THE OMNI SHOW

Ken Case: You can tell from the version number eight that OmniGraffle has some history to it now. I pulled back the OmniGraffle one boxes that we used to ship as box product on shelves, right? And kind of looked over, all right, what was the box art that we had? What did the manual have to say about OmniGraffle? And think about what we can do to make the app as approachable as possible while still preserving all of the power, because we don't want to lose anything in this process.

Andrew J. Mason: You're listening to the Omni Show where we connect with the amazing community surrounding the OmniGroup's award-winning products. My name's Andrew J. Mason, and today we hear about the OmniGroup's 2026 roadmap.

Well, welcome everybody to this episode of The Omni Show. My name's Andrew J. Mason, and today we have the CEO of the OmniGroup with us to talk about the 2026 Roadmap blog post. Ken, always an honor to have you with us. Thank you again for hanging out with us today.

Ken Case: Oh, thank you. It's always fun to be here.

Andrew J. Mason: I love this time of year because it's our chance to pause and take a breath and think about not only where we're continuing to head as we're always forward-looking, but also about the ground that we've traveled to get here. And as you look back on everything the team's kind of shipped and explored and worked on recently, do you have a defining theme or kind of a sense that emerges over what's happened over last year's roadmap?

Ken Case: Oh, last year was a pretty fun year. There were certainly some visible releases, of course, that we shipped out to the public with some great improvements to OmniFocus with planned dates and so on. But we also did a lot of heads down working behind the scenes stuff on features like OmniLinks and Apple Intelligence. And part of that was inspired by what was happening in the world as Apple announced new things and we started thinking about them. And part of that was just inspired by thinking about what our customers had been looking for for years. So I was reflecting on our conversations with customers about collaborating with OmniGraffle and how they might want that collaboration to work. And that led to us developing OmniLinks. And of course, OmniLinks was something that took a lot of time to think about and sort of refine before we finally shipped it in OmniOutliner 6 as a starting place, but that's of course not the ending place. OmniLinks will be coming to the whole suite over time.

Andrew J. Mason: Yeah, very much in progress too. And if you really want to deep dive into the whole OmniLinks scenario and what that's going to really enable for us, I actually encourage people to take a listen to, I think it was two episodes back now, you and Sal just kind of like jumped into this is what it can enable in terms of collaboration and how it enables new ways of working together, which I think is really great. But maybe just give a quick little overview of some other things that people can expect or have been thinking about when it comes to OmniLinks as it's moving forward.

Ken Case: Sure. Yeah. So obviously in that last episode, we were talking specifically about what we had shipped in OmniOutliner and what you could do right then. But as we think about OmniLinks, of course, they're not going to be limited to OmniOutliner. You'll be able to select a shape in OmniGraffle on a canvas and say, "Okay, well, I would like to link to that." And then you can copy that link and paste it into OmniOutliner if you want to have OmniOutliner documents reference your OmniGraffle content or into another place in OmniGraffle. So you can have diagrams that refer to other diagrams or kind of go from one place to another that way. Or the links can go to an outside system altogether. So maybe you share it with your company in a group chat or put it in your local Wiki or something, right? We call it guidebook for our internal documentation for things. And if somebody might want to reference the original document, like maybe I've pasted the PDF into the page or a ping representation of the diagram, but maybe we have a link that says, "Oh, and if you want to get back to the original Graffle content, just click this link and the OmniLink will take you there." And so it's meant to be a real time saver for people to be able to share this stuff with themselves, of course, across these documents, and then with other people in their teams. And I'm pretty excited about where that can go, both as a collaboration mechanism and also as a way to make apps more efficient. So one of the challenges that we've had when it comes to attachments in our apps, if somebody brings in a big folder worth of content and drops that into OmniOutliner as an attachment, well, now that document has gotten really big because it's embedded and every time you edit and save, it's rewriting all of that same data again and again. If you can just link to that instead, which OmniLinks enables, you can't right this second now, but that's part of the planned roadmap for how OmniLinks will develop, then that syncing of that data happens once and it happens separately from every time you edit your document and write around and browse to it. And of course, the same thing applies for OmniFocus. So when people are using OmniFocus and they're referencing content that right now maybe they have to embed in the database in order to have it show up in their notes, well, instead they can link to it and have that linked content then be synced once rather than slow down syncing all of the time.

