh, my God, I just got this urgent email, so let me do this. Oh, and there’s a deadline. I’m going to stay up and do this.” When you keep a decision journal, what you’re actually creating over time is process, you’re like, “Oh, this is how I deal with this. This is the right way to figure out what to work on next.” We forget the degree to which, in knowledge work, we just wing it all the time.

It’s not like we have, “Here’s how I build cars. How do I improve that?” It’s the equivalent in knowledge work, if the way we built cars was just put a bunch of tools and parts in a warehouse, threw a bunch of engineers in there like, “Guys, build me some cars. Let’s go.” Everyone was just running around like, “Hey, can I have the wrench?” That’s the way we do knowledge work. So, if in that world, you’re starting to actually think, “How do I figure out what to work on? What didn’t work? What did work?” you start to think about that clearly.

It’s like the one-eyed man in the world of blind people, you’re going to have this huge advantage, you’re like, “Oh, my God, I’m just really…why are people working so hard? Like, I’m really killing it over here, and I’m not even working,” because no one else is doing this. They’re just getting after it with Slack and email in their calendar, and just saying yes to everything, and trying to be busy. So, there’s a huge advantage once you start thinking process-centric within knowledge work.

Pete Mockaitis
That’s beautiful. And to The ONE Thing, that is one of my favorite questions I think about often, “What’s the one thing I can do such that by doing it everything else becomes easier or unnecessary?” And I think that is one handy question. I’ve learned it’s not applicable in all situations, in all domains. But I’m curious, have you discovered any other organizing principles or questions that tend to serve people pretty well, pretty often?

Cal Newport
Well, I mean, first as an aside, have you heard Jeff Bezos’ version of The ONE Thing idea?

Pete Mockaitis
Well, no, until you articulate it. Lay it on me.

Cal Newport
So, this is like the big idea within Amazon when to figure out “What are we going to work on? And what are we not going to work on?” Bezos has this thing, “Is this something that’s going to make our beer taste better? And if it’s not something that makes our beer taste better, we shouldn’t be in that business.” And the case study he’s referring to was when, I guess, German brewers, beer brewers used to generate their own electricity. And then at some point, they plugged into a grid instead of generating their own electricity. There’s a lot of annoyance and logistical overhead with running your own generators and dynamos.

Pete Mockaitis
It sounds tricky.

Cal Newport
It’s tricky, right? And they said, “Oh, we should just plug into the grid.” Why? “Because making our own electricity doesn’t make our beer taste better so let’s not put any energy into that. We want all of the people we hire to have their energy into making our beer taste better.” And so, Bezos brought that over to Amazon, “We should be focusing on the things that makes us money, that our customers really care about. Anything else, if we can outsource it, we should, or just not do it at all.”

And so, I really love that way, like, “What makes our beer taste better?” But that brings me to, I think back to your question, one of the other big principles is obsess over quality. And what this is really doing is, basically, in knowledge work, in some sense, figuring out, “What’s your equivalent of brewing beer?” Like, figuring out, “Me, as an individual employee, what’s the thing I do that’s most valuable? And if there’s nothing really there that’s valuable, what’s something I can learn to do that’s going to be really valuable?”

And once you identify that, you can focus more of your energy in, “My goal is not to be really responsive. My goal is not to make sure that everyone gets everything they need from me as fast as possible. My goal is not to be in every meeting where you need me. No, my goal is to do this thing better. I want to do this better and better because this bottom line helps our organization.” And one of the keys behind this idea is focusing on something that’s really valuable to your company or your organization, is like the foundation on which all radical engagements with slow productivity will eventually be built because it gives you leverage.

It gives you control over your job. It makes your value clear. You’re playing the right game. It allows you to focus on what matters and not these sort of accessibility routines that everyone else is trying to do with their email and with their meetings. And when you really begin to care on making your beer taste better, all of the busyness becomes unnatural to you. So, you say, “I don’t want to be on email or in meetings. That’s getting in the way of getting better at these marketing strategies or at writing this code.”

And so, slowness becomes natural, and as you get better, you get more leverage to make your work slower. So, that idea of figure out like what your equivalent is of brewing beer, what’s the thing you do best and focus on that, that unlocks almost everything else.

Pete Mockaitis
That’s cool. So, if I’m doing marketing, what’s giving me more impressions per dollar, or more purchases per, whatever, what’s boosting my conversion rate, etc. Or if you’re creating products, it’s like the beer tastes better, what will delight the customer all the more, and make them say, “This company rocks. I love their stuff. I would tell more people about their stuff. I’m going to buy more of their stuff.” Very cool.

All right. Well, so we’ve talked about, so we got three principles here. We’ve spent some good time on do fewer things, and we hit the obsess over quality. Can you unpack the third one for us a bit?

Cal Newport
That’s work at a natural pace. And the argument here, it’s a psychological argument, the way that we work in knowledge work, which is all out, all day long, year-round, is really unnatural. It’s unnatural in a sort of literal sense that human beings throughout our whole history as a species are used to having huge variations and intensity of what we’re doing. There’s really intense periods during the day and really quiet periods. Some months are much more intense than other months. In the winter, we’re kind of hunkering down. And in the fall, we’re doing the harvest, and it’s super busy. And we have all this variation, that’s what we’re wired for.

And then we got mills and factories. And in mills and factories, it made more money if people just worked as hard as they could as much as they could. And so, we switched for the first time in human history to just like work hard all day long, but it was very unnatural and very intolerable. We had to invent labor unions and regulatory frameworks just to try to make these jobs survivable, essentially.

When knowledge work emerged in the mid-20th century, we said, “Okay, how are we going to organize this labor?” And we said, “Well, let’s just do the factory thing.” Because that’s what was going on, that’s what was in the air. The core of the economy was industrial manufacturing. So, it’s like, “Great. We’ll just approach knowledge work like we do building Model Ts, eight-hour days, work as hard as you can.” Like, if you’re resting at all during the day, that’s bad. Pseudo-productivity activity matters, and it’s the same all year round.

