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April 4, 2022, 6 a.m.
How Stephen Dolan Uses OmniFocus

Today, we’re hanging out with Stephen Dolan. Stephen is the chief of staff at Tuple, a company that makes remote pair screen-sharing software for programmers / developers.

Show Notes:

In this episode, Stephen shares how he uses OmniFocus to manage operations at Tuple, plan his daily tasks, and keep others accountable. You’re sure to enjoy Stephen's perspective on OmniFocus and his ability to articulate it with clarity.
Some other people, places, and things mentioned in this episode:


Andrew J. Mason: You're listening to The Omni Show where we connect with the amazing communities surrounding The Omni Group's award-winning products. My name's Andrew J. Mason. And today we talk with chief of staff at a software company named Tuple, Stephen Dolan. Hey, everybody. Welcome to another episode of The Omni Show. My name's Andrew J. Mason and today we have the honor of speaking with Stephen Dolan. He's the chief of staff at a very cool software company, Tuple. We'll learn more about that. And he's an OmniFocus user and coach. Stephen, welcome to the show.

Stephen Dolan: Thanks so much, Andrew. It's great to be here.

Andrew J. Mason: Let's jump right in. Stephen, talked to us about what Tuple is and what you do there as chief of staff.

Stephen Dolan: Yeah, so Tuple is a pair programming application for macOS and soon Linux as well. Basically, it's a better version of Zoom for when you're programming. You'll have blurry video or high latency or something that makes it just a little bit hard to work with text in these other video conferencing platforms. And Tuple's priority is really, really high quality, no UI Chrome or buttons or screens to get in your way. It just lets you do the work with really high fidelity sharing with other developers, if you want to bring in designers or other people that are working with you and collaborate. That's really all it is. And it's a huge business because of that. I mean, it's just, it's so hard. There's so many hard problems in this kind a space that it's really interesting.

Andrew J. Mason: And so the story goes, I reach out to Ben originally the CEO of Tuple who loves OmniFocus. And he says, listen, as much as I would love to do this show, there's somebody I think on staff that deserves it even more and would be a much better communicator than I am about this. So how did you end up in Tuple?

Stephen Dolan: I definitely had a sort of a winding road to get to chief of staff. I'm actually formally schooled in computer science. So development, websites, all that kind of stuff, and spent a lot of time doing some web development early in my career, moved into more of an account management or customer success kind of role. And then funnily enough, I actually saw Ben Orenstein, the CEO of Tuple on Twitter. He had paraphrased the role of chief of staff as a chief of getting things done or getting stuff done. So immediately I was like, well, I've got to reach out to this guy. Like, this is me. I want to be paid to do GTD to use OmniFocus because every company I had been at, I'm always the person people are like, oh, how does he get so much done? Or, oh my gosh, how do you remember to follow up with me on that?

Stephen Dolan: Or can you show me what your system looks like? And this just felt like a great way to get in the door somewhere where someone could really use the help. And I knew it was something I was good at. And I guess a little more than six months later now I've been chief of staff at Tuple for a while and just kind of jump around to different areas of the business, whatever needs help.

Stephen Dolan: There's like a commando mode where Ben just throws me into unknown waters and you assess, and I build up a ton of OmniFocus projects and then start knocking them down to that advisor force multiplier role, making sure that when Ben makes a commitment on behalf of himself or Tuple that I track it in my OmniFocus. And in our touch bases, I'm reminding him, Hey, remember you committed to doing this. Or, Hey, are we making progress on this initiative you said the company wanted to tackle this quarter. So it's a lot of varied tasks, but I think that's the cool part about being so into getting things done and having a great tool like OmniFocus to back it up is it feels pretty effortless. Like my job feels pretty easy, but it's impressive from the outside looking in, how many things can be juggled at one time.

Andrew J. Mason: That's really interesting. So I'd be curious. What portions of your life do you find yourself managing with OmniFocus and do you and Ben use Tuple to manage OmniFocus together?

Stephen Dolan: Yeah, absolutely. I mean, everything is in OmniFocus for me. So there's work projects, there's projects for anything we want to pick up in other areas of the business that maybe don't have a dedicated role, but that kind of falls to the office of the CEO. So marketing up until we have our new marketing person starting in a couple weeks and sales is my domain, is handled pretty much entirely in OmniFocus. So there's a lot that goes into there, but if it's not in OmniFocus, it's generally not be being made progress on as quickly as I'd like.

