THE OMNI SHOW

Stehpen Dolan: The instinct to work out of my inbox is a little bit harder to suppress when things are really busy. And so these daily reports that run and tell me where I'm completing tasks from help me at the end of the day, just get a look back of, "Oh man, I completed zero tasks today. I know I've been working for eight hours, but I ticked to zero boxes today. What can I do tomorrow to set myself up for more success? Is that a review right now? Or maybe shifting a meeting that I have tomorrow so that I'm not in meetings all day?" That sort of thing has been, I think, the most impactful that I definitely would've scoffed at and said is a waste of time last time we spoke.

Andrew J. Mason: You're listening to The Omni Show where we connect with the amazing community surrounding the Omni Group's award-winning products. My name's Andrew J. Mason, and today we learned how Daniel Von Fange uses OmniGraffle. Well welcome everybody to this episode of the Omni Show. My name's Andrew J. Mason, and today we are honored to be able to have Stephen Dolan, back in the house with us via video versus audio today. And, Stephen, I would say the biggest change since we've last talked to each other is your shift from Chief of Staff to CEO of Tuple. Talk to us about that and welcome to the show.

Stehpen Dolan: Thanks so much, Andrew. It's great to be back. Yes, definitely big professional shifts, big life shifts since the last time we talked. I think the last time we spoke I was dad of one and so we've doubled that, made life a bit more tricky on that front. And also since we last spoke, I had a couple shifts, one into role as Tuple's COO, so I took over for one of the co-founders in that respect and then maybe a year later took over as CEO and so now it's the whole thing. We haven't back filled any of those roles, so it certainly has been an increase in throughput of my task management system for sure.

Andrew J. Mason: Let's dive in. Let's talk about that. So back in 2022, you described your OmniFocus setup as pretty simple. Would you still describe it in that way today or has it grown more complex as the responsibilities have been added on?

Stehpen Dolan: Actually I would say I have gained way more confidence in the simplicity of my system because there are some things around the edges, some of the cool Omni automation stuff, obviously AI has changed a lot in that landscape since the last time we spoke, and so I'm trying to incorporate that and see where that fits into a setup like mine and more generally into getting things done. But overall setup is still the same. I've got my same core perspectives, it's robust, it works, it gets out of my way. I don't have to fuss with the tool and there's never a better time to not mess with your system than when your life is chaotic and you're having a bunch of stuff thrown at you. So I would say more confident than ever that simple is better because I didn't have to pause and get into a new tool or do anything like that with all these changes.

Andrew J. Mason: That's incredible. It's funny that scale doesn't break the system for you and that's honestly, you mentioned the phrase confident as ever the idea that being able to increase reps and speed and time and velocity is not something that's destroying your ability to stay with it on the system. What's one thing, you mentioned on the automation and on the edge, is what's one thing that you're doing today that maybe would've surprised you in 2022 for your system?

Stehpen Dolan: I wrote an Omni automation script that every day reports out to me a bit of how many tasks did you complete directly from your inbox and what's the distribution look like of task completion across your projects? How many projects got completed that day? And it's a thing that I think last time we spoke would've said, "Don't waste your time with this stuff. Just work the system in the way that works for you." And I think that's true, but a bit of what's happened with my professional and personal shift is that I'm finding I have less focus time to just sit down and work the system. There's a lot of latest and loudest, which is okay, GTD allows you to handle that stuff I think with more elegance than you can in any other system. But the instinct to work out of my inbox is a little bit harder to suppress when things are really busy. And so these daily reports that run and tell me where I'm completing tasks from, help me at the end of the day, just get a look back of, "Oh man, I completed zero tasks today. I know I've been working for eight hours, but I ticked to zero boxes today. What can I do tomorrow to set myself up for more success? Is that a review right now? Or maybe shifting a meeting that I have tomorrow so that I'm not in meetings all day?" That sort of thing has been I think the most impactful that I definitely would've scoffed at and said is a waste of time last time we spoke.

