THE OMNI SHOW

Ken Case: We would often get questions about, "Oh well, could you add this feature? We think this would be a good improvement." And wherever possible, of course, we would say, "Okay, yeah, let's see what we can do." But sometimes what we would realize is, well, in order to implement that particular feature, we would have to break compatibility with OmniFocus 3. But it's now been over a year since we shipped 4.0, and we've done all these other great releases and we think it's appropriate to start pulling in some of those great changes that people have been asking for some time and in some cases for decades.

Andrew J. Mason: You're listening to The Omni Show. Get to know the growing community surrounding The Omni Group's award-winning products. My name's Andrew J. Mason, and today we have the 2025 Omni Group Roadmap blog post with Ken Case. Well, welcome everybody to this episode of The Omni Show. My name's Andrew J. Mason, and today we have the CEO of The Omni Group with us to talk about the 2025 Roadmap blog post. Ken, always awesome to have you with us. Thank you for hanging out with us today.

Ken Case: Oh, you bet. It's always fun to have these conversations.

Andrew J. Mason: Looking back I guess over our last year, 2024, is there any specific moment or achievement that happens to stand out to you the most personally, and why would that be?

Ken Case: Well, of course it has to be Apple nominating us for Mac App of the Year recognition in the App Store. We're one of three finalists, so that's a wonderful place to be. We didn't win, but on the other hand, it was a huge recognition and it reflected I think the team's effort to really try to make an app that was approachable for new users and in this redesign that we did for OmniFocus 4, and it was nice to have Apple recognize that effort.

Andrew J. Mason: Absolutely, and it really is an astonishing feat I mean that's worthy of celebration even just for the nomination. And you mentioned in the blog post as well, this marks five years of the team working remotely. And noticing the impacts on that and team collaboration, how has this shift in our culture, has this impacted our innovation in ways that were maybe unexpected for you in a positive way?

Ken Case: It's hard for me to identify specifics around that area because now it feels so settled. We've just gotten so used to this pattern now. Of course, it's much easier for anybody who is working out of the office, which we've had people working remotely for decades now, but it was awkward to have them at meetings and so on where a bunch of us were in the office around a whiteboard and we'd be doing stuff and they might be participating remotely. And we had experimented with things like these rolling robots that you could remote into and you would see them going down the hall and coming to the meeting and joining us there. So you'd see their face on a screen and participating that way, but it doesn't feel like a level playing field for that person, I think. Whereas now with everybody always working remotely, the meetings truly are a level playing field. We all feel like Brady Bunch Squares maybe, but we're all visible there at the same time and nobody feeling left out the conversation or partially left out.

Andrew J. Mason: We've talked about this on other episodes too, this idea of work-life integration as well, where it's just time zones are distributed and now people are able to jump in and jump out when it makes sense in a way that actually benefits everybody, which is very cool. Talk to me a little bit about OmniFocus. I know we've made a lot of progress with OmniFocus this year, 4.0 and 4.x releases continuing to come out. You've already mentioned that the changes up until this point have really kept the owners of previous versions of OmniFocus in mind. Dig into that a little bit. What does that mean for us?

Ken Case: Sure. So as we were designing version 4.O, we often, as we were going through feedback with the customers that were testing and they were helping us test during the public test period, we would often get questions about, "Oh well, could you add this feature? We think this would be a good improvement." And wherever possible, of course we would say, "Okay, yeah, let's see what we can do." But sometimes what we would realize is, well, in order to implement that particular feature, we would have to break compatibility with OmniFocus 3. And we didn't want to do that for the initial 4.0 release because we wanted to make the transition from 3 to 4 as smooth and easy as possible. So anyone who was already using 3 could run version 4, figure out what they'd like to have. Also, easy for the testers. They might not want to rely on this product that's still in testing for other full-time use and have to make this one-way migration that then blocked them from going back to the production version if something came up that they needed. So through that whole process we were very careful to prioritize keeping compatibility with version 3 and not making any changes that would break that compatibility. And we've maintained that for this first year of development as well. So as we did 4.1, 4.2, 4.3, 4.4 and 4.5, we were also looking at some of those same feature lists and like, well, no, not yet because we don't want to break compatibility. So we'll put that on hold until later. But it's now been over a year since we shipped 4.O. We've done all these other great releases and we think it's appropriate to start pulling in some of those great changes that people have been asking for some time in some cases for decades.