Andrew J. Mason: That's so cool. And when did you come across The Omni Group originally?

Stephen Dolan: Yeah, I don't remember specifically when it was. I remember it was OmniFocus two. That was the version when I first came across it and I had already been doing, getting things done on whiteboards in my room at home. I remember my parents' house I had whiteboards all over the room, one from my project list, one for my next actions, one for my tags. I did the strict David Allen implementation. And in college I got a Mac and of course Omni Group is just prolific when you Google for any kind of Mac software. So I came across OmniGraffle and then OmniFocus when I was looking for a GTD app for macOS. And I mean, since then I love this kind of stuff. So I've tried all kinds of different tools, but I always end up coming right back to where I started. The very first thing I found was OmniFocus and that's where I'm still at today.

Andrew J. Mason: This is great. This is good stuff. And what words of wisdom do you have for someone who's first starting out? They maybe have just cracked open OmniFocus or even are in that space where they're like, you know what I've taken on more to do, then I know how to do and can manage in my head myself. What do you tell that person as a first step?

Stephen Dolan: Yeah, I guess the easy maybe cop out answer is definitely read, Getting Things Done by David Allen. I mean, that's what got me started. That's what gives you that framework, the methodology that you can structure your entire OmniFocus in with the folders, and the projects, and tasks, and repetition, and deferrals, and due dates. There's just so many things when you open up the tool for the first time and different perspectives. I think that reading and understanding Getting Things Done is the first component.

Stephen Dolan: And then keep your system really simple. You always want to dive in and dig into every feature, at least I do. I'm going through all the settings menus and I'm trying to play with every single feature, but where I've ended up after all these years using the tool has kind of always sling shotted me back to a very simple implementation. I have two main perspectives that I'm working out of on a day to day basis. I have very few tags. It's just, if you do the basics and you do them really, really well, that's 99% of what you need to feel really effective, to feel really stress free and actually implement getting things done.

Andrew J. Mason: You made a really good point. I don't want to gloss over it. I just kind of want to repeat it and bring some more attention to it. This idea that sometimes we just make things more complex than they are. Do you think maybe it's just to make ourselves feel more important or why do we do that?

Stephen Dolan: Absolutely. I think a lot of people fall into the trap of thinking their world is more complex than it is because it makes you feel better. Like, oh, I'm doing so many things. My projects are so hard to get done. I have to plan out so many steps at once. And I've done that and I've tried to live in my OmniFocus in that way and it can support it, which is maybe one of the trickiest pieces is it's actually pretty easy to do that. But I've always found that if you can just simplify the work that you're doing and maybe pull it up one level or push it down one level in the folder, project task kind of stack, there's generally a way to do it with less and actually do the work, but still keep track of everything. Still keep it out of your head, but not over complex your system with too much functionality or using the features too heavily, and any given feature too heavily.

Andrew J. Mason: That's such a hard balance to strike too though, because it's like, those that are moving the fastest notice drag the most. And so any little thing that I can do this hack, this tip, this trick that can give me that much more productivity, of course I'm interested in it.

Stephen Dolan: Yeah. And don't get me wrong. I love reading the blog posts where someone is talking about, oh, I can enter in 30 seconds on my microwave and an OmniFocus task appears within 15 seconds reminding me to go and turn it off. I think those things are so cool. And I've done a lot of that too. With the new Omni automation stuff is so super difficult for me to stay away from and kind of stay responsible and actually do the work I need to get done rather than just spending all day on that website, going through the samples and trying to code some stuff up myself.

Stephen Dolan: I love that, but I do think there's a balance you have to strike between like, for me, it's a hobby. I enjoy doing that kind of stuff. So I don't chalk it up as I'm doing this and it's going to end up saving me time. So it'll be a profitable venture. For me, it's like, this is going to be a waste of time. I'm going to try and automate this silly thing, and I'm never going to get the time back, but I'm going to enjoy it while I'm doing it. And I'll end up with something cool that maybe I can write a blog post about. And that's totally fine.