Andrew J. Mason: This is incredible because it gives you a little bit of that insight into the Covey urgent versus important idea that's happening here and where am I? What caused you to say, "You know what, if I have my eyes on this metric, it's probably a pretty good insight as to whether or not I'm allowing myself to be hijacked by that information."?

Stehpen Dolan: One of my last steps of my weekly review each week is what could I have done better in my system and what did I do well? And this stemmed from one of those, what could I have done better over the last week? It was basically a recognition that I had been working with unclarified tasks out of my inbox and had kind of diluted down my system to not using my forecast as just the things I have to do and mostly working out of my next perspective, but instead, I was basically just working out of my forecast view using due dates and abusing them a bit because it was like, "Well, I don't have to do this thing tomorrow, but if it doesn't have a due date, I'm not going to look at it because there's too much going on." And so it was just this... it bubbled up from a weekly review for sure. And I would encourage anyone doing a weekly review to take some time at the end of that review and do that reflection because it's every time I have improved my system or tweaked it slightly, I would say most frequently it comes from that reflection period, not from some arbitrary like, "I'm going to spend an hour and change my system," kind of a block.

Andrew J. Mason: It's like going to the gym. It's one of those steps that probably isn't the most glamorous, but once you do it you're like, "Okay, I'm not upset that I spent my time there actually asking these questions." You are juggling a lot of areas. How do you decide or evaluate which projects actually deserve your personal focus versus delegating or deferring it off to somebody else?

Stehpen Dolan: Certainly still a challenge that I would say I don't have full confidence in my ability to do well today. I think that's a constant evolution and has a lot to do with how much do you trust your team and how bought into the system are these people to that you're working with? Because that level of follow through can impact my ability for my brain to let the task go and put it in a delegated list versus managing the project more aggressively. I think there's a spectrum there. It could be as simple as a waiting on task that is waiting for this person to complete this project. And then for a lower trust relationship, I think you can get as granular as check in with this person every other day on this project or ping them on this slack thread to make sure they follow up. And so I think adapting to being in the loop with the entire company and what everyone is working on and trying to both stay out of people's way and let them be autonomous and bring the thing that I think I can do well, which is this sort of clarifying what's next, removing blockers, pulling people out of the weeds when it's necessary. For the way that I handle being a CEO, it's really just who I feel wants the most help and needs the most help is where I focus my attention. Now, my personal work because I still have to do things like file the company's taxes and answer security questionnaires and handle some of the sales stuff. And so there's certainly work that I have to do generally, and so those things generally take a back seat to helping the rest of the team unless there's something that's urgent. But generally I would say I follow the energy of the team who I'm feeling like wants or needs the most help and that can change on a day-to-day basis or an hour by hour basis.

Andrew J. Mason: There is some art to that science, I would say. It's one of those things where somebody that isn't quite ready today may be very much ready tomorrow, especially in the terms of only doing what only you can do kind of a thing and being able to gauge or judge where that lands, I feel like that is a dance. Sometimes it's cyclical. Sometimes they were more ready versus less ready today because of other things that have shifted in the workflow. So how do you actually decide what is next for you? Let's say you know what, you've got the inbox cleared out. Is there a tag-based system you use? Is it a gut instinct or just something else entirely where you're like, "Okay, this is really what I need to be doing the next today."?

Stehpen Dolan: I think that is the thing where my system tells me the list and I don't try and push priority too much into the list. Basically the only prioritization I do today is if something has a due date, it means bad will happen if I don't get it done by that day, whether that's I'll feel really bad about a commitment I made to myself or someone else, or I will miss filing our family's taxes. Those are the kinds of things that get due dates. And then my next list is, the goal for me is to keep that list small enough that every time I look at the list I could scan it and just pick whatever feels most important because I think something I've struggled with over time is using tags like priority, effort, energy, complexity. There are all kinds of ways that I've seen people recommend doing this thing and for me, it never survives how I'm feeling in that moment. It always changes. This morning I've had two cups of coffee and I've got a lot of energy and maybe the thing I'm looking for is kind energy independent and I can just work on a thing that feels fun to me. It feels like a thing I want to have my best brain on for early in the morning. And then this afternoon, the thing I would be optimizing for is some mix of three different categories of that thing, or I just came off of a hard meeting I wasn't expecting and so I need something that just speaks to me that was related to that meeting that I couldn't put a tag on, but when I look at the list, I pick it next. And so I would say it's pretty ad hoc. I let my brain do that part of the picking what's next, and it's very custom based on the context of that minute. But the thing that enables me to do that is not having a next actions list that's like a hundred things long. And the way I do that is by pretty aggressively using on hold for projects that I'm not actively working to bring to completion that week, the next two weeks, sort of that one to two week is my window for an active project.