So, we adopted this way of working. It was actually super unnatural and required all these safety mechanisms. We adopted the same thing without the safety mechanism, and it’s an exhausting way to work. It doesn’t, over time, produce more productive effort even if in the moment it seems more satisfyingly frenetic. So, work at a natural pace says, “You need more variation in your intensity on all sorts of time scales. It shouldn’t all just be all out.”

It also says, “You should take longer to work on your projects, that we make our timelines too small. Give yourself more time so that you have room for these up and down variations.” Like, this is the way all the great thinkers through time past work, up and down in intensity over time until eventually something good came out. That’s how we produce things with our brain, not the Model T model of just, “Clock in and turn that wrench as fast as you can until you clock out.”

Pete Mockaitis
Okay. Well, so then any sense for how do we tune in to knowing if we’re overall too much or overall too little? I know there’s going to be variability, busy seasons, lighter seasons, but any clues that we might focus in on to go, “Ooh, let’s crank it up,” or, “Let’s tone it down”?

Cal Newport
Well, that’s not the hard part. The hard part for people, actually, is just being comfortable with the idea that you shouldn’t always be cranked up. And then once you have that realization, there’s a lot more variation that just becomes natural. So, like a couple of things you can do. One, just start doubling your timelines for everything you agree to do. Instead of doing the typical trick of, “In theory, what’s the fastest possible time I could get this done?” and then falling in love with that timeline, “Oh, my God, that’d be great. If I could get this done before Christmas, this would be great,” and then we commit to this impossible timeline.

Double everything. So, give yourself much more breathing room. And, two, actually engineer seasonality. You don’t have to tell people about this if you work for someone else, but just schedule out your project so that the summer is going to be slower, but you’re really going to be getting after November. You can just start engineering variations in your workload. No one is tracking your workload so carefully.

There’s no graph somewhere in the central office, where they’re like, “I’m looking at Pete’s daily work project touches here, and they’re down in July versus whatever.” People, it’s all just chaos. They don’t know what’s going on. So, take longer and engineer seasonality explicitly into your project flow and your workflows. Just doing that is going to be like taking a deep breath.

Pete Mockaitis
Lovely. Cal, tell me, anything else you really want to make sure to mention before we shift gears and hear about a few of your favorite things?

Cal Newport
Well, I mean, again, I think the key thing to keep in mind is don’t use the word productivity so confidently.

Pete Mockaitis
You live it.

Cal Newport
I mean, there’s a lot of talk where people are like, “I want to be more productive,” or, “Productivity is bad,” but people aren’t really defining their terms, and that’s a big problem. We all just assume we all know what productivity means, but we don’t. Like, when people say, “I want to be more productive,” what they really mean often is, like, “I want to produce more stuff over time.” When people are critiquing productivity, what they’re often doing is critiquing a sort of industrial notion of productivity, like, “The effort per day needs to be large.”

We’re not talking about the same things. Like, let’s define our terms. This is why I think it’s helpful to say pseudo-productivity is what we’re doing. Pseudo-productivity is different than quantitative productivity, which is what we used to do. Slow productivity is itself an alternative. Like, once we get clear about terms, a lot of the absurdity of what we’re doing just becomes self-evident. Like, a lot of this idea of, “I want to do this now instead of that. I’m going to do fewer things. I’m going to have more variation.”

When we realize that’s in contrast to pseudo-productivity, and that’s a part of slow productivity. Just having the terms clear, I think, really makes it better, much easier for us to make progress. So, that’s my final thing I would say is don’t be too confident that you know what people mean when they use the word productivity. I actually push on it, “What specifically are we talking about here?”

Pete Mockaitis
Lovely. Thank you. Now, could you share a favorite quote, something you find inspiring?

Cal Newport
Well, there’s an obvious answer to this question because I actually wrote a book with this quote in the title, so maybe I’m telegraphing I like this. Steve Martin, doing Charlie Rose interview about his memoir, “Born Standing Up.” And Steve Martin says, “People are always asking me, ‘How do you succeed in the entertainment industry?’” And he says, “The answer I give them is never what they want to hear. What they want to hear is, like, ‘Here’s how you find the right agent,’ or, ‘Here’s how you like get onto the writing staff.’”

And he says, “No, what I tell them is, ‘Be so good they can’t ignore you. If you do that, all the other good things will follow.’” I wrote a book called “So Good They Can’t Ignore You” 10 years ago, 12 years ago now that was just inspired by that quote because that’s how important it is to me, because I ultimately think, especially in creative work, that’s what it all comes down to, “Be so good they can’t ignore you. The other stuff will work itself out if that’s where you’re focused.”

Pete Mockaitis
And a favorite study or experiment or bit of research?

Cal Newport
Well, this always shifts, but there’s a new study someone just showed me, which I found very satisfying, because I don’t use social media, and I’ve often argued with people for various reasons why I should. And one of the reasons they give me is, like, “Well, this is how, like, you’re an academic, and this is how people know about you, and know about your work. You have to be yelling at people on Twitter about Trump. And if you’re not, you can’t be a successful academic.”

A new study just came out where they studied the citation count of academics correlated to Twitter engagement, and found Twitter engagement does not lead to more citations. It does not lead to more notice to academics’ work. What does matter? Doing really good important work. And so, I found that study very satisfying. You’re not going to be able to tweet your way into intellectual significance. You just have to do good stuff.

Pete Mockaitis
And a favorite book?

Cal Newport
A book I just read, which I really liked, was Abraham Joshua Heschel’s The Sabbath. It’s a 1950’s-era book by a great Jewish theologian, talking about the Shabbat. But I found a lot of secular resonance in this book because he was looking at the theology of Shabbat, taking a day off of work, like as it said in Genesis, right in the Bible. And he has this really cool argument. I wrote an essay about it.

