THE OMNI SHOW

Ken Case: And other years we had more homework and other things we had to do. We had to learn the whole new systems and so on, and just start to think about building our apps differently. And so, which kind of year was it? Was it a gifts year or was it a homework year? That was kind of the question we would ask sometimes.

Andrew J. Mason: You're listening to The Omni Show, where we connect with the amazing community surrounding the Omni Group's award-winning products. My name's Andrew J. Mason, and today we have our Omni Roadmap 2025 post WW DC update with Ken Case. Well, welcome everybody to this episode of The Omni Show. If you'd like to stay productive, today in the house, we have the man that you'll probably like to high five at some point in your life and say, "Thank you," to Ken Case, the CEO of Omni Group is here with us chatting about our Roadmap 2025 post WW DC update. Ken, how are you, sir?

Ken Case: I'm doing great. It's been a fun year so far and it was a very fun WW DC last month.

Andrew J. Mason: Yeah. I mean, there's a lot that's been covered in here and I really like the opening idea that you mentioned as we dig into this blog post and kind of unpack all the ideas that are in there, this phrase that you used about the philosophy that, "Gifts are nice but dividends are earned." It's almost something that I could sit down and really ponder for a while. But unpack that for us a little bit. What does that statement mean?

Ken Case: Some years back, we used to have some regular conversations with other developers about how some years at WW DC we would have a year of gifts where we got some presents from Apple that we got to unpack and open and integrate with our apps and boom, here's some new functionality, here's some new features, and they were wonderful gifts from Apple. And other years, we had more homework and other things we had to do... We had to learn the whole new systems and so on and just start to think about building our apps differently. And so, which kind of year was it? Was it a gifts year or was it a homework year? That was kind of the question we would ask sometimes at the end of WW DC. But this year, we added this sort of third position, which is a year of dividends. And the difference is, dividend, of course, is something where you've invested in something. And then, with the notion that there would be some future payoff. And now, years down the road, here's the payoff, you start to get dividends from the work that you invested earlier. So, that's where some of our work over the past five years and more around things like investing in SwiftUI for revamping all of our applications, making sure they're not still using older stuff that's starting to fade away in Apple's ecosystem, but instead using the most modern tools and modern interfaces and so on, was really starting to pay off as well as the investments we've made in things like on the automation to try to make our apps more powerful and flexible and be able to adapt to new situations.

Andrew J. Mason: I see it as foundational something like Omni Automation or SwiftUI. I remember a couple of years ago when Apple's first announcing this, it's like, "Okay, we might not see immediate results right now. But over time, over the future, we're going to start to see hopefully some payoff in being able to invest in these new technologies in this way." One of the things, and I do want to get back into the dividends idea, but one question before we do this idea that Apple had introduced an entirely new kind of theming Liquid Glass design language into their offering this year, any initial thoughts and it is so fresh and it might not actually even look the way that it's looking now as they continue to iterate over it, but any initial thoughts on how that might influence your UI/UX design approach and just looking at things moving forward?

Ken Case: We certainly have seen that it is still evolving. It evolves from beta-1 to beta-2, which is the current data that we have available to us as developers. And I'm sure it will continue to evolve over the summer and it'll perhaps even after it ships. We saw with iOS 7's new interface that it evolves some more with iOS 8 and iOS 9. And it's not ever a static endpoint of, "Oh, this is the final design forever." This is something that as we get into the system, as Apple gets into the system, as their customers get into the system, they start to get feedback about what's working, what isn't working, and think about how can they improve the system. So, of course, we're thinking about that as we think about the design of our apps, where does this make sense to apply in general? I think based on Apple's direction, they're not expecting people to use Liquid Glass everywhere. It's not built for that kind of use really, the legibility would be in trouble and so on. But it is meant to use in sparing ways for specific features. And right now, I'm kind of talking about this specific glass effect. There are other things that now fall into this design system called Liquid Glass that are things like how the toolbars work, how sidebars work and so on. Those do affect the system more broadly. Of course, all of that then is stuff we have to think about as we design our apps, how do we make sure that we look at home in the system as it goes this way? We are native apps, so there aren't other systems we're having to worry about. We just want to make sure we're fitting in with the platform that we're on. It's easier in a sense because with Liquid Glass, because now Apple has the same design system across all of their platforms, whereas before we had to deal with the design system on one platform being different from another end. On this platform, maybe you can see the edges of buttons on that platform you can't or all sorts of things that are... Then, we had to kind of design a little bit differently in different places to accommodate. We still, of course, have to design differently on different platforms. Every platform has its own input mechanisms, its own screen sizes from the size of the watch and how much you can tap on there or see there. That's very different from what you would see on my Big Mac screen or even more so on the Apple Vision Pro where I've got this infinite canvas that I'm playing with. But so, those platform differences don't go away completely, but it gets easier if a lot of the design language at least is similar.