Andrew J. Mason: That's excellent. It's a mindfulness toward the customer that didn't show up for me initially when I first heard about it. I'm like, oh, my gosh. Okay, I didn't even realize that, yeah, compatibility is something that we need to take into consideration when we're adding to features or changing things. OmniGraffle 8 actually showed up on the radar as well, and you've mentioned in the blog post has incorporated literally decades of user feedback. Talk to us a little bit about the behind the scenes of how you're approaching its redesign at this point.

Ken Case: For a while there, our customer support team really wanted us to avoid using the word voting for a feature or a request or something because the process that we use for designing the next version of an app is not just based on votes. It's not just a democratic thing. It's based on thinking about what the designs and needs are and then what set of features might work together and so on. But on the other hand, we actually do track how many times something comes up from a customer, and I think a vote is a reasonable way to think of that. So what a vote does in that case is it doesn't determine what we're going to do, but it does determine what might get our attention, and so what we're going to look at when we're designing the next version. So we'll go through this database of a few decades now of feedback and we'll look at the things that have received the most requests over time. We'll also just look at things that are more recent to give them a little bit more weight because maybe some of the things that were asked for two decades ago, the whole landscape has changed and people don't need that anymore. But often it's just based on, all right, well how many people have asked for this and how long have they been waiting for it, and what is their use case, does it make sense for the product? And then we go in and think about, okay, what else are we building and how can we make this all fit together and what are our overall product directions that we're also trying to fit in with? And what do I mean by that? I mean things like deciding that our apps should be cross-platform, universal apps that where one purchase gets you the same app everywhere and ideally the feature set is as complete as possible everywhere. We don't want just a tiny crippled version of OmniGraffle on your iPad. We want it to be as full an experience as makes sense for that device. And it has a smaller screen, so maybe it doesn't make as much sense as on Mac or on an Apple Vision Pro. And we have to think about what the device characteristics are around touch input and all of those sorts of things. There are lots of things that are platform-specific no matter what, but it gives us a chance then to think about, okay, well, we really want to bring a unified experience to all of the devices. We want to rebuild the way you get to different features, hopefully in a way that you learn it once on one platform and when you go to another platform, even if the interactions are slightly different, you're touching instead of mousing and so on, you know where to look for things. The information architecture is the same and the features are overall the same, and so you know where you're looking even if the navigation and the actual input is slightly different. That's part of what has gone on behind the scenes as we've been rethinking how we did OmniGraffle 8.

Andrew J. Mason: That leans a lot into the next question that we were thinking about and asking. First of all, just to say, I appreciate the craftsmanship that goes into making something as compatible as it possibly can be across devices as well as showing that we're listening to customer feedback by when you say voting, we're listening because we're tracking it. We are there along with them seeing, okay, is this something that really becomes a need over time or something that more and more people are saying is a need? One of the things that we mentioned was this need to have a consistent user experience across different platforms. And one of the things that makes that challenging is the different structures of file systems and how things change and shift as you move from one platform to the next, and the inability to control what other systems that people use to manage their files with. So how has the Omni team approached and overcome challenges for linking to documents that are inside or outside of Omni's system and what are we doing to overcome them?

