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Feb. 15, 2021, 6 a.m.
Roadmap 2021 Special with Ken Case

On January 21 we published the Omni Roadmap 2021, where we looked back at 2020 and look forward to all the items planned for this year. Ken Case, CEO of the Omni Group — and author of the roadmap — joins the show to go into further detail.

Show Notes:

2020 - What a year! From migrating our entire suite to run natively on Apple's new M1-powered Macs to integrating a streamlined way to handle licensing and subscriptions - Omni Group accomplished a lot.

We recap all the progress from 2020, and Andrew tries his hardest to get Ken to spill the beans on upcoming application features.

And, like every year, we expect that Apple will announce new features at WWDC, and we will have surprise work to do. Which we don’t mind — it’s part of the fun of making apps! (We love those new features as much as you do.)

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

Previous roadmap blog posts:

2020 2019 2018 2017 2016 2015


Andrew J. Mason: You know, Ken, whenever I'm talking about the Roadmap blog post from Omni, I always liken it to a mini version of the Apple keynote, where you talk about here's what we've done, a couple of things that we've accomplished in this last year, and then we're turning our sights towards the future. And we've released OmniPlan Four.

Ken Case: We opened a store in Shanghai.

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's Andrew J. Mason. And today we talk with Ken Case, CEO of the Omni group about the 2021 roadmap.

Andrew J. Mason: We're so excited to be talking with Ken Case today. And I promised him before the show begins that I would just, much like an FBI investigator, just trying to find, down at the CSI-detail level, is there anything? I've been studying this, this blog post with a fine-tooth comb, just trying to think, is there anything that I can read between the lines and kind of pull out from the blog post just about the future?

Ken Case: Ut-oh. Setting expectations a little high there. I don't know.

Andrew J. Mason: All kidding aside, I really am a fan of these roadmap posts. I know that there's plenty of people who look forward to these and it's got to be cathartic for you to write them as well. I mean, just this acknowledgement of, okay, here's what's true, here's where we've been. Here's what we've seen. Is there any portion of you that just says, ah, there we go. I've taken a snapshot of the last sprint, now we're looking to the future. Here's what we see kind of from here.

Ken Case: So I think there is an element of, yes, there's a sense of completion, but what I more often feel as I finished the roadmap is, okay, I'm ready to code now, let's get going. And I think about all of the hopes that I've sort of captured as I've been building that roadmap up and writing it down and how much we have to do. And I'm just impatient to get started and keep going. I mean, we've already started on what I described, but yeah, get it to all of you.

Andrew J. Mason: Well, now that 2020 is over and we're on our way through 2021, are there any takeaways or thoughts that you have surrounding the entire year so far?

Ken Case: Yeah. Well, I will say that going through 2020 has given me a whole new appreciation for the historical context leading up to the roaring twenties, that after everybody's been stuck at home depressed for a year, when the pandemic finally ended, they're ready to get back to work, that the economy really boomed for the next decade. Now, of course, that led to the crash of '29 and a whole nother [crosstalk 00:02:41].

Andrew J. Mason: Yikes. Maybe not a complete metaphor, but that idea of just this, we're ready to kind of rebound moving forward thing.

Ken Case: One of the things I've been sort of thinking about is what a different position we would be in if this pandemic had happened 30 years ago or even 10 ago before we had our fast network connections for these video conferences. Some parts of the economy have been hit very hard. Anyone in the service sector, anyone in restaurants, a lot of places have had to close up shop and go out of business. So I don't want to overlook that, but I have to imagine that if we were trying to do our work where even we're doing programming work, but without the tools that we have available to us today, it would have been a lot harder, 10 years ago, 20 years ago. And so that just makes me really thankful for it hitting as late as it did. Not that I wanted it to come at all, but.

Andrew J. Mason: No, no. Not at all. But I just so grateful for the progress that feels like it's been made. And the bright future that we believe is ahead. I mean, there's not really a way to underestimate the scope of what your team's taken on in the last few months. I mean, it's like millions, I want to say millions of lines of code across all the apps. It's so easy to gloss over something like the M1 transition or the subscriptions that's been introduced, but I don't want to say there's an urgency, but there's a work with the purpose. It's like, what's next? What's next? What's next?