Andrew J. Mason: The holding that thought about other things that Apple has already announced and brought out. Let's also rewind and talk about how we've been cruising on OmniFocus this year. So, we've been really cruising. We've got 4.6, and then released just recently before WW DC, and then cruising into 4.7. And so, do you mind just recapping what 4.6 has offered to us that's available now in case somebody hasn't upgraded OmniFocus recently? And maybe, what to expect in 4.7 and beyond?

Ken Case: Sure. Well, the stuff that we introduced in 4.6 are some improved functionality around notes and attachments. You can now resize an attachment, so particularly the image attachments were previously the app would pick a size for you. It was based on what size the image actually was stored on disk or what was taken, and then how much space there was available and it would try to stretch and fill into that space. But its choice wasn't always the choice that made sense for every context. And now, you can say, "Okay, well I'd like all of these images to be smaller thumbnails or this one, I do want to be a really big image that success is central content. Maybe it has text in it and stuff that you're trying to read. And so, we added a lot more capability around that, and that came then to not just OmniFocus on the Mac where this support for images has been around the longest but also to all the other platforms because of our investment in bringing rich text to the iPhone and the iPad and the Apple Vision Pro. So, this stuff around images much got much better. We also realized that there were some frustrations about how editing a note particularly with links worked. And so, we tried to make it a lot easier to interact with links to be able to easily remove a link or do something different with it than just as soon as you touched it, tapped on it, clicked on it, whatever, having it automatically open that sometimes got in the way of actually trying to edit it and change things around. And so, we made some improvements around images, links and refined how we paste things. One of the other problems that would come up is if you copied and pasted a bunch of content from another app in particular, often it would come in with things that you didn't really want, colors that didn't make sense in your OmniFocus database that was just now calling out to itself too much or other sorts of things. And so, we wanted to be a little bit smarter about stripping things that you don't necessarily want from the other context. So, we'll look at kind of the whole thing and we'll look at what colors were used. And if a color applied to the whole thing we're like, "Okay, well then that color probably didn't matter." It wasn't a meaningful color change. It was just you copied it from a webpage where they decided to use purple text on a green background or whatever. And so, we automatically then simplify the styles. If you wish, there still many... There are options where you can decide I want to keep the original styles intact exactly when you paste or as a default or there's another option where you can say, "I want to strip everything all the time. I don't want to preserve red text even if it's just one word in the middle," which currently we try to do because we think that's probably meaningful if it's only applying to one word, not to everything. Guessing about semantic meaning is kind of hard, but we do our best and that's sort of where those options are. And then, we try to give you flexibility to make a better decision knowing what you know about your own workflow.

Andrew J. Mason: Yeah, that's incredible. The level of detail that goes into trying to intuit something like that and figure out, okay, this is probably what the user intends or what they're hoping for when they're pasting something in. And I love what you said about how adding that feature into one space has the potentiality to add it into multiple spaces. And talk to me a little bit about 4.7 as we're starting to look to the future as well. You mentioned some definite directions that we're thinking about taking OmniFocus, and then also maybe some hope to haves coming up too.

