Connect with the amazing community surrounding the Omni Group’s award-winning products.

July 10, 2023, 4:30 a.m.
Omni Roadmap, July 2023

On today’s episode of The Omni Show, Andrew and Omni Group's CEO, Ken Case, dissect the key takeaways from Apple's WWDC and how visionOS is set to redefine the tech landscape. Ken envisions a future rich in augmented reality, drawing parallels with the revolutionary transformation seen with the iPhone.

Show Notes:

They also dive into the App Store’s 15th anniversary and the eagerly anticipated debut of OmniFocus 4, highlighting their steadfast dedication to seamless design and staying ahead of tech progression.

Some other people, places, and things mentioned in this episode:

- OmniGraffle Test Builds
- Vision Pro
- OmniFocus
- Swift (programming language)


Andrew J. Mason: You are 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 hang out with Ken Case talking about the WWDC Roadmap blog post wrap-up. Welcome everybody to this episode of The Omni Show. My name's Andrew J. Mason, and today we have CEO of The Omni Group in the house with us to talk about his latest WWDC blog post wrap-up. Ken, always awesome to have you with us. Thank you for hanging out.

Ken Case: Oh, thank you. This is a fun time of year for us and it's fun to be able to sit down and take a few minutes to share it with you all.

Andrew J. Mason: Absolutely. And for those of us that maybe are new to these wrap-up shows, maybe they haven't heard us break down what's new after a WWDC, if you don't mind level setting with everybody just talking a little bit about how this conference helps us level set and recalibrate the software and the company moving forward.

Ken Case: Sure. Well, for those who don't know, WWDC is Apple's Worldwide Developers Conference and it's something that they've been doing every year now for a few decades and ever since we became Apple developers. When Apple acquired NeXT back at the end of 1996, I have been to every WWDC since, paying close attention, except for two years, the year where my oldest daughter was born, and that [inaudible 00:01:28], obviously there was a higher priority there, and last year when she graduated I did not go down either. Her graduation from the University of Washington was more important. But other than that, I've been to every WWDC because for us it's our insight into what's coming next, and it's important for us to understand that, what's coming next for the platform because we want the work that we're doing, all the time and effort that we're investing to last as long as possible. And so if we're not paying attention to where the platform is going and it starts steering off in a direction, we're going a different direction, our stuff is not going to last very long and that's not good for our customers, that's not good for us. So we pay very close attention each year to what's coming at WWDC and then think about, well, how does that affect our plans for the rest of the year until the next one rolls around?

Andrew J. Mason: That makes good sense and I don't think anybody would really fault you for the two times that you missed WWDC, "Where's Ken?" "He's at the birth of his daughter, I apologize." I think that's okay. Talk to us a little bit about what WWDC has traditionally done and has done this year in regards to the timeline of development of software. I know maybe forefront everybody's mind is OmniFocus. Last year the introduction of Swift did a few things and just talk to us about where we find ourselves this year.

Ken Case: Sure. Well, of course we started this process of redesigning and rebuilding OmniFocus back three years ago, right after that WWDC when Apple announced Apple Silicon and we knew these new Macs were coming. They announced changes to the Mac platform with Macs 11, we finally were moving away from the Macs 10 era getting some new designs and of course we'd already started working somewhat with Swift UI. And so that seemed like a really good opportunity to take it a step back and think, "Well, if we were building apps new today for the Mac, how would we build them? How would we be writing them and so on?" Now we're not building new apps. We've been doing this for a couple decades, but we didn't want to be stuck in this world. I mean, I remembered the transition from Mac OS 9 to Mac OS 10 and how a lot of developers kind of got lost or left behind in that transition because they weren't really thinking about, "Well, how do we reinvent our products now as the platform shifts and continues to evolve?" And so what does that mean in this case? Well, obviously it's not just about the Mac evolving because one of the things that Apple has done since then is they've really branched out to a lot of platforms and we wanted to be there on all of them. So we were there on day one when the iPhone App Store launched and we're coming up on the 15th anniversary. And we were there on day one when the iPad launched, and we wanted to of course be there and we brought all of our products to both of those platforms, but that left us spread pretty thinly where we now had a bunch of native code that we were doing on the Mac and a bunch of native code for the iPhone and iPad that were all a bit different. And that required a lot of careful design, a lot of careful investing. Anyway, it seemed like with Swift UI being a new cross-platform framework and with all of the platforms getting a bit more evolved, it was time to step back and think, "Well, how would we do this today?" And so that's what we started three years ago and that's sort of what we're hopefully wrapping up now as we come close to the end of this redesign project on OmniFocus and of course other products along the way.