But he has this argument that’s like, “Look, you take a day off from work. This is not instrumental. This is not you have to take a day off work so that you’ll be able to do work better when you get back. It’s not instrumental. You take a day off of work so that you can appreciate all the other stuff in life that’s important.” In Genesis, it was like God looked at what he had done and said, “It is good.” It’s like gratitude and presence.

I just thought it was, from 70 years ago, looking at something that was written 3,000 years ago, is a really sort of timeless idea that it’s not just, not everything is just the work, and breaks from work is not just about making the work better. It’s about all the other stuff that’s important to you. And it’s a slim book, it’s beautifully written, it has these original woodcut illustrations which are fantastic. A really cool read. I recommend it.

Pete Mockaitis
All right. And a favorite tool, something you use to be awesome at your job?

Cal Newport
I recently have gone down the mechanical keyboard rabbit hole.

Pete Mockaitis
Oh, yeah.

Cal Newport
Yeah, because I wore off on my MacBook, I wore all the keys off because I write a lot, and the plastic was cheap in this generation. I wore every key off. You can’t see any key. And so, I got a cover for it with the keys on it, and I wore all those off too. So, I finally bought a nice, a NuPhy, N-U-P-H-Y mechanical keyboard, and, oh, I love it. Just the click and the clack. It’s substantial. I love writing on it. Your fingers spring back up with the keys so that you can type faster. I don’t know, I’ve enjoyed it. I write all the time. I enjoy writing more on this than I did when I was on just the MacBook keyboard, so I love my NuPhy wireless mechanical keyboard.

Pete Mockaitis
Alrighty. And is there a key nugget you share that really seems to connect and resonate with folks; you find it’s quoted back to you often?

Cal Newport
I think people, really, like more recently, one of the things that come back to a lot is this idea that activity doesn’t matter, busyness isn’t monetizable, your email inbox is not going to be remembered 10 years from now, but what you produce that you’re proud of, that’s everything, and just this idea of output over activity. That’s what keeps coming back to me. That’s what people seem to be quoting when they’re talking about this book or calling into my podcast, so I like that. Busyness is maybe satisfying in the moment, but is forgotten in the mist of history.

Pete Mockaitis
Okay. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Cal Newport
Do fewer things. Like, trust this idea that if you cut down the number of things you’re working on right now, you will look back when this year is over and be much more impressed, and proud of what actually got accomplished.

Pete Mockaitis
Cal, this is fantastic stuff. I wish you much fun and slow productivity.

Cal Newport
Thanks, Pete. I’m going to go slowly get some things done.

1014: How to Make Meetings Better for Everyone with Calendly’s Darren Chait

By Podcasts One Comment

Darren Chait discusses how to make meetings more engaging using data from Calendly’s State of Meetings 2024 research.

You’ll Learn

  1. Why 81% of respondents want more meetings 
  2. Three meetings to keep—and the one to stop 
  3. Surprising statistics on meeting etiquette 

About Darren 

Darren Chait is the VP of Marketing at Calendly, leading the world-class marketing organization. Previously, he was a co-founder of Hugo, the leading meeting workflow solution powering meetings for tens of thousands of customers backed by Google, Slack and Atlassian.

In a prior life, Darren was a corporate lawyer at one of Australia’s leading law firms, where he attended meetings for a living – the start of his passion for meetings and the future of work.

Resources Mentioned

Thank You, Sponsors!

Pete Mockaitis
Darren, welcome.

Darren Chait
Thanks, Pete. Thanks for having me.

Pete Mockaitis
Well, I’m so excited to get into your unique vantage point, your insights, your wisdom. So, you work at Calendly, which is my all-time favorite meeting scheduling software. Use it in two businesses. So, great job, guys.

Darren Chait
Good to hear those. Thank you.

Pete Mockaitis
I’m curious, while you’ve been there, how many meetings have been scheduled in Calendly?

Darren Chait
Personally? Thousands.

Pete Mockaitis
Thousands? Millions?

Darren Chait
Well, yeah. I’d say thousands. I’ve been at Calendly for two and a half years. I think I probably would have exceeded hundreds. I spend a lot of my day in meetings, like we all do, which is why it’s such a good topic for discussion. And I really try and schedule most via Calendly because who’s got time to jump around with the back and forth and try to coordinate multiple schedules? And being an Australian, living between the US and Australia, time zones are a nightmare. So, I need Calendly to work, and luckily, so do other folks.

Pete Mockaitis
And how many meetings has the Calendly software product platform scheduled for humanity?

Darren Chait
That’s a very good question. That’s not a number that we’ve actually published before. So, you’ve heard it here first, if I had to do the math quickly, I wonder if we’ve crossed a billion, it’s possible, but I’m not sure. So, keep that one between us, all right? But I want to look into that. It’s the number I should know off the top of my head.

Pete Mockaitis
All right. Well, we’ll say rounded to the nearest billion and one million.

Darren Chait
Exactly, that’s right. It’s closer to a billion than zero, but it could even be more. I’ll have to check on that one.

Pete Mockaitis
All right, so that’s cool. So, a billion meetings, and you’ve been in many yourself, personally there. I’d love to hear, off the top of your head, what are some of the most striking, surprising, fascinating discoveries you’ve made about us workers and meetings from your vantage point here?

Darren Chait
We’ve recently published a report on this. We do it every year, and the 2024 State of Meetings Report, went in and asked over a thousand workers a whole lot of questions about meetings. And what I love about this process, this piece of content is because we do it year on year, things are changing right in front of us.

So, the number one thing that jumped out at me, which I can’t reconcile, I don’t know what your thoughts are, Pete, but 81% of workers want more meetings. Here we are talking about meetings being the bane of our existence, competing with productive work, there’s a million and one memes about meetings that should have been emails and those sorts of things, but the overwhelming majority say, “Give me more.”