Ken Case: Well, 4.7 is right around the corner in terms of testing. It's not ready to ship just yet. There's a lot of work involved in what we're doing. But the 4.7 release is the first time in almost a decade I guess that we have made changes to our data file format that we wanted to do a data migration that would add capabilities that customers have been asking for, for a long time that we've wanted to provide for a long time. But we were trying to be very careful, particularly around the release of 4.0 itself, not to require a new data format and have people have trouble if they migrated to 4.0, then they couldn't continue to sync with their old OmniFocus 3 data and so on. So, we've been trying to be very careful about when to do this migration. And when we got to the beginning of this year, we thought, "Well, this was a pretty good time." We've got things into a pretty good state with where we are on OmniFocus 4 or 5 at that time. And so, what are the things that I'm talking about? Well, we wanted to add better scheduling around repeat dates. So, now you can say something repeats not just indefinitely, but it ends on a particular date, really great for maybe you're taking a class at college and you want things to repeat every week until the end of the quarter, and then you want it to be done and you don't want to have to go delete it by hand every time. I mean, that's what people have been doing, so that's an extra convenient thing. We also have tags that can now be mutually exclusive. So, if you have tags that are, for example, fees, prioritization tags, it doesn't make sense to have something that's tagged both high priority and low priority at the same time. You wouldn't be able to say that when I tag something as high priority to automatically overrides any previous priority that was there. And now, your low priority thing is high priority or vice versa if you change it back. Mutually, exclusive tags is another big long wave feature that we now have in there. And then, the third big data change that we're making in this release, and this is the one that actually has taken us the longest to kind of... Because it touches so many things throughout the interface, is adding a planned date feature. So, not just in the past OmniFocus tasks already have a lot of dates associated with them. They have the date they're to do, which is perhaps the most important one, but they also have a date that they have been deferred to. So, that is when something will become available. You're saying, "I can't do this before then, so I don't really want to hear about it or be reminded about it until all that's done." They also have dates for when they were last modified so that you can easily create a perspective that'll show you things that you've touched recently or when it was added to your database, when it was completed or dropped, all of these sorts of things in there. And so, we've been a little bit hesitant given how many dates were already associated with each item to add any more dates. But the more we've talked with customers and talked with them about their workflows and how they use forecast in particular, it's become clear that none of the dates quite matched the way people wanted to plan their tasks and actually schedule, "When am I going to do this work?" Not when is it due, not when does it become available, but when do I want to set the time aside in my schedule to actually get this done? And so, that's the plan date that we're adding and part of the design changes that we made in OmniFocus 4 data, when the first place were to make it easier to optionally add fields to your interface and to your outline, to your inspectors and decide whether something matters to you or not. So, this is an optional feature. Not everybody will want to use it or has to use it, but if you are one of those folks who have sort of fallen into this trap of, "Well, maybe I'll use deferred dates for this, but then that's not really working the way I want. Okay, maybe I'll use due dates now. I've got due dates all over my database and it's just cluttered everything up." Maybe plan dates is the right answer for you. That's our hope.

Andrew J. Mason: So cool. And I love that it's the philosophy of can but not must. There's so many people that it can work for and it'll be helpful for. But again, not a must if it's not for you. So, I love this kind of extensibility that shows up here. And talk to us a little bit about what's happening or the latest with OmniFocus for the web.

Ken Case: As we think a little bit about all these changes coming in 4.7, they're not just changes to the app itself, but also to this documentation. Of course, we have to update all of our documentation to talk about the new plan dates, talk about the priorities. And then, the app interface and the documentation that all has to get localized into the 12 languages we support. And so, this effort gets... There's a core effort that is adding the feature itself, and then there's a lot of supporting effort to make things much better. And one of the sort of subtle pieces of that is that OmniFocus for the web also has to be updated. And OmniFocus for web, we were already working on updating it to have the new design that OmniFocus 4 has, but we don't yet have some of the flexibility that new design has in place for making fields optional and so on. And so, we're figuring some of that out, but we're adding of course, the basic functionality before anybody can migrate their database to support plan dates and mutually exclusive tags and end dates on repeats. We have to have OmniFocus for the web also working for them, if they're using OmniFocus for the web and it needs to be able to understand what that data means. And so, if nothing else, we have to get the backend working and behaving the same way. And then, we need to start exposing all those features up through OmniFocus for the web's interface just like we had to do on all the other platforms.

Andrew J. Mason: I want to take the pins, the two pins that I had taken from earlier in the conversation and ask you the question, what do dividends and gifts look like for the other apps that we have going on here? You mentioned a whole new kind of Liquid Glass interface in the blog post to consider for all four of the products across the different four platforms, or you mentioned you had five, so that's like 17 different spaces to consider. Can you share a little bit more about what's going on with all of the other apps and kind of just a state of the union for each as they're moving forward?