Andrew J. Mason: I love too, that you have given a pretty decent portion and a nod to what was happening last year over the development of Omni's integration of AI. And I mean Apple Intelligence, not artificial intelligence, but there is a really great kind of philosophy showing up of like can but not must, that's out here. And I think it's a really thoughtful long-term way of approaching this that I super appreciate in that the idea of how Apple's approaching all of this AI portion, but also the ability that we're giving people with things like OmniAutomation plugins. Talk a little bit more about how we've been approaching Apple Intelligence when it comes to both privacy, but also things like large language models.

Ken Case: It's something we can't ignore given what's been going on with the industry, and there's a lot of interesting power there. And at the same time, there are a lot of concerns about, is it safe to use? What are the privacy aspects and so on? One of the great things about Apple Intelligence that has helped us feel comfortable sort of aligning and integrating into our apps is that almost all of the Apple Intelligence stuff, all of the stuff that we integrate with anyway, is stuff that happens on your own device. So it's powered by your device, you're not burning down forests somewhere else, you're just using the capabilities and the energy that your laptop is already using and you're applying it to whatever problems you're trying to use it for. Because it's happening on your own device, that means the data is also under your control. It's not going to somebody else's server. You don't have problems where your data is accidentally leaking because somebody said, "Well, we designed this in order to make sure that it's not going to scan your sensitive emails. It'll skip that and filter that out." And then, "Oh, sorry, we had a bug and it did get exposed to the cloud and copied to somebody else's device." And those sorts of risks just feel really dangerous to me, I guess, as somebody who does care about our customer's privacy and the ability to keep their data confidential. So we want people to be able to be fully in control of their data even when they're using AI. But we also want people to be able to choose not to use AI at all because there are certainly good reasons that some people have for wanting to avoid it in certain circumstances. So we just basically want to give that choice to our customers because there's so many different ways that it can be used. And while we have tried to address as many of the problems that we can think of, other people may think of different problems that might be appropriate. And in some fields, maybe there are no problems and it's okay to just go to town and use it all you want, but that's where it needs to be left to the customer to decide, I think.

Andrew J. Mason: I think putting that in the hands of the customer is such a wise thing and also a shout-out to all of the people on Slack that are caution to the wind. I see them throwing down the MCP servers and all sorts of things that are like, "Wow, that is bleeding edge," but it has to depend on the person's level of comfortability. We don't want to force that on anybody. So I think it's just such a thoughtful way to approach it. A couple of other changes that have happened over the last year, including Liquid Glass with OmniOutliner 6 and a couple of other really cool advances that I think are worth a mention here. Do you mind just kind of shaving through some of the other things that have been happening?

Ken Case: Sure. Yeah. So of course we go into every year knowing that our plans will have to adapt to whatever Apple announces in June at WWDC, their developer conference, the worldwide developer conference. So last year they announced some things around Apple Intelligence, but they also announced Liquid Glass, which is the first time that Apple has really sat down and tried to create a cohesive user experience across all of their platforms at the same time. They have done this on one platform or another in sequence before, but not really where they tried to look at all of it at the same time and say, "Here's a system." So that's an ambitious project and this is the first iteration. So there are some areas that are still rough on some platforms and different areas on different platforms. But I think the project as a whole is a good idea. It's great that buttons look like buttons again to me now. I can see where the edges of buttons are. They're not just colored labels floating out in space and you don't know whether the color label actually means that it's interactive or if there's some other reason that it's colored and so on. So things like that, there are some nice moves forward. There are certainly some concerns that people have had around Liquid Glass, but overall, I feel like the direction is a good direction and it's been improving. And so we first adopted some Liquid Glass support in OmniFocus 4 aid, which shipped alongside the new operating system. So I'll note that Liquid Glass only applies to people who are using Apple's latest operating system. So if you're using an older operating system, none of this affects you, but when you upgrade to the latest one, then all of Apple's system is designed with this Liquid Glass stuff in mind, or they tried to. And of course now we want our apps to fit in with that system as well, so that it looks at home and in place. And so now we've done that with OmniFocus and OmniOutliner. And of course we look forward to bringing Liquid Glass to OmniGraffle and OmniPlan.