Andrew J. Mason: That's a great way to frame it. Do you have anything that you would say is instructional for other people on their journey of productivity? I don't know if you'd view it as a failure or an obstacle, but just something that, Hey, I tried it this way. It didn't quite work out for me the way that I found it would. And if you tried to, I would just suggest just skipping it.

Stephen Dolan: I really think that just going too big, utilizing too many tags, too many perspectives, too much automation, specifically like integrating with other tools. Something that I've come to in the last year or two, as you start working with all these other systems, because as time goes on, there's just more and more products that are, oh, you can keep all of your development tickets here and all of your support tickets here and all your meetings here. And everything is trying to pull your external brain, which is OmniFocus for me into a million different places. So there's this poll that I think is a mistake you can make of, well, if a ticket gets created in Jira or Linear, whatever people are using these days, let me type it into my OmniFocus and I'm going to duplicate it all there because that's my external brain.

Stephen Dolan: I think the place where I've come to now is I have a daily repeating task, check my Jira tickets, check my Linear tickets, check my Pipedrive tickets, whatever external systems you, or your company, or your spouse uses, you can still have it in OmniFocus. And that can be your external brain where you know I'm not going to miss this. I live in OmniFocus. And as long as I tick the box every day, I know that I've done it. And I know I'm not missing anything without having to build this kind of house of cards of integrations and things that no matter how good you are at developing them, no matter how much help you get in the Omni Slack from really smart people who do this all day, at some point, it's going to fall down. It's going to break. You're going to have to maintain it. You're going to go on vacation. It's not going to work. And I think keeping it simple is, that's probably the main thing I would advise. And it's the mistake I've made many times, is making it a little bit too complex.

Andrew J. Mason: Now the other side of this coin, the dangers of kind of overdoing the complexity or making things more complex than they need to be. Is there anything that you feel like is really unique to you and your system? So I've looked all over the internet. I've seen blog posts and how people do things. This one, I haven't really come across. This is just the way that I do it in my system, but I don't see anybody else doing it this way.

Stephen Dolan: I do keep my system pretty minimal. So there's not a lot that I think people wouldn't do. I would say the main thing that differentiates... Ever since I was working with Ben, the CEO of Tuple and my boss now I've been coaching a few people, his friends or other people who are struggling with that. And the thing I see over and over again, there are a few common anti patterns that people will use in whatever system they're using, OmniFocus or other apps. I think one thing is not using positive enough language in your projects and tasks, things that really excite you when you see them. So I use tons of emoji and I'm sure some people are very polarized by that. Like, I don't want to see emojis. I see them all over. I hate when people use them in email, I get that.

Stephen Dolan: I get that take. But for me, when I open up my list of tasks and my tags all have little pictograms on them, and my projects are really positively oriented. It's not marketing site. It is launch a beautiful marketing site that people love, something that at the end, I want to be able to say that to myself. And I want to affirm that every time I'm working on a task, this is the goal you're heading towards. And I think that's something that not enough people pay attention to. You can have a really well organized system and everything can be there. But when you get to the last step of GTD execute, you have to, in some sense, trick your brain into actually using the systems you've spent all this time putting together. And I think emoji, fun language, using actual outcome statements for projects, those are all things that I do really liberally and try and make myself stick to consistently. And I think they help quite a lot.

Andrew J. Mason: Agreed. There's just something different between writing down a project that says publish multiple blog posts versus open Google Docs and write a really horrible first draft. There's something in your brain that just activates and says, no, I could do that. That's great.

Stephen Dolan: Exactly. I think there's this cycle where motivation breeds action and action breeds motivation. A lot of people think I have to get motivated before I can do anything. So they'll do all kinds of tricks and things to get themselves motivated. But for me, it's the reverse. If I do some small action on any project, generally, you'll find yourself doing more. So in that kind of scenario because I have seen that again, that's another thing very commonly when I'd be coaching people is their tasks are way too big. It is write a blog post. That's so much. Your brain is never going to want to do that. That does not sound fun. You know you need to do it, but it's never going to be fun, but create a Google Doc. That's fine. That's easy. I can open up a URL and create a Google Doc to throw a draft in or write a really bad first draft.

