Software is a permanent fixture for many of us, and while we often implement software platforms to enhance our productivity, it can in fact hinder it. Robert Peake, GTD® veteran who has an extensive background in software and technology, talks with Todd Brown about how best to navigate software platforms to support your GTD practice and overall productivity.

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0:00:05.4 Todd Brown: Hello, everyone, and welcome to this Change Your Game with GTD podcast. My name is Todd Brown, and I’m here, as always, with Robert Peake.

0:00:12.6 Robert Peake: Hello!

0:00:14.6 TB: Our goal in this podcast series is to provide you with our thoughts, with some guidance, with some of the practical tips and tricks, with some of the theory, with our own experiences and the experiences of the people that we’ve worked with over the years, in getting the most out of the Getting Things Done methodology by helping you to enable stress-free productivity, so getting more of the right things done, in less time, with less stress. That’s what we’re heading for. And Robert, as you and I were talking just before we hit record, the topics that you’d suggested that I liked a lot was how software helps and hurts when it comes to GTD. So that was your topic. Why don’t I let you riff a little while on what that means, what sort of brought it to mind, and what it means to you?

0:01:04.2 RP: Those feel like one of those essay assignments you get in school, right? “What does software mean to you?”, or “What does software helping and hurting mean to you? In this essay, I’m going to tell you about what… ” And then you repeat it. Anyway… I’m in a whimsical mood, clearly. Yeah, it just came to mind because, well, a lot of my career has been around software: Developing it, implementing it, debugging it.

0:01:32.9 RP: And I think… There’s this thinker, Venkat Rao, who says “Software is eating the world.” More than hardware, more than anything else, it has just become the driving force behind so much change in our world, and of course, change being a neutral term, change can be good or bad. And software! Software can be good or bad, in the sense that it’s buggy or not, but also in the sense that it’s either appropriate or not, or even within a certain piece of software, that certain features are appropriate or not to what you’re trying to get done and what you want to accomplish, so…

0:02:10.3 RP: I’ve done a lot of work with software, and I’ve done a lot of coaching one-to-one with people who have implemented different software solutions to try and make their life easier and more productive and more stress-free, and generally, with software, there’s this thing that you do… There’s some upfront initial investment, in setup, in learning it, etcetera. And the idea is that after that initial figuring it out, installing it, etcetera, period, that there’s gonna be a pay-off, that it’s just gonna be absolutely… Have been worth it to do that because things will go faster, things will be smoother, etcetera.

0:02:45.2 RP: And what I’ve found is, because software is… Has made such a profound impact, and now in the age of machine learning and big data and the implications of those two worlds coming together, there’s some almost magical types of things. I still love that image recognition can tell me who’s in a photo. I love and I’m plenty creeped out by… So even more, there’s that magical sense of “Software can fix it, software can solve it.” But in the world of personal productivity, as well as wellbeing, we’re dealing with fundamentally human problems, and so the human element of that, there are certain parts of it that really can’t just be fixed by an app, if you like.

0:03:38.1 RP: They can’t just be installed away. And so looking at the interface between what you want in terms of behavior chains, what you want in terms of optimizing your own thinking process, your own relationship to your commitments and aspirations and goals, and orientating yourself throughout the day to stay positive and productive, and interfacing that with pieces of software that may help with that. I also found there’s a lot of pieces of software that may hinder with that, or more appropriately, the way people use it, the way people use that software may actually hinder or cause a lot of problems and challenges with how people actually getting them what they said they wanted to get done.

0:04:22.0 RP: So I just think it’s a really interesting tangle, because there’s great potential on either sides of that equation, frankly, that I’ve found. So I thought it’d be fun to explore and it’d be fun to talk a bit more about it, so that’s the kind of philosophical high-level umbrella that I think got me here in terms of my thinking is just, “Wow, there’s… It really can be both.” I dunno, I’d be curious, your experience, you’ve done an awful lot of coaching, as well as, obviously, running your own systems, and a lot of seminars and consulting work inside of companies. What have you seen out there in terms of… Any war stories, success stories about software helping and hurting with the goal of being more effective?