Ken Case: We've tried to support links to our documents for quite a long time. All of our apps have the ability to select something and then say, "I want to copy, a link to this content," and then you can paste it somewhere. But the question is, where can you paste it and how well does it work? And that answer is, well, it works pretty well for OmniFocus if it's you using it in your own database. We have wherever you've synced your database, we have the same reference points and when we see a link, we know what to open and that works out just fine. But it's more awkward if you're trying to do a link to some content in OmniOutliner or OmniGraffle because those links would refer to a document, and we didn't know where to find the document. So we might try to look for an open document and then that would work, but if the document wasn't open, then the link would fail, and of course, this would be a surprising interaction for people. So as we were thinking about how do we solve this, first, the problem got more complicated because people started using more devices. And so when you're on one device, it's easy to refer to where a document lives on that device. But as you start to go to another device and maybe your username is something different or you're sharing the document with somebody else and they definitely have a different username, so their document folder lives in a different place, we couldn't just use the path on disk the way like a file URL would use to reference it anymore. So what we are building for these document links is something that lets you reference the document by its name and then by the location that it lives in, and so basically just a reference to its folder or one of its parent folders and then a path down to the document. As long as that document is now synced between devices, and we have lots of ways to sync things between devices these days, we have of course things like iCloud Drive, pre-syncing your own documents, but in our work development teams often share documents and whole trees of documents through Git. We'll check things into a Git repository and then check it out on the other side. Whatever the mechanism is that your team is using to share our documents, we want to be able to work with that. We don't want to say, "No, you have to throw it into our sync system in order to link to it. That just gets intrusive and invasive and nobody's going to want to do that. So instead we just say, "Well, what do you want to name this folder," whatever it is. Pick a folder that contains a document, any parent folder up through the hierarchy, and then we'll store a reference that says what the path was within that folder and then a name for the folder. And when you go to another device and you follow that link, we'll ask, "Okay, we haven't seen this folder before. Where do we find it? I'm looking for Andrew's notes folder and where is that on this machine?" And so once they found it, then we bookmark a reference to it so we will be able to use it again later without having to prompt every time. From then on, whenever you click a link to something in Andrew's documents folder, well, it can just open it again. So that lets lots of documents talk to each other. They can cross-reference each other now. It lets a shared document links with other team members. That's a much better system and we're looking forward to rolling that out through all of our apps.

Andrew J. Mason: Again, a foundational work that is one of those things that you don't think about it when it's working correctly, but it's versatile enough to work possibly regardless of what system the person's using to sync up their files, which is so, so cool. And it opens up a lot of doors of possibility in the future as well, which is nice. I want to shift over to Omni Automation. I know it seems to get a continual focus. And with features like install links and the Omni Automation Vids that are showing up, how have you seen automation really start to transform the way that people have been using the Omni apps?

Ken Case: Well, our goal with automation, I know it sometimes seems esoteric to people, but really the goal is simple. We want to make routine things easy for people. So if you have something that feels like drudgery, it feels less like drudgery if the computer does that drudgery for you. It automates that work, and all you have to do then is maybe initiate it, or maybe you don't even have to initiate it because what you've done is added a trigger that the system initiates for you on your behalf. So there are all sorts of automation triggers now built into the shortcut system. Things like, oh, I've connected to Bluetooth in my car, and I would like to automatically fire off this thing that starts playing my favorite podcast or whatever. In OmniFocus, that means now that you can, in this latest release that we're doing, we just added a Shortcuts entry point for saying, "I would like to do a sync right now." So whenever you connect to a Wi-Fi network, for example, you could have OmniFocus automatically sync. Or you could say, "I want it to sync daily or hourly," and OmniFocus will often try to sync on its own and based on push notifications and things like that. But we're not in control of when that happens. Our app doesn't run in the background on iOS or iPadOS or visionOS. It can't run in the background. It's a hidden app on the Mac, and people usually don't usually have sync troubles. But sometimes with an irregularly used device, maybe they haven't used their iPad for a few weeks and they pull it up and now it's a few weeks out of date unless they open the app, well, this would let the system just automatically sync it up every day whether you're using it or not, and make sure that device is ready to go as soon as you do pick it up. Those sorts of automations I think just make life more practical. And of course, we've seen this through the years, not just with the most recent automation additions. With people using it for creating project templates and then instantiating projects from those templates, like, "Here's my packing list for a trip," and maybe the automation prompts them with a few questions like, "Okay, where are you going," and notices which season it is and so whether you should pack warm things or some things and so on.

Andrew J. Mason: Yeah, and if somebody is listening to this and they're like, "Man, that does sound cool. I'd love an entry-level jump into that," I do want to point the attention over to the Automation Vids and even a couple of past episodes where we've talked about automation a little bit. William Gallagher, I remember David Sparks, both of those are champions for entry-level automation. So if you hear this stuff, and you think, man, this sounds really cool, this is a couple of directions and we could put those in the show notes as well for people to check this out. You've also spoken about Apple Intelligence and how it's provided new opportunities for workflows within Omni's apps, like exposing those nouns and verbs for use in Shortcuts. Share a little bit more about what that is and how that works. Nouns and verbs, what does that mean?