Stephen Dolan: That's a good one too, because you give yourself permission to not write the final draft, just to put some words on paper. And no matter how small it is because people have the concern well, write a Google Doc. That's too granular. I don't want to plan out 100 project steps for a blog post and you don't have to.

Stephen Dolan: I think what you'll find is just put the next action there, open a Google Doc. Once you open it, you're going to want to put some words down. You're going to want to write an outline. You're going to naturally find yourself in that cycle of motivation and action. And I think it's all about engaging that initial pursuit, making a really positively worded project statement that you want to complete, making a really simple next action that you could give the instruction to a robotic version of yourself, a very low budget robot version of yourself, and they could complete it. I think that's absolutely key to once you have these beautiful systems in place and these nice project structures that OmniFocus lets you have, how do you use it? How are you effective with it? Whether your system's simple or complex, I don't think it matters. I think getting that engagement going at the very end of the process is critical.

Andrew J. Mason: Well, it's obvious that you're passionate about productivity in general. What do you think that passion comes from? How does that happen over time that you just begin to define yourself and say like, oh yeah, Stephen, he's the guy that is good at productivity.

Stephen Dolan: Yeah. I don't know. Maybe the sad answer is its kind of an ego thing. Once you become known as the person who can just get anything done and doesn't get overwhelmed and never forget something, that's kind of a cool, I love when people compliment the way that I can get things done and follow up with them. That just makes me feel really good. So maybe it's kind of chasing the dragon to some extent, like let me just always stay on top of it. Because if I'm off the wagon, I'm not going to get that praise anymore. But I think living in this stress free way that GTD promises when you're on the wagon and you're doing a really good job, I think is just so addictive. I describe it and use this analogy to people of dental hygiene, right? We're not born knowing we need to brush our teeth.

Stephen Dolan: Why do we keep doing it? Well, some people will say just marketing and sure. But part of it is once you start and form that habit, you like the way it feels to have clean teeth. And it's a nice feeling. And I think that in a similar way, no one's born putting projects and next actions onto a list. You don't pop out of the womb and immediately open up your OmniFocus. Who knows maybe my son will, maybe I'll already have his license purchased before he is born. But I think that there's a component of this where once you're making impeccable agreements with yourself and with other people, there's this stress free way of living that when you're not in that state, you really feel it. You don't feel it so much beforehand, but once you've lived in that way, it's really addictive.

Stephen Dolan: It's I can feel when I haven't done a weekly review. It's like, it's painful. It's uncomfortable. Doesn't mean I always do it. I still can live in that discomfort. We were moving to a new home over the last couple weeks and I skipped my weekly review for two weeks. It felt really bad. I knew I was doing a bad thing for myself mentally, but I still did it. But I think that's part of it is just, you get kind of addicted to how great it feels when you're really on point, when everything is impeccable, when you know what you have committed to and what you need to follow up on.

Andrew J. Mason: We talked a little bit about a good first tip for somebody that's getting started. Do you have any tips for somebody let's say you're coaching them in OmniFocus and they say, I know I have a project that needs to be done, but how or where I begin, that's a mystery to me. What advice might you have for somebody who's in that situation?

Stephen Dolan: Yeah, I think the common and easiest thing to do is something we already talked a little bit about with that granularity of tasks and tricking yourself into engage. But when in doubt, you're probably safe to say you should hoist everything up one level in OmniFocus. So we have this folder, project task hierarchy in OmniFocus. And I find that when someone will open up a to-do list when I'm coaching them or when I'm just working with someone other at Tuple that I'm just helping out work through a project, I think that there's a tendency to make things that should be a project tasks with no real next action. So you're spinning in your head every time you're opening that up, thinking what is the next step or to make folders that aren't necessarily correlated to your areas of focus. And that's a GTD term. For me, my areas of focus at work are really varied and they change in my week through reviews.

Stephen Dolan: If I'm focusing on sales, and marketing, and hiring, those might be my three areas of focus at work. Those would each have a folder and then I'd have individual projects which are outcome oriented in each of those folders. And it helps me keep track of it mentally, gauge how much time I'm spending in each area. But I think that's a huge pitfall that a lot of people fall into. As you get more and more projects, you'll be tempted to do a worse and worse job of defining them and taking the time to really curate your system. Because it does take time. I think I heard Kelly Forrester on one of the GTD podcasts or the interviews that they release saying that realistically, it's not unreasonable for someone in an executive position or a management position to spend two to four hours just curating their system throughout the week.