Pete Mockaitis
Fascinating. Okay, now I imagine that the devil’s in the details in terms of do they want more meetings like the ones they’re having right now? Or are they looking for something else on the menu that they haven’t received yet to appease their appetite?

Darren Chait
Yeah, exactly. It’s both. So, number one, firstly, productive meetings was the caveat there. We want more productive meetings. Are we having productive meetings today? Yes and no. But I think there’s a more interesting take, which was my opinion, anyway. We sort of said, “Why? Like, how do meetings help you?”

And if you look at all the different reasons why people love meetings, 51% said connection with colleagues, 44% said more collaboration, and the list goes on. And what it really led me to think is that we’re in this new world where we’re now post-COVID, we can’t blame COVID anymore, but it’s certainly reset the way we work. We have many, many, many remote-first companies out there, many, many, many hybrid companies, and some companies that are operating in a traditional office environment, but we’re really just seeking out connection.

So, yes, we want more productive meetings, but based on what respondents said in this particular survey, and what I hear talking to folks every day, meetings are how we stay connected. It’s how we build relationships at work, it’s how we make the work we do human. So, I guess it’s not that surprising if you think about it like that.

Pete Mockaitis
Okay. So, we like more meetings, in so far as they are productive and connecting. Got it. And can you lay it out for us, just how much time are we spending in meetings these days?

Darren Chait
Most of us, in terms of the respondents, are only having one or two meetings a day, but about half are having three or more meetings a day, and I guess it comes down to what you do for work, right? So, this year for 20% told us, they’re spending more than six hours per week in meetings, which, 20% doesn’t seem like a whole lot. But I think there’s a few things to consider.

Firstly, the folks that are customer-facing, we heard way higher. We saw five, six hours a day in some cases. The folks that aren’t customer-facing, so in roles that they don’t need to be talking to customers, just internally, is where we saw those numbers of one or two meetings a day.

The other thing is you might have two meetings a day at two hours in total, which doesn’t sound like much, but think about the time needed to prepare for the meeting, to travel to the meeting, in some cases, attend, take notes, travel from, identify what the follow-ups were, share them out, and before you know it, your two hours of meetings a day could be closer to four. And that’s why the cost of these meetings and making them productive and valuable matters so much.

Pete Mockaitis
All right. Well, let’s talk about making them productive and valuable. What are some of your top insights and discoveries here associated with what makes meetings excellent versus bad?

Darren Chait
The fundamental question is whether you need a meeting at all. It’s 2024, we have a ton of technology at our fingertips, there’s so many different ways to collaborate and communicate, but in many cases, we just jump straight back to the calendar.

I used to tell my team, I’m in a different role, there’s only three reasons you need a meeting, the three D’s: debate, discussion, and decision-making. So, if that’s not going to happen, does it need to be a meeting? Can I send them a video, right, with, “Here’s what I want you to know, the background on this particular topic,” or, “Here is the plan for next quarter,” or, “Here is some feedback on something I’ve read.”

If I don’t need debate, discussion, or decision-making, I can share that asynchronously via video. And there’s many other different ways we can achieve that. So, if you don’t need to have a meeting at all, that’s the number one way you can reduce the cost of those meetings.

Pete Mockaitis
And I suppose connection as well, it doesn’t fit into the nice 3D framework, and it’s not necessarily about making productive value creation happen, but that is a key source of reason and value of a meeting going down.

Darren Chait
That’s a very good point. I think you’re right, and it sounds like that’s what people are craving. So, even if we could do everything async, we would be losing out on that element of connection. But then, again, is a meeting always the best way to achieve that connection? Can we catch up spontaneously? Can I give you a call? Can I text you and say it’d be great to have a one-on-one and check how things are tracking and hop on the phone? Different style of meetings can, obviously, favor connection and can be achieved that way.

But a traditional meeting, if I have eight people in the room, in a meeting room with some slides up on the screen and so on, debatable the level of connection you get there. But it’s a good point and something to keep in mind.

Pete Mockaitis
Okay. So, with the three D’s – the debate, the discussion, the decisions – what are some inappropriate meetings then, meetings we’re having where this is not occurring that should perhaps sound the alarm bell for us, and make us say, “Wait a sec, maybe this meeting should not exist anymore”?

Darren Chait
The knowledge sharing meeting, I think that’s the one. worst culprit. So, where I’m just coming to share information, “So, can everyone come because I need to present the 2025 plan for whatever with you?” And you come along, and everyone’s happy because I’ve got some interest in the 2025 plan, and I go and tell you a story for 30 minutes, 45 minutes, 60 minutes, and that was helpful to know. I need to know your plan.

But do we really need everyone in a meeting on the schedule that I dictated, joining the Zoom call, or traveling to the meeting, sitting there at the same time, perhaps having distractions because I’ve determined the time that they have to listen, and really, they’re just gleaning this information from me. Could I not have shared that some other way? So, that’s one. I think that jumps out at me a lot.

The other alarm bell for me when I look at a meeting is the attendees – too many or too few. Too many is where everyone has some sort of, you know, interest in the topic. They all join this meeting and you’re never going to have any real debate or discussion, right? There’s 20 people in the room. Even if there’s 12 people in the room, that’s just not going to happen. We can’t have this productive discussion with, effectively, a conference that we’re running.

Or, too few people in the room, or the wrong people in the room. How are we going to make a decision? I can’t go and talk about planning or strategy when Pete clearly is a stakeholder who couldn’t attend and has to be a part of the decision, or talk about what we’re doing for social next year where there’s no social media marketing folks there. So, the attendees is the second red flag that jumps out at me.

And then, I guess, the third thing I’ll say, which is back to really tips for a great meeting, they sound obvious, but we don’t do them well, which is goals for that meeting. So, when you actually look, and ask yourself, you shouldn’t have to ask yourself, it should be clear, but if you have to ask yourself what the goal of the meeting is. If you can’t answer that very quickly, we shouldn’t have had that meeting. We didn’t need that meeting in the first place.

