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Aug. 11, 2020, 10 a.m.
Omni Roadmap, July 2020

Our world is constantly changing, and each year we have to be prepared to adjust our plans based on what we encounter along the way. On July 8 we published an update to our 2020 Omni Roadmap, and in this episode of the Omni Show we talk with Ken Case about some of this year's twists and turns and how we've adapted.

Show Notes:

We've shipped Omni Automation in all our apps. A great resource for learning more about Omni Automation is

Here are links to some of the referenced news from Apple, announced during WWDC:

You can find Ken on Twitter @kcase and on our Slack group. You can also find @omnigroup on Twitter.


Andrew J. Mason: Okay, let's see. I can never find the restart button. Ah, there it is. All right. Here goes. Hey, computer, play the Omni Show. Episode 60.

Andrew J. Mason: You're listening to the Omni Show. Get to know the people and stories behind the Omni Group's award-winning productivity apps for Mac and iOS. My name is Andrew J. Mason. And today we're talking with Ken Case, CEO of the Omni Group. Well, welcome everybody, back to the Omni Show. Like I said, my name is Andrew J. Mason, and you may recognize my voice from the Getting Things Done Podcast.

Andrew J. Mason: I am so honored and excited to have Ken Case with us here today to really take some time and break down 2020 so far, as well as cover some of the future roadmap for the rest of the year. Ken, thank you so much for being here today.

Ken Case: Thank you, Andrew. And welcome to the Omni show.

Andrew J. Mason: Yeah, thank you. I wanted to start off with a fun question. At least for this episode, I thought wouldn't it be fun if we had guests come up with their own code name for a brand new operating system. We know macOS 11, Big Sur just came out and they codenamed it Big Sur. What would your code name for a brand new Mac OS operating system be?

Ken Case: Oh, man, I don't know about that. I can tell you what I named the Mac mini that I installed macOS 11 on. It's kind of an obvious reference, but I had to call it Spinal Tap. But I don't think that would be a very good name for the operating system.

Andrew J. Mason: And you're 2020, outside of what you've accomplished as a team so far, you've got to be so proud of that. I mean, all of the amazing software releases and all of the different features and everything that's been added, so proud of that. But let's step aside for a second and talk a bit about the work culture at Omni. How have things changed and shifted? What's current reality for you guys?

Ken Case: Oh, absolutely so much change. We're based out of Seattle, which was for a time in the early part of this year in March---or February, I guess, really---the sort-of identified epicenter of this pandemic spreading through the US. Which, I say "identified" because we've learned since then, of course, that it was not the only place where the pandemic was spreading. At that time, it was spreading in New York and it was spreading in California. But we had an identified case here in February and we were starting to wonder, is this something we should be worried about as we go to gatherings and so on?

Ken Case: And I remember the last Friday in February, I'm telling people, "Well, I just looked at the Department of Health's website. They say there's one person. There were eight people originally that they were kind of monitoring. The others turned out to be okay, so it doesn't look too bad." And then, coming back, looking at the Department of Health's website again on Sunday, before we came back to work on Monday and seeing that it had already gone from one known case to eight known cases, and I went, "Oh, all right, well, this is, it's a virus, this is exponential growth. This is going to get out of control quickly if we're not really careful about trying to stamp it out."

Ken Case: I announced that day on Sunday, the first Sunday in March now that we would not be returning, working for at least the next few weeks. We would stay home and work from home. And so, that's what we've all been doing since the beginning of March.

Andrew J. Mason: And how has the team fared with that change?

Ken Case: Well, of course we had to get used to doing all of our work remotely using teleconferencing for everything. There were some kinds of work that just didn't make sense anymore. We had previously had a kitchen staff when we were serving lunches and dinners, too, and breakfast to people. And unfortunately, we had to close all of that down. And so, at this point we have shut down our offices and we're just working from home.

Ken Case: And that was, that was a hard transition. For me personally, just to realize we had to make that choice. But I'm thankful that we have been able to make it through that transition, that we do have a solid team and all of our core engineering team, almost all of our testers, almost all of our support people, and so on, were able to stay on. The places that were hardest hit actually, were our marketing team---and of course the kitchen. And the marketing team is the team that was working on this podcast before, so that explains part of the delay between then and now.

Andrew J. Mason: Well, Ken, I so appreciate the fact that you take the time to break down not only the overall general roadmap each half-year, but also your logic and intention behind those changes. Why is this sort of a state of the company address so important to do in this particular long form way that you do it?

Ken Case: Well, I just think it's important to communicate to everyone. Both internally and externally. This is something that we use inside the company, as well as we think about what are we working on? And are we aligned with what we set our priorities be?