Ken Case: Sure. So as we think about things like how Shortcuts, the app, has worked, over a few years ago, if you looked at the Shortcuts app, it was built on a bunch of recipes and you would say, "Here's an action I want to do in an app," and you might get a result back that was text or a graphic or something, but there were only a few predefined kinds of results you would get back and that it could then operate with. So as I think about the vocabulary that you're using in Shortcuts, that's what I'm thinking about when I call these things, nouns and verbs. The nouns are the things you're acting on, the objects that maybe are input to a step of the shortcut to automation or the result that comes out of it. And then the verbs are the individual actions that you might do with something like what is the next step? You might want to open it, you might want to edit it, you might want to be trying to find it in the first place. And of course, then other verbs that are specific to certain apps, like, "I want to complete this item in OmniFocus." Complete doesn't make sense in OmniGraffle for a shape, but it does make sense for a task in OmniFocus. And so getting specific in OmniFocus, those nouns will be things like tasks, individual actions, projects that collect those actions together, perspectives that are of ways that you view all of your content and you have different views on your database, tags, folders, those are the nouns of OmniFocus. And then the verbs are things like open, edit, delete, add, complete. But OmniGraffle will have a very different vocabulary because it's not working with these actions, these tasks, these projects. It's working with shapes and canvases and maybe in layers or organized into groups and things like that, and so it has a different set of nouns, a different set of vocabulary for things like grouping and ungrouping and laying out. And those are the things then that we expose to the system. And what that means is we expose it to the Shortcuts app, for one thing. The Shortcuts app notices these definitions that we've exposed. These are called app intents and app entities, and app entities being the nouns and app intents being the verbs. And then the Apple Intelligence work that they're doing coming forward that they've talked about with Siri, as Siri gets Apple Intelligence support, then in theory it should be able to start working with these nouns and verbs. So you can say, "Okay, well I'd like you to gather these projects and send it over here," or, "Gather these email messages and now send them to OmniFocus," and have it figure out a flow for you rather than you having to do it by hand in Shortcuts. But I want to be careful to note that all of this is stuff that is initiated by the user. It's not stuff where we invoke Apple Intelligence without your prompting. In fact, often we don't even know Apple Intelligence is the technology that's being used when it talks to our app and says, "Okay, well the system asks for me to apply some verb to some noun." We apply that verb to that noun, but we don't know whether it came from Shortcuts or whether it came from Siri or what.

Andrew J. Mason: So the idea of almost building a dictionary of this collection, this database of things that can happen and things that are doing the happening and handing it over to Apple to do in whatever way that it deems necessary for the apps.

Ken Case: Right, and then in theory, they're training Siri on all of these nouns and verbs. And then Siri, through this process of AI learning, is starting to put things together so you can express your goals at a higher level and have it outline the steps that it'll take to get there.

Andrew J. Mason: So cool. I guess as we wrap up, what is one thing, or multiple things if you want, that you are hoping that people are going to take from this year's Roadmap blog post, maybe not even in terms of features or things that are upcoming, but how they're approaching productivity and their workflows?

Ken Case: I want everybody to hear that we really appreciate everybody who's using our products and giving us feedback along the way and telling us what it is that they want and need, and to know that we're listening, and we're trying to continually improve each of our products as we go forward. That's what we really love doing the most, and a big part of the reward is hearing from our customers that, yes, what we did made a difference to them.

Andrew J. Mason: 100%.

Ken Case: So thank you to everyone who's given us feedback.

Andrew J. Mason: Yes, thank all of you that happened to be listening to this. We so appreciate it. Ken, thanks to you too for joining us for a little bit for the show just to break down the blog post and talk through what 2025 might hold and where we've come so far. I appreciate that.

Ken Case: All right. Well, thank you.

Andrew J. Mason: Everybody, that is our Roadmap. If you haven't checked or read through it yet, you can head over to omnigroup.com/blog, look at the Roadmap blog post and check it out and learn more about where we've come from and what we're hoping for this year as we move forward. Hey, and thank all of you for listening today too. You can find us on Mastodon at The Omni Show at omnigroup.com. You can also find out everything that's happening with The Omni Group at omnigroup.com/blog.