So, what do we need to walk out of this room with, virtual or physical? If we haven’t achieved this, this meeting has been a waste of time. If you can’t express that for a meeting, at least once it’s started, I think we’re making a mistake here.

Pete Mockaitis
So, when it comes to the right number and the right people in the meeting, you have some work there associated with folks having a specific role. Could you expand on that?

Darren Chait
So, one of the downsides to virtual meetings in 2024 is the risk of multitasking and distraction. We know that 52% of workers report multitasking always or often in virtual meetings. Now, yeah, it doesn’t surprise me, but when you look at it like that in the numbers, it’s mind blowing. That means, in every meeting I go to, more than half the folks in the room are doing something else.

Pete Mockaitis
When they’re remote?

Darren Chait
Yeah, they’re doing both. Now, how well can we do both? Well, I won’t debate you on that topic, I know we’ve all got different views there, but you don’t have 100% of their attention. And I’ve got a goal here for this meeting, we don’t want to walk out of the room without achieving this meeting, but I know half the people there are doing something else. So, that’s number one.

And then, to more directly answer your question around engagement level for different types of meetings, if I have an assigned role in that meeting, we saw more than 90% say that they’re engaged in that meeting, “I’m actively listening.” So, an assigned role, I might be chairing, I might be taking notes, I might be presenting a piece of it, everyone’s kind of listening. Very few said otherwise.

But if I don’t have an assigned role in that meeting, it’s almost inverted. We see, at this point, almost 30% of folks who are somewhat disengaged or completely disengaged. And that role, again, could be part of a brainstorm, providing a status update. Again, taking notes, whatever the role is, it makes a very, very big difference.

The reason I like this stat, it sounds obvious, again, naturally, if people don’t need to be there, number one, they’re not going to be engaged. But even if people need to be there, it’s really important to run these meetings in a way where other folks are involved, where there’s collaboration happening, if you want everyone to be engaged. And as I mentioned, particularly for virtual meetings, you’re competing with that 52% who are doing something else otherwise.

Pete Mockaitis
Well, that’s kind of fascinating, and there’s a whole lot of debate right now like, “Everybody come back to the office!” “No, we don’t want to come back to the office!” Or some people are like, “No, we’re fine, you don’t need to go back to the office.” So, that’s sort of raging now in 2024, and probably will continue in 2025.

And so, I can imagine, if those people who are calling the meetings are aware of these phenomena, that’s probably sort of annoying to them, “No, I would like you to be physically in the space such that you cannot be multitasking.” But, at the same time, I think some people really do perhaps think and function better when we’re multitasking.

I’ve been to meetings where someone’s on his walking treadmill desk, and it’s like, “More power to you. I think your brain is working better when you’re moving, and that’s cool.” Or folks are able to just kind of move around a little bit, or fidget with some things, or ponder. I think, I don’t know, I don’t have any evidence in terms of scientific randomized control trials on this, but I think some people just happen to be in a more comfortable thinking, working groove when they have the flexibility to be in their own space.

And yet, having a little bit of that forced pressure of, “No, you’re here and there’s no escaping. There is no multitasking available in this room without you looking rude and embarrassing yourself.” So, it is really juicy and personal what’s at stake here.

Darren Chait
I have two views on that. I think fascinating point. One is what sort of multitasking, right? So, I’m a big fan of the walking meeting. A lot of my team will know, I’ll put in the AirPods and go for a walk and have a conversation at the same time. Certain meetings, right? That works great when we’re catching up about the week and I’m helping to hear and unblock.

But if I’m going to have a really direct conversation with you about feedback or performance, or we’re trying to solve a problem that might be financial and we’re sharing our screen, obviously, you can’t do it that way. Similarly, if I’m sitting in a meeting and I’m now working on writing a piece of content, there’s no way I’m listening or engaged with what you’re saying. No part of my brain can do that. So, I think it comes down to definitions of multitasking. It’s a fair point that some types of multitasking can be productive.

The other side I was going to mention is around remote, and Calendly, full disclosure, Calendly is a remote-first company. What we mean by remote-first is we designed a workplace, a way of working, that takes into account the fact that our team is remote. And I think what we learned through the pandemic, many companies sort of just picked up their culture and dropped it in online and ran into a lot of issues. Different businesses have different views on the topic, and that’s why many companies have required their employee base back to the office, either full-time or part-time.

If you design a meeting culture around the way you’re set up, I don’t think it makes any difference. So, if I’m running highly collaborative meetings where everyone’s engaged and has a role to play in that meeting, I’m going to see the same levels of engagement, or higher even, than I would if I force everyone into the room such that they can’t be on another device, such that they can’t be doing something else.

And to your point, Pete, many people do better because you think better when you’re on your treadmill while you’re in that meeting or when you go for your walking meeting, and we allow for that. So, I guess what I’m saying here is your meeting culture and the way you meet has to be purposeful and intentional based on the way your organization operates.

Pete Mockaitis
And to your point about our own idiosyncrasies and perceptions, you’ve actually got some fun tidbits about etiquette, like what we consider to be rude or unacceptable. This is fun, because I think some people wonder, “Is it okay if I do this on this meeting?” Well, you actually have some answers. Lay the numbers on us, Darren.

Darren Chait
So, in general, we asked a whole lot of questions around, “Is it okay to eat in a meeting? Is it okay to schedule over lunch?” and those sorts of questions, things we do all the time. And let me run you through some of this data.

So, in general, we saw that 23% think eating in a meeting on camera is totally fine.

Pete Mockaitis
Okay, so 77% thinks it’s not fine.

Darren Chait
No, no, no. But, if you’re on mute and your camera’s off, that’s fine.

Pete Mockaitis
And they’ll never know.