Ken Case: Well, that's a really easy thing not to spend time reflecting on because once it's done, it's done, it's shipped and we're always looking ahead at what can we do next and so on. But looking back as well, I think it's important to pause and sort of celebrate some of the improvements we did bring. So M1, of course, was one of those things, having all of our apps ready on day one for the M1 was a really important thing that we did. And the M1 itself was not the hard part of that work. The hard part is something that's just happened over the years of keeping all of that code maintained and ready for changes like this. If that code had been out of date and we had to do a bunch of work just to bring it to the latest operating system, then we would not have been ready on day one.

Ken Case: Another big project that we spent a lot of time working on this year, but it was really kind of a behind the scenes problem, because it's not about how you use our apps, it's about how you purchase our apps and license them in the first place. We want that process to be as invisible as possible. So we don't spend a lot of time talking about it or emphasizing it, but there were aspects of our old licensing system that really got in the way for our customers. We were providing a license code for each purchase that you made. And then if you had a large team that was buying hundreds and hundreds of copies, they suddenly had to maintain a spreadsheet of a bunch of license codes and keep trying to keep track of that. And so this year we have also shipped a sign-in based licensing system where you just list the people on your team, they sign in and when they sign in and it unlocks the apps for them, and that's a much better experience for the teams who are trying to buy our software.

Andrew J. Mason: Well, speaking of signing in and unlocking, what else happened that has to do with that this year?

Ken Case: This is the year that we let you start subscribing to our apps instead of purchasing them upfront. And there are some people who really prefer the subscription model. And so we like having that option available for when people need it. It's not the only option. We didn't want to make it exclusive. I think that's limiting customers choices in a way that we don't want to do, but having the option available made life a lot easier. And at the same time we made our apps, let you license them across platforms at the same time. So you could subscribe to OmniFocus and get it on the Mac, on the iPhone, on the iPad and on the web.

Ken Case: Well, now that option is now available on all of our apps. You can license OmniGraffle and if you're a subscriber, you get it on all platforms at the same time. And that's the way we plan to be selling all of our apps in the future. We're not there for the front purchases yet because that requires revisiting pricing and other sorts of things. But we are there now for OmniPlan, which is our most recent release, the one we shipped this summer. And I guess that's another big accomplishment worth reviewing, but we will be there over the coming years with OmniFocus, OmniGraffle and on the OmniOutliner as well.

Andrew J. Mason: Well, something like that really is huge for the future user base, because, if you're not sure you want to make the full investment, you can just do a month or two and dip your toe in the water and see if it's right for you.

Ken Case: Yeah. And some companies prefer to have a model where they know exactly how much there'll be spending every year and they don't have to worry about, is this the year that a new major version is coming up that I need to pay an upgrade price for.

Andrew J. Mason: That's awesome. And talk about this rewrite that's happened or happening.

Ken Case: As you look at the way our apps are put together, there's some central core areas of the apps, which implement the application logic, the parts that describe for OmniFocus, for example, that you have projects, then you have tags, then you have due dates and all those sorts of things. Those are all common logic that work across all of our platforms, Mac, iPad, iPhone, the watch and the web. But then we also have these application platform-specific parts that have to do with how do you interact with the user on this particular device? So we have logic that interprets keyboard keystrokes, and we have logic that draws things through the screen and so on. And all of that logic is different on every platform or has been. And the thing that we're doing right now is rebuilding a lot of that logic.

Ken Case: So a lot of the user interface, interaction pieces still preserving all of the hard won things that we have figured out over time with respect to the way the app actually works with due dates and so on. And I should mention the thinking logic, the network logic, file formats, all of that stuff is common shared code. but we have this opportunity now to kind of rethink how we do all the rest of it. What is the best way to get stuff to the screen? What is the best way to capture input and so on? And that's what we've taken on. So it's a portion of those millions of lines.

Andrew J. Mason: Got it. Okay. And I don't know the metrics, but I believe somewhere I was reading a review for the apps on the M1 processor and this is just slightly paraphrased. I don't know the exact wording, but they said something along the lines of stupid fast, which I don't know what kind of benchmark that is, but stupid fast seems like a pretty good thing to me.