Ken Case: I think it's important to write down where we think we're going and what are the steps along the way that are important? So that we know what steps we should be taking and how to prioritize things. And then, to share that with, of course, all of our customers I think is important so that customers can decide, yeah, are we, do we think that is a good idea or a bad idea? Are we on board with this vision or do we think Omni is making a mistake and we want to give some feedback about it.

Ken Case: And so, I really appreciate sharing with people. I love hearing from people what they think about it. That's why I, at the end of every roadmap blog post, I include my contact information so that you can reach out to me directly and share that feedback, so I can hear how our customers are responding.

Andrew J. Mason: Well, speaking as a customer, I honestly so appreciate being able to look into the lens of where we feel like things are headed. Specifically, let's talk about that first half of 2020. A pandemic aside, still an unheard of level of features released and productivity. Something to be so proud of. What have we accomplished this year so far in our apps?

Ken Case: Sure. We, of course, started the year hard at work on a number of features. Of course, we were working on all of the apps. But one of the big, big pushes that we've been working on for years now has been Omni Automation. And that's the ability to add plugins and scripts to our apps that let people enhance their own workflows and make their own lives a little bit easier. You can add, oh, for example, I saw somebody post, share a plugin just the other day that was for adding a reading list to OmniFocus.

Ken Case: Say you need to read a book by a particular date, maybe for a class or something. And so, you plug in, here's the book title, here are the number of pages I need to read, here's the start date, the end date, maybe what page I'm already on.

Ken Case: And then, it would break that down into tasks for each day saying, okay, well, here's what pages I have to read for this day. And that day. It would put due dates on each one and different dates on each one. And so, with just a little bit of clear input guidance, now you get this fully formed project that helps guide you again, back through the rest of your time, working on this project. That sort of automation I think is just a great way to make lives easier.

Ken Case: We've been working on automation now across all of our product lines. What has it been about four years? And OmniFocus was the last one to complete this integration and very, very pleased to finally have it across all of the apps. Lets all of the apps work together because you can go with the script that calls the script in one of the other apps or plugin that calls into, for example, you can collect some information from OmniPlan and send it over to OmniFocus or from OmniOutliner to OmniPlan to OmniFocus. All of those sorts of things are now possible with this.

Ken Case: And of course, it's not just between our apps, but because it's JavaScript and because it can load arbitrary URLs, it can talk to web services and collect data, present data and so on. That was a big, fun project. And maybe I'll just start with that and see, is this something that you've looked at at all and played with, or...?

Andrew J. Mason: I have, and it intrigues me because I know enough scripting to be dangerous and break down the entire operating system, but I really am thankful for the community that's surrounding it. There is a website people can go to, right? It's Omni Automation?

Ken Case: Yes, It's the site where Sal Soghoian---who is well known among the people who've done scripting on the Apple platforms for years because he used to shepherd automation on macOS 10 and macOS 9 before that. I don't remember how many years before that… For those who don't know, Omni came to the Mac platform really with macOS 10. We had come from the NeXT side of the merge between NeXT and Apple. And so, when Apple acquired NeXT and Steve Jobs returned to Apple, that was when we came, too. So he [Sal] was there before that.

Andrew J. Mason: Oh, I see. I didn't know that. Is that causation or correlation, do you think?

Ken Case: All just correlation.

Andrew J. Mason: Okay. Okay. Oh, even then it seemed to have worked out pretty well, so that's good.

Ken Case: We certainly came to the platform because NeXT was coming. I think it was kind of accidental that Steve ended up in charge of Apple in the sense that I don't think it was anticipated when Apple bought NeXT. Not to make this conversation all about Steve.

Andrew J. Mason: Of course, but I mean, we talk about correlation and the cool thing about these scripts are that correlating. I mean, there are a lot of people surrounding this, right? I mean, there's a community growing.

Ken Case: Yeah. Well, that's one of the great things about this, really, is people can build these things that are things that people share with each other then, and you don't have to be a scripter yourself in order to benefit from it. You can use a script that somebody else has written or a plugin that somebody else has written. Like "Complete and Await Reply," for example, which will complete a task and then create a followup task and tag it so that you can easily find it again later.

Ken Case: That kind of thing is stuff that everybody gets to benefit from. I don't know whether, in some of these cases---like the reading list example that I gave earlier. I don't know how often that one person was creating a reading list like that, whether it was something that they're doing all the time, so it really does save them time or if it was just a fun project to work on.

Ken Case: But now that they've written it, anybody can use it. And so, it certainly is going to save time for the community at large, in the long run, right? And saving time is yeah, really what all this is about.