Darren Chait
Most people thought that was okay, 68% said that’s fine, “I just don’t want to see you taking those bites.” I thought that was interesting. I’ve definitely been a bit self-reflective after that because I’ve probably been guilty of that over the years. But some more, I guess, relevant ones to the way we work, the dynamics with camera on and camera off is really fascinating. So, when most people have their camera on, 39% said it’s okay for you to have your camera off, but, obviously, 61% said the opposite.

Pete Mockaitis
So, 61% said, “I want those cameras on.”

Darren Chait
Yep, that’s right. “If some people’s cameras are on, yours better be on,” that’s what they’re saying. And that kind of makes sense, right? You’re trying to build connection here. You know you’re remote in these examples, they’re virtual meetings. It’s hard to do that when you’re the one that’s not there. You think about the real world parallel. So, I wasn’t too surprised by that, the people weighed it up.

Pete Mockaitis
Yeah, what would the real world parallel be, like you just have a black bag over your head? It’s like, “Okay, I’m not available to be looked at.”

Darren Chait
It’s true. It’s true. Again, it’s funny with technology because, just a few years ago, if you weren’t in the office, hopping on the phone is totally acceptable with no camera. But now that we have the likes of Zoom at our fingertips, no longer good.

Pete Mockaitis
Well, and I think it gets to the notion of, “Well, hey, if this was a properly sized meeting with the proper people in attendance, it makes sense for everyone there to be on their camera,” in most contexts, as I think through it. And yet if it’s like, “Well, you invited 80 people to this meeting when, really, only nine are there,” it’s sort of like the other 71 are more so spectators, so, like, it seems to make sense to turn the cameras off at that point.

Darren Chait
And that’s why I blame the media organizer, or the onus is on the media organizer. If you have a meeting where folks consistently have their camera off, or if they are doing things while the meeting is running, rather than go to the attendees, and say, “Why are you doing this?” you should be looking at yourself, and saying, “Hang on, what is it about this meeting that disengages, that means that folks can go and do something else, or have their camera off?”

So, I think that’s the feedback there. I think related to multitasking point, before I shared some data with you around how many people are typically multitasking during a meeting, but what surprised me is 70% said that’s okay. They don’t have a problem with it. So, then 30% said, “Nope, everyone should be there.” I don’t personally agree with that.

Again, if you’re running a great meeting and everyone needs to be there, I think that number should be lower. But I think it’s a sign of the fact that we’re not all running those great meetings. We’re all attending many meetings. We don’t have enough hours in the day to get our work done because we’re attending all of these meetings that maybe I didn’t need to be in and that’s why I’m multitasking and that’s why I think it’s okay.

Pete Mockaitis
Okay. So, that’s some good stuff about inside a meeting. Anything else you want to share about best or worst practices when you’re inside a meeting?

Darren Chait
So, generally, I mean, from a data standpoint, we asked some questions about folks calling in when they’re not at their desk, but others are at their desks, only 37% thought that was okay. I was offended by that one. Again, I’m a fan of that walking meeting. If people are at their desks, you should be calling in the same way and so on, so similar sorts of insights.

But really, we’re just seeing the same trends again and again in terms of great meetings, great engagement, everyone needs to be there, everyone’s there. Poor meetings, unclear goals, not everyone needs to be in the room, didn’t need to be in a meeting, everyone disengages, and technology has made that so much easier, because I can click one button and turn my camera off. And again, I can’t do that in the live meeting like we discussed.

Pete Mockaitis
And that’s really intriguing. The word “should” is so heavy, like, with judgment, you know. And I guess it varies how strongly people hold these “shoulds.” Like, is it more like, “I’d kind of prefer if it were on,” versus, “I can’t believe this unprofessionalism on the other side”?

But I think that really highlights the need to have these conversations because we might very well be entering into this situation, blindly unaware, it’s like, “Well, no, I got my video camera off because, I mean, it’s during lunchtime and I’m hungry and I’m going to get really cranky if I don’t eat. You’re going to have a dumber Pete if I don’t eat. So, this is all in everyone’s best interest for me to be eating right now.”

So, I’m just thinking, “Hey, I’m making prudent decisions that make sense for me and my team and organization.” And unbeknownst to me, I’m getting some judgments from others participating in the meeting, so it sounds extra super important that we have those conversations candidly and upfront so that we’re not incurring the negativity that can just be unspoken and foment and grow, you know?

Darren Chait
Well said. And it gets even more complicated culturally because different demographic factors drive different opinions. I saw in the research, for example, 72% of folks in the US feel like it’s okay to eat off camera, but only 64% in the UK felt that way. So, if you’re meeting with Americans, have your lunch. If you’re meeting with Brits, maybe not a good idea. And there’s generational differences and all sorts of others. So, to your point, being clear on expectations and the way we’re operating this meeting matters because you’re never going to make everyone happy.

Pete Mockaitis
Yeah. Yeah, that’s handy. Well, I think it’s just good that the fact that you have this report gets some people thinking and perhaps more likely to discuss, “Oh, hey, I had no idea that a reasonable portion of you might find my behavior completely unacceptable. Why don’t we go ahead and chat about that, shall we?”

Darren Chait
We actually had that a few weeks ago. We have a weekly meeting with the team, and a lot of the team don’t have their camera on, and there’s 40-something people in this meeting, and I get it. Everyone’s got busy. This meeting has just been dropped on their calendar. We haven’t really found a time that suits everyone. It’s impossible with so many folks, and about half of them come with camera on, half come with camera off.

And for the people that are presenting content in that meeting or sharing and driving the discussion, it’s really difficult because there’s no feedback, right? When I’m chatting live with video, we can read each other’s faces and body language and build a great relationship. If you’re just a name, it becomes really hard.

So, we did two things at the same time. One is we set expectations. I said to the team, “Hey, I really want to make this into a meeting that you have your camera on, and I’ll explain why.” And I gave that rationale. And at the same time, we redesigned the way we ran that meeting so it was a lot more collaborative, we had a lot more engagement. Even though it’s a big team, we’d have breakouts most times, we’d have polls running, we’d have an open agenda that anyone could add to.