Andrew J. Mason: Does on hold serve as your someday maybe or is that a separate category as well, and if it is separate, how do those distinguish for you?

Stehpen Dolan: I would say kind of a mix. I use someday, maybe for very long-term things that are pretty ill-defined, just a free space for me to dump things. Also, that's where I end up deleting most things from when I'm doing my once a month deeper review of on hold projects, those lists when they come up, I'll clear things out like, "Yeah, it sounded really great to learn the flute. I don't think I'm going to be able to do that. It'll come up again if I need it." On whole projects are more of this thing is fleshed out. It's an outcome that I'm pretty sure I want to achieve and maybe I've even talked with other people about it or other people have brought it to me, maybe I want to follow up with someone before I close it out. But realistically, I'm not pushing that forward this week. And so I'll just on hold it to get it out of my view knowing that the worst thing that's going to happen is I don't see it again until my weekly review this week. So again, all these things build on and don't work without the other one. Like the simple system only works if you have a small enough next actions list that you can reasonably go through and pick the next important thing. And you can only keep that list small if you're pretty aggressive about on holding projects that aren't actively moving forward. And you can only do that reliably if you're doing your weekly review reliably and consistently.

Andrew J. Mason: If you ever get the sense that either some sort of burnout or task fatigue is starting to creep in, how do you adjust your system or how you interact with your system to accommodate that mental load, that bandwidth that's needed there? A little bit of the same question as earlier, but maybe attacking it from a different angle.

Stehpen Dolan: The thing that I've found most effective that I would say I do a bad job of utilizing is, in a professional context, utilizing your team. So if I'm struggling and I'm feeling like I can't quite get the energy to get through a project I need or a task I'm working on, I'll post something to the team saying, "I could really use a buddy to pair through this." Tuple is a pair programming app, and so we sell it to developers and they use it to code. But I think the thing I found is that you can pair on anything. That value of looking at a complex thing and having multiple brains on a problem applies to my task system, our taxes, whatever it may be. And so I've tried to take a little bit of that framing and apply it to when I'm stuck on a hard problem in my to-do list too. It's not applicable to everything. If the project I'm working on is what do I want for my career? Maybe I'm not going to post to the team and be like, "Help me work through this thing." But if it's something more tactical, I have found that to be a really great way to unblock or just get some energy or just the injection of talking to another human about a thing. It can be therapeutic to talk through a problem and then you suddenly realize as you're explaining it, "Actually, I just don't... this isn't important to me anymore." Or "Actually the thing I'm blocked on is really that I need to talk to this other person about this thing." And so just explaining what you're going through to someone else can be helpful too.

Andrew J. Mason: That's wild. So there's a sense in which the process is the solution because of that. That's interesting. Talk to me about what would you consider thinking back through 2022, '23, '24 and today, is there anything that you would categorize as weird or unexpected OmniFocus kind of an experiment that you tried, you're like, "Oh, let's give that a go in my system and see how that takes shape." And not necessarily that it was a mistake or the wrong thing or whatever, but you're like, "Okay, now that I think back about that, that was kind of an interesting foray into that world and not necessarily for me."