Andrew J. Mason: WWDC happens. Did you already have a process for assimilating all of this new information into what the roadmap currently looks like? And then, just deciding in that direction? I mean, pre-pandemic, I would have asked if there were like offsite retreats and trust falls and fire walks or anything like that, but what's your process look like?

Ken Case: I would have to say more of the latter than the former. It's not so much a process as a space that we try to leave ourselves. Of course, this reminds me of a lot of, of GTD and the whole notion of "mind like water," right? That if you can sort of leave a space in your life, if you have things organized enough, when the rock hits the pond and the ripples start going, you can react appropriately to those ripples. Here we are, WWDC. Sometimes is just a small rock hitting the pond and we see some small ripples. And sometimes it's an avalanche pouring in.

Andrew J. Mason: And then we see, okay, wow, they're really visually updating so much in macOS. And you see not only this challenge of, well, we were going to update things anyway, but there's a pretty decent opportunity here. Let's talk about that.

Ken Case: Sure. Yeah. We've been thinking for a while now about how can we make our apps easier for customers to use, make them more consistent across platforms, really leverage the current strengths of the platforms. Like when we originally designed for the iPad, we were not trying to design for a keyboard because the iPad wasn't designed around having a keyboard, it was designed around touching the screen to do all your typing.

Ken Case: But I know certainly in my iPad use now, I always have this new Magic Keyboard attached to it. And sure I fold it up sometimes and don't use it, but it's always available now. And there's a trackpad associated with it. We used to not even have pointers. So. User interface changes and leveraging the strengths of each platform. We had been thinking about that already before WWDC, because those things have changed a lot over the course of the last decade that we've been working on all of our apps, really.

Ken Case: All of our apps are now over a decade old. Our youngest app is OmniFocus, which was introduced in 2007. As we were thinking about that, and we'd started making some mock ups of new designs and so on, but it was hard to get too committed to any particular design, knowing that WDDC was right around the corner and, oh, well, what if they change something again? What's going to happen there?

Ken Case: We had some drafts and mock ups and we were sharing them around and redoing them and thinking about, okay, what works well with this and what doesn't work so well? And then, WWDC did hit, and we got to watch the sessions. We got to see the introduction of macOS 11, which after 20 years of macOS 10, I am really happy to be ready to move on to version 11.

Ken Case: And of course, 11 brings a new look and feel to a lot of the things that we've become accustomed to on the platform, whether it's the way alert panels work or the toolbars, or even the title bars that you drag windows around, all of that has changed at least somewhat. While, at the same time, not being so dramatically different that it's completely unfamiliar.

Ken Case: I think anybody sitting down at macOS 11---I've been using it now for a couple of weeks (since the first day of WWDC) and I love it. I'm enjoying using it every day. And I think it did not take me very long at all to adapt to it. There's still some work we have to do to adapt all of our apps to it, but the design system as a whole, it's cohesive and works well.

Andrew J. Mason: All right. And this is cool, so then not only that, but they're also redoing a bunch of code base for these upcoming Apple processors. Can you break down what that means for the job that your team has ahead of themselves, but also the outcome of what that job will mean for us end users once we're there?

Ken Case: Yeah. For those who, I'll try to give a little bit of background, at least, I don't want to make this podcast all about macOS 11, but for those who aren't aware, macOS 11 has all of the same frameworks available---as far as I know---that macOS 10 had, right? It has the same active frameworks. It has the same catalyst framework that lets it run UI kit code that was supported from iPad. It has a lot of the same driver kits and so on.

Ken Case: But it also has something that was introduced last year was this new SwiftUI framework, which goes along with the new Swift language that Apple introduced about six years ago now. And SwiftUI is a radical rethink of how to build apps for Apple platforms in a cross platform native way. You're still using native widgets and everything else, but instead of building the app by laying out exactly, "I want this button to be this many pixels wide and I want it to be aligned with this other button," and so on (the way we were building software with AppKit or UIKit), you simply say, "I want two aligned buttons and here are their labels." And then, you let the operating system itself kind of figure out where should those things go? Or two grouped buttons.

Ken Case: And because you're describing your goals rather than the process, that leaves the process up to Apple's frameworks to kind of figure out well, where would we like this to go on this platform? And they can make platform changes based on whether you're using it on an Apple TV, the hugest screen, or a Mac or an iPad or an iPhone, or even all the way down to the Apple Watch. It can be the same SwiftUI code. Now, obviously it's going to work very differently on each of those because the interfaces are different. You don't have a keyboard on your Apple Watch. And you can identify things that are platform specific. Like you can say, "Here's the keyboard shortcut that I want it to be associated with that button or that action." And it will take effect on things that have keyboards and not on things that don't.