And both of those things together, a terribly designed scientific trial, both of those things together changed the way this meeting operated. So, I think it comes down to, as we keep saying, right, being clear on expectations and why it matters, but also creating meetings where we want to be there, we get value out of them, and naturally I’m going to be engaged.

Pete Mockaitis
Okay. Well, Darren, let’s dork out a little bit, if I may, on tech tools. So, Calendly is one of the finest software as a service tool as I’m aware of on the planet. So, yep, I said it. I made it, Darren. You can quote me if you like.

Darren Chait
It must be true then. I’ll take that. I was going to say, just capture that.

Pete Mockaitis
So, yeah, it sounds like you’re doing some cool stuff with regard to the open agenda, the polls. Lay it on us, in terms of when you’re in meeting, what are some cool tech features you’re utilizing, and how’s it go down?

Darren Chait
So, firstly, talking about Calendly, as you and hopefully many of the listeners are familiar, we make scheduling automation software, so we make them very easy to book meetings with you and with your team and co-workers from your website, directly by sharing a link, balancing multiple schedules, round-robining, allowing lead routing, whatever the use case is, we want to make scheduling very easy.

And the reason I share this with you is some of my favorite features and tools out there related to meetings actually happen in the pre- and post-. So, I know one of the common reasons I hear why people buy Calendly reminds me of great meeting practice, which is confirming the meeting, sharing out content before the meeting, and sending that thank-you or that follow-up after the meeting.

But, in general, whatever tooling you’re using to do that, you got to do it, you just got to do it. You have to make sure that everyone knows why they’re coming, what the goal is, and making sure they’re actually attending, and then that you capture the value afterwards. So, sure, use Calendly’s workflows by all means, but otherwise, find a way to do it.

Outside Calendly, we spoke earlier about avoiding the meeting. Here at Calendly, we’re big fans of Loom. Loom is an asynchronous video collaboration tool. They’re actually now part of Atlassian, but you can buy Loom independently too and they’ve got a free tier I believe. And the reason I love Loom is it helps me avoid those meetings when I don’t need meetings, but it does it in what I would call a high bandwidth way.

So, here’s what I mean. If I want to share something with you, Pete, I can go and send you an email or a message, say, a Slack message, and say, “Hey, Pete, I want you to know what I’m thinking about this topic, and here’s some feedback on this work,” you just deliver in bullet points. You’re going to come to work. Firstly, I can do it on my schedule, time zone, the way I work, when whatever my workday looks like.

But you’re going to come to work, you’re going to read this message, and you’re going to have 50 questions, right? You’re going to wonder if what I really meant was this or that, if I’m unhappy about that, what the tone was there. Or, I can send you a video, which is what Loom allows me to do. I can record a video, and say, “Hey Pete, great work there. I want you to be even better because you’re next in line for that director promotion. Here are some tips to make your amazing work absolutely incredible.” And I can run through that.

And, very quickly, you’re seeing my tone, my body language, the words in between, the real words, and you’ve got a completely different message delivered, and we’ve avoided that meeting with all those questions. So, async video tools like Loom, I’m a big fan.

Pete Mockaitis
I love Loom so much, and I’m amazed at just how much you could accomplish there. We bought a company about a year ago, and much communication between buyer and sellers is like, “Hey, so here’s kind of how I’m thinking about the financing situation, dah, dah, dah.”

And so, like, we’re going into all these details of a spreadsheet, and so it’s like, “Huh, this is kind of high stakes kind of a communication, and yet we all recognize that, yeah, this is the best way to do it. We want to say, ‘Wait, what was that sell? Where did you get that number? Where’s that coming from?” And we can’t find the right time to meet together quickly, but it’s like, so it really kept our back-and-forths moving faster as opposed to, “Oh, I guess we could all meet Thursday.” “No, give me the Loom Monday, and then we’ll all have our comments Monday evening.”

Darren Chait
Exactly. I love it. What a great testimonial. So, I think that’s an absolute secret for success.

Pete Mockaitis
Cool. All right. So, Loom or something like it enables you to, very quickly, easily do a screen record share. You can see your face in a bubble and mark up documents or spreadsheets or work products of any sort. Very cool. Any other favorite tools?

Darren Chait
So, at my core, I’m a marketer. I crave voice of customer. I want to hear from the customer all the time. So, looking for solutions that allow me to do more of that, and there’s lots out there and it depends on the nature of customer and so on. So, without going to a specific solution, because I think it depends on the company, if you can find a tool that helps you record customer conversations and allows you to share them around internally, that is game-changing. That helps us organize.

Because, in my marketing org, I can go and tell you what the customer says, I can give you slide deck after slide deck, spreadsheet after spreadsheet, until you’ve heard a real human standing right there, talk about the value they get from your product or service, the challenges they have with your product and service, nothing aligns you more like a marketer. But it’s also an area that we’re very interested in directionally at Calendly.

We are moving beyond just scheduling. We are very interested in tasks around meetings, preparation, engagement, and follow-up. I think you’ve got to find ways to capture what’s discussed in meetings and circulate them and surface them and share them to create that organization that’s always working for the customer.

Pete Mockaitis
That’s cool. So, when you say record the voice of the customer. Is that just as simple as, “Hey, we’re on a Zoom, or a Google Meet, or whatever, and I’m clicking record, and now here’s the snippet”? So, what you’re saying is there’s tools that make it even simpler than that?

Darren Chait
Totally, yeah. I know a lot of enterprise organizations use Gong, for example, where sales calls are recorded, you can search and share snippets so there definitely are. But, again, it’s a bit like some of the meeting features and workflows I mentioned earlier. It’s a way of working more than a particular tool that matters. And we really have seen total change in the way we work and collaborate and how customer-centric we are as we’ve created that culture of sharing meetings.