0:05:09.4 TB: Yeah, I… It’s interesting. What came to mind as you were talking about that is that you and I do share a background in technology, so my first role, actually, in my first job back in the 80s was, I was a developer. I was a programmer for quite a few years, and I worked in IT for about 10 years. I don’t do it actively so much anymore, but one of the things that, as you were talking about, I was reflecting on for a long time in my own head… The software could be the solution. I was a classic early adopter; if it was new and cool, I wanted to own it. And in my head, I was like, “Okay, well, if I… This new tool, it just sounds so cool.”

0:05:53.4 TB: I didn’t really come to this conclusion at the time, but I think a subconscious desire was that if I bought the right bit of software and configured it the right way, it was going to basically take all of the work out of whatever it was that I needed to do. That was somehow… The ultimate goal was efficiency that led to a zen-like state of productivity, where the tool was doing absolutely everything and I was not engaged at all.

0:06:22.2 TB: Now, that was… As I say, I didn’t really consciously think about it in those terms at the time. But a bit like you, over the years, what I’ve come to realize is that the tool… Or the tools, better said, because today, pretty much everybody’s system is a multi-tool suite. And when I say suite, I don’t mean necessarily… A bit like the Google suite or the Microsoft suite or whatever, where it’s tools from the same supplier. It could, in many cases, be tools that have been glued together or cello-taped together by you. But the tool set is a facilitation… Can help to facilitate what you do, but it’s not the solution.

0:07:10.9 TB: And then, more directly in answer to your question, I think… What I’ve seen is a lot of people who… I think one of the surprises for a lot of people is how… In my coaching with folks in the work that I do with clients? I’m looking to strip back what they’re doing with the software to that sweet spot, which is right on the border between… We wanted to do what’s helpful for you, but we absolutely do not wanna try to, for example, learn every feature of Outlook, nor of whatever Gmail or whatever. We wanna make sure that the things that you’re using every day are not so complex that that gets in the way of your being productive.

0:07:58.0 TB: And quite often, I think… When people come out of coaching engagements for this or out of seminars for this, and they’ve had a system set up for themselves, but quite often say, “I’m surprised how little of the tool I really need to be focused on.” That’s not to say they didn’t learn anything new about the tool; almost everybody does. New ways to think about using email and list-making, and whether it’s Teams or Slack or whatever, these sort of groupware-type things. They have learned new things about all of those tools, but they’re surprised, as I say, that it’s not hugely complex.

0:08:40.0 TB: And I think there’s probably some magic in there. The answer is probably in there somewhere, that what we’re trying to do is get to the stage in the development of our own thinking and of our own systems, where our thinking and our practices are matched and complemented by the tool that we have in front of us, and that tool is providing us with what we need, and that magic is a thing, it doesn’t require… That magic does not require the… Using all of the features of any given bit of software.

0:09:16.8 RP: Yeah, absolutely right, absolutely right. And of course, there is that, as you say, “Christmas morning, opening it up, seeing what it all can do” factor. There’s nothing wrong with exploring the features, but the question is, are you exploring and playing around, or are you looking to implement something you know you want? And I’m amazed. Half of people lose sight of implementing what they want, which is something that’ll be fast and efficient and streamlined, in the process of exploring the new toy, as it were.

0:09:49.6 RP: One of the things that occurs to me on a practical basis, when clients often do come to me, either in a tangle, either in a tangle because they’ve set up maybe more context than they need, or they’re doing lots of bells-and-whistle stuff, or they’re tied up in lots of pop-up reminders, or somehow they’ve gotten into a bit of a muddle, where suddenly their system feels like a drag, is that there’s really two scenarios, two thought experiments you wanna flash forward into when evaluating the features of a tool, and how you’re using it, and that kind of thing. And one is, I’m doing my day-to-day work. I’m doing my work. Where do I go to get what I need, to know what my options are?

0:10:37.8 RP: If you’ve got 30 different contacts and seven different sub-tags, and it’s all color-coded blue, purple and green, or whatever, I would say “No no, you’ve just come into the office, where do you go?” But if they say, “Well, I gotta click here, here, here, here, here, and here,” it’s like, count the clicks. And is that really effective? And then the other one is in the weekly review. It’s like, okay, now it’s weekly review time. You’re gonna go through these 11 steps. You’re gonna be looking at these different parts of your system. How fast and efficient and fluid is that?