Ken Case: But it's obviously a very different way to build software, but it's a way that I think in the end, it will save everybody a lot of time. The challenge of course, is, the devil is in the details. We still have very high standards when it comes to wanting to say, "I want this button to be, to look exactly like this or to be polished exactly like that."

Ken Case: Either we have to let go of some of that and just give Apple the control and say, "All right, it's up to you, Apple, to decide how this should look." And accept that maybe it's not as polished as we would have made it, had we been able to do that on our own. Or we have to spend a lot of time tweaking it and trying to convince SwiftUI that all right, "Here's what we mean when we, and here are some extra constraints that give you the hints you need to make this look the way we want it to look on each platform."

Andrew J. Mason: I'm not entirely sure how deep the audience really likes to go. But just out of personal curiosity, is there a sense in which the operating system or the code likes to let you just kind of give it some ideas and then it'll do what it wants to do? After you get past a certain point, does it feel like you're almost fighting the operating system?

Ken Case: You do get to have at least some of that level of control, it intentionally has things like "I want to set the font size bigger" or to this exact value, or "I want to set the color." There are these modifiers that you can use to adjust the base controls that you're placing. But if you go beyond what it knows how to do, it could feel like you're fighting the system. It does feel a bit like you're the fighting system.

Ken Case: And of course, we're not experts on this yet. It's too new. Or we're too new to it. Apple introduced this last year, but it was completely new. We did use it in our iPad apps and iPhone apps last year for a couple of our screens and some of the new stuff that we were doing around OmniPresence integration with the new Files app, for example, we did using SwiftUI. It's not as though we're completely new to it, but we haven't spent the last year programming it and becoming experts in it. Let's put it that way.

Andrew J. Mason: And so, I guess there's never a great time to learn that.

Ken Case: It's time to make that leap. Exactly. Because I think in the long run, it will save us a lot of time and let us build a much higher quality product and focus on what makes our apps unique rather than what makes our apps work on the platform.

Andrew J. Mason: Do you ever get a sense in which it's like, "Oh man, we just got used to this environment and now it's, it's changing. It's switching up on us?"

Ken Case: Yeah, well it has been 20 years since macOS 10 was introduced and we started using AppKit for everything. Really, we were using AppKit back in '89. This is a big shift for us in some ways, but it's a lot of fun.

Andrew J. Mason: I want to dive specifically into what was one of my favorite upcoming features. And I say was just because it's shifted slightly, but in a great direction. In OmniFocus, you were hoping to have tasks become shareable. This is still on the roadmap, but with one pretty big change.

Ken Case: Yeah. One of the other big projects that we were working on in the first half of this year was OmniFocus collaboration. Now, I shouldn't say just the first half of this year, we've been working on that off and on---alongside other things that we've been working on, of course---for the last several years.

Ken Case: Our goal in the past had been, we want to be able to share a single task with another single person. Maybe I want to delegate this task to somebody. And I want to be able to see status updates. I want to know when it's checked off, that kind of thing. That was how we had originally designed that feature.

Ken Case: As we got to the point of, "OK, now let's actually get this into the app," we had laid some of the groundwork for how we would sync that information. We had done a lot of work on how would this look in the app and that experience work. But as we really started adding it to the app, we realized that isn't really, that isn't the feature that we want. What I want is to be able to share an entire project of tasks so I can add new tasks to it and other people can see what that is. And I want to be able to share the project with an entire team, not just with one other person. It's a really, we're looking at building team support at OmniFocus with shared projects.

Andrew J. Mason: I've been looking at this particular feature and there is a lot of buzz and a lot of people talking online about this. I'm excited about it, as well. Just to add my voice, thank you for that.

Ken Case: Oh, you bet. Yeah. It's important. As we were thinking through this, the most obvious way to do this, like if I just sync my OmniFocus database with somebody else, we can all see the same task. But the problem with that is I can't tell when somebody else is making a change to the task. I mean, I guess I could watch my change perspective, modified perspective and just kind of see everything that has changed recently. But ideally, I would like to be able to tell, well, what's changed since the last time I looked at it? How can I review somebody else's changes? That kind of thing. And so, it's not just a matter of designing and sharing of these projects, but of designing a workflow where you can watch, understand what has changed and be able to react to it.

Andrew J. Mason: I appreciate you going that deep with that answer because sometimes we don't appreciate everything that goes into something like that. It's not just a sharing feature. There's also, the tracking the status updates and the communication that goes both ways or multiple ways. Talk to me about OmniPlan. I know that there's some changes happening there, too.