Ken Case: The M1 processor is stupid fast, but I don't know that it's the processor itself, it's kind of the whole architecture. This thing that Apple has put together, that includes the central processor, the memory architecture, the video architecture, all of these different pieces that have to work together to run an application. When Apple has pulled them together into the M1, they're able to work together much more efficiently and so things like memory access, they're much faster. And that's part of what makes our code running on the M1 go faster. And particularly not just faster, there is a faster element to it, but Apple's original goal, their stated goal was more efficient so that you can get more done on a certain amount of battery life, for example. Your battery can last longer or whatever it is you need to do there.

Andrew J. Mason: And I heard that Omni was actually featured at the Apple launch event?

Ken Case: Yeah. I was fortunate enough to be invited to talk about some of my experience with the M1 in Apple's launch event. And I enjoyed that a lot because it really was an exciting process to bring our apps to the M1 processor. We didn't actually have access to the M1 final version. We had the prototype development kits that Apple was offering to developers over the summer. But we brought it all of our apps over to the development kit and we tested them out and then told Apple, wow, this is really wonderful what we're seeing. And they said, well, would you like to talk about it, so that's what we did.

Andrew J. Mason: And I heard you actually had a musical solo of some sort there.

Ken Case: They were like two seconds of harp playing. Yes. Just a quick glissando.

Andrew J. Mason: Now how game changing is this really? I mean, for somebody that doesn't understand the scope of this new hardware architecture, this is a really big deal, right?

Ken Case: Oh, absolutely. M1 is, well is version one, that's what that one stands for. On the other side, on the Apple, the iPad and iPhone we're on like the A14 at this point?

Andrew J. Mason: The A14. Yeah.

Ken Case: So imagine when we get to the M2, M3 with what we're already seeing in the M1. It's a promising roadmap ahead of us for the hardware roadmap that Apple's looking forward to. They've told us that they're planning to transition all Macs over the next two years, this year or next year.

Andrew J. Mason: And that's what's exciting to me because you hear people saying stuff like the M1 Mac mini outpaced my Macbook Pro.

Ken Case: Yeah, absolutely. We found that like the Macbook Air is actually faster to do builds of our software with than the old Mac Pro $20,000 machine that you can get with a lot more cores than everything else, just because of this architecture that it has.

Andrew J. Mason: Now, I know our community wouldn't forgive me if I didn't do the due diligence and asking, is there anything that didn't show up in the blog posts that, man, I wish I had a way to kind of share that about the future. Just trying to see if there's any hidden meanings or things I can read into and just something to just kind of pick from.

Ken Case: I don't have a lot more, well, I don't have anything to announce at this time, let's put it that way. I will say that one of our big focal points over the last several roadmaps, if you look through the history of our roadmaps has been about improving the integration between our apps and a big part of that has been building Omni Automation, which lets you write JavaScript plugins for any of our apps. And those plugins can call out and talk to any of our other apps as well as other third-party apps that understand URL communication, or any web apps that understand, have a web API, a rest-based API. So that's a way that you can use our apps with a bunch of other tools right now, ours and others. And I look forward to seeing how that ecosystem develops over time.

Ken Case: We're actually building some pieces, like if you look at our current test builds that are out right now, we've added, in December we added to rest support for calling web APIs. Here in January, we're adding support for storing authentication credentials in a more secure way so that one plugin can't read another plugins authentication credentials and so on. And other changes like that, I think are just going to make this ecosystem grow. And I look forward to seeing what people do.

Andrew J. Mason: I'll go ahead and use this opportunity to plug Sal Soghoian's episode, when he laid out this overall framework for Omni automation, the temptation, if you watch his first video where he presents OmniGraffle and he uses a lot of JavaScript, honestly, just to draw a circle, you saw people in the audience, not yawning, but like, okay. A circle, great, big deal. But then he starts to get a lot more interesting in terms of the examples that he started creating. And you're like, my gosh, anything really is possible with this.

Ken Case: Yeah. It gets a lot more interesting when you take that sort of JavaScript and now it's going out and talking to your router and finding out what network devices are currently connected to each other. And then it's drawing a graph of that on your canvas in OmniGraffle. That's the kind of thing you can do when you start building tools out of this automation technology.