0:11:05.2 RP: Is that really working for you as well? And I found that those two places, when doing system design is begin with the end in mind to some extent, and we do that with everything. We do that with data design. It’s like, “Okay, well, we’re gonna build a structure to hold some information. How are you gonna wanna get that out? What are the reports gonna look like?”, and that’s gonna inform how we build the structure. Likewise, when you’re building a system structure, it’s like, “Well, how are you gonna wanna get that out? What situations are you gonna be and how are you gonna be viewing that?” And that, I think, goes a long way toward helping people realize that…

0:11:43.9 RP: At the end of the day, all of these tools, you gotta say to yourself, particularly in the list-keeping tool, How is it better than paper? How is this better than a really, really simple technology that’s endured for centuries for a reason, ’cause it’s super fast and easy to write on, to crumple up, to strike a line through, etcetera, with. How is it really better? And there definitely are some good answers that… “Well, it integrates with email, and it lets me copy-paste it over here, and it lets me do that, and it lets me put in hyperlinks.” Great, but when you start to get into some of the stuff where you go… “Do you really need that? Or could you just have done that on paper, actually, a lot faster than what you just showed me, through the kinda circuitous way you had to go to get what you wanted out of the system?”

0:12:32.1 RP: So those are some of my litmus tests. “Does it work really fast for a weekly review?” “Does it work really fast day-to-day?” “Are these features truly better than paper?” “Are they slower or are they faster?” “Is there an integration of something else that really makes your life better, or is it just kinda cool that that’s possible?” And so those are the kinda things that I start to ask clients when they recognize… Fortunately, they often do recognize that they’ve gotten into a bit of a tangle, and that the software’s starting to hurt. I’m curious, your thoughts on how you… Someone comes to you with “Hey, I’m not sure about this tool,” or “I’m not sure I’m using this tool well,” or just even if you have any war stories, of people that have gotten themselves into a muddle. How do you help people that are hurting with software?

0:13:28.1 TB: Yeah, well… Pain, when it comes to software, I suppose, comes in many forms. It takes me back to one of the very first coachings that I ever did with somebody who had implemented a tool. And… Sorry, let me… A little bit of sidebar quickly, ’cause I think one of the ideas that you talked about earlier is gonna be important in making sense of this story. I think quite often, when we are in the flush of that, “Oh, that new feature in that’s so cool, and that’s gonna be really neat, and that’s gonna… ” I think part of what drives that is, there’s a little bit of a dopamine hit about the new, of course.

0:14:10.6 TB: But I think as well, it gives us the sense… And maybe we are… The sense is incorrect, that that feature, whatever it is, is gonna give us a sense of control that we don’t really currently have, okay? And quite often, what I find is, those features… Yeah, they might give you a sense of control over something, but in the bigger picture, that control is either not something that you really particularly wanna control, or, and this is where I come into the story, or it’s gonna give you the ability to create what, at the moment, feels like an upgrade, but, in the bigger picture, is not. And so on to the story, so…

0:14:53.2 TB: Doing this coaching with this person, and he had a tool, a very well-known tool, and it was the kind of tool that would allow you to create lists, create links between lists, put tasks and folders, put… Create categories for things, whatever. And so the ability to layer metadata on your items was pretty extraordinary. And he showed me this, and he… As part of the coaching, of course, one of the things that we do is we do a deep dive into, “What are you doing now? So what’s your current tool set?

0:15:32.2 TB: What are you doing now?” And he gave me a quick demo of this, and it was all interlinked! Every task had two categories and was in a nested folder structure that was six deep, and there were hyperlinks all over the place to take you to various things within the app and outside the app, and… As an intellectual exercise, it looked to me like it was actually quite fun for him to do it, to put it all together, but as you might imagine, none of these interconnections was maintained with any kind of rigor, and so it was… It had just become… This is a phrase I’ve heard David Allen use quite a bit. It had just become organizational spaghetti. It was just… [laughter] It was all over the place.