Stephen Dolan: And that hurts, especially for people like Ben, who's a developer historically and wants to be doing things all the time. The acknowledgement that you just have so many things coming into your life from external sources, so many polls on your attention that you have to take time to curate those and pull them up to the right level of abstraction, really think through where you're putting these things in your OmniFocus system. I think that's a pitfall that a lot of people fall into because it takes time and no one wants to spend time on this stuff at the end of the day. If you're really motivated to get something done, there's a part of you that just says, well, why am I spending time on a minute to-do list when I could just be doing the thing? And it's the effectiveness you get on the backend, but you have to spend the appropriate amount of time upfront so that that effectiveness on the backend is really maximized.

Andrew J. Mason: I know you mentioned that your system is relatively simple, but I did fail to ask, are there any custom perspectives or views that you engage with regularly? Do you have something that is like your go-to rhythm when you're using OmniFocus?

Stephen Dolan: I use the forecast perspective pretty heavily. That's like my first stop, because the only things in my system that have due dates are items where something bad's going to happen if I don't get it done on that date. It's not a, I want to do it on this day or I want to be reminded about it. That's another trap that I would say people fall into. So forecast is my first stop for the day. It's what things have I committed to people that I'm going to do, even if it's a loose commitment, like I'll follow up with you no later than end of week next week. I would see that the next week in my forecast view, as well as some things, I use the today tag in the forecast view. So I have like a today tag with a little fire emoji and I have things on that, like exercise or check those queues, right?

Stephen Dolan: Check Help Scout, check Pipedrive, whatever systems you're using. I have those in a today tag, so that's kind of my tickler there. And then when I'm just sitting down for a working session to get things done, it's a next perspective. And that's just the next action in a project that's active that's not on hold and doesn't have an agendas tag. So I definitely leverage the custom perspectives, but it's so that I can structure my projects in a way that makes sense to me. So the next is supposed to be things I can do on my own. I don't need someone else's involvement. These are things I can actually work on. I should be able to just look at that list, pick the most important thing and do it. And it should be very simple.

Stephen Dolan: If I'm in a meeting with a person or on a call with a person, then I have a people perspective. And that's just things in an agenda's list for those people or with a tag that I'm waiting on that person for something. So I generally have tags for the people I communicate most with in my personal life. Our dogs vet has a tag. My doctor has a tag. Ben has a tag. Avery has a tag. I am pretty liberal with people tags, but it just lets me curate that perspective so that when I'm talking with my wife, I can pull up her tag. And I know exactly all the things I need to go over with her if there are anything, same thing with Ben.

Stephen Dolan: That classic moment on a call where the person you're with says anything else you need from me? And you just kind of sit there like, no, I don't think so. But I can open up the perspective and I know exactly the five things I'm waiting on them for, the two things I want to talk about them with. So that's really it. It's those three, the forecast view, and then next, and people. That's my daily driver set of perspectives.

Andrew J. Mason: Stephen, thank you so much for your time with us today. I know it's been super valuable. I hope people have gotten some really good tips and tricks to listen to as they're thinking about their systems as well. And how can somebody connect with you if they're interested in finding out more about what you're up to?

Stephen Dolan: Yeah. Well, if you're a manager of engineers, or a developer, or the owner of a company that has developers, you should be using Tuple because pair programming is far above and away, better than Zoom for the people doing that kind out of work. If you're interested in that, you can go to It's If you want to chat with me, I've got some blog posts, I've got some coaching I've started doing with people for OmniFocus specifically and helping set that up. And my email and Twitter and all that kind of stuff is just And it's Stephen spelled S-T-E-P-H-E-N and Dolan,

Andrew J. Mason: That's perfect. Thanks so much, Stephen.

Stephen Dolan: Thanks so much, Andrew. It was great.

Andrew J. Mason: Hey, and thank all of you for listening today too. As always, you can drop us a line @theomnishow on Twitter. We'd love to hear from you there. You can also find out everything that's happening with The Omni Group at