Andrew J. Mason: I can't wait to see what happens. Talk to me about the last paragraph or two in the blog post, where you allude very lightly to some design tweaks that are happening within the apps, starting with OmniPlan, having what's called an outline view. What is an outline view and why is this exciting as we're moving into Big Sur and the guts of the apps are being reprogrammed from the ground up?

Ken Case: Sure. So I'll just break that down quickly. If you, in an app is a thing that draws through the screen and interacts with the user. So sorry for using that rather technical term without any clear explanation, but now it's, I guess, our chance to do that. So an outline view is a part of the app that is drawing an outline. And in Finder, for example, you can put the finder into outline mode and you'll see it draw an outline view of your folders and the files that are contained inside. In OmniOutliner, of course, the whole central interface is an outline view. You're working with an outline and you want to work with it in a nice, rich way.

Ken Case: So what I was talking about there at the end of the roadmap is bringing that outline view, a nice rich outline view that's editable and everything else to iPad, not just for OmniOutliner, where we've had it now for a decade, but for all of the other apps. So OmniPlan can use an outline view just like it does on Mac for looking through your projects and arranging stuff inside them. OmniFocus can use an outline view for organizing your tasks there. And we've actually had an outline view in OmniFocus now since the beginning of OmniFocus on the iPhone, but it was not a very good outline view. That's really what that paragraph is talking about. So now, instead of just being an outline view where you see an indented set of tasks and so on, you can collapse and expand those items, you can edit them in place. You can drag and drop them into other places and so on. Some of those interactions worked already, but none of them were as complete as they were on, say the Mac or in OmniOutliner, the dedicated app. And we really want that sort of capability to be available wherever it makes sense in our apps.

Andrew J. Mason: That sounds phenomenal. As an OmniFocus user, I'm guilty of over-structuring my areas of responsibility. So, folders within folders, within folders. So swipe, swipe, swipe to get to a certain level of detail. I love the granularity that that gives you the ability to slice the data and see it in a certain way. But sometimes it's a round trip to go back and forth.

Ken Case: Yeah, hopefully you won't have to do nearly as much navigation because you can do a lot more stuff right there in place. You're not going into a detail mode and then coming back and then going into another detail mode and then coming back and so on as you're adding tasks and manipulating them.

Andrew J. Mason: I think everybody can appreciate good design when they see it. But just as a beginner, this is probably a super basic question, but is there a tension there between the amount of real estate that shows up on the screen versus the level of complexity of all the different details that can be shown at once?

Ken Case: Yeah. There's a constant tension there between approachability, discoverability. Maybe I should explain what these steps are. So approachability to me is how easy is it to just sit down and start using an app without knowing anything about it, without having to go read the manual and then go into depth. Discoverability is finding features that are in the app that you're trying to use. So sometimes we call this the blank canvas problem. OmniGraffle used to, when you first launched the app, it would just bring up a blank canvas where you could drag on your shapes and connect them and so on, but people didn't know what to do at that point. They see this blank screen, but what am I supposed to do now? And they'd have to go find the other pieces.

Ken Case: So in order to make those activities discoverable, you started giving them some screen real estate that lets you drag stuff from the stencils onto the canvas, or maybe the inspectors you open up so that people can see, Oh, I can change what the shape is from a square to a circle or I can, after the fact, and I can also hook these things up, I can change the stroke. I can change the fill, all those sorts of details. The more of those things are visible, the more discoverable they are, but now you're making it harder for people to approach and know what they're supposed to be focused on in the first place, if you're not careful. And so you kind of want to design it with an incremental design that opens up easily and lets you discover things as you're ready to use them, but doesn't overwhelm you with all that detail right upfront. And that's part of that struggle that we're constantly working with as we try to design an app.

Andrew J. Mason: See, this brings me back to a blog post. A couple of years ago, I think you introduced a term that was new to me. I'm sure a lot of people have heard of it, but I've since he used it in consulting roles to sound way smarter than I am, this term of progressive disclosure where there's only so much you need to see, and then you show that to the user only at the exact time they needed to see it and so as not to overwhelm them with options. So in over my head, but is that partially what we're talking about?