Andrew J. Mason: Way to parlay into 2026 brings us to where we're at. I know that OmniGraffle has a really deep legacy. And as you talk about all the ongoing design and modernization with Liquid Glass and those things, how are you balancing those decades of, there's power user expectations with also this need to like, we want to make sure that we're moving the app forward in a way that's meaningful to everybody.

Ken Case: Yeah. It's a really interesting problem that we spend a lot of time kind of thinking about, particularly in the context of OmniGraffle. This is the big app that we're doing next is OmniGraffle 8, the big app release. And you can tell from the version number eight, OmniGraffle has some history to it now. We've been working on it for over 25 years. And as part of this effort, we went back, I pulled back the OmniGraffle 1 boxes that we used to ship as box product on shelves and kind of looked over, all right, what was the box art that we had? What did the manual have to say about OmniGraffle? What was our initial kind of goal for this to be approachable for somebody new to this whole problem space? And what did we think was important at the time? Not that we want to just go back to that old version. We've learned some things between now and then, but we do want to kind of look at some of these things again with fresh eyes and think about what we can do to make the app as approachable as possible while still preserving all the power because we don't want to lose anything in this process that people have come to rely on over the past two and a half decades out of the app. And so we want it all to be fresh and easy to use for new customers. We want it to feel good for customers who are experts in it and have been using it forever and we don't want them to feel lost or wonder, "Is this new version worth the upgrade or not?" And so change is always a little worrisome that way, right? There's the risk that you had something that you liked and you're changing it and now you've broken it in some way, you've made it worse. But I think change is important because I don't think we have gotten things perfect yet. We weren't in a perfect place with the old version, so of course we want to change it. We want to make it better and how can we make sure we're making it better and not introducing things that make things harder for people. And so as we adopt Liquid Glass, for example, or as we redesign different features, we try to keep all of that tension in mind. We try to listen very carefully to what our customers have told us over the years about how they're using the app and what it is that they want out of it, where their frustrations are, so how we can improve those things. And then we kind of have to just listen to our own experience with the app. It's something we use ourselves to... We don't as often hear from customers saying, "Oh yeah, I love this part about your app." It's just not the way people are wired. So they don't say, "Oh yeah, I use that feature every day and it just works perfectly." And so, "Don't mess with that. That part's already there. Please don't ruin it." They'll tell us after we ruin it.

Andrew J. Mason: It's the silence after it. Yeah. Silence when it's working and then raise the volume when it's not.

Ken Case: And so we have to kind of pay attention to our own instincts as we do that and like, "Okay, what is it that we're using and what is it that works well and what is it that maybe didn't work so well that we tried last time around?"

Andrew J. Mason: I love that this iterative approach that shows up where it's like we're bringing things to an app, we're paying attention to that app, making it a focus, making it where it needs to be, but also you're re-asking the question, how do we make it better? And this is part of the stay humble, stay hungry thing where it's like, if we ever come up to an ultimate answer with that, then okay, we've done our job wrong because this is something that's a conversation. It's not just a once and done snapshot. And so being able to bring that conversation from OmniOutliner most recently and focusing into the direction of OmniGraffle, I mean, would we be expecting things like the OmniLinks? And you mentioned Liquid Glass already, so that's coming over, but any other could expects or might want to seize showing up here in OmniGraffle as well?