Andrew J. Mason: That's awesome. And can you give us some more specific details about how things are progressing with OmniFocus?

Ken Case: When it comes to that test flight, where we are right now, we have finished our feature set for everything, which is we have a lot of new features in version four and we're pretty excited about what's coming and some of the features are completely new and other features are new to a platform. As we did this work of cross pollinating the platform so that we have things like focus on every platform that we have, things like nearby on every platform, but then we also did completely new features like bringing history to all of the platforms. Those are just some examples, but now what we're wrapping up is the design freeze, and that's where everything is starting to look like the way it's supposed to look, and you're able to safely take screenshots and share that with people, which lets us get going in parallel with things like our documentation and our marketing work because obviously we don't want to be building screenshots in our documentation that are showing broken interface code or interface code is still changing. And so design freeze is almost done at which point we can turn our attention to usability and that's all of the other bugs that are very important to using the app like keyboard shortcuts and things like that. And whenever those break, obviously those are some of the bugs that we hear about most these days from our test flight customers, like when tapping breaks and obviously we don't want to ship with tapping broken, but tapping doesn't fix screenshots either. So we always have to make this balance between, "Well, we want to keep people engaged and we want to keep the test useful enough that people are going to be in it." So we have been fixing some usability bugs all along, but there are some that we've put off that we can finally sit down and focus on as soon as we're not worrying about, "Okay, is every pixel in the right place?" I imagine this part is going to start speeding up as we get closer and closer now to where we're going. So the usability bugs sorted out any remaining stability issues or performance issues, [inaudible 00:06:44] as well. And then we'll be right around the corner from shipping.

Andrew J. Mason: That's excellent. So that's OmniFocus. I've also heard that OmniGraffle is in testing as well. What feedback have you learned from on that?

Ken Case: We certainly have had feedback along the way. I think OmniGraffle is a really interesting product for people to test because so often if you're really trying to test with it that you're building documents that you're trying to share with other people, and if you have a different version of the app that now has so many features, you can't really share those with other people very well. People just rely on it so much for the content that they're creating in it that it's really a lot harder for people to feel comfortable diving in and testing. So a lot of the testing feedback has just had to come from us ourselves internally, even though we have opened up the gates and we invited other people to come to us. And I think we might have a hundred testers now, but it's a far cry from the 10,000 testers that filled up the test flight on OmniFocus. We have learned some great things from it. People will tell us when we accidentally break something, they'll let us know right away, "Hey, we're working on this and I can't do this thing." Or they'll let us know if a workflow change that we have made around our tools or our pallets or whatever is doesn't feel right to them or doesn't seem to be working quite right. We hear about those things and we hear about things that people just wonder or wish that the app had. One of the fun things about this release in particular is that we've had the chance to sit down and bring some long requested features to OmniGraffle. And so it's fun to have those now in test flight, have people actually trying them out and telling us, "Yeah, this is finally solving this need that we have had," for however many decades in some cases.

Andrew J. Mason: I love that even though Omni is not a new company, there's that new mindset that says, "How would we do this today in a way that makes it most accessible for everybody?" I so appreciate that. I also like this mindset that says, "Hey, we're going to skate to where the puck's going. We're willing to slow down a little bit in order to speed up." Tell me more about that thought process.

Ken Case: That is a great summary, part of why we did this. We didn't want to be continuing to have our platforms diverge and have to... every time we implemented a new feature, we would have to design it multiple times, implement it multiple times, and it just was slowing everything down. And that was appropriate at the start when the capabilities were very different. But as time's gone along, we certainly want OmniFocus to feel like it's OmniFocus no matter what platform you're on, and as all of the platforms have gotten more parody in their capabilities, it feels like pretty much every feature ought to be on every platform. There are a few features that are still exclusive to one platform or another, and of course the experience is different just because the devices are different. But you don't want to say, "Oh, well you can do location alerts on this platform, but not that platform," or "You can do your map here and not there," or "You can do focus on here but not there quick entry," and on and on.