Stehpen Dolan: I can't think of anything from those earlier years, but I will say I've tried a bunch of very weird stuff around that whole AI sphere that I mentioned earlier that I would say has not panned out. Nothing has felt great yet, but it feels like there's potential there. Some of the weird stuff is I wrote an Omni Automation script to export my database with the right views and perspectives and things, like customized a bit for my context out as JSON, which is a task format that's easily readable by computers and systems and things like that. And then I wrote a little AI with the right context to understand that JSON and my idea was like, "Man, if I can just start my day, tell it how I'm feeling and then give it this entire dump of my task database with enough context, I should be able to have it walk me through and ask me the right questions. How's your energy? Oh, I saw that you had a chat with Jack yesterday. Do you want to maybe ping him about this and get started?" And I think that we are not that far away from a world where that could happen. And so I'm trying to expand my mind and start experimenting with that. But everything I've tried so far has definitely felt like you described weird and not quite right. It would tell me to do things that didn't really make sense in the content of what I was working on or it would hallucinate a task that wasn't there. And when I asked it about it'd be like, "Oh yeah, sorry that wasn't in your list. This is just a thing I was suggesting you might want to try." So not quite there yet, but there's a lot of cool stuff I think that's going to be happening over the next few years. And I would encourage anyone who hasn't played with it or tried prompting one of these assistance with a problem that you're working through, especially in the getting things done context like, "I'm working on this really gnarly thing, I'm getting things done, help me make this into a great list of projects and next actions." I have found that to be really great. That's like a great pairing buddy I was alluding to earlier of just working through something that feels really gnarly, can be great for a machine like that to guide you through.

Andrew J. Mason: Talk to me about when you're coaching other people in OmniFocus, is there a common mistake that you see even really, really experienced users make? So not maybe necessarily the most common mistake anybody would make, but as you're coaching people through how to use OmniFocus you're like, "Okay, you're a veteran, but this seems to be an issue for a lot of people even if they have advanced usage cases."

Stehpen Dolan: I think the main issue I encounter with people who have been in a system for a long time like OmniFocus and feel like they know the system well is probably one of two categories. And these will probably not be surprising to folks who have listened to me talk on the show before. But one is making it too complicated, too many tags, too many folders, too much hierarchy, too many custom perspectives, too many automations. I think all of those tools are incredible. In fact, that's why I use OmniFocus and legitimately can't use another task manager, even though I've done the thing of trying every now and then. I love those tools, but I think you have to use them extremely diligently. And I've found that if you feel like you know how to use a tool and you have a lot going on, it's really tempting to spend a lot of time tweaking the system, introducing new things, and then suddenly it makes it just that much harder for you to manage it. So you skip a weekly review so you slide into having too many tasks. So it's just this snowball effect. On the other side of that, so not the system side, but just the getting things done side. I think people do a really good job of the capture part of getting things done because it feels like the accessible and understandable part of the process, maybe outside of engage because that's what people are doing as well. But the step between capture and clarify where one of the results of clarifying is just to toss something out, I think is something that experts use particularly poorly.

Andrew J. Mason: Who?

Stehpen Dolan: I remember on a podcast, the Getting Things Done podcast, there was one that they replayed from a talk David Allen gave where he said something like he throws away 70% of the stuff he captures. And I remember that just blowing my mind and it really changed my use of my systems, my tools, getting things done in general. And I think every time I've coached an expert, a thing that I didn't use to ask but that I ask now is how many things do you throw away? And almost without fail, the answer is "Not really anything, should I? Like why would I do that?" And I think that's a trap you can fall into. You're basically just pushing the decision to throw something away until it feels overwhelming and you're less likely you're able to make that decision versus in the moment thinking, "Is this just going to come back up? I did the job that getting things done does and I got it out of my head into my system, I captured it. Do I really need to keep it in the system? Do I need to clarify? Do I need to spend the time organizing it?" I think being more aggressive with yourself and biasing more towards throwing things away. You can always come back, things will always pop back up. Capture commitments, obviously. If I tell you, "I'll follow up with you after this podcast in an email by 4:00 PM." Capture that and maybe don't throw it away. That's a good thing to just keep in your system. But if it's an idea that I had for a moment and it did a great job of capturing, but I feel like we'll probably come back in a month and I'm not really stressing about it, I find tossing that kind of thing, not having it in the system just makes everything flow way better.