Ken Case: Sure. So, we've already talked a fair bit about OmniFocus, so I guess I'll skip kind of through that, although I'll, maybe I'll quickly note that all of this Liquid Glass work that we're talking about and so on, that's not in either 4.6 or 4.7, of course, that's what we're looking at for releases then down the road afterward. But releases that we want to get done by the end of the summer if possible. Then, OmniGraffle, of course, we've spent the last several years in a public test where we're testing new features around how you can now have reference objects that when you change an object in one place under your document, it will now change all of the other instances that have been copied from that or it was the reference object. And now, you decided, "Oh, you know what? Here's a new version of that desk or something." And now, all of the desks throughout your document have this functionality to them. It's a really great feature, and that's something we've been working on for a while along with things like being able to skew shapes and so on. So, those are some of the general features that are just about the capabilities of what you do in a document itself. But another big piece, the work we've been doing for OmniGraffle aid is to make it a universal app, much like OmniFocus is now and OmniPlan is now where you purchase the app once and you use that licenses it across all the platforms. It's one version. It's not OmniGraffle... Well, what's currently shipping is OmniGraffle 7 on the Mac and OmniGraffle 3 on the iPhone and their separate purchases and you can sync the data back and forth and so on, but it's a little bit hard to keep track, much like Apple's operating systems were hard to keep track of until this release. And I didn't touch on that in the roadmap at all, but it's really great that Apple is now just calling it iOS 26, iPadOS 26 and VisionOS 26 and WatchOS 26 that all of them are now just OS 26 instead of... And they're all synced up at the same time. You kind of know what was released at the same time as which other things. Well, we have the same problem with our non-universal apps with OmniGraffle 7. You have to remember that OmniGraffle 3 is the equivalent version on iOS and those are the ones with the compatible data format and so on. We're fixing all that with OmniGraffle 8. It will be OmniGraffle 8 everywhere, and we're, of course, bringing it to the Apple Vision Pro as well, which is a platform that we're currently available on as a compatible iPad app, but that's not quite the same as having in native experience where you can use the whole intimate canvas. So, we've been doing a bunch of work on OmniGraffle 8 to make that possible and to rebuild all of our palettes into a system that can work better across all of these different platforms. The design considerations I was talking about earlier with big screens versus small screens, all of that comes into play, especially with OmniGraffle, which has more of these palettes than any of our other apps. OmniFocus has quite a few, but OmniGraffle has maybe twice as many. And because all of that work involved translating those rebuilding, redesigning and rebuilding those palettes using SwiftUI, so that they would be cross-platform, that means that we now are reaping a bit of a dividend because SwiftUI is Apple's recommended way to use Liquid Glass in your interface. And so, all of this becomes much more easy to adapt Apple's latest interface work, then the end of the latest design than if we were still doing things separately on each platform. Of course, we're looking at some of the same things around what we're doing with OmniOutliner, and though OmniPlan is already universal, that's the app that became universal first. It's the one that we're... After we make the rounds and finish this up with making OmniGraffle universal, making OmniOutliner universal, then we'll be back to doing the next version of OmniPlan.

Andrew J. Mason: It's one of those things where if you could look back and say, "I am so grateful, I am so grateful that you get everybody moved to Swift because I can imagine trying to maintain each of these individually, these different platforms and products as they're all being updated like this."

Ken Case: In the past, we have had to make some hard decisions because we weren't using SwiftUI yet because we had to develop the iPad app completely separately from the Mac app. And it was just too much work to do that for as many products as we had. And so, we've now focused down onto four products that have the biggest audiences for us. And so, that's where we're at, at the moment. Wouldn't it be nice if we had had SwiftUI a decade or two ago and could have kept some of those other products alive as well?

Andrew J. Mason: Yeah, it's so cool to be able to see from here on out the delta of work that doesn't have to be done because this groundwork, this foundation has been laid for the company. It's so cool to see that. One RIB app highlight that you had mentioned is integrating deeper with App Intents and Spotlights in OS 26, how are we as a company thinking about extending its logic into these new contexts? What does that look like and how does that even work for us?

Ken Case: The way App Intents are designed from Apple's point of view, last year they were presented as a way that you could integrate with shortcuts and that you'd be able to integrate with Apple Intelligence. But really, they were a set of APIs that let the system call into your app, and it didn't have to be just Apple Intelligence or Siri or whatever doing the calling in, and it didn't have to be just shortcuts doing it. Those were just where it started. Now, what we're seeing is that Spotlight is able to do it as well. So, when you pull up Spotlight and you start to type in something, you can now match our App Intents and say, "Oh, okay, you would like to duplicate this file, or any App Intents that we have built for any of our products now are surfaced through the Spotlight system." Going forward, you can imagine that Apple might have other ideas in mind for how App Intents could be exposed. So, really they're just a great extension point for integrating our apps with the operating system and exposing more of their functionality and features. So, one of the things that we're doing right away is we are migrating our Omni Automation shortcuts interfaces, which were previously done through Apple's older SiriKit interface to their new App Intents interface. And that means that they won't just be available in shortcuts, but they'll also be available in Spotlight in other places, so you can quickly invoke these plugins or other code.