Ken Case: Exactly. Yes, absolutely. That is one of the techniques at least that we can use to try to help solve that problem. Another technique is just to reduce complexity. So where that makes sense, we certainly want to do that. We don't want our apps to be overly complicated. That's a word we definitely want avoid. But some problems that our customers are trying to solve are complex. And so they sometimes need a complex array of tools available to help them tackle those problems. And that's where the power and simplicity have to be balanced and hopefully we can find a way to balance those along with using techniques like progressive disclosure so that when somebody starts with the app, they can start simply. For example, in OmniFocus you could just work in the inbox and do all of your work out of the inbox for a while.

Ken Case: I just did a blog post about that right before the roadmap podcast. But then as you start to use the app more and more and you realize, well, okay, I have a more complicated need than that. I have a problem I'm trying to solve that goes beyond just something I can do in the inbox. Well then you start to learn about outlining and grouping things into projects, or maybe you learn about tagging or about due dates or about filtering and all these other features that are there all along, but that we don't want to overwhelm somebody with when they first come to start using the app.

Andrew J. Mason: It makes sense. And you heard the term just-in-time learning and you think of GTD where it's about put the thing in the front of the door of your mind just when you need it so you'll bump into it basically. And a lot of it has to do with guessing kind of the right options and the right information within the right context.

Ken Case: And there are examples of this all over the Mac. Like this is an important characteristic of the Mac platform. Like even in something as simple as the open-and save dialogues, when you first use the save dialogue in say, Apple's built-in text editor, you'll get a little window that just prompts you for what file name do you want to use and then it has a pop-up button that says, well, what folder do you want to store it in. And for simple use, that's kind of all you need. But if you want, then you can expand that panel and you get a fuller dialogue that gives you the options of saving in different formats and browsing the entire file system instead of being limited to the options in that pop-up and so on.

Andrew J. Mason: Is there any cost analysis over like the muscle memory of your existing user base where it's like, where is that thing? It used to be over here? I don't see it anymore. And now it's hidden away or tucked behind some other option. Is there a trade off there between that simplicity and that keeping things fresh and up to date and continuing to develop them in a way that makes sense to your existing user base?

Ken Case: Yeah, absolutely. Yeah. Every time we make changes, we have to also weigh what is the cost to the customers that have already learned the old ways of doing things and are they going to feel like we moved everything out from where they just learned the way it was and now we shifted everything on them and do they really want to spend time learning where things are now instead. It's something we have to be careful of each time we redesign something.

Andrew J. Mason: Got it. And just in preparation for this, hearing this idea that good design is more like a conversation than it is like an end all be all. So it's like a version is like, okay, there it is. That's the end. We've made the ultimate, but really, it's this ongoing conversation that changes over time. The operating system elements change from, I have no idea what I'm talking about right now, skew morphism to flat or something. I don't know. But this is something that continues to evolve over time.

Ken Case: Yeah, absolutely. And we never fully achieve any of our designs. Maybe that's the way to put it. Is that truly the case? There's some simple problems where, maybe we have finished the problem, we've achieved the design and we're done, and we can just consider that thing done for all time. Or we consider it done because it met our needs and then we show it to somebody else and then they have slightly different needs and so they start asking for other things and now we have to evolve that design somewhat. And yeah, you're right. It's a conversation. And we have to draw the line somewhere and say, well, this is good enough for now. Let's ship that and then next year we'll ship something with some of the other things that we've been thinking about that we, otherwise we would never ship anything.

Andrew J. Mason: Well said. And speaking of shipping anything, I think it is just about time. So I will let you get back to it. Ken, thank you so much for joining us for this episode. I'm grateful to hear the bright future, but also just so much possibility and groundwork laid out with all of these apps together. Thanks for your time, Ken.

Ken Case: Thank you, Andrew.

Andrew J. Mason: My pleasure. It's a great roadmap and I'm excited to see it come to fruition. And thank all of you for listening today. Hey, we're curious, are you enjoying the shows? Are you enjoying learning how people are getting things done utilizing Omni software and products? Drop us a line at the Omni Show on Twitter. We'd love to hear from you there. You can also find out everything that's happening with the Omni group at