0:16:21.8 TB: And so, going back to your previous question, I think quite often, what I find myself doing in the early phases of an engagement with a client is, we’re just gonna go back to the basics. Now that might mean, literally, as you said earlier, that might mean we start over with paper. Could be, could be. Not in all cases, by any means. But we’re gonna strip it back, we’re gonna strip back the toolset to the really core features, and really start from there. It might be, by the way, but that doesn’t mean we’re changing tool. We could be making use of the very same tool, but we’re just gonna make use of it in more fundamental ways, and then let the complexity build over time, not over the course of 10 or 15 minutes, but over time, let the complexity build in your system, I would say, as it becomes really clear to you that that complexity is, on balance, bringing benefit.

0:17:18.7 TB: And that, of course… I think what you said earlier is really important, we should be open to experimenting, to playing, to trying. We shouldn’t be just locked into our toolset forever. But at the same time, I think we wanna be clear that there needs to be… It needs to be reasonably… You need to have some reasonable confidence that there’s a payoff as you’re implementing the additional complexity, that that additional complexity is leading to being more clear-headed, more focused, giving you more perspective, being more in control. I think that’s… Yeah, that’s what I’d say, in a very big and ragged nutshell.

0:17:54.5 RP: No, that’s great. No, that makes a lot of sense. The admonition that comes to mind is “Complexity, if you build it, you must maintain it.” [laughter] Just thinking that as you’re adding in these features and things can go a long way toward being kind to your future self, and there’s a lot of subtle ways to do that, and one of them is to say, “You know what? Looks cool, but I’m just gonna stick with some fundamentals for now, because it’s fast and smooth, and future me knows how to do it.” And trialling things is a great way to do it: Considering it an experiment, even setting a reminder in the calendar, “Hey, I’ve been trying using the purple flags for a week, how’s that going?”

0:18:42.1 RP: So that you can evaluate and not just fall into suddenly creating a habit. It’s amazing how fast we create habits for ourselves as human beings, but… Creating a suboptimal habit, just because you’ve done it a few times. So yeah, I think that’s such great advice, Todd, and yeah. How to avoid having to eat your own organizational spaghetti later on that you’ve cooked up for yourself; it’s all of your own making.

0:19:11.0 RP: Yeah. And the question to ask is, “How’s your brain? How’s your brain doing with all of this?” It’s amazing how we get out of touch with how the brain is actually doing it, ’cause we can’t cope with and adapt to so much, and we can cope with and adapt to systems that we’ve created for ourselves that are not ideal or optimal. We’ve talked a lot about how software can hurt, obviously there’s… I think some of the ways in which software helps are really self-evident, we go, “Well, things are a lot faster,” or, “I can copy and paste rather than writing out longhand,” or, “I can link from this to that, and that’s really useful later that I can get to it later.”

0:19:53.3 RP: But I wonder if there are any kind of specific, specific things in software, because we’ve both been around for quite a long enough time that software has changed, productivity software has changed and had gotten better. Is there anything in particular that stands out to you where you go, “Oh yeah, this is a major upgrade,” or, “This can really help people,” or, “This is definitely better than paper or a more simple system”? Any thoughts on how software helps?

0:20:18.6 TB: Oh yeah. Look, I’m a big fan, I wouldn’t class myself any more as an early adopter. I am willing to sit back, let other people be the pioneers with the arrows in their backs, and then come back and tell me about the experience. So I’m not quite there. I’m not really an early adopter anymore, but what I will say is, I love having a system which really feels like it complements my preferences the way I like to work, feels like it’s more or less a seamless integration for me, I’m a big fan.

0:20:56.9 TB: It’s funny, I’m thinking back to… Let’s just talk about list-keeping, ’cause anybody’s GTD system has to have that as some element of it, whether it’s on paper or whether it’s in the digital space. But let’s talk about the digital space, and it takes me back to… I’m gonna go back 25, 30 years now. Lotus, most probably best known for the… For Lotus 1-2-3, the spreadsheet program way back in the day, and Lotus Notes more recently. But Lotus had a product called Agenda, and Agenda ran on the PC. And Agenda was basically… This was pre, most people having network connectivity, and it was a standalone thing. But it was…

0:21:41.3 TB: It basically did list-keeping, it allowed you to put things in folders, it allowed you to put things in categories, and I thought it was absolutely magical. And I was thinking about this the other day, because when you see list tools, they’re our greatest hits, right? “Can I put things in categories? Can I put things in folders? Can I group things together? Can I link things? Can I have external links to other things?” Those kinds of things are very, very common, and critical.