Ken Case: Oh, of course. Yeah. The big features that sort of talked about us with Liquid Glass, with OmniLinks, of course, those are going to come to all of our suite, including OmniGraffle, and be adapted to what makes sense in OmniGraffle for them. So in OmniOutliner, the OmniLinks are kind of based around this notion of connected folders, and we'd had resource folders in the past where you could say, "Okay, I want to be able to store some templates wherever I want and be able to sync them around to all my devices. So when I go to a new device and open an outline, I can base it off this template that I spent some time working on in the past." Well, in OmniGraffle, I already kind of spoiled this, right? We have the same thing going on with stencils that you might share between your documents or among your team, and you might want to put those stencils in a connected folder. We also use it for plugins. We use it for, if you have some OmniAutomation plugins that are doing some interesting things and you want to sync that across all of your devices, you store them in a connected folder and that way you can easily reference them. And that connected folder technology is the same foundation that's used now for plugin stuff, for stencils, for templates, for OmniLinks, of course, and for the future things that I referenced earlier, like being able to have attachments that are linked attachments rather than embedded attachments that are lighter weight in terms of performance, the performance implications on whatever document you're editing at the time. So yeah, that's all pretty exciting. And of course, OmniGraffle itself has a lot of stuff that is specific to the OmniGraffle space. So as we're designing OmniGraffle, it has over the last two and a half decades developed a lot of functionality. And so we ended up with a lot of inspectors and other kinds of controls and interfaces and so on. We don't want to take those things away from people, but we also don't want it to be so cluttered and busy with all of this information that it's hard to find the essential controls, like what are just the simplest pieces. And so some things we've done in this coming release to make that easier for people to approach and discover is when you select something, we'll display just a little strip of controls right underneath that selected shape that say, "Okay, well, here's where you can change the shape's color or its shape itself or the stroke on the shape or what does it feel like?" Or the text, right? And so kind of the basic functionality then is right there at hand. It's obvious and it's near the mouse where you are, you were selecting things, you don't have to click somewhere on the canvas and then go over to the inspector and then come back back and forth. And those sorts of little refinements I think can help the experience with a very mature app, while not taking anything away from all of those pallets and so on, that in fact we have now gone through and rebuilt all of those using Swift UI so that we can make them universal and bring all of that same capability, the capability of the Mac app to the iPad app and to the iPhone app to the Apple Vision Pro app and have them all feel like a unified experience. So we can have one set of documentation that applies to the whole suite rather than sort of documenting it separately for each platform, which there I was phrasing it from the point of view of the work we have to do, documenting it separately. From the point of the view of the user, you have to learn it separately. You're learning it for the Mac and then you're learning it again on the iPhone and then again on the iPad and so on. That's not the experience we want. We want people to be able to apply their learning from one platform to all of the platforms as it becomes a universal app and a universal purchase. One of the struggles that some customers have had in the past is they would buy the Pro app maybe for the Mac because that's where they're doing most of their editing and they need most of the power. And then they would get like these simpler app for the other platforms. And this isn't just for OmniGraffle. We see this in OmniOutliner in all of our apps really. Because they were using the Pro app on the Mac, well now they try to do something on the iPhone with one of those documents and it says, "Oh, you need the Pro App for this." And they're like, "Well, I don't want to spend this money again. I don't use it that much on the iPhone that it feels like it's worth it to me or I don't use those Pro features enough to feel like it's worth it." What exactly is it about this document that makes a pro? And at least a whole bunch of questions, which as we make this now a universal purchase for all of our apps, we've done... OmniGraffle is the last one. We've now done OmniPlan first and then we did OmniFocus with version four. So OmniPlan 4, OmniFocus 4 were Universal. Now OmniOutliner 6 is Universal and OmniGraffle 8 will be the last one to become Universal. And that means if you have purchased OmniGraffle 8 Pro on the Mac, you have it on all of the platforms, on the iPhone, the iPad and Apple Vision Pro.