Andrew J. Mason: This really does feel like an effort in reducing friction as much as possible, having... if it shows up on one platform, if it's on the Mac, then you can expect it to be on iPad OS, iOS or Vision OS. And speaking of Vision OS, I'd love to talk about no promises here, but I know this is an area of interest for the Omni group. What sorts of things does an operating system like this make possible?

Ken Case: Well, it's exciting for me to see this happen if you haven't already figured this out. I'm a bit of a computer nerd, so I've always been fascinated with, "Where is this stuff going? What's going to happen next? What can we play with this stuff?" And so as various VR experiences have come out... I guess I've been playing in various VR experiments since the late '80s, early '90s, the graphics lab at the University of Washington I used to work at and so on. It's been a pretty fun time to see over the last decade or so some of the gaming stuff come along on the PC platform or on some of the consoles as well. But we still have never really seen a good productive platform for doing this sort of experience that is really designed for productivity and for being able to accomplish work to be the bicycle of the mind that Steve Jobs talked about, computers being some decades back. That's the platform we're interested in developing for... As a computer nerd, I was interested in the others just to see where things are going to end and to play with it. But now that Apple is jumping in here with Vision OS, its systems is designed to augment your reality as it exists to not cut you off from communicating from the people around you. You don't have to wear this headset that blocks off your vision, but you instead see through it and you just see your computing world sort of superimposed on the real world. That starts to get a lot more interesting and exciting for us as developers.

Andrew J. Mason: You mentioned in the blog post that you received the Vision OS SDK and within about an hour had some version of an Omni software app or environment running. What did the team think when they saw, okay, this is what the apps might feel like when they're in this new environment?

Ken Case: Well, to be clear, this is what the apps as their built today would look and feel like if we make no changes by the time that... and so obviously part of the reason we wanted to do this is we wanted to see, "Well, what do they look like and then how do we think they should look? What do we need to change so that they feel at home on this new computing platform?" And there's a lot to do, so to be clear. But a lot of the work that we want to do is made so much easier now by the fact that we're using Swift UI in so many places. And so the investment of the last few years has really paid off now in terms of us feeling like we can bring this code over and it will adapt to yet another platform in a way that makes sense for that platform, that's part of how Swift UI is designed to be a declarative language where you say what you're trying to accomplish rather than, "Here's where this exact pixel should go." Now those pixels are very different. We're very happy to be using this system that will now adapt to yet another platform. Not that there won't be any work on our part that will be some design work and so on, and not everything can be shared and we still have yet to figure out, "Well, what are the platform specific things that we want to leverage and how do we want that to look?" But we've already started thinking about that and imagining what would happen if you have a much larger canvas that you're working with in OmniGraffle or in OmniPlan, for example. What happens if you maybe want to drop some 3D things on an OmniGraffle canvas or maybe have some of the plains of the layers that are in OmniGraffle, it already has documents that are separated into multiple layers. What if you bring some of those layers out at different Z level or perhaps even give them different transformation so that at different angles of positioned differently in 3D space than the others and so on and so forth. There's a lot to think about and work on. I don't want to make any promises about what may or may not show, we still have yet to actually experiment with real hardware. The simulator's one thing because we're still looking at it and an environment where the screen itself is still 2D, it's still flat and we don't truly get to see around it in the same way as we can imagine it, but it makes it a little easier to imagine and we can kind of see how the code runs on the operating system, at least.

Andrew J. Mason: Two things really strike me. One is this, moving from two to three D and the possibilities that brings to our software. And two, I'd love any thoughts, again, no promises here, but about how this might change the way people interact with software or more specifically are software.