Andrew J. Mason: Now that's interesting to me. And this wasn't on my list of questions, but you bring up a good point. How much do you let context dictate the behavior that you need to engage in? And what I mean by that is we have three kids and when we first started, and the example I always use is something really granular, like brush their teeth does show up in my system just because if I don't, teeth might fall out. So it feels like, "Well, wouldn't that begin to remind you based on the fact that you're interacting with them and seeing them every day?" But something like that does get glossed by. Where's the line between, "You know what? What I'll see that. I'm in the grocery store, I'll know what aisle it is," That sort of a thing versus over capture show up for you.

Stehpen Dolan: So for the teeth brushing example, how that would show up for me in OmniFocus is actually how can I... It would be a project to make that habit more... how do I entrench tooth brushing as a habit for my kid? Not necessarily add a recurring task on my list, but how do I make it so that my son will remind me to brush his teeth every night? And so maybe that's like, "Oh, maybe I'll order a book about brushing teeth and cavities and things and read that to him for a week and see if that sticks." And so that specific example resonates a lot because it started out as a recurring task, but in one of my weekly reviews, I was noticing that it was just going three days, I wouldn't uncheck it or I wouldn't check it off, it would just be there. And I don't know that it was serving me personally the utility of earning a spot in the list. And so I brought it up one level of how can I not have this in my list? Well, if I delegate this task to my two-year-old, basically. So that's one very micro tactical thing from what he said. But regarding all the other lists of grocery contexts and errand contexts, I think it's pretty personal. When I coach people, I take a variety of approaches here and so I could speak to my own. For my wife and I and our family for that kind of thing we use Apple reminders. So this actually doesn't go in OmniFocus. And it might, if there was a collaboration layer to it where my wife could have her OmniFocus and I could have mine and we could share lists and things like that more easily, maybe we would move it there. But my wife and I have agreed to the commitment that, "If you need me to get something from the grocery store," and we could stop at any time when I'm picking up my son from daycare or if I'm out and about, "it just goes on the groceries reminders list." And that's just the contract we've agreed to and it works for us and I wouldn't want to duplicate that into OmniFocus or anything like that. And so I would say it's a lot of personal preference about who you're working with and how old they are and how technical they are. I think a physical list would be better if I had my mom living with us when she's older. It would be like, "Cool, if you want something from the store, write it on the list on the refrigerator and I'll make sure that I look at that at least once a day." It's just making impeccable agreements there with the people that you interact with in these other contexts I think is probably the best way to go about it.

Andrew J. Mason: This is so helpful because it's not just about tooth brushing or picking things up from the grocery store because this more implicit agreement stuff shows up at the company level, at the career level where, "Okay, what have I been doing on repeat or been settling for and repeat that. If I were just to ask a new question, it might erase it from the system entirely." I think you've uncovered a really great question for me to ask and at least systematize at some level, but I don't feel like I have it, so thank you. Stephen, thank you so much for joining us. This has been a blast. It's good, first of all to catch up with you even after three years to realize that number one, you're doing well, and then number two, Tuple I believe is in really, really good hands. How can folks catch up with you, be in your orbit, find out more about you?

Stehpen Dolan: Well, I have my website, stephendolan.com, you can read some stuff I've written about my system. There hasn't been a lot there because like I said, it hasn't changed that much since I have written a lot of this content. So if you want to catch up with me, it's good to read that. You can book coaching sessions, intro calls, that kind of thing there too. If you want to get in about Tuple, if pair programming sounds like a thing you want to get involved with, you can go to Tuple.app. And recently I found it strangely pleasant to connect with people on LinkedIn, so maybe that's the real thing that three years ago you wouldn't have caught me saying, "Maybe connect with me on LinkedIn," and we can chat about getting things done and what everyone's up to there.

Andrew J. Mason: That sounds amazing. Thank you so much, Stephen, for joining us. This is great.

Stehpen Dolan: Thanks for having me.

Andrew J. Mason: Hey, and thank all of you for listening today too. You can find us on Mastodon at the Omni Show at omnigroup.com. You can also find out everything that's happening with the Omni Group at omnigroup.com/blog.