Andrew J. Mason: So cool to get to hear that. I mean, it represents a body of work and I love that for an app or even a suite of apps that are as mature as they are. I learned the term progressive disclosure from you. I'm not a designer. So it's the first time I've heard somebody say that term where it's like you're bringing information to a person in this place that they need it, but you're also having this continuous question about how do we make it easy for users without alienating the long-term Pro users that we have on this thing. And it is a dance, but I love how thoughtfully and continuously we're having this conversation and it is an ever-ending one. And as if any of this wasn't enough for a year, I know that there are people out there that as soon as the blog code post came out, they hit command F or search or whatever on their keyboard and typed in the word Kanban. I know it for a fact. I just believe that that happens and happy to say that if they did that, they would see the words show up there, as well as even a couple of other elements that we're looking to actively work on in this coming year, such as data centers. But do you mind speaking a few words to those two elements as well?

Ken Case: Sure, absolutely. So make sure I'll start with the data centers first because that's something that is actively in test right now. We've put out some notes on social media, folks that follow us there, you might have already seen them and we've had some volunteers that, "Sure, yeah, I would love to try a closer server. Could you sign me up for this test and let's see how it goes?" And as we have moved people over to these servers, which are currently in Europe and in Southeast Asia, then we checked back in and like, "Okay, how's it going? Did that work well? How's the experience for you?" And so far it's just been universally positive like, "Oh yeah, this is amazing. I assume this is what it must have been like for people in the US all along, this sort of sync time. Suddenly my watch syncs better." All sorts of things that people were having struggles with that were caused by the latency of trying to send these bits around the globe and talk to a server that was on the other side of the world. So placing these servers closer to the customers who are using them, I think is so far the experiment seems to be going well. Let's just put it that way. The future is not certain because it's not been yet, but the roadmap is about what direction we're headed in, what we're working on and where we're trying to get to. And so looking at it from that point of view, of course, yes, we're working on Kanban. And for those who don't know, Kanban is a way of visualizing things a little bit differently. So if you have a bunch of tasks, instead of viewing them as a list of tasks in an outline the way that we have traditionally done things in OmniFocus, this would be viewing them as more like cards that you would arrange on a board and you drag them around from one column to another to represent different changes in their state and so on. And so obviously in the context of OmniFocus, we want to maintain all of the power and flexibility that we're used to having with OmniFocus and our outline lists, but we want to give people the chance to visualize things a little bit differently. So that's how we've been thinking about Kanban.

Andrew J. Mason: If people dig into the blog post itself, they're going to even see even more, if you can believe it, beyond what's been listed and talked about here in this episode. So I do encourage you to dig in and just kind of see if there's any other details that might appeal to or apply to you in your certain situation. But as always, I'm really, really grateful, Ken, that you even spend a half... I don't know why I pit this picture of you like this incredibly busy on the go person, but it is productivity software and these are tools that help you get the most out of your day. And I know that you're busy making productivity software. So I'm just grateful and honored that you would spend this time just kind of breaking down what the year would look like for us, maybe some great things to look forward to, but also to look back in the past and pat ourselves on the back and say, "Yay, we're making progress. This is great."

Ken Case: Well, I just want to say I'm grateful to everyone who's listening or watching this, right? Because the work we do isn't possible if there's nobody out there who cares about what we're doing.

Andrew J. Mason: That's right.

Ken Case: So of course we care about what we're doing and we're trying to make the best software we can, but ultimately it comes down to, is it the best software for you? And so if you're listening to this and if you have feedback about any of this, of course I would love to hear from you and that's what makes doing all this worthwhile for us.

Andrew J. Mason: Yeah. Thank all of you. And yeah, thank you Ken too as well. This has been great. Hey, and thank all of you for listening today too. You can find us on Mastodon at TheOminShow@OmniGroup.com. You can also find out everything that's happening with the OmniGroup at OmniGroup.com/blog.