Ken Case: And some other examples, if we look at OmniFocus, you could imagine... You can open multiple windows, first of all, and they can each be positioned wherever you want in 3D space, which means you can leave a window in one room and put another window in a different room. So you can put a window with your OmniFocus shopping list right by your fridge, and you can put it in another window with your to-do laundry and stuff, actually by the laundry and so on. Now, I don't know that people will actually want to wear their Vision Pro everywhere they're going around their house. So will that actually be a useful thing for people to do? Maybe not with this generation of hardware, but this is just the first generation of hardware at some point. I can imagine, maybe if it's as easy as putting on my glasses, then I would want to wear it as I'm off doing the laundry. And so why wouldn't I have a reminder there that says, "I need to refill the soap," or whatever.

Andrew J. Mason: Just even thinking about the concept of iterations, the first iPhone comes out and it's great, but already iPhone 3G, which was just a few years later, looks so much more different and offered so many more capabilities once they got that moving in the right direction.

Ken Case: I mean, right now I think it's easy to forget how constraining the screens that we carry around are, these physical screens that we're putting our windows on. And if instead those windows can go anywhere in your physical world and all you're carrying around is a much lighter and smaller headset that makes a lot more places that you could think about placing these windows and using them.

Andrew J. Mason: And what other earmarks or milestones are happening through the rest of this year along with Apple? So we just had WWDC, what else is happening in this world?

Ken Case: Sure. So of course I already mentioned that right around the corner. We're coming up on the 15th anniversary, and that's not really a milestone in terms of us shifting anything new, but it is kind of an opportunity to look back and think of, "Wow, here's how much has happened over the last 15 years." As you mentioned, the difference from the original iPhone to even the iPhone 3G. And then from the 3G to where we are now, it's incredible to look at. So we'll probably share some fun screenshots of that original iPhone app that we had and so on. I don't want to give away cheeky spoilers, although maybe it's not spoilers by the time the... that's just right around the corner. So by the time this makes it into production, maybe it's right around the same time. Of course, looking a little further ahead... In the fall, Apple will be releasing new updates to all of their operating systems. And of course that's what they shared with us at WWDC, where here are the new versions of Mac OS, iOS, Watch OS and iPad OS. So of course we'll be updating all of ours for those. And still the top focus on our plates would be the OmniFocus 4 release that we're building towards. And OmniGraffle 8. OmniGraffle 8 won't be this year, but I think we can look forward to OmniFocus 4 coming later this year.

Andrew J. Mason: Can I just say that this team does such a great job of intentionally asking the question? We mentioned it earlier about if there's a new user coming to Omni, how do we make sure that that experience is a good one for them? If we had it over to do again from scratch, what would we do here? And I think that speaks to why the staying power of Omni has been as much as it has, as well as this resistance to want to take the quick win. "Hey, we upgraded something," versus, "No, we're going to skate to where the puck's going so that in the next four years when Swift is a really big thing, all of our apps are natively programmed in it." That's a big deal.

Ken Case: Well, and we wanted to do that both from the implementation side and from the user experience side. If somebody's coming to the app new today, what can we do that makes it easier for them to get into that? They don't have to know about the 10, 15 years of history of OmniFocus and various design decisions and can just sit down and hopefully start using it as easily as they can use reminders, and then they can grow into the other features as they need them. And so that's really the essential part of the experience that we've tried to keep in mind with every design decision that we've been making.

Andrew J. Mason: Well, Ken, I so appreciate the breakdown of the WWDC blog post and where we're at. I'll have to admit that the nerd slice of me did kind of light up a little bit when they brought up the headset saying, "Aha, okay, well we've been waiting for this. I'm excited about this." Any final thoughts or ideas as we let you go?

Ken Case: Yeah. And again, I don't expect it to happen overnight. Much like the Apple 2 didn't happen overnight. The original MAC didn't happen overnight. Even the iPhone people were pretty excited about it, but it took several years before it really became anywhere near as huge as it is now. And I don't necessarily expect that this becomes as huge as the iPhone did, but I think it could easily become as big as the MAC is. So we'll find out.

Andrew J. Mason: Definitely exciting times. Ken, thank you so much for hanging out with us today.

Ken Case: Thank you. It's been a lot of fun.

Andrew J. Mason: Hey, and thank all of you for listening today too. You can drop us a line on Twitter at the Omni Show. You can also find out everything that's happening with the Omni Group at