Ken Case: OmniPlan is, we're coming up on version four now. It's the app that we released just before we released OmniFocus. It's been 14 years or so that we've been working on OmniPlan. We've received a lot of feedback over the years. But one of the big pieces of feedback was, if I'm planning a project and I've laid out my timeline of the work that needs to get done, it helps me figure out the dependencies and what resources I need when, and I can see all of that on this timeline, Gantt chart, but what I would like to know as project manager, is how much is this going to cost me each month? And how much will I be spending in July? How much in August? How much in September? And so on.

Ken Case: And I could look at that chart and sort of work out the numbers myself by hand. We did have support for tracking how much things cost on a task by task basis and project, entire project basis and so on.

Ken Case: But it was across the entire length of each of those things that you had to kind of work out those numbers yourselves. We decided, well, this is an obvious feature to automate and bring into OmniPlan itself. And I'm very pleased to share that in OmniPlan 4, you can see these intervals marked right on the Gantt chart that say, "Okay, well this month, this task, or this group of tasks will cost this amount of money. Or "this many hours," if you're just working on an hourly basis, maybe it's an internal project. You've already got all of the resources, but you need to know how much will be spent on one thing versus another thing? That is the big thing in OmniPlan 4.

Ken Case: There are of course lots of other things, things like repeating tasks, fold up tasks, so when you have something that's repeating, it doesn't sit there, cluttering up your entire Gantt chart. But you can still kind of see that this repeating thing is happening. Lots of stuff, I invite people to check it out. It's already in public tests and has been for a while. Anybody can download it from our website. But it will be shipping very soon, possibly by the time this podcast goes live. We shall see.

Andrew J. Mason: You heard it here first. Or maybe second, we're not sure when this release date is going to be. I've got a friend who swears by OmniGraffle loves to use it. I'm interested in trying it, too. But I'm a little bit gun shy about the investment because of like release dates. I don't know when new things are coming out. You have some changes coming up there. Talk to me about this.

Ken Case: Yeah, well, that's a concern that everybody has because our apps are an investment. One of the things that we do to try to protect the investment people are making is if somebody buys one of our apps and we come out with a major upgrade within the next six months, we give everybody that upgrade for free, who has purchased the app recently.

Ken Case: That's one kind of protection that we have to make sure that you're not losing your investment. But even if you're out of that particular upgrade period, like if you bought OmniGraffle last year and we shipped some new version of it later this year, every customer that has ever purchased one of our apps get a 50% discount on any newer version. That's another way to protect that sort of traditional license investment.

Ken Case: Over this year, one of the other big changes that we have been working on has been to add subscriptions to our online store. We now support team subscriptions. And as we launch OmniPlan 4, we will be adding support for personal subscriptions, as well, on our website.

Ken Case: If you would rather not have to make a big investment now, and then worry that that investment's going to go out of date, or you just feel some uncertainty about it, you can do this on a month by month basis and say, "I just want us to subscribe to the app right now," or, "I want a year's long subscription," maybe. And whenever any new upgrades become available, your subscription automatically switches over to the latest and greatest version of our app. If you subscribe to OmniGraffle or OmniFocus, or OmniOutliner or OmniPlan, you will have the latest version as soon as it becomes available. It's a different model. You are not paying up front, you're paying as you go and you get the latest thing as you go.

Andrew J. Mason: See, that is awesome. I love that as an option for people to have. One final question, anything that you didn't share that you'd love to share before we wrap up today?

Ken Case: I do just want to reiterate that I think the future of the Mac right now is looking brighter than it has in years. I'm really looking forward to having Mac on new hardware that Apple, where Apple is building the silicon and making improvements every year, the same way that they've been making improvements to the iPhone and iPad every year.

Ken Case: As somebody who spends so much of my working day, every day on a Mac, every time I look over at my iPad and how much faster it gets every year, I'm a little bit jealous on the Mac side of things that I can't just use the iPad for everything. And now suddenly, that same sort of improvement will be coming to the Mac, as well as being able to run every bit of iPhone and iPad software directly on the Mac.

Ken Case: It's certainly the place we want to be with our apps. We're just really looking forward to what the next few years will bring.

Andrew J. Mason: Excellent. I cannot agree more with that statement. Ken, thank you so much for hanging out with us today on the show.

Ken Case: Oh, well, thank you. And I really appreciate your taking the time to talk with me about all of this.

Andrew J. Mason: Absolutely. And it's my pleasure, too. Thanks to everybody for listening today. If you want to keep up with us and what we're up to check out the Omni Group at or head to the @theomnishow on Twitter.