0:22:08.7 TB: I think in order to have an effective list-keeping system, I think about how painful it would be in my own system if it were difficult for me to take an email and from that email to create a reminder of some sort. And I think it’s one of the reasons, by the way, that in the world of Microsoft Teams and in the world of Slack and similar products, I think one of the things that is slowly being addressed is the fact that it’s a little bit tough at the moment to take a post out of Teams and create, for example, a reminder from it in some other bit of software.

0:22:48.7 TB: And by the way, literally just yesterday, I got a ping, I got an email, I haven’t looked into this yet, but apparently Microsoft has put a new feature into Teams which allows you to create reminders in the Planner, stroke to-do, stroke, whatever universe, which is gonna mean that maybe those barriers are starting to come down. But… So, I think one of the… List features, list tools on one hand, again, there’s not a huge amount that’s new, but what is becoming even more common and is gonna make a big difference, I think, for us is the degree to which all of these list tools are very well-integrated with the rest of our toolset, and the more friction-free that integration becomes, the better it’s gonna be, the faster and more effective we’re gonna be able to work. That’s my take. What do you think?

0:23:39.1 RP: Yeah, yeah, no, I like that. Yeah, I think for me… Well, I’m amazed that, for example, I can be out on a walk and take a picture of a plant and beam it into space and have it come back and tell me not only the Latin name, but the 40 different weird common names for that plant, so I love some of what technology is doing in terms of learning, actual learning in that sense of being able to classify things, being able to help us filter and sort things. And at the same time, I’m a bit wary of it because for example, the new Gmail inboxes where it’s trying to sort different things, or Cortana, where these services are trying to say, “Hey, you haven’t responded to this email for a few days,” or, “Hey, there’s this thing over here,” or, “Hey, that sounds like a question.”

0:24:34.0 RP: In a sense, trying to be a little bit of a system for you, and trying also to parse and sort, “This looks like an important email, this looks like one that’s not so important,” etcetera. And the reason I’m wary of that is, well, for one thing, we had the problem of spam for decades now, many decades now, and we all still have to look at our junk folders, we all still have to go there, ’cause every once in a while something slips through, and the reason for that is that humans are ingenious and constantly finding ways to circumvent and do stuff to defeat the systems they create for filtration.

0:25:19.3 RP: And also just one of the biggest things I’ve discovered in coaching is that the human brain… No two human brains really work the same at all. Neurodiversity is just a reality of how we think about things and how we wanna state things. I’ve almost never said, “Okay, state that in your own terms,” and it was exactly the way I was thinking of it, for anyone’s project or task or action or anything, they never did it exactly the way I was thinking of it, they have their own way of thinking about it.

0:25:48.2 RP: So I guess what I’m coming to is that, increasingly I think we’re seeing a real trend toward machine learning trying to help solve the problem as it were, of just a tremendous amount of information and people feeling like, “Well, I can’t possibly respond to everything, and some of it obviously is spam and… ” My concern is just that there’s an increasing talent for, “Well, maybe I can let a few things slip through the cracks if the computer doesn’t catch it.” And I think that’s dangerous. I do think that’s dangerous. I do think we’re always gonna have to check our junk filters, and no matter how much technology can support us in telling us what it thinks might be going on, that we really still are ultimately responsible for doing the thinking that we can’t… We can’t outsource true intelligence, we can only beef up the views of what’s there through artificial intelligence.

0:26:44.3 RP: And the ultimate goal of AI is what they call “unsupervised learning.” They have this program that plays the Japanese board game Go, that has reached a state… This program has reached a state where it actually learns how to play the game better from playing itself, than it does from playing other humans or from analyzing other games that humans have played, it’s actually reached a level where it learns more from itself than it learns more from other people. I don’t think our email inboxes are ever gonna get there.