Because the thing about meetings, right, I should have said at the beginning, is we love to hate them. Yes, they drive all of these great outcomes for our business, but it’s where business gets done. If you think about external meetings, every meeting you have with someone outside your business is somehow tied to making money, or recruiting to have the right team to make money, or build relationships that ultimately may lead to customer acquisition, whatever it is.

So, the fact that we’re letting the value of these meetings dissipate into thin air when the meetings end doesn’t make sense. So, we need to capture them, and the same rationale is, the same reasons why we have to make sure we take notes, we have to make sure that we have follow-ups, and make sure those follow-ups actually happen and so on. So, just all of these ways of working and tools out there are all really reminding us of the fact of the value of every meeting.

Pete Mockaitis
Okay. And so, inside a meeting with remote technology operating, you mentioned open agenda, polls, whatever. So, these are just the features baked into your Zoom or Google Meet or whatever you’re using?

Darren Chait
Yep, yep. In many cases, yep.

Pete Mockaitis
Okay, just making the most of them. Like, they’re there for you. Go ahead and learn about them. Try them out.

Darren Chait
Yep, and like that, we won’t be eating in meetings anymore, right, because I’ll be so engaged in what we’re talking about.

Pete Mockaitis
“I get to vote! I’m excited!” It might not be immediately that transformational.

Darren Chait
Yeah, that’s it.

Pete Mockaitis
It may or may not be that immediately transformational.

Darren Chait
There you go. That’s the disclaimer.

Pete Mockaitis
But you’re right, it is fun. It’s intriguing. I don’t know about you, but something about real-time data, there’s a little bit of a reveal. If it’s an interesting question, like, “Oh, hey, how many of you are calling in from the West Coast?” It’s like, “Okay, I don’t know.” But like, if I’m genuinely wondering in terms of like, “Hey, we came up with 12 ideas. I’d love for everyone to vote on which ones they think are the most likely to be high impact and they want to start on first.” Like, I don’t know about you, but that just gets my heart thumping a little bit. Like, “Ooh, who’s going to be the winner?” It’s like election night, like county by county.

Darren Chait
You know what though, Pete, if you said, “Does anyone have any views on how we should prioritize this?” Silence. Right?

Pete Mockaitis
Totally.

Darren Chait
We use a lot of Miro here as well. Miro is an online whiteboarding tool, and there’s a few of them around as well, and some of them are embedded in other products and so on. The reason I like Miro is it allows a very fluid, freeform way to collaborate in the form of whiteboards. But they have a lot of great real-time tools you can share.

You can share your Miro board for your Zoom or directly, and it’s great for voting. People can put stickies. They can contribute to a conversation. They can drive that collaboration in a real way. So, that’s what you’re reminding me of as you’re talking about that behavior because it definitely does exist.

Pete Mockaitis
Very nice. Well, Darren, tell me, any other key things you want to make sure to mention, any top do’s or don’ts?

Darren Chait
So, one other thing to mention that we noticed in the research this year, and again, I’m not surprised, but also really cool at the same time. We asked, in general, we asked all the respondents in this survey their views on the role of AI in meetings, if they’re interested in the use of AI in meetings.

2023, 17% said yes. This year, almost 50% said yes. But we’re all learning so much about AI every day and the advent of all the big players in tech in AI. It’s now very clear, to these respondents at least, that it’s here, we’re heading there. Most products are releasing AI features now, particularly those in the meeting space, Calendly included, and we’re coming up there soon.

So, I think it’s fascinating to see that AI has unlocked a ton more powerful online, and it’s a logical place to start, right, to make us more productive in our meetings, more effective. So, that trend in just 12 months was really surprising to me.

Pete Mockaitis
All right. Well, now can you share with us a favorite quote, something you find inspiring?

Darren Chait
One of my favorite quotes, in general, in business, comes from, it’s actually been quoted many times by many people so I won’t try to attribute it, which is not to confuse work with progress. So, something I often think about is, “Is this just work keeping me busy or is this actual progress or output?” So, “Don’t mistake work with progress” is one of my favorite business quotes.

Pete Mockaitis
All right. And a favorite book?

Darren Chait
Team of Teams, General Stanley McChrystal. Definitely a bit of a less conventional business book, but a must-read if you’re leading a team.

Pete Mockaitis
And a favorite habit?

Darren Chait
I don’t end my day until I’ve got a plan for the next day. I think, especially with time zones and the likes of Slack and other tools now that bombard us when we’re not online, you always wake up, you always start your day feeling behind. So, I, at least, want to start my day having clarity for the goals for the next day.

Pete Mockaitis
And if folks want to learn more or get in touch, where would you point them?

Darren Chait
Absolutely. So, obviously, if you want to learn more about Calendly, Calendly.com. But on LinkedIn, always happy to connect and chat and nerd out on these topics, and we can, yeah, definitely dive more into what we’ve learned. You can also, if you go to Calendly.com. If you scroll all the way to the bottom of the page, you’ll see a link or other resources to the State of Meetings 2024 so you can dive into this data. And there’s many more thoughts and perspectives here that we didn’t have time for, but you can nerd out on the State of Meetings yourself as well.

Pete Mockaitis
Okay. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Darren Chait
Go through your calendar, and look at those meetings that are competing for productive time. See what you can cut, and then choose a favorite meeting and see if you can make it that much better. Go and look at who’s attending. Look at your process around setting agendas and planning. Look at the tooling that you’re using to power that meeting, scheduling all the way through to follow-ups, and see if you can get that favorite meeting performing that much better. And no doubt you will, you’ll see the results and you’ll move on to the next one. So, meetings really are a hack for team productivity, and I encourage you to try it out.

Pete Mockaitis
All right. Darren, thank you. I wish you many excellent meetings.

Darren Chait
Thanks, Pete. Likewise. Great to chat.