Andrew J. Mason: I love how we're getting the opportunity to really stay not only doing this foundational work, as you mentioned, the homework that leads to dividends, but also getting to see the gifts that show up as well from Apple. And one of the things I'm curious about, I think this probably also landed in the homework category for you, but it's kind of a big deal, and it was just mentioned as a sentence or two inside of the blog post, was this idea of extending the syncing and improving the syncing in multiple continents. That's a small sentence, but do you mind unpacking what that entails and what that looks like and maybe some of the stuff to consider when you're thinking about OmniSync in different countries?

Ken Case: So, this is still very much work in progress, it's work that we're doing. But one of the things that we have realized is we've had a lot of contact with customers about OmniFocus and how long it takes to sync here and there is that most people who are on the same continent as where our servers were, we're not having trouble. I mean, a few were, anyway. There are all sorts of situations that can make your network slower for whatever reason. But if you're on another continent, there's not really not much that they can do or we can do, if you're trying to run a connection from one side of the world to the other and you're trying to sync data over that in some sort of time-sensitive way. I think we have sync times between continents usually at under 20 seconds for simple sort of transactions. But we would love for that to be more like the 3 seconds that we typically see here in the US. And sometimes, I see more like a quarter of a second, but I'm right here in Seattle, the servers in Seattle, it's a lot easier for me to see that kind of result. So, we want that result to be possible for anyone, and it is possible for anyone. Sometimes, we'll help people by talking to them through how they can set up their own sync server for the data. You can run something like WebDAV Nav server on your Mac, and then connect to that by setting up your sync settings to sync with your Mac rather than syncing with our servers across the world. But we know most people don't want to have to run their own servers, even if it's as simple as running a little Mac app and kind of configuring the username and password, then you still have to worry about is your Mac available? Is it on the same network? All of the things when you're trying to sync. We have set up a few test servers now in Singapore over in Amsterdam so that we can start to work with customers who are in other parts of the world and say, "Well, how is your connection if you go use this other server instead?" And it's not something that is fully developed yet. I really want this to be something where the customer can choose themselves, which server they think will be closest to them can migrate their data from one server to another automatically, and things like that, or maybe not automatically, maybe by their choice, but certainly easier than having some sort of support interaction to do it. So, that's what that project's about. And, of course, that involves managing services that are across the world from ourselves. So, that's a new thing for us to deal with. But there are some great services out there that make that easier.

Andrew J. Mason: It's so incredible to see because as a customer, you just think about is it fast? Is it slow? And just the trickle down of all the different decisions that need to be made in order to provide the best possible experience for somebody. It's so cool because I don't necessarily always think about that, but getting to see it play out and getting to hear kind of what goes into it is really interesting to me. Wrapping up in the blog post, you teased kind of this idea that, shoot, poof, there goes half of 2025 and 2026 will be here before we know it. And literally today as we're recording, this is I think the halfway day or the halfway point of the year, which is blowing my mind that we're in July already. But if you were to accelerate to the end of 2025, 2026 is just starting, you're looking back and you're saying, "Wow, I'm so glad we've made the progress that we did." What do you hope or believe would be true in that situation?

Ken Case: Well, I think we will have, of course, the improvements from OmniFocus 4.7 chip by then. I hope that we will easily by then have shipped the changes beyond 4.7, where we're talking about integrating Liquid Glass and how we also can integrate some of the other new features like these foundation models that let us leverage Apple's Apple Intelligence on their local device to do things in a way that preserves customers privacy and so on, and make that available to users. And, of course, I want to get back to our road map from the start of the year where we were talking about features like Kanban and OmniFocus. And so, I can't wait I guess to get to that and get that out as well, but we have plenty to do. So, it's not just that, of course, also OmniGraffle 8, I hope we're now kind of closing in on bringing it to the other platforms. Right now, the test flight is just for the Mac. Obviously, all this time, we've been working towards making it available universally. Soon we hope to have test builds available for the iPad, the iPhone, and the Apple Vision Pro. And then, of course, we have OmniOutliner 6 coming around soon.

Andrew J. Mason: It's so crazy to me the amount of work that's getting done, it's the difference between busy and productive. I feel like even though the crew's productive, they're not too busy to make time for a call like this. So, I appreciate you just pausing and giving us, not just an update, but a thoughtful look at where we've been so far in 2025 and where you hope to head as our team in 2026 and just excited to see what the future holds, even though it's a busy summer, I know that, but stuff's coming out of it. And so, I'm grateful to see that. So, thanks for spending some time with us today, Ken. This has been a blast.

Ken Case: Oh, you bet. Thank you. And thanks to everyone listening. The reason we do this is because we want to build stuff that you'll find useful. So, let us know if we're doing our jobs.

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