0:27:16.1 RP: I just don’t think that’s ever gonna happen. I think there’s always gonna need to be supervised learning, as it were, in the space of setting up filters and setting up rules and dealing with information flow in that way. And I think we really need to do the supervising and we really need to continually be in there going, again, “Is this helping me? Is this showing me the right stuff? Is it really accurate? And is 90% accurate really good enough? Or is it possible I’m gonna miss an email from my mother-in-law and really have a big problem?” or the CEO, or whoever.

0:27:46.9 RP: So, a little bit of a rant, maybe slightly a side bar, but I think the thing I see really coming at us is this enrichment of data through machine learning, and just a little caveat in there of, “Hey, your commitments are still yours,” whether the computer catches it or not, you’ve gotta catch it and it’s gotta make sense to your brain. I think softwares are just gonna be getting in some ways more complex, more feature-rich, more interesting, and some of it is gonna look like magic, “Wow, that’s amazing that it knew, that it knew what I was thinking about.”

0:28:23.0 RP: And so even more, I think, this caveat that we’re talking about of, “Hey, just ’cause it’s shiny and new, does it really help you manage your day-to-day commitments in a really effective watertight way, or are you at risk of basically trying to delegate some of your responsibilities to a machine?”

0:28:41.7 TB: Good stuff, good stuff. Well, listen, we’re coming at the end of our time. Let’s put ourselves just very briefly in the shoes of someone who’s got a toolset, and they’re thinking about, “How do I evaluate this, how well it’s serving me, how well… Do I need to make any changes?” Well, what would you say to somebody like that? What kinds of questions would you encourage them to ask in order to make that evaluation?

0:29:05.5 RP: Yeah. It’s an important one. I think it’s really helpful to have a sense of what you wanna be experiencing, in relation to the tool, how you wanna be working, it’s like, “What’s your day-to-day state like?” It’s like, “Well, it’s fast and easy to find the actions in this context. Well, when I get interrupted, I can go right back to where I need to go. It’s really obvious when my inboxes have piled up when I need to process those down.”

0:29:38.2 RP: Rather than just going into the tool and saying, “What can the tool do for me?” Having a vision for your relationship to your trusted system as a whole, the tool is being one part, from the outset, that if you really have that, and you might even write it down, it’s like, “I feel this tool feels like, it’s really fast and frictionless, and I’ve put in the right stuff for the right times, and it’s really easy to understand when I should be in calendar and when I should be over in my lists and… ” whatever like that, you actually can spell out, what’s the vision, what’s the vision for the use of this tool?

0:30:12.2 RP: And then, evaluate everything against that so that you’re in charge of designing and crafting your productivity system, rather than going with the flow, ’cause I see a lot of going with the flow and the flow is of course, software developers wanna sell you on more and more and more and more features, that’s all they can do is add, add features and fix bugs to make their thing better. But more isn’t always better, particularly if you lose sight of that, again, that vision for what the system is gonna be like to use. I don’t know, how about you?

0:30:47.6 TB: Yeah, I like all that. I think what I would add, another thought would be, make use of the 5-phase model in GTD: Capture, clarify, organize, reflect, engage, and think about the tool in terms of which element of that model is it going to facilitate, make easier. I think a lot of people get… That framework can be quite helpful. “Is this something that’s going to help me capture better? Is it something that’s going to help me facilitate clarifying so that I can make decisions about things?

0:31:20.6 TB: Is it gonna help me to organize better?” And by the way, a tool, of course, can wear multiple hats, it could be something that helps you both clarify and organize, for example, or capture and clarify. But I think that can be quite helpful is to use that framework. Well, thank you everyone, for being with us today for this episode of the Change Your Game with GTD podcast. Please do subscribe, and come visit us on the web as well at, the website, you can sign up there for our newsletter, and that will get you not only notifications about these episodes, but also about the various blogs that we produce.

0:32:05.4 TB: We produce content generally speaking, once or twice a week, and our goal in all of that is to serve you best, it’s to help you on your journey and to enable stress-free productivity as we say. So for now, on behalf of Robert and me, thank you again for joining us, we’ll look forward to seeing you next time